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NameDescriptionAddressPhone
Step Into Adventure
Key West SeaplanesTop Pick
 
A scenic tour, charter flight or almost any adventure you'd like to have is possible when you use Key West Seaplanes. These amphibious craft can land on...
3194 South Roosevelt Blvd. 305-294-4014
Fury Water AdventuresFury Water Adventures is home to the Glass Bottom Boat that takes you on an eco-tour of the reef that doesn't involve you actually getting into the water,... 2 Duval Street 800-994-8898
Sebago Key WestGetting out on the water in Key West is one of the highlights of a Key West vacation. And, for a great on-the-water adventure, Sebago Key West offers a full... 205 Elizabeth Street #1 305-292-2400
Sightseeing Steps
Harborwalk and Historic Seaport at Key West BightTop Pick
 
If you only have time visit one part of town, the Historic Seaport area is the place I always suggest. The Key West Harbor (Bight) was once a working waterfront...
Along the waterfront from Front St. to Grinnell St.
Key West SeaplanesTop Pick
 
A scenic tour, charter flight or almost any adventure you'd like to have is possible when you use Key West Seaplanes. These amphibious craft can land on...
3194 South Roosevelt Blvd. 305-294-4014
Curry MansionThe Curry Mansion was built beginning in 1855 and was the home of William Curry, Key West's first millionaire. Today, the mansion, listed on the National... 511 Caroline Street 305-294-5349
Fury Water AdventuresFury Water Adventures is home to the Glass Bottom Boat that takes you on an eco-tour of the reef that doesn't involve you actually getting into the water,... 2 Duval Street 800-994-8898
Garrison BightHome to several charter fishing boats, 2 marinas and 2 Thai restaurants, Garrison Bight is not much to look at, but a good place to go to find a charter boat... North Roosevelt Blvd. and Palm Avenue
Key West Cemetery
 
Filled with flowers, plantings, sculpture, gravestones and vaults, the Key West Cemetery can be a place for a walking tour all its own. Pick up or print out a...
Bordered by Olivia and Frances Streets and Windsor and Passover Lanes
Key West Ghost and Mysteries Tour
 
Operated by the same great people from the Trails and Tales tour, this haunted walking tour is just the right mix of scary and fun. Key West is full of ghosts,...
310 Duval Street 305-292-2040
Key West Public LibraryI've never actually taken advantage of the library's services, but while I'm out walking I often take advantage of the peaceful gardens and... 700 Fleming Street 305-292-3595
Mallory Square
 
Home to Key West's famous Sunset Celebration, Mallory Square during the day is a wide open space bounded by a number of attractions and clear turquoise,...
Mallory Square
Nancy Forrester's Secret Garden
 
Nancy's Secret Garden has RE-OPENED as a sanctuary featuring Nancy's precious collection of parrots, macaws and at least one cute cockatoo too. While...
518 Elizabeth St. 305-294-0015
Sebago Key WestGetting out on the water in Key West is one of the highlights of a Key West vacation. And, for a great on-the-water adventure, Sebago Key West offers a full... 205 Elizabeth Street #1 305-292-2400
Southernmost HouseThe Southernmost House stands guard at the southernmost corner of Duval Street. Built as a private home in 1896, this spectacular Victorian spent a number of... 1400 Duval Street 305-296-3141
Southernmost PointThe Southernmost Point buoy is one of the most popular photo op stops in Key West. While it isn't much more than a painted concrete(?) marker, there is... South Street and Whitehead Street
White Street Pier and the AIDS Memorial
 
The White Street Pier is one of my favorite spots to visit. At the entrance to the pier, you'll find the Key West AIDS memorial; a somber testament to the...
White Street at Atlantic Boulevard and the Atlantic Ocean
Step Into History
Fort Zachary TaylorTop Pick
 
Fort "Zach" has it all: a beautiful, although slightly rocky beach, a fascinating historic fort where you can take an informative self-guided tour, a...
300 Truman Annex 305-295-0037
Hemingway HouseTop Pick
 
One of the most popular tourist destinations on the island and for good reason. The guided tour of Ernest Hemingway's Key West home is interesting for more...
907 Whitehead Street 305-294-1136
Mel Fisher Maritime Heritage Society and MuseumTop Pick
 
In Key West, much of the history you have a chance to learn about and experience is from long ago. The Mel Fisher story, told in full at this fascinating...
200 Greene Street 305-294-2633
African CemeteryIn 1860, three ships carrying Africans meant to be sold into slavery, were captured and sent to Key West. Many died at sea and another 294 died after they... Higgs Beach. Atlantic Avenue at White Street
Audubon House and Tropical GardensFilled with art and antiques, this house also features the 28 first edition works by James Audobon, which are my favorites. There is a fascinating history to... 205 Whitehead Street 305-294-2116
Charles "Sonny" McCoy Indigenous ParkAcross from the beach, this small piece of property preserves and showcases over 75 native Florida Keys native trees and plants. It's a great addition to a... Atlantic Boulevard at White Street
Cork and StogieDouble your pleasure at Cork and Stogie where you can visit the Southernmost Cigar Store AND the Southernmost Wine Shop all at once! The cigar making industry... 1218 Duval Street 305-517-6419
East Martello Towers and Museum
 
Fascinating history and art museum located on the east end of the island near the airport. In addition to artifacts from every phase of Key West history, the...
3501 South Roosevelt Boulevard 305-296-3913
Harborwalk and Historic Seaport at Key West Bight
 
If you only have time visit one part of town, the Historic Seaport area is the place I always suggest. The Key West Harbor (Bight) was once a working waterfront...
Along the waterfront from Front St. to Grinnell St.
Key West Cemetery
 
Filled with flowers, plantings, sculpture, gravestones and vaults, the Key West Cemetery can be a place for a walking tour all its own. Pick up or print out a...
Bordered by Olivia and Frances Streets and Windsor and Passover Lanes
Key West Ghost and Mysteries Tour
 
Operated by the same great people from the Trails and Tales tour, this haunted walking tour is just the right mix of scary and fun. Key West is full of ghosts,...
310 Duval Street 305-292-2040
Key West Lighthouse and Keeper's MuseumAt 86 feet tall, it's an 88-step climb to the top of this 1847 lighthouse, where you'll find unparalelled views from the observation deck. The... 938 Whitehead Street 305-295-6616
Key West Shipwreck MuseumMore for kids than adults, with historic "characters" telling tales of wrecks and rescues; with artifacts of actual wrecks. The walk to the top of... 1 Whitehead Street 305-292-8990
Little White House
 
Harry Truman's tropical weekend getaway offers a glimpse into both Key West and American history. The house is located in what is now the gated community...
111 Front Street 305-294-9911
Oldest House MuseumLocated right on Duval Street, the Oldest House, built c. 1829 and moved to it's current Duval Street location c. 1836, is a true piece of Key West... 322 Duval Street 305-294-9501
West Martello Tower
 
The West Martello Tower, located at Higgs Beach is home to the Key West Garden Club's Botanical Gardens. The self-guided tour is free, although donations...
1100 Atlantic Boulevard 305-294-3210
White Street Pier and the AIDS Memorial
 
The White Street Pier is one of my favorite spots to visit. At the entrance to the pier, you'll find the Key West AIDS memorial; a somber testament to the...
White Street at Atlantic Boulevard and the Atlantic Ocean
Sandy Steps
Fort Zachary TaylorTop Pick
 
Fort "Zach" has it all: a beautiful, although slightly rocky beach, a fascinating historic fort where you can take an informative self-guided tour, a...
300 Truman Annex 305-295-0037
Dog BeachTiny beach where dogs bring their owners so they (the dogs) can go swimming. Lots of fun to watch the doggies play in the water and with each other. Right next... Vernon and Waddell Streets
Higgs Beach
 
My favorite thing about Higgs Beach is watching the ongoing volleyball games that seem to spring up from nowhere. I'm not sure what the rules are about...
Atlantic Avenue, just west of White Street
Rest BeachOn the opposite side of the White Street Pier from Higgs Beach, Rest Beach is a small area bordered by grassy dunes. Other than what I've seen riding past... Atlantic Avenue, just east of White Street
Smathers Beach
 
The longest stretch of sand on the island. Not as big as many in Florida go, but the most "beach-like" beach in Key West, stretching a half mile (1000...
South Roosevelt Boulevard, from Bertha Street to the airport (almost)
South Beach
 
A very nice, albeit small-ish beach at the end of Duval Street. Chair rentals, volleyball and beach amenities are enhanced by the presence of the Southernmost...
Duval Street at the Atlantic Ocean
Sipping Steps
Afterdeck at Louie's BackyardTop Pick
 
The Afterdeck at Louie's Backyard is a very special place. The bar itself is small (about a dozen seats) but the deck is expansive with seating for well...
700 Waddell Avenue 305-294-1061
Schooner Wharf BarTop Pick
 
When they say "the last little piece of old Key West" they're not kidding. When you're at Schooner Wharf, you can get a feel for what Key...
202 William Street 305-292-3302
Sloppy Joe'sTop Pick
 
An institution with a rich history and some of the hardest working bartenders and servers on the island. Talented musicians play all day with rock and roll...
201 Duval Street 305-294-5717
801 Bourbon Bar
 
An Entertainment Complex on the corner of Duval and Petronia, 801 is one of "the" places to go for the gay community and it also welcomes visitors,...
801 Duval Street 305-294-4737
Aqua Nightclub
 
Bar and nightclub featuring their famous "Reality is a Drag" show nightly. Aqua has a daily happy hour from 3 - 8PM featuring drink specials and...
711 Duval Street 305-294-0555
Bagatelle
 
Located in an historic Victorian house right on Duval, Bagatelle is a great spot for people watching, and an even great spot for breakfast (served 'til...
115 Duval Street 305-296-6609
Bobby's Monkey BarCasual neighborhood bar often referred to as the "Gay Cheers". Locals and tourists, gay and straight, mingle, mix and chill. Play some pool, have a... 900 Simonton Street 305-294-2655
Bottlecap LoungeThe Bottlecap is on Simonton, only a block off Duval, but has a definite "off the beaten path" feel to it. Tables and bar stools inside and out. Dance... 1128 Simonton Street 305-296-2807
Bourbon Street PubA mainstay in the gay community, Bourbon St. Pub has a lot of fun to offer everyone. 4 separate bars (the Garden Bar is for men only), hot male dancers on stage... 724 Duval Street 305-293-9800
The Bull, Whistle Bar, Garden of EdenLocated on the corner of Duval and Caroline Streets, this three-story collection of classic Key West drinking establishments is practically a required stop for... 427 Caroline Street 305-296-4565
Captain Tony's Saloon
 
Captain Tony's is one of the most famous, most revered saloon's in Key West. What is now Captain Tony's was once Sloppy Joe's. The history...
428 Greene Street 305-294-1838
Caroline's CaféA fun open-air bar and casual restaurant on lower Duval between Caroline and Eaton. Great for people watching and known for its generous portions,... 310 Duval Street 305-294-7511
Chart Room BarTucked away along one of the paths that meander through the Pier House Resort, the Chart Room is an off-the-beaten path sort of place, right at the party end of... 1 Duval Street
Cork and StogieDouble your pleasure at Cork and Stogie where you can visit the Southernmost Cigar Store AND the Southernmost Wine Shop all at once! The cigar making industry... 1218 Duval Street 305-517-6419
Cowboy Bill's Honky Tonk SaloonA reopened, refreshed and slightly downsized Cowboy Bills is still kicking it as the go-to place for country music fans! Expansive country music venue... 618 Duval Street 305-295-8219
Dante's
 
Fully outdoor dining and drinking establishment with the added feature of a pool that is open for use to all Dante's customers. The pool adds to the...
951 Caroline Street 305-423-2001
El Meson de PepeCuban food, Cuban culture and Cuban music all thrive right off Mallory Square. My favorite time to be here is when the salsa band starts playing every night... 410 Wall Street 305-295-2620
Fat TuesdayIt's amazing to see just how many varieties of frozen daiquiris and other concoctions you can choose from at Fat Tuesday; and that's before you start... 305 Duval Street 305-296-9373
Flying Monkey SaloonAdjacent to Fogarty's on lower Duval, The Flying Monkey Saloon is home to frozen cocktails and a cooling mist that lightly sprays. Between the two,... 227 Duval Street 305-294-7525
The Gardens HotelWhat is currently the Gardens Hotel on the corner of Angela and Simonton streets used to be the home of Peggy Mills, who created a wondrous botanical garden... 526 Angela Street 305-294-2661
Grand VinGrand Vin is the "grande dame" of Key West wine bars. Many an afternoon has been spent sitting on the porch, sipping several glasses (or is it... 1107 Duval Street 308-296-1020
Green Parrot
 
Probably the best spot for music in Key West with national acts performing blues, jazz and funk every week. Great drink prices and a happening locals scene...
601 Whitehead Street 305-294-6133
Half Shell Raw BarThe Half Shell used to be one of my favorite spots, but again, with a menu change and "improvements" that were made, I don't enjoy it as much as... 231 Margaret Street 305-294-7496
Hogs Breath SaloonGreat spot for live music all day and night in a funky outside venue. Not one of my picks for dining (he inside restaurant is rarely full) but great vibe,... 400 Front Street #C 305-296-4222
Hot Tin Roof
 
Elegant, upscale and romantic, Hot Tin Roof offers an extraordinary dining experience. The views are second to none from this second floor, waterfront location...
00 Duval Street 305-296-7701
Irish Kevin'sA raucous establishment with almost continuous entertainment designed to make you howl with laughter (or run out the door in embarrassment), Irish Kevin's... 211 Duval Street #C 305-292-1262
Jack FlatsA true sports bar with a stunning collection of gigantic TVs, great drinks and what some say is the best burger in Key West. If you're going to watch a... 509 Duval Street 305-294-7955
LaTeDa
 
On the upper end of Duval, the bar at LaTeDa is one of my favorite spots for people-watching any time of day. The design of the bar makes conversation easy and...
1125 Duval Street 305-296-6706
Margaritaville
 
This is Jimmy Buffett's original Margaritaville and is a hugely popular destination for Key West visitors. You can stop here for a nice cold brew,...
500 Duval Street (305) 292-1435
Pier House Beach Bar and Grill
 
One of my favorite places to meet friends for drinks or lunch, this is a casual, comfortable spot right next to the Pier House beach. With a view of the water,...
1 Duval Street
Rick'sRick's is a true Entertainment Complex with entertainment to suit nearly every taste. Take a stroll around and find the spot you like the best. 208 Duval Street 305-296-5513
Rum Bar/Speakeasy InnThe Rum Bar, in the lobby of the Speakeasy Inn is a neat little bar with a serious emphasis on RUM. There are over 50 rums to try on their own or mixed in a... 1117 Duval Street 305-296-2680
Salute on the Beach
 
A true beach-front dining option, that's one of our favorite spots for lunch and a cold beverage after a nice long walk. It's fun to watch the...
1000 Atlantic Boulevard 305-292-1117
Smallest BarOfficially, there is room for two at the bar, but in reality, you'll be amazed at how many people can pack into this tiny, quirky little spot. Go with... 124 Duval Street 305-509-2904
Sunset Pier
 
Sunset Pier doesn't need a sunset to make it great, although it is a fantastic spot for that. Stretching out into the water from the Ocean Key House, at...
00 Duval Street 305-296-7701
Tavern 'N TownLocated in the Marriott Beachside Hotel on N. Roosevelt Blvd. near Stock Island, if you're staying in Old Town, it's probably best to bike or cab to... 841 North Roosevelt Boulevard 305-296-8100
Turtle Kralls Restaurant and BarI've been back and forth with my feelings about Turtle Kralls since they renovated, changed the menu and took most of the charm out of the building. Lately... 231 Margaret Street #1 305-294-2640
Vino's on Duval
 
Fabulous, intimate little wine bars are popping up all over town and Vino's is my personal favorite. The cozy, comfortable bar was build by hand and...
810 Duval Street 305-294-7568
Virgilio'sSophisticated stop for sipping martinis, fine wines or whatever you heart desires. The sound of jazz, blues or reggae complements the atmosphere. Grab a bite... 524 Duval Street 305-296-8118
Willy T'sPerfect for people watching on Duval. Talented troubadours like Gerd Rube and Fremont John are regular performers. A great spot for relaxed refreshment and Key... 525 Duval Street 305-294-7674
Dining Steps
AmbrosiaTop Pick
 
Many, including me, rate the sushi at Ambrosia as the best we've ever had - anywhere. It really is that good. With the freshest of fish and seafood...
1401 Simonton Street 305-293-0304
Antonia'sTop Pick
 
Cozy and elegant, it's often difficult to get a table at Antonia's. While you may stop looking once you see the pasta selections, the fish, shellfish...
615 Duval Street 305-294-6666
Blackfin BistroTop Pick
 
Blackfin is absolutely one of my favorite dining establishments on the island. It's at the top of the list any time of day or night. Breakfast is served...
918 Duval Street 305-509-7408
FireflyTop Pick
 
One of the newest dining establishments in Key West is also one of the best. Firefly, situated on Petronia St, in Bahama Village, between Blue Heaven and...
223 Petronia St. 305-849-0104
Michael'sTop Pick
 
One of my personal favorite dinner destinations with delicious steaks and an array of fish and seafood options to tempt your palate. If you're lucky...
532 Margaret Street 305-295-1300
5 Brothers Grocery and Sandwich ShopNeighborhood grocery store that caters to the locals, 5 Brothers has spectacular Cuban, pulled pork and fish sandwiches, delicious café con leche and... 930 Southard Street 305-296-5205
A&B Lobster HouseA high-end restaurant with an excellent reputation and high prices to match, with lovely views of the Key West Harbor (Bight), if you have the right table. This... 700 Front Street 305-294-5880
AbbondanzaTraditional Italian food served in a cozy indoor setting. Some people are particularly fond of their giant meatballs and other swear by the generous portions of... 1208 Simonton Street 305-292-1199
Afterdeck at Louie's Backyard
 
The Afterdeck at Louie's Backyard is a very special place. The bar itself is small (about a dozen seats) but the deck is expansive with seating for well...
700 Waddell Avenue 305-294-1061
Alonzo's Oyster Bar
 
Casual waterfront dining and home to one of the best deals for Happy Hour on the island. The key lime oysters are my favorite and that's just the...
700 Front Street 305-294-5880
Amigo'sOpen until midnight, this tortilla bar is perfect for a late bite. Square tortillas are filled with a range of flavorful meats, beans and cheeses that satisfy... 425 Greene Street 305-292-2009
Azur
 
With one of the two chef/owners on-site at all times during the day and evening, you can be assured that the utmost care will be taken to provide you with a...
425 Grinnell Street 305-292-2987
Bagatelle
 
Located in an historic Victorian house right on Duval, Bagatelle is a great spot for people watching, and an even great spot for breakfast (served 'til...
115 Duval Street 305-296-6609
Banana CaféFor years, only open for breakfast and lunch, Banana Café is now serving dinner Tuesday through Saturday. It's rare to find a fine French restaurant... 1215 Duval Street 305-294-7227
BenihanaBenihana restaurants can be found in many American cities but the Benihana in Key West is very special. Located overlooking the Atlantic Ocean, this traditional... 3591 South Roosevelt Boulevard 305-294-6400
Blue HeavenBlue Heaven is one of the most famous, most popular restaurants on the island. Some days, that means a 2 hour wait for breakfast. No matter, have a delicious... 729 Thomas Street 305-296-8666
BO's Fish WagonIf you weren't looking for it, you might walk right by BO's, thinking it is a pile of junk in the middle of the sidewalk on Caroline St. On the other... 801 Caroline Street 305-294-9272
Café SoleAnother chef-owned and operated restaurant located in the heart of an Old Town neighborhood, not far from the cemetery. Café Sole is a romantic spot with... 1029 Southard Street 305-294-0230
Caroline's CaféA fun open-air bar and casual restaurant on lower Duval between Caroline and Eaton. Great for people watching and known for its generous portions,... 310 Duval Street 305-294-7511
Chico's CantinaOn the Overseas Highway, just across the bridge to Stock Island, you'll find the most popular Mexican restaurant In the lower Keys. Featuring regional... 5230 U.S. 1 305-296-4714
The CommodoreThe Commodore is also located along the Harborwalk and offers wonderful views of the water, boats, the setting sun and twinkling lights of the evening. With a... 700 Front Street #104 305-294-9191
Conch Republic Seafood RestaurantI'm a BIG fan of stopping here for drinks, especially during daily BOGO happy hours. It's the perfect place to relax, have a cocktail and a plate of... 631 Greene Street 305-294-4403
Croissant's de FranceBakery, coffee shop, bistro - Croissant's de France is all three. Breakfast is the meal I enjoy the most here, but the real draw is the fantastic bakery... 816 Duval Street 305-294-2624
Cuban Coffee QueenA food stand located just about 25 steps away from the Harborwalk at the Historic Seaport, the Cuban Coffee Queen has quickly developed an excellent reputation... 284 Margaret Street 305-294-7787
Dante's
 
Fully outdoor dining and drinking establishment with the added feature of a pool that is open for use to all Dante's customers. The pool adds to the...
951 Caroline Street 305-423-2001
Eaton Street Seafood Market
 
Eaton Street Seafood Market is THE place to purchase fish and seafood in Old Town. Carrying only the freshest, locally caught fish and seafood, Eaton Street...
801 Eaton Street 305-295-3474 (fish)
El Meson de PepeCuban food, Cuban culture and Cuban music all thrive right off Mallory Square. My favorite time to be here is when the salsa band starts playing every night... 410 Wall Street 305-295-2620
El Siboney
 
Popular spot for authentic Cuban food in an off-the-beaten-path, neighborhood location. El Siboney is a must-do for many Key West visitors seeking true local...
900 Catherine Street 305-296-4184
The Flaming Buoy Filet Co.
 
At the corner of Virginia and Packer streets, a few blocks from Upper Duval and seemingly far from the hustle and bustle of the tourist areas, this small...
1100 Packer Street 305-295-7970
Fogarty's
 
Fogarty's is a favorite stop for a casual, reasonably priced lunch or dinner. Sitting in the courtyard at the corner of Duval and Caroline, directly across...
227 Duval Street 305-294-7525
The Grand CaféThe Grand Café is right in the middle of the action of lower Duval. Housed in a pretty Victorian, with outdoor dining on the patio out front, the Grand... 314 Duval Street
Half Shell Raw BarThe Half Shell used to be one of my favorite spots, but again, with a menu change and "improvements" that were made, I don't enjoy it as much as... 231 Margaret Street 305-294-7496
Harpoon Harry's
 
Harpoon Harry's is a hot spot for locals and tourists looking for great food and great prices. Harry's is also one of the friendliest places in Key...
832 Caroline Street 305-294-8744
Hogfish Bar and Grill
 
The Hogfish is my favorite Stock Island dining establishment. Located off the main drag and a bit out of the way, I recommend a bike, cab or car to get here. A...
6810 Front Street 305-293-4041
Hot Tin Roof
 
Elegant, upscale and romantic, Hot Tin Roof offers an extraordinary dining experience. The views are second to none from this second floor, waterfront location...
00 Duval Street 305-296-7701
Hurricane HoleDockside dining at this full service marina on Stock Island. The restaurant recently added a play area for the youngsters, making this a perfect place to bring... 5130 U.S. 1 305-294-0200
Jack FlatsA true sports bar with a stunning collection of gigantic TVs, great drinks and what some say is the best burger in Key West. If you're going to watch a... 509 Duval Street 305-294-7955
La CreperieThe location on the corner of Petronia and Thomas St. is smack dab in the middle of a thriving dining district. When the owners lost the original store-front... 300 Petronia Street 305-517-6799
La Trattoria
 
"La Trat" as it's known to locals, is popular, busy and delicious. The menu is extensive, featuring pastas, veal, fish and shellfish, along...
524 Duval Street 305-296-1075
La Trattoria OceansideA newly-opened (Summer 2011) restaurant by the people who bring you La Trattoria on Duval, this is sure to be a huge hit. Delicious food, stunning ocean views,... 3591 South Roosevelt Boulevard 305-295-6789
LaTeDa
 
On the upper end of Duval, the bar at LaTeDa is one of my favorite spots for people-watching any time of day. The design of the bar makes conversation easy and...
1125 Duval Street 305-296-6706
Louie's Backyard
 
One of my absolute favorite places to be in Key West is on the Afterdeck at Louie's, where you are literally sitting over the Atlantic Ocean and the view...
700 Waddell Avenue 305-294-1061
Mangia MangiaA cozy neighborhood spot for fresh homemade pasta, creative sauces, delicious seafood and house specialities. The food is exceptional, portions large and prices... 900 Southard Street 305-294-2469
Margaritaville
 
This is Jimmy Buffett's original Margaritaville and is a hugely popular destination for Key West visitors. You can stop here for a nice cold brew,...
500 Duval Street (305) 292-1435
Martin's
 
Martin's front room has a cool urban vibe, while garden seating is decidedly "island". Dinner is classic and delightful, with a German accent....
917 Duval Street 305-295-0111
Mo's RestaurantSuper-casual spot for Caribbean/Haitian specialities and some real Key West flavor. Located on White Street, this is not your typical tourist destination, but... 1116 White Street 305-296-8955
nine-one-five
 
nine-one-five is another one of those places that has some items on their menu that I crave and simply must have. The restaurant is consistently ranked among...
915 Duval Street 305-296-0669
Paradise PizzaParadise Pizza is in the perfect location for people staying at any of the large hotels near lower Duval as well as those indulging in late night fun in the... 503 Greene Street 305-292-4100
Pat Croce's Rum BarrelRum Barrel will be closing April 2017....Bar food menu with some interesting sandwich and entrée choices. My experience with the food has been uneven,... 528 Front Street 305-292-7862
Pepe's CaféEstablished in 1909, Pepe's really is the oldest (eldest) dining establishment in Key West and retains that "old Key West" feel. Good food, great... 806 Caroline Street 305-294-7192
Pier House Beach Bar and Grill
 
One of my favorite places to meet friends for drinks or lunch, this is a casual, comfortable spot right next to the Pier House beach. With a view of the water,...
1 Duval Street
Prime 951One of the newer fine-dining establishments in Key West that has a reputation as one of the best. They are best known for their beef (hence the name) and sleek,... 951 Caroline Street 305-296-4000
The Rooftop CaféA beautiful and romantic setting, with trees growing up through the deck and a nice big bar serving luscious libations. The Rooftop is a great place for lunch... 308 Front Street 305-294-2042
Salute on the Beach
 
A true beach-front dining option, that's one of our favorite spots for lunch and a cold beverage after a nice long walk. It's fun to watch the...
1000 Atlantic Boulevard 305-292-1117
Sandy'sLocated on White Street, Sandy's is a walk-up, food-to-go sort of spot, open 24 hours. Their Cuban sandwich is famous for a reason, but everything here is... 1026 White Street 305-294-0159
Santiago's BodegaThe first restaurant devoted exclusively to tapas is also an island favorite. Open continuously from 11 AM, the menu remains the same into the evening. With so... 207 Petronia Street 305-296-7691
Sarabeth'sThe original Sarabeth's is on Central Park South in New York City, but the Key West version has settled into island life just fine. Most popular for... 530 Simonton Street 305-293-8181
Seven Fish
 
Newly located in a newly built, angular, almost art-deco designed space on Truman Avenue, this perennial favorite on the Key West dining scene now has more...
921 Truman Avenue 305-296-2777
Southernmost Beach Café
 
A fun and casual option for any meal, it's one of our go-to spots for a light breakfast or a quick bite at the bar in the afternoon. We love watching the...
1405 Duval Street 305-295-6550
Tavern 'N TownLocated in the Marriott Beachside Hotel on N. Roosevelt Blvd. near Stock Island, if you're staying in Old Town, it's probably best to bike or cab to... 841 North Roosevelt Boulevard 305-296-8100
Thai IslandAuthentic Thai food and fresh sushi in a waterfront restaurant, a 1.5 mile walk (~3000 steps) from Mallory Square, this newer spot is finding its footing. 711 Eisenhower Drive 305-296-9198
Thai LifeFloating in the waters of Garrison Bight, Thai Life has become a popular spot for local Thai food aficionados. A little over a mile from the corner of Truman... 1801 North Roosevelt Boulevard 305-296-9907
Turtle Kralls Restaurant and BarI've been back and forth with my feelings about Turtle Kralls since they renovated, changed the menu and took most of the charm out of the building. Lately... 231 Margaret Street #1 305-294-2640
Two Friends Patio RestaurantCasual spot to stop in for a bite. Portions are large and service is quick. Stop in for Karaoke on Tuesday nights and your friends can watch on the webcam! 512 Front Street 305-296-3124
Virgilio'sSophisticated stop for sipping martinis, fine wines or whatever you heart desires. The sound of jazz, blues or reggae complements the atmosphere. Grab a bite... 524 Duval Street 305-296-8118
Willy T'sPerfect for people watching on Duval. Talented troubadours like Gerd Rube and Fremont John are regular performers. A great spot for relaxed refreshment and Key... 525 Duval Street 305-294-7674
Musical Steps
Green ParrotTop Pick
 
Probably the best spot for music in Key West with national acts performing blues, jazz and funk every week. Great drink prices and a happening locals scene...
601 Whitehead Street 305-294-6133
Schooner Wharf BarTop Pick
 
When they say "the last little piece of old Key West" they're not kidding. When you're at Schooner Wharf, you can get a feel for what Key...
202 William Street 305-292-3302
Sloppy Joe'sTop Pick
 
An institution with a rich history and some of the hardest working bartenders and servers on the island. Talented musicians play all day with rock and roll...
201 Duval Street 305-294-5717
Captain Tony's Saloon
 
Captain Tony's is one of the most famous, most revered saloon's in Key West. What is now Captain Tony's was once Sloppy Joe's. The history...
428 Greene Street 305-294-1838
Cowboy Bill's Honky Tonk SaloonA reopened, refreshed and slightly downsized Cowboy Bills is still kicking it as the go-to place for country music fans! Expansive country music venue... 618 Duval Street 305-295-8219
Hogs Breath SaloonGreat spot for live music all day and night in a funky outside venue. Not one of my picks for dining (he inside restaurant is rarely full) but great vibe,... 400 Front Street #C 305-296-4222
Margaritaville
 
This is Jimmy Buffett's original Margaritaville and is a hugely popular destination for Key West visitors. You can stop here for a nice cold brew,...
500 Duval Street (305) 292-1435
Tavern 'N TownLocated in the Marriott Beachside Hotel on N. Roosevelt Blvd. near Stock Island, if you're staying in Old Town, it's probably best to bike or cab to... 841 North Roosevelt Boulevard 305-296-8100
Virgilio'sSophisticated stop for sipping martinis, fine wines or whatever you heart desires. The sound of jazz, blues or reggae complements the atmosphere. Grab a bite... 524 Duval Street 305-296-8118
Willy T'sPerfect for people watching on Duval. Talented troubadours like Gerd Rube and Fremont John are regular performers. A great spot for relaxed refreshment and Key... 525 Duval Street 305-294-7674
Dancing Steps
Sloppy Joe'sTop Pick
 
An institution with a rich history and some of the hardest working bartenders and servers on the island. Talented musicians play all day with rock and roll...
201 Duval Street 305-294-5717
Aqua Nightclub
 
Bar and nightclub featuring their famous "Reality is a Drag" show nightly. Aqua has a daily happy hour from 3 - 8PM featuring drink specials and...
711 Duval Street 305-294-0555
Cowboy Bill's Honky Tonk SaloonA reopened, refreshed and slightly downsized Cowboy Bills is still kicking it as the go-to place for country music fans! Expansive country music venue... 618 Duval Street 305-295-8219
Rick'sRick's is a true Entertainment Complex with entertainment to suit nearly every taste. Take a stroll around and find the spot you like the best. 208 Duval Street 305-296-5513
Step Out
801 Bourbon BarTop Pick
 
An Entertainment Complex on the corner of Duval and Petronia, 801 is one of "the" places to go for the gay community and it also welcomes visitors,...
801 Duval Street 305-294-4737
Aqua NightclubTop Pick
 
Bar and nightclub featuring their famous "Reality is a Drag" show nightly. Aqua has a daily happy hour from 3 - 8PM featuring drink specials and...
711 Duval Street 305-294-0555
Bobby's Monkey BarCasual neighborhood bar often referred to as the "Gay Cheers". Locals and tourists, gay and straight, mingle, mix and chill. Play some pool, have a... 900 Simonton Street 305-294-2655
Bourbon Street PubA mainstay in the gay community, Bourbon St. Pub has a lot of fun to offer everyone. 4 separate bars (the Garden Bar is for men only), hot male dancers on stage... 724 Duval Street 305-293-9800
LaTeDa
 
On the upper end of Duval, the bar at LaTeDa is one of my favorite spots for people-watching any time of day. The design of the bar makes conversation easy and...
1125 Duval Street 305-296-6706
Shopping Steps
5 Brothers Grocery and Sandwich ShopNeighborhood grocery store that caters to the locals, 5 Brothers has spectacular Cuban, pulled pork and fish sandwiches, delicious café con leche and... 930 Southard Street 305-296-5205
Cork and StogieDouble your pleasure at Cork and Stogie where you can visit the Southernmost Cigar Store AND the Southernmost Wine Shop all at once! The cigar making industry... 1218 Duval Street 305-517-6419
Diamonds InternationalWith locations throughout the Caribbean and in Alaska, Diamonds International caters mainly to the cruise ship crowd. That never stopped me from shopping here,... 122 Duval Street 305-293-1111
Eaton Street Seafood Market
 
Eaton Street Seafood Market is THE place to purchase fish and seafood in Old Town. Carrying only the freshest, locally caught fish and seafood, Eaton Street...
801 Eaton Street 305-295-3474 (fish)
Fairvilla MegastoreAdult toys, costumes, accessories, implements, lotions and potions of all types are there for the taking (buying) with a friendly, well-informed and... 520 Front Street 305-292-0448
Fast Buck FreddiesFast Buck Freddies has CLOSED, but the listing remains to commemorate this beloved shopping emporium..... It's impossible for me to visit Key West without... 500 Duval Street 305-294-2007
Fast Buck Freddies Home StoreA beautiful selection of furniture and home accessories at very reasonable prices. You might feel like moving in to the showroom, it's that nice, but it... 920 Caroline Street 305-294-5049
In One Era
 
Antiques and vintage fabulous-ness in every corner (and on the ceiling) of the perfectly-located shop on the corner of Thomas and Petronia, directly across from...
227 Petronia Street 305-293-0208
Island BooksIsland Books is the last independent book store standing in town. Island Books is positively packed with piles and piles of books of all types, all of which I... 513 1/2 Fleming Street 305-294-2904
Kino Sandal FactoryThe Kino Sandal Factory is tucked away off a courtyard, down an alley, but it is worth following the old brick streets to get to the home of the most... 107 Fitzpatrick Street 305-294-5044
Lily PulitzerPreppy pastel prints and classic styles for the country club set define the Lily Pulitzer style. It's unlikely you'd wear your Lily fashions while in... 600 Front Street 305-295-0995
Little SwitzerlandTwo locations for the Caribbean jewelry store group that carries beautiful baubles of all shapes, sizes and colors and a wonderful selection of fine watches. I... 423 Front Street, 271 Front Street at the Westin Key West 305-292-2345, 305-293-8600
Local ColorA big selection of sundresses and separates, many in linen, along with some men's selections, all in tropical fabrics. The big draw here is the HUGE... 276 Margaret Street 305-292-3635
Margaritaville
 
This is Jimmy Buffett's original Margaritaville and is a hugely popular destination for Key West visitors. You can stop here for a nice cold brew,...
500 Duval Street (305) 292-1435
Peppers of Key WestA hot sauce "bar" where you can taste (if you dare) sauces hot enough to make you cry and then have some that are even hotter. Some people actually do... 602 Greene Street 305-295-9333
The Restaurant StoreFamily owned and operated, this is truly a store for chefs. Stocked with everything a great chef would ever want or need, less elaborate, more affordable and... 1111 Eaton Street 305-294-7994
Shell WarehouseYou won't find many shells on the beaches of Key West, due to the reef that also keeps the heavy waves farther out to sea. But, if you are a shell... 1 Whitehead Street 305-296-4776
Sole Man
 
If you're going to be doing some serious walking in Key West, you'll enjoy it more if you have some serious footwear for your excursions. For that,...
610 Duval Street #5 305-292-2505
Walgreens/The Strand Movie TheaterYears ago, what is currently a Walgreens used to be The Strand, an 800 seat movie theater. It's all Walgreens inside, but the façade has been... 527 Duval Street 305-292-2979
wanderlust boutique and galleryA beautiful boutique filled with jewelry, clothing, paintings and art created by local artists, with a few items (a fantastic shoe selection!) that are not... 310 Petronia Street 305-509-7065
Natural Steps
Audubon House and Tropical GardensFilled with art and antiques, this house also features the 28 first edition works by James Audobon, which are my favorites. There is a fascinating history to... 205 Whitehead Street 305-294-2116
Charles "Sonny" McCoy Indigenous ParkAcross from the beach, this small piece of property preserves and showcases over 75 native Florida Keys native trees and plants. It's a great addition to a... Atlantic Boulevard at White Street
Florida Keys Eco-Discovery CenterOn the waterfront at the end of Southard St. just before the entrance to Fort Zachary Taylor, the Florida Keys Eco Discovery Center has fascinating exhibits... 33 East Quay Road 305-809-4750
Fort Zachary Taylor
 
Fort "Zach" has it all: a beautiful, although slightly rocky beach, a fascinating historic fort where you can take an informative self-guided tour, a...
300 Truman Annex 305-295-0037
Fury Water AdventuresFury Water Adventures is home to the Glass Bottom Boat that takes you on an eco-tour of the reef that doesn't involve you actually getting into the water,... 2 Duval Street 800-994-8898
The Gardens HotelWhat is currently the Gardens Hotel on the corner of Angela and Simonton streets used to be the home of Peggy Mills, who created a wondrous botanical garden... 526 Angela Street 305-294-2661
Key West AquariumMainly for the kids, the Key West Aquarium offers up close and personal contact with creatures of the sea, the most popular of which is the touch tank where you... 1 Whitehead Street 305-296-2051
Key West Nature and Butterfly ConservatoryAn extremely popular attraction where you can walk and sit in a beautiful conservatory filled with plants and flowers, and yes, butterflies. So many... 1316 Duval Street
Key West Nature PreserveA "rustic" walk along a battered wooded path leading to the Atlantic, where you'll see lots if trees and plants, along with lizards, snakes and... Atlantic Boulevard, between White Street and Bertha Street
Key West Tropical Forest & Botanical GardenThe designated wildlife sanctuary and arboretum is home to a wide variety of local flora and fauna. Managed by the Key West Botanical Society the Gardens this... 5210 College Road 305-296-1504
Nancy Forrester's Secret Garden
 
Nancy's Secret Garden has RE-OPENED as a sanctuary featuring Nancy's precious collection of parrots, macaws and at least one cute cockatoo too. While...
518 Elizabeth St. 305-294-0015
Sebago Key WestGetting out on the water in Key West is one of the highlights of a Key West vacation. And, for a great on-the-water adventure, Sebago Key West offers a full... 205 Elizabeth Street #1 305-292-2400
West Martello Tower
 
The West Martello Tower, located at Higgs Beach is home to the Key West Garden Club's Botanical Gardens. The self-guided tour is free, although donations...
1100 Atlantic Boulevard 305-294-3210
Artistic Steps
Alan S. Maltz GalleryAlan Maltz, the Official Wildlife Photographer of Florida and Fine Art Phtographer for the State of Florida, makes his home in Key West. Alan's gallery on... 1210 Duval Street 305-294-0005
East Martello Towers and Museum
 
Fascinating history and art museum located on the east end of the island near the airport. In addition to artifacts from every phase of Key West history, the...
3501 South Roosevelt Boulevard 305-296-3913
Key West Cemetery
 
Filled with flowers, plantings, sculpture, gravestones and vaults, the Key West Cemetery can be a place for a walking tour all its own. Pick up or print out a...
Bordered by Olivia and Frances Streets and Windsor and Passover Lanes
Museum of Art and History at the Custom HouseBuilt in 1891, the building itself is a beautiful example of what Key West was capable of building at a time when wrecking ruled the economy and Key West was... 281 Front Street 305-295-6616
wanderlust boutique and galleryA beautiful boutique filled with jewelry, clothing, paintings and art created by local artists, with a few items (a fantastic shoe selection!) that are not... 310 Petronia Street 305-509-7065
Wyland GalleryInternationally known marine artist, painter and sculptor Wyland keeps a home in the Keys. He regularly puts on exhibitions in his Key West gallery, where you... 623 Duval Street 305-292-4998
Wyland MuralIn addition to his paintings and sculptures, the artist Wyland is known for his murals of whales and other sea creatures. He has painted 100 of them throughout... 201 William Street at the end of Lazy Way Land at the Key West Bight
Architectural Steps
Curry MansionThe Curry Mansion was built beginning in 1855 and was the home of William Curry, Key West's first millionaire. Today, the mansion, listed on the National... 511 Caroline Street 305-294-5349
Southernmost HouseThe Southernmost House stands guard at the southernmost corner of Duval Street. Built as a private home in 1896, this spectacular Victorian spent a number of... 1400 Duval Street 305-296-3141
Tropic CinemaOn Eaton Street, right off Duval, you'll find the wonderful Tropic Cinema. With 4 screens, there's a good mix first run Hollywood features, art house,... 416 Eaton Street 877-761-3456
Walgreens/The Strand Movie TheaterYears ago, what is currently a Walgreens used to be The Strand, an 800 seat movie theater. It's all Walgreens inside, but the façade has been... 527 Duval Street 305-292-2979
Small Steps
Florida Keys Eco-Discovery CenterOn the waterfront at the end of Southard St. just before the entrance to Fort Zachary Taylor, the Florida Keys Eco Discovery Center has fascinating exhibits... 33 East Quay Road 305-809-4750
Key West AquariumMainly for the kids, the Key West Aquarium offers up close and personal contact with creatures of the sea, the most popular of which is the touch tank where you... 1 Whitehead Street 305-296-2051
Key West Shipwreck MuseumMore for kids than adults, with historic "characters" telling tales of wrecks and rescues; with artifacts of actual wrecks. The walk to the top of... 1 Whitehead Street 305-292-8990
Wheels and Other Cool Stuff
Angela Street Parking LotSmall public lot in the center of Old Town. This lot will put you a mere 25 steps from Duval Street and very close to one of my favorite restaurants,... 530 Angela Street
Green Street Parking LotLarge privately run lot on Greene Street between Elizabeth and Simonton Streets. This lot is closest to Sloppy Joe's and shares it's home with the... 605 Greene Street
Higgs Beach Parking LotThis southernmost parking lot is perfect if you're looking to spend a day at the beach. From this lot, you are on the doorstep of Salute on the Beach, a... 900 Atlantic Boulevard
Island Comfort MobilityWe know it's not easy or possible for everyone to walk to see the sights of Key West and so does Island Comfort Mobility. This fantastic service provides... 5170 US Highway 1 305-453-6456
Island Joe's Cafe and Coffee Roasting Company
 
Island Joe's coffee shop is closed, but well-known local writer, Joe D. Wells is still roasting his coffee, which can be found in Fausto's, Publix and...
305-294-1190
Key West Bight Parking LotLarge lot that encompasses an area bounded by Caroline, Margaret and William Streets. When you park in this lot, you are directly in front of the Wyland Mural,... 201 William Street
Mallory Square Parking LotThis small public lot right takes you right to hub of the sunset celebration. You are also nearby a number of attractions, such as the Key West Aquarium and the... 400 Wall Street
Old Town Parking GarageConvenient, covered parking garage, at the corner of Grinnell and Caroline Streets. If driving in from New Town, it's easiest to reach if you take the Palm... 300 Grinnell Street
Paradise PortersA wonderful service for anyone who needs help with their luggage and other bags prior to check-in or after an early check-out. Paradise Porters will pick-up,... 100 Grinnell Street 305-293-4000
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