Rams Head Southernmost
American Restaurants • Brunch
Rams Head was founded in Annapolis, Maryland and has been family owned and operated since 1989. With roots in Key West, Rams Head is proud to be part of the local community and is committed to providing the best in Food, Fun, and Beer.
Rams Head was founded in Annapolis, Maryland and has been family owned and operated since 1989. With roots in Key West, Rams Head is proud to be part of the local community and is committed to providing the best in Food, Fun, and Beer.
Sloppy Joes
Craft Beer • Live Music
As one of Key West’s most iconic locations and the favorite watering hole of Ernest Hemingway, Sloppy Joe’s boasts visitors from all over the world who come to enjoy their favorite beverage, true Key West atmosphere, and high quality cuisine. There’s always a party in the main bar and Joe’s Tap Room sports a large variety of crafted and specialty beers. Live musical entertainment begins at 12 in the afternoon and rocks until 2:00 a.m.!
As one of Key West’s most iconic locations and the favorite watering hole of Ernest Hemingway, Sloppy Joe’s boasts visitors from all over the world who come to enjoy their favorite beverage, true Key West atmosphere, and high quality cuisine. There’s always a party in the main bar and Joe’s Tap Room sports a large variety of crafted and specialty beers. Live musical entertainment begins at 12 in the afternoon and rocks until 2:00 a.m.!
El Meson de Pepe
Caribbean Restaurants • Cuban Restaurants
Specializing in Cuban Conch cuisine, this family owned, Key West restaurant and Chef Pepe Diaz hae been bringing in locals and tourists alike since 1984. Chef Diaz dishes up such favorites as Picadillo, Ropa Vieja, Fambas Ala Plancha, Paella ala Pepe and his own family recipe for flan, and let’s not forget the island’s best Mojitos! Set in Mallory Square overlooking the harbor with live Latin music, El Meson is not to be missed.
Specializing in Cuban Conch cuisine, this family owned, Key West restaurant and Chef Pepe Diaz hae been bringing in locals and tourists alike since 1984. Chef Diaz dishes up such favorites as Picadillo, Ropa Vieja, Fambas Ala Plancha, Paella ala Pepe and his own family recipe for flan, and let’s not forget the island’s best Mojitos! Set in Mallory Square overlooking the harbor with live Latin music, El Meson is not to be missed.
Irish Kevin’s
Live Music
This is the place for great friends and ice cold Guinness! From intimate business deals and family celebrations, Irish Kevin’s is a rustic second home to all its guests. With a high standard of hospitality and knowledgeable servers, it’s easy to kick-back, relax, and enjoy the delicious authentic Irish cuisine and the incredible set of live entertainment each night.
This is the place for great friends and ice cold Guinness! From intimate business deals and family celebrations, Irish Kevin’s is a rustic second home to all its guests. With a high standard of hospitality and knowledgeable servers, it’s easy to kick-back, relax, and enjoy the delicious authentic Irish cuisine and the incredible set of live entertainment each night.
Bar 1
Join us at Bar 1 for a casual drink with friends or a hands-on craft cocktail class. Mix, shake, and sip as you explore premium spirits and create signature drinks in a fun, interactive setting.
Join us at Bar 1 for a casual drink with friends or a hands-on craft cocktail class. Mix, shake, and sip as you explore premium spirits and create signature drinks in a fun, interactive setting.
Willie T's
Happy Hour Bars
Live music fills the air daily at Willie T’s. Popular for its outdoor setting on Duval Street, this bar is well known for it’s famous mojitos. The ceilings and walls are adorned with dollar bills from patrons past. Stop on through, they serve up happy hour daily from 4pm-7pm.
Live music fills the air daily at Willie T’s. Popular for its outdoor setting on Duval Street, this bar is well known for it’s famous mojitos. The ceilings and walls are adorned with dollar bills from patrons past. Stop on through, they serve up happy hour daily from 4pm-7pm.
Island Dogs Bar
Burgers • Craft Beer
Island Dog welcomes both locals and tourist for a laid back experience, with affordable drink and delicious food. Come and enjoy live music every weekend!
Island Dog welcomes both locals and tourist for a laid back experience, with affordable drink and delicious food. Come and enjoy live music every weekend!
Tipsy Rooster Liquor Store & Bar
Cocktail Bars
Drink Now….Its cocktail time all the time in Key West! Enjoy specialty cocktails made with house-infused liquors and a pizza while relaxing in the sand. Or you can stop by the liquor store and buy the perfect ingredients to make your own Key West cocktail.
Drink Now….Its cocktail time all the time in Key West! Enjoy specialty cocktails made with house-infused liquors and a pizza while relaxing in the sand. Or you can stop by the liquor store and buy the perfect ingredients to make your own Key West cocktail.
Key West First Legal Rum Distillery
Distilleries
Tastings, Souvenirs, Tours and more! Rated in USA Today's Ten Best! Come taste history at the Key West First Legal Rum Distillery. Hand made, bottled and labeled proudly in Key West, FL! Come in and enjoy a FREE tasting! Their Legal rum represents the true essence of the 1920’s in Key West... when rum was the drink just like it is today. They have something for the whole family including homemade soda tastings for the kids!
Tastings, Souvenirs, Tours and more! Rated in USA Today's Ten Best! Come taste history at the Key West First Legal Rum Distillery. Hand made, bottled and labeled proudly in Key West, FL! Come in and enjoy a FREE tasting! Their Legal rum represents the true essence of the 1920’s in Key West... when rum was the drink just like it is today. They have something for the whole family including homemade soda tastings for the kids!
The Chart Room
Dive Bars • Happy Hour Bars
If you are looking for a no fluff, no frills bar…this is the place! Off the beaten path, this watering hole embraces the history of Key West and its characters. For nearly 40 years, this small dive bar has been on the grounds of the Pier House Resort. Famous faces like Jimmy Buffett and Capt. Tony have gathered here to laugh, lie and take aim at others. Free popcorn, peanuts and hot dogs await any visitor.
If you are looking for a no fluff, no frills bar…this is the place! Off the beaten path, this watering hole embraces the history of Key West and its characters. For nearly 40 years, this small dive bar has been on the grounds of the Pier House Resort. Famous faces like Jimmy Buffett and Capt. Tony have gathered here to laugh, lie and take aim at others. Free popcorn, peanuts and hot dogs await any visitor.
Shots and Giggles
Craft Beer • Wine Bars
Shots and Giggles is a local's favorite bar in Key West, FL. Nestled next to Tattoos & Scars Saloon right off of Greene St., Shots and Giggles is known for its relaxed atmosphere, cold drinks, and always having the game on any of their 5 TVs.
Shots and Giggles is a local's favorite bar in Key West, FL. Nestled next to Tattoos & Scars Saloon right off of Greene St., Shots and Giggles is known for its relaxed atmosphere, cold drinks, and always having the game on any of their 5 TVs.
Rick’s Entertainment Complex
Dive Bars • Happy Hour Bars
Rick’s Entertainment Complex has the perfect combination of everything Key West… dance clubs, VIP bars, adult entertainment, premium drink bars, balcony bars sporting incredible views of Duval, and live rock n’ roll entertainment. With eight different bars its a place to taste a little bit of everything, a variety of music venues, and many party zones all under the same roof.
Rick’s Entertainment Complex has the perfect combination of everything Key West… dance clubs, VIP bars, adult entertainment, premium drink bars, balcony bars sporting incredible views of Duval, and live rock n’ roll entertainment. With eight different bars its a place to taste a little bit of everything, a variety of music venues, and many party zones all under the same roof.
430 Duval
Caribbean Restaurants • Local Seafood
A sophisticated and unique space found in the grand lobby of Crowne Plaza La Concha brings a city chic vibe to Key West. Offering enticing island inspired small plates with bold Caribbean spices and fresh local seafood! 430 Lounge bar is open from 12PM to 11PM daily, with an enticing happy hour starting at 4:30PM, their bar mixologists offer refreshing signature 430 Duval cocktails! Their Sleek Lounge area seats small and large parties or you can cozy up at the grand bar.
A sophisticated and unique space found in the grand lobby of Crowne Plaza La Concha brings a city chic vibe to Key West. Offering enticing island inspired small plates with bold Caribbean spices and fresh local seafood! 430 Lounge bar is open from 12PM to 11PM daily, with an enticing happy hour starting at 4:30PM, their bar mixologists offer refreshing signature 430 Duval cocktails! Their Sleek Lounge area seats small and large parties or you can cozy up at the grand bar.
Salty Frog's Bar & Grill
Salty Frog's is a laid-back beach bar and grill offering great food, friendly service and southern hospitality. Experience the perfect blend of coastal charm and midwestern warmth. From delicious food to a welcoming atmosphere, Salty Frog's is your go-to spot for a good time in the Florida Keys.
Salty Frog's is a laid-back beach bar and grill offering great food, friendly service and southern hospitality. Experience the perfect blend of coastal charm and midwestern warmth. From delicious food to a welcoming atmosphere, Salty Frog's is your go-to spot for a good time in the Florida Keys.
Hurricane Hole
American Restaurants • Burgers
From the dockside bar and grill, complete marina, wide range of watersports options and upstairs restaurant overlooking the harbor, Hurricane Hole Marina is a treasure waiting to be discovered from sunup to sundown. Known as "The Hole" by locals the complex is a one-stop dining and recreational shop for those wishing to experience the best the Keys has to offer. So, plan to relax, stay awhile, and have fun.
From the dockside bar and grill, complete marina, wide range of watersports options and upstairs restaurant overlooking the harbor, Hurricane Hole Marina is a treasure waiting to be discovered from sunup to sundown. Known as "The Hole" by locals the complex is a one-stop dining and recreational shop for those wishing to experience the best the Keys has to offer. So, plan to relax, stay awhile, and have fun.
The Rum Bar
Cocktail Bars
Situated in the home of the late Raul Vaquez, a cigar selector and rum-runner of the early 1920’s, the Rum Bar has the largest selection of rums on the island. Spectacular cocktails, not just rum, await you as you sit quietly on the porch watching the passerby’s on Duval Street. Located on the first floor of the Speakeasy Inn, this laid back spot is a must see on your visit.
Situated in the home of the late Raul Vaquez, a cigar selector and rum-runner of the early 1920’s, the Rum Bar has the largest selection of rums on the island. Spectacular cocktails, not just rum, await you as you sit quietly on the porch watching the passerby’s on Duval Street. Located on the first floor of the Speakeasy Inn, this laid back spot is a must see on your visit.
Aqua Nightclub
Happy Hour Bars • Lounges
Reality is a drag! Are you looking for the best music, lights, sounds and DJ’s in town? Aqua Nightclub is the premier gay nightspot in Key West. Its friendly staff welcomes all patrons– as well as gays, lesbians, young and old. The club is home to the Aquanettes, who perform drag shows nightly. Happy hour is daily from 3pm to 8pm. Must be over 21 to enter.
Reality is a drag! Are you looking for the best music, lights, sounds and DJ’s in town? Aqua Nightclub is the premier gay nightspot in Key West. Its friendly staff welcomes all patrons– as well as gays, lesbians, young and old. The club is home to the Aquanettes, who perform drag shows nightly. Happy hour is daily from 3pm to 8pm. Must be over 21 to enter.
Sunset Tiki Bar
American Restaurants • Happy Hour Bars
Known as where the boardwalk ends and the sunset begins, the Sunset Tiki Bar and Grille is the ultimate hidden gem! Located on the harbor the Sunset Tiki bar is open 7 days a week from 10am-10pm. Savor one of the best views of sunset while listening to live tropical music every evening. Stroll on back to the docks of the Galleon Resort and bask in the great views on the deck or by the pool and enjoy not only one but two happy hours daily.
Known as where the boardwalk ends and the sunset begins, the Sunset Tiki Bar and Grille is the ultimate hidden gem! Located on the harbor the Sunset Tiki bar is open 7 days a week from 10am-10pm. Savor one of the best views of sunset while listening to live tropical music every evening. Stroll on back to the docks of the Galleon Resort and bask in the great views on the deck or by the pool and enjoy not only one but two happy hours daily.
22&Co
Cocktail Bars
22&Co in old town Key West features fresh cocktails, fun bartenders, tutus, flamingos, and unicorns. Need we say more?
22&Co in old town Key West features fresh cocktails, fun bartenders, tutus, flamingos, and unicorns. Need we say more?
Hog’s Breath Saloon
American Restaurants • Craft Beer
For 25 years, the Hog’s Breath Saloon has served cold drinks, delicious food and live music in their outdoor tropical setting and in the rustic, cool interior of the bar! “Hog’s breath is better than no breath at all!” Enjoy the cool, air -conditioned interior or have a drink outside! Check out their three live webcams or purchase one of their famous t-shirts in the mercantile store!
For 25 years, the Hog’s Breath Saloon has served cold drinks, delicious food and live music in their outdoor tropical setting and in the rustic, cool interior of the bar! “Hog’s breath is better than no breath at all!” Enjoy the cool, air -conditioned interior or have a drink outside! Check out their three live webcams or purchase one of their famous t-shirts in the mercantile store!
Fat Tuesday
Frozen Cocktails • Happy Hour Bars
Straight from Bourbon Street in New Orleans and dropped in the middle of Duval Street comes Fat Tuesday Key West. WARNING: Don’t be a victim of a brain freeze while slurping on one of its famous frozen daiquiris on a hot summer day. Have your own private party as you dance to their house DJ nightly. Fat Tuesday offers happy hour Monday–Friday from 4-7pm. Open everyday from 10am.
Straight from Bourbon Street in New Orleans and dropped in the middle of Duval Street comes Fat Tuesday Key West. WARNING: Don’t be a victim of a brain freeze while slurping on one of its famous frozen daiquiris on a hot summer day. Have your own private party as you dance to their house DJ nightly. Fat Tuesday offers happy hour Monday–Friday from 4-7pm. Open everyday from 10am.
Schooner Wharf Bar
Dive Bars • Happy Hour Bars
Coined the "Last Little Piece of Old Key West, " it is located in the heart of the Historic Seaport on the water. The Schooner Wharf offers you and your dog a great place to drink, eat and watch the beautiful tall ships come and go. Charles Kuralut called the Schooner Wharf, This must be the center of the universe.” Once you visit, you know why.
Coined the "Last Little Piece of Old Key West, " it is located in the heart of the Historic Seaport on the water. The Schooner Wharf offers you and your dog a great place to drink, eat and watch the beautiful tall ships come and go. Charles Kuralut called the Schooner Wharf, This must be the center of the universe.” Once you visit, you know why.
Salty Oyster
American Restaurants • Cocktail Bars
From Key West pinks by the dock to a Mango Overboard in your private cabana, Salty Oyster Dockside Bar & Grill offers fresh fare and tasty drinks in a comfortable atmosphere, just steps from the pool.
From Key West pinks by the dock to a Mango Overboard in your private cabana, Salty Oyster Dockside Bar & Grill offers fresh fare and tasty drinks in a comfortable atmosphere, just steps from the pool.
Little Room Jazz Club
Cocktail Bars • Live Music
Little Room Jazz Club is an intimate jazz venue offering live performances multiple nights each week. Known for its cozy atmosphere, craft cocktails and small plates inspired by American soul food, this club is a go-to spot for jazz lovers and anyone seeking a relaxed, music-filled night in Key West.
Little Room Jazz Club is an intimate jazz venue offering live performances multiple nights each week. Known for its cozy atmosphere, craft cocktails and small plates inspired by American soul food, this club is a go-to spot for jazz lovers and anyone seeking a relaxed, music-filled night in Key West.
Flying Monkeys Saloon
Frozen Cocktails
An outside bar, located at the historical Fogarty House, Flying Monkey’s Saloon is a popular spot for locals. One of the only open air bars located right on Duval Street, it is a great place to people watch. Flying Monkeys also offers a variety of frozen drinks for that warm sunny day. Open all day, happy hour nightly.
An outside bar, located at the historical Fogarty House, Flying Monkey’s Saloon is a popular spot for locals. One of the only open air bars located right on Duval Street, it is a great place to people watch. Flying Monkeys also offers a variety of frozen drinks for that warm sunny day. Open all day, happy hour nightly.
The Roost
Cocktail Bars • Craft Beer
The Roost is your friendly neighborhood liquor store and bar with classic craft cocktails, fine wine, and small bites located just steps from Duval Street in Old Town Key West. They offer something for everyone such as delicious small plates of smoked salmon, caviar service, and more… along with an extensive liquor store!
The Roost is your friendly neighborhood liquor store and bar with classic craft cocktails, fine wine, and small bites located just steps from Duval Street in Old Town Key West. They offer something for everyone such as delicious small plates of smoked salmon, caviar service, and more… along with an extensive liquor store!
Louie's Upper Deck
American Restaurants • Caribbean Restaurants
Magical panoramic views of the Atlantic Ocean await you at the Upper Deck at Louie’s. Fine wines by the glass or bottle are served as a perfect compliment to the small plates of focaccia, carpaccio, oven-fresh gourmet pizzas and more. Open 5-10pm, Tuesday through Saturday. A local and visitor favorite for over 25 years.
Magical panoramic views of the Atlantic Ocean await you at the Upper Deck at Louie’s. Fine wines by the glass or bottle are served as a perfect compliment to the small plates of focaccia, carpaccio, oven-fresh gourmet pizzas and more. Open 5-10pm, Tuesday through Saturday. A local and visitor favorite for over 25 years.
Captain Tony’s Saloon
Dive Bars • Happy Hour Bars
The original Sloppy Joe’s Bar, this historical saloon has been loved for decades by locals and visitors alike, as well as iconic figures like Tennessee Williams, Truman Capote, and, of course, Ernest Hemingway. Capt. Tony was an avid fisherman, rumrunner, casino manager, and even the mayor of Key West, who built the saloon with the intention of offering ice cold drinks to his fellow Key Westers—a tradition that everyone still loves to participate in!
The original Sloppy Joe’s Bar, this historical saloon has been loved for decades by locals and visitors alike, as well as iconic figures like Tennessee Williams, Truman Capote, and, of course, Ernest Hemingway. Capt. Tony was an avid fisherman, rumrunner, casino manager, and even the mayor of Key West, who built the saloon with the intention of offering ice cold drinks to his fellow Key Westers—a tradition that everyone still loves to participate in!
Waterfront Brewery
American Restaurants • Burgers
Opened in 2015, the Waterfront Brewery is a working brewery, restaurant, and entertainment center located in the heart of old town overlooking the Key West Historic Seaport and Bight. They’re constantly coming up with new brews, many of which have won awards! The food is as lovingly handcrafted as their beers! Bring your friends for some games, fun, and relaxation while admiring the spectacular view. They aren’t called “Waterfront” for nothing!
Opened in 2015, the Waterfront Brewery is a working brewery, restaurant, and entertainment center located in the heart of old town overlooking the Key West Historic Seaport and Bight. They’re constantly coming up with new brews, many of which have won awards! The food is as lovingly handcrafted as their beers! Bring your friends for some games, fun, and relaxation while admiring the spectacular view. They aren’t called “Waterfront” for nothing!
Old Town Tavern & Beer Garden
Burgers • Craft Beer
The lively bar where you can mingle with the locals. Air conditioned, smoke free, indoor high tables or cozy benches? Outdoors in the Beer Garden against the rail to watch the comings and goings of Duval Street or at a garden table? They are also pet friendly!
The lively bar where you can mingle with the locals. Air conditioned, smoke free, indoor high tables or cozy benches? Outdoors in the Beer Garden against the rail to watch the comings and goings of Duval Street or at a garden table? They are also pet friendly!
