Our Picks for the Best Vacation Experience in Key West

We love sharing our island with our guests! Concierge service is complementary with your stay at the Tropical Inn, so let us help you get the most out of your visit. We can make suggestions for the best attractions, activities, restaurants, and more, or if you have your own dream itinerary, we can almost always make it happen. We know all the best “locals’ favorites,” so you can experience Key West like a native!

Now, it’s no secret that Key West has become known as a party town. While that’s true, it’s the myriad other things to see and do here that make the island a treasure-trove of enriching experiences. Home to a colorful mix of eccentric, free-spirited, and independent-minded types, Key West is, quite simply, a fascinating place unlike any other. You’ll be amazed at the wealth of exciting discoveries awaiting you!


The Island Vibe

Every night is Saturday night in Key West, and the party gets started daily with the Sunset Celebration at Mallory Square. The tradition arose in the late 1960s, a time when carefree hippies found their way to Key West in search of Paradise. Gathering at “The Pier” each evening as the sun went down to celebrate the close of another glorious day — and enjoy a communal high — “See you at Sunset” had a special connotation. Today, it is an invitation to join in spontaneous cameraderie as street performers, tourists, artists, food vendors, and locals gather to entertain and be entertained.

Key West has historically had a free-wheeling, raffish charm, and its irrepressible joie de vivre is not confined to its nights. Seems there is always something to be celebrated here, even if it’s just another day of being on the planet. And one is never far from like-minded spirits ready to share the occasion.

There are literally hundreds of bars on this little two-by-four-mile island, ranging from sophisticated piano bars at waterfront resorts to quirky neighborhood hangouts that cater to the locals. Most activities, from bike tours to movies, offer the opportunity to partake in the libation of one’s choice. There’s even a bar-hopping tradition, known as the “Duval Crawl”, a nod to Duval Street, the heart of the entertainment zone.



Stroll hand in hand – be seduced by the magic of as you poke around quiet lanes overgrown with lush tropical vegetation, discovering the “real Key West”.

Bike – get around like a local. Pretend you live in a sherbet-colored cottage with a hammock on the porch or a grand clapboard mansion, decked out in gingerbread trim and built by a sea captain.

Scooter – another “Key West like a local” experience!

Trolley – ride it for the loop, learning about the island’s history and highlights in about an hour and a half, or hop on and off at your own points of interest, making a day of it.

Off-island day trip – if you didn’t arrive by car, there’s an economical place to rent one, just down the street. We’ve created a self-guided tour just for our guests that will take you to some of the most off-beat and quirky “locals secret” places in the Lower Keys.


Water Sports


Kayaking in the National Wildlife Sanctuary

Jet skiing around the island – a 22 mile tour gives you a different perspective

Snorkel the reef, the patch reefs of the backcountry, or the rock piles right off the beach at “Fort Zach”

Dolphin watching


Standup paddle boarding

Diving – reefs and wrecks




Flats – sight cast in the shallow waters of the Backcountry for the elusive tarpon-permit-bonefish Grand Slam!

Reefs and wrecks – target grouper, tuna, snapper for the table or sailfish for the thrill

Offshore – stalk the big game fish of the deep blue Gulfstream waters




Fort Zachary Taylor State Park – “Fort Zach” to the locals who love it – is our favorite, and the beach closest to the Inn. Rock piles not far offshore make snorkeling right off the beach a convenient alternative to a trip out to the reef.

South Beach – at the Atlantic end of Duval Street, featuring a cool beachside restaurant, is less than a half-mile away.

Smathers Beach, Higgs Beach, and Rest Beach – on the Atlantic side of the island, an easy bike ride from the Inn. Smathers is the largest, where you’ll find parasailing, small sailboat rentals, and a wide sidewalk for scenic walking, jogging, roller blading, or biking. On windy days, this is where the kiteboarders congregate. It’s also Spring Break Central in March and the site of most beach weddings.


Sunset Sails


By all means, do “Sunset” at Mallory Square, the Top of the La Concha, Fort Zach, or the Afterdeck at Louie’s Backyard – all the traditional places. Then, one day of your stay, add billowing sails and gently rolling seas for the ultimate sunset celebration! Choose your favorite ambience, libations included:

Sail into history on a classic tall ship
Enjoy wine tasting on the water on a sleek sailboat
Party hearty on a catamaran with live music
Or, for a particularly memorable experience, pair your sunset sail with a gourmet dinner prepared just for you by the captain of a 32-foot motor yacht!



Indulge in a day of pampering! The major resorts dotting the island all have their own versions, one more decadent than the next, to melt away your stresses. Or enjoy a more intimate, Thai-vibe at a great little spa just around the corner from the Inn. And, if yours is one of our more spacious accommodations, consider having a massage therapist come to you, in the privacy of your own space.




Key West is closer to Cuba than to the nearest Walmart! Take home something exotic from the island’s diversity of unique shops. Trinkets to treasures, discover that special “find” that you’ll wonder how you ever lived without!




Fish tacos from a street cart? Gourmet fare in a dramatically lighted lush, tropical garden? White tablecloths, tiki torches, and a sea breeze on the beach of an offshore island? A decidedly decadent dessert by flickering candlelight, chosen from a sexy menu of innuendos?

Whatever your pleasure, Key West is blessed with an amazing array of world-class dining options. Ask us about our favorites!


Museums, Exhibits, and Historic Places


Tropical Inn – Built in the late 1800s and listed on the National Register of Historic Places. Enrich your Key West experience by staying in a landmark property (sorry, we just couldn’t resist)!

Dry Tortugas and Fort Jefferson National Park Fly out on the seaplane for a unique experience (our pick for “most fun thing to do in Key West”) or take the ferry and make it a day trip! Dr. Samuel Mudd, accused conspirator who attended the injuries of John Wilkes Booth suffered during his assassination of President Abraham Lincoln, was imprisoned here (hence the expression, “his name is Mudd”) … and there’s great snorkeling in the surrounding moat!

Fort Zachary Taylor Historic State Park – The site of not only the local’s favorite beach, but a Civil War era fort, one of a series built in the mid-1800s to defend the nation’s southeastern coastline.

Florida Keys Eco-Discovery Center – Free admission, thanks to NOAA’s use of your tax dollars! Located adjacent “Fort Zach”. Stop in to learn about the ecology of the Keys’ natural habitats, from the upland pinelands and hardwood hammock to the beach dune and mangrove shoreline, where landscape gives way to the underwater environments of the seagrass flats, hardbottom, coral reef and deep shelf communities.

Custom House – Best kept secret in Key West, in our humble opinion! On display are rotating exhibits by local artists, a photographic history of Key West, depictions of life in Key West during the early 20th Century by Mario Sanchez (Key West native that is one of the country’s most sought after folk artists), and a collection of Hemingway memorabilia unrivaled even at Papa’s own home over on Whitehead Street!

Ernest Hemingway House – The literary icon that called Key West home for awhile as he wrote Green Hills of Africa and parts of A Farewell to Arms and Death in the Afternoon. A glimpse of his writing studio in the carriage house is inspirational. Try to imagine his life here with second wife, Pauline. And, oh, those polydactyl cats!

Mel Fischer Museum – “Today’s the day!” was Mel’s favorite shout, to keep his crew inspired. Then, one day – after 16 persistent years — in 1985, it was! Imagine the adventure of the search and discovery of the treasures of the Spanish galleon, Nuestra Senora de Atocha, laden with gold, silver, and jewels of South American empires and lost to a hurricane in the Florida Straits in 1622 … see the booty … capture the excitement for the pirate in your soul!

Truman’s Little Whitehouse – In the mid-1940s, President Harry Truman discovered Key West, in response to a need for climatic treatment of health concerns. He quickly realized that “where the President is, the White House is”. In 1946, he offhandedly proposed moving the White House to Key West. Obviously, that didn’t happen, but you can take a walk through his world, imagining how refreshingly uncomplicated things were … not that long ago …

Audubon House – John James Audubon, the famous ornithologist, naturalist, and illustrator, visited the Florida Keys and Dry Tortugas in 1832. Eighteen new illustrations for his “Birds of America” folio were created in Key West, many of them in the Audubon House garden.

Key west Lighthouse and Keeper’s Quarters Museum – Built in 1847 to aid to ships navigating dangerous reefs off the lower Keys. Climb to the top for a unique perspective of the island.

Fort East Martello and West Martello Tower – Civil war era fort never completed, now housing displays of Key West history and artwork by renowned folk artist and Key West native, Mario Sanchez.


The Arts


Cultural activities are year-round features in Key West, peaking during high season. Who knew there is so much talent here at “the end of the road”?

Not-to-be-missed are:

Historic home tours
Live theater and musical performances
Literary events
Art galleries

Curtains up!

Red Barn Theater: Live theater December through May
Waterfront Playhouse: Live theater December though May
Tennessee Williams Fine Arts Center: auditorium, special events
Tropic Cinema: year round select first-run, indie, and classic films


Night Life


Like the songs says: “When the sun goes down, everything gets hotter”! Mellow to maniacal, Key West has it to your liking, and there’s music everywhere. Take yours in a quiet piano bar, dance the night away to techno, or do the “Duval Crawl”, lured from one venue to the next along one of America’s most famous promenades.

The party isn’t over until you’ve partaken of a long-standing tradition in Key West: a drag show. Catch the high-camp, kitschy-karaoke version at the 801 Saloon or a Vegas – worthy female impersonator in a cabaret setting at La Te Da.

And what historic town would be worth its salt without a ghost tour or two?


Special Events


There is almost always something special going on in Key West – too many to list here. For a month-by-month guide to planning your visit, check out the More Special Events page of our Web site.


Get Married!

Did you know that Key West is second only to Las Vegas as a wedding destination? What could be more romantic than an intimate ceremony on the beach or in the sequestered privacy of the Tropical Inn’s own garden? Have a look at our Weddings page.


… or do nothing at all …


Italians, the most exuberant and passionate culture on earth, have a wonderful expression, “Il dolce far niente” – the sweetness of doing nothing. Our guests succeed at raising that expression to an art form!