Romantic Key West Vacations

Vitalising heat, easy living and a litle slice of paradise


On a Romantic Key West vacations you can enjoy a relaxing Caribbean-like climate, romantic sunsets, a rich history, fine dining, galleries, theaters, short film showings and unique accommodations. Do check out our Key West honeymoon page for much more on romantic Key West getaways.

Just off the tip of Florida, the Keys are a 110 mile long archipelago filled with 800 islands, warm water, and a languid tropical air. Stretching between the Atlantic and the Gulf waters, US Hwy 1 takes you over the photogenic seas and links the Upper, Middle, Lower Keys and a Key West romantic getaway.

Check out our report on top 10 things to do, cocktail bars, best beaches for swimming and snorkeling, romantic restaurants and accommodations.

Top 10 things to do and see on a Key West romantic getaway  

  1. Walked from the Gulf of Mexico to the Atlantic along Duval Street
  3. Stop at Sloppy Joe’s bar for a mojito to soak up the atmosphere Hemingway loved
  5. Set foot on the southernmost point in the US and try to make out Cuba, just 90 miles away
  7. Spend an afternoon the Butterfly and Nature Conservatory
  9. Tour Nobel Prize–winning author Ernest Hemingway's former home, populated by 60 descendants of his famous polydactyl cats.
  11. Climb 88 steps to the top of the Key West Lighthouse for a bird’s eye view of the island
  13. Take the Conch Tour Train - a great way to see the historic Old Town, Hemingway House and the Historic Seaport
  15. Wander around the historic Seaport district
  17. Attend the daily ‘Sunset’ celebration at Mallory Square
  19. Observe Florida key's famous sunset from the water, sailing on a catamaran, an historic tall sail schooner, privately chartered boat or a glassbottom boat down to the Southernmost Point. Toast the end of another romantic day with complimentary champagne


Romantic Key West vacations: More About the Old Town

The 19th century Old Town is the original Key West neighborhood and includes the Key West Historic District. This is where you can find the classic bungalows and guest mansions. The palm-lined streets are filled with gingerbread mansions, tin-roofed conch houses, sidewalk cafes, open-air bars, legendary pubs and world-class restaurants.

This is is the bustling section of Key West which housed Hemingway, John Audubon and Tennessee Williams and is still home to writers, artists and Conchs (locals) who come for the fishing, diving and drinking. Key West has been a home and inspiration to some of the world’s top artists for over two hundred years. Their work can be seen in galleries and museums all over this creative island paradise.


Things to do and see in the Old Town on romantic Key West vacations

Hemingway's House and gardens (pictured on the left): here you can see the typewriter on which Ernest wrote: "For Whom The Bell Tolls). In the garden is the old urinal from the original Sloppy Joe's, which Hemingaway dragged back to the house to annoy his wife, Pauline. His house is overrun with the six-toed dependents of his cat Snowball.

Mallory Square is at the center of Key West's historic waterfront and stages every evening the famous Key West sunset celebration. Each day at dusk (around two hours before sunset) visitors gather at this seaside spot to watch the spectacular sunset and enjoy multicultural happenings with lively street performances and to watch the sun sink into the Gulf of Mexico. It's a great place to watch the sunset and street performers (actors, flame throwers, musicians jugglers, mimes, musicians and street artists) but with hundreds of participants it's not the best spot for solitude and contemplation.

Truman Annex is walking distance to shops, elegant and tropical restaurants, bars, beaches and museums that make Key West unique. This is where the winter White House for President Harry S. Truman during its days as part of Naval Station Key West Naval Station is located. You can visit the "Little White House" and the Botanical Gardens (an acre of tropical foliage and trees surrounded by the original 1890 wrought iron fence).

On romantic Key West vacations it's impossible to miss Duval Street. A bar and restaurant district that includes many different entertainment options, all within walking distance of each other.

Don't miss St. Paul's Church on 401 Duval Street Key West, FL 33040. This is the first church to be built in Key West and has some spectacular stained glass windows.

From Duval Street and the waterfront, to hidden Old Town gems or the Historic Seaport, restaurants occupy old homes and other buildings featuring widely diverse architectural styles.

Key West vacations: Romantic restaurants.

The Hot Tin Roof features a relaxed elegance with dramatic water and sunset views. Its menu is highlighted with a mix of seafood and landfare prepared in a unique culinary style dubbed as "conch-fusion."

Phone: (305) 296-7701
0 Duval Street (Ocean Key Resort & Spa)
Key West , FL 33040

Mangia Mangia - Acclaimed Pasta Cafe.

Family style Italian cafe with abundant portions of fresh homemade pasta & low prices! Critical Acclaim from Zagat, Fodors & Frommers. Wine Spectator Award of Excellence since '94. Off Duval in quiet Old Town, cozy tropical patio; a local favorite

Phone: 305-294-2469
900 Southard Street
Key West , FL 33040

For the full romantic Key West vacations experience try La Trattoria, centrally located romantic eatery on Duval Street serving gourmet Italian dinners since 1984. It has as been honored numerous times (including in 2004) with the People’s Choice Award as one of Key West's favorite Italian restaurants, best romantic dinner & where the locals eat!


524 Duval Street
Key West , FL 33040
Phone: (305)296-1075

Follow up with Virgilio's Cocktail Lounge, Key West Hot Spot serving up chilled martinis, single malt scotches, fine wines and hot entertainment. Live jazz, blues, and lounge music.

Appelrouth Lane
Key West , FL 33040
Phone: 305-296-8118

Romantic Key West vacations are also renowned for its Gourmet Dinner Cruises.

Key West vacations and Key West romantic getaway: Best Beaches

Key West vacations are not known for its spacious sugar white beaches like the Bahamas. There are better places just a few miles north in the Florida Keys - Bahia Honda National Park has one of the few stretches of white sand beach in this archipelago of sharp coral reef.

Higgs Beach is one of the nicer public beaches.


Smathers Beach has lovely white sand imported from the Bahamas, a beautiful blue/green sea and a marvelous view - great for taking lots of pictures with an ideal backdrop, and is perfect for those special weddings.

There is seaweed on the shoreline, but once you get passed it, the water is nice. It is not the biggest beach in the world and it does not compare with South Beach in Miami, but it also doesn't have the amount of people on it as South Beach. It is quite and perfect for just relaxing in the hot sun, walking along and splashing in the shallows.

Fort Zachary Taylor is recommended for swimming and a splendid fort to visit on Key West vacations. This is a Florida State Park and National Historic Landmark centered on a Civil War-era fort located near the southern tip of Key West, Florida,


More about activities and things to do on Romantic Key West vacations:

Snorkeling is a great thing to indulge in on Key West Vacations. It's coral reefs are part of the world's third largest reef system and are located in shallow water - under 20 feet. The seas at the reef are typically calm, crystal clear, and warm.

Take a day trip to Fort Jefferson and the Dry Tortugas on your Romantic Key West vacations.

The Dry Tortugas National Park is a collection of seven uninhabited island 70 miles west of Key West. Fort Jefferson is located on Garden Key, one of the seven coral reef islands. This is one of forts that were originally constructed to protect against piracy. Fast ferries provide access to this remote site, leaving daily from Key West’s historic Seaport. Once on the island, visitors are free to wander the grounds of the fort and lighthouse, take a 45-minute tour of the facility provided by the Park Service, or hit the stunning beach, where snorkeling in the crystal clear waters is a favorite activity.

If it's isolation you want, then you cannot do better than the Dry Tortugas.

Stroll in the Key West Cemetery.

It's considered worthy of visiting because it offers a slice of history and authenticity and because it's one of the most unusual cemeteries. The cemetery has unusual epitaphs, unique headstones, original sculptures, spooky statues, all set amongst winding pathways and whitewashed tombs.


Key West vacations: Romantic hotels and Bungalows

Marquesa Hotel

A gracious historic district hotel dating back to 1884 possessing high ceilings, ceiling fans and marble baths. This Key West romantic getaway has an inventive contemporary restaurant with grilled fish specialties.

600 Fleming St.
Key West, Lower Keys, Florida
T: +1 305 292-1919. 27 rooms in 4 houses, US$ 245-

Paradise Inn

A Key West Inn and Guesthouse where you can unwind in the Jacuzzi, cool off beneath the palms in our fountain-fed pool, or walk just one block to the excitement of Duval Street.

Key West, Lower Keys, FL
T: +1 800 888 9648. 18 rooms, b&b only.US$ 240-

This bed and breakfast style inn, is a traditional Caribbean compound made up of historically significant cigar maker cottages that have been meticulously renovated into one and two bedroom accommodations, set in a secluded environment. Additional suites are located in two authentically reproduced Bahamian-style houses with vine covered porches, sundecks and shaded balconies.

Little Palm Island (Spa & Resort)

Here you can enjoy your Key West romantic getaway on a five acre private island with thatched roofed suites and British colonial furnishings.

28500 Overseas Highway
Little Torch Key, Lower Keys, Florida
T: +1 305 872 2524. 30 duplexes. US$ 895-


Getting to your Romantic Key West vacations

Key West romantic getaway by Air:

There are direct flights or connections to Key West International Airport from a host of Florida cities: Miami, Ft. Lauderdale, Ft. Pierce, Ft. Myers, West Palm, Naples, Orlando - Kissimmee, Tampa, St. Pete - Clearwater, Zyphrhills, Atlanta and Nassau.

Key West romantic getaway by Land / driving directions

If you're driving from Miami International Airport , take LeJeune Road south to 836 West. Take the Florida Turnpike south toward Key West. The Turnpike ends at US 1 in Florida City. Follow U.S. 1 south as far as it goes and you will be in Key West.

From Ft. Lauderdale-Hollywood International Airport , exit the airport and follow the signs for 595 West. Take 595 to the Florida Turnpike and follow the signs for the Florida Keys and Key West.

From the north , take the Florida Turnpike south and follow the signs for Homestead and Key West. The Florida Turnpike ends at US 1 in Florida City.Follow U.S. 1 south into the Florida Keys.

From Florida's west coast , take 1-75 Alligator Alley east to the Miami exit, and south to the Turnpike Extension.

Key West romantic getaway by Water:

Key West Express operates high-speed passenger ferries from Ft. Myers Beach and Marco Island. The ferries dock at the Key West Bight Ferry Terminal in the heart of the Historic Seaport District

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