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Visiting Key West: A Tropical Vacation in the U.S.

To feel like you’re in the Caribbean without leaving the country, head to Key West for your next vacation. It’s hard to beat this tropical paradise, which has a fascinating history, charming architecture, easily walkable streets, beautiful beaches and gloriously clear water, and delicious food.

Key West is perfect for those who like to snorkel, scuba dive, or fish. It’s also an amazing destination for U.S. honeymoons and romantic couples’ trips. And despite its party reputation, Key West is great for family trips as well, with plenty of interesting historical sites and activities to do.

KEY WEST, Florida Keys — The southernmost city in the continental United States, Key West lies at the tip of the 125-mile Florida Keys island chain and is located just 90 miles from Cuba. With an average temperature of 77 degrees, the island is a popular visitor destination. Attractions include a rich cultural community, historic architecture and a relaxed, laidback charm. (Rob O’Neal/Florida Keys News Bureau)

The “Conch Republic” is a relaxed yet fun-filled spot that packs a lot into its small island. As soon as you arrive in Key West, your shoulders will drop and you’ll breathe a little more deeply as you soak in the carefree atmosphere, sunshine, and coastal breezes.

If you’re headed here on a road trip from Miami or points north, be sure to stop at the “Mile 0” sign as you reach the end of U.S. Highway 1 and grab a selfie!

Things to Do in Key West

While many people think of Key West as a party capital—and you can certainly have a good time here—there is so much more to this lovely laidback paradise. Head away from the crowds along the main drag of Duval Street to wander through more peaceful areas and enjoy the brightly colored architecture, tropical foliage, and funky vibe.

Visitors in Key West, Fla., ride the Conch Tour Train as it passes in front of Sloppy Joe’s Bar, former watering hole of author Ernest Hemingway. The faux train and Old Town Trolley are two of the island’s primary motorized tour operations. Key West is the southernmost city in the continental United States. Photo by Bob Krist/Florida Keys News Bureau

You can also get an overview of the area by taking the Conch Train Tour, an open-air “train” that guides you past more than 100 top sites over an hour and a half. If you’d prefer a walking tour, there are plenty to choose from including Hidden Key West Walking Tours, Florida Keys Ventures Key West Walking Tours, and Hemingway in Key West Tours. You can also search on GetYourGuide or Viator.

Some of the most popular Key West activities include visiting the Southernmost Point in the United States for a picture next to the giant buoy, touring the Ernest Hemingway Home and Museum (look for the 6-toed cats, descendants of his cat), and climbing to the top of the Key West Lighthouse.

A family poses for a photograph at the Southernmost Point marker in Key West, Fla., one of the most photographed icons in the Florida Keys. The concrete buoy, which commemorates the southernmost spot of land in the continental United States, is painted with letters proclaiming that it stands 90 miles from Cuba and more than 150 miles from Miami. FOR EDITORIAL USE ONLY. Photo by Laurence Norah/Florida Keys News Bureau

There are all sorts of museums and historic sites in Key West. Museums include the Shipwreck Museum, the Sails to Rail Museum, the Key West Museum of Art, the Fort East Martello Museum, the Oldest House Museum and Gardens, the History of Diving Museum, the Key West Firehouse Museum, the Key West Heritage House, and the Custom House.

Another interesting stop in Key West is the Mel Fisher Maritime Museum, which chronicles treasure hunter Mel Fisher’s searches for sunken treasure—and displays some of his incredible finds.

KEY WEST, Florida Keys — Visitors enjoy a sunny afternoon at the beach at Fort Zachary Taylor Historic State Park in Key West, Fla. The beach area, a favorite of locals and visitors, has a sandy bottom and is protected by several jetties. The park also is a popular location for destination weddings and for watching sunset over the water. (Rob O’Neal/Florida Keys News Bureau)

For stunning ocean views and a lovely beach plus some history, check out Fort Zachary Taylor Historic State Park at the southern end of the key (entry fee of $6 per car). Other good beaches in Key West include Smathers Beach on the Atlantic coast—the largest public beach on the key—Higgs Beach, and South Beach, which is on the Gulf at the foot of Duval Street.

A unique thing to do in Key West is explore President Truman’s Little White House. During Truman’s presidency, he loved Key West so much that he spent 175 days here. He wasn’t the only president to stay here, however; it also hosted Presidents Taft, Eisenhower, Kennedy, Carter, and Clinton. Guided tours are available.

Visitors stroll outside the Harry S Truman Little White House Museum in Key West, Fla. In 1946, Truman began visiting the island for rest and relaxation and returned for 175 days during his presidency. Photo by Andy Newman/Florida Keys News Bureau

History buffs will also enjoy touring the Key West Cemetery, established in 1847. Located in Old Town and easy walking distance from other attractions, it offers guided tours. You can also do a self-guided tour by getting a free map at the entrance. The 19-acre parklike grounds are home to tens of thousands of inground and above-ground tombs holding a diverse collection of people from all walks of life and heritages.

Anyone who loves to read must stop in at Books & Books, a great local bookstore that is owned by famous author Judy Blume (who can often be spotted working behind the counter!). It’s the perfect place for families to stock up on quality books for children and teens, or anyone to find great vacation reads.

Natural attractions in Key West include the Audubon House and Tropical Gardens, the Key West Aquarium, the Key West Tropical Forest and Botanical Gardens, the Key West Wildlife Center, and the Key West Butterfly and Nature Conservatory. One of the most romantic things to do in Key West for couples is to book a “Flamingle” at the Conservatory and get up close and personal with Rhett and Scarlett, the famous flamingo couple.

An aerial photo of Fort Jefferson in Dry Tortugas National Park, situated 70 miles west of Key West. The unspoiled Dry Tortugas area, covering 100 square miles in the Gulf of Mexico, comprises one of America’s most remote national parks. Accessible to the public only by boat or seaplane, it is home to rare migratory birds and a wealth of marine life. The park’s awe-inspiring centerpiece is Civil War–era Fort Jefferson, sometimes called the Gibraltar of the Gulf. FOR EDITORIAL USE ONLY. Photo by Laurence Norah/Florida Keys News Bureau

Consider heading offshore to Dry Tortugas National Park and Fort Jefferson on a fun Key West day trip. You can book a tour or take the Yankee Freedom Ferry, a catamaran that has an air-conditioned cabin plus shaded and unshaded sundeck areas, food and drinks available, and comfortable seating as well as restrooms and fresh water showers for washing off. There’s all sorts of fun to be had in the Dry Tortugas, including snorkeling, birding, exploring, and relaxing on pristine beaches. You can even camp here.

Watersports abound here. Scuba diving and snorkeling in Key West is very popular due to the offshore reefs and wrecks. Some of the most popular spots include Sand Key, Ten-Fathom Ledge, Kedge Ledge, The Cayman Salvor, Joe’s Tugboat, Nine Foot Stake, and Vandenberg, which is the second-biggest ship ever to be used as an artificial reef. You can even snorkel off the shore at the Key West Marine Park, on the southern side.

KEY WEST, Florida Keys— Snorkelers visit Sand Key Light roughly 7 miles off Key West, Fla. The original structure was built in the early 1800s and has been rebuilt or upgraded regularly. Coral-lined reef tracts surround the lighthouse in clear, shallow water where diving and snorkeling are popular. (Rob O’Neal/Florida Keys News Bureau)

You can also go deep sea fishing like “Papa Hemingway;” rent jet skis, paddleboards, and kayaks; take guided kayak tours through mangrove swamps; take a glass bottom boat tour; charter a boat to explore the surrounding water; or relax on a sunset sail. Sebago Watersports offers several sunset sail choices on spacious catamarans, with complimentary drinks, appetizers, and live music.

Golfers will enjoy playing at the Key West Golf Club, an 18-hole par 70 course designed by Rees Jones. Fairways and greens are in excellent condition, and the course is both beautiful and challenging. Clubs are available for rental if you don’t want to pack yours.

Will Soto performs a juggling and high-wire act at the Sunset Celebration in Key West, Fla. Soto has been entertaining for over 30 years at the nightly celebration in Mallory Square that draws crowds of people to watch buskers perform, browse vendors wares and applaud as the sun sinks below the horizon beyond Key West Harbor. Photo by Rob O’Neal/Florida Keys News Bureau.

Be sure not to miss the Sunset Celebration at Mallory Square, which features all sorts of activities and performers entertaining the crowds who gather to watch the glorious sunsets and watch for the elusive green flash as the sun sinks into the sea. You’ll find Mallory Square along the water at the foot of Duval Street.

After sunset, there are plenty of nightlife options in Key West. You can bar hop along Duval Street or see live music at laidback places like the Green Parrot, which features local musicians (see “Key West Bars” below for more details).

Romantic things to do on a Key West honeymoon or vacation include relaxing on the beach, taking your time over a leisurely brunch, watching the sun set, riding bikes along the water, taking a sunset cruise, enjoying dinner with a water view (see below for a top romantic restaurant), and seeing a concert at Coffee Butler Amphitheater.

Couples can also book a Flamingle (see above) or a Sunset Experience at the Key West Lighthouse, 90 minutes of private access to the lighthouse to watch the sunset from the highest point on the island. This also comes with a bottle of wine and appetizers or sweets.

KEY WEST, Florida Keys — The Key West Lighthouse, opened in 1848 and decommissioned in 1969, today is restored as the Key West Lighthouse and Keeper’s Quarters Museum. Visitors can climb 88 steps to the top of the lighthouse to get a 360-degree view of the island, including the Ernest Hemingway Home & Museum that stands directly across Whitehead Street. (Rob O’Neal/Florida Keys News Bureau)

Where to Stay in Key West

The iconic Pier House Resort & Spa is perfect for honeymoons and romantic trips, close to all the action but set along the waterfront with a private white sand beach and protected swimming area. Centrally located at the foot of Duval Street, this tranquil oasis features posh accommodations and a swanky full-service spa as well as a pool, a fitness center, and 3 restaurants and bars including the famous Chart Room (home of Jimmy Buffett’s first gig).

Private beach at Pier House Resort & Spa

Lounge on the beach, swim in the ocean, relax at the beach bar, and dine overlooking the water at the outstanding One Duval restaurant for breakfast, lunch, or dinner. Oceanview Suites have separate living rooms with sofabeds plus excellent water views from private furnished balconies. The unique Dockside Suite is located on the edge of the building for incredible sunset views from the expanded infinity balcony. Key West honeymoon packages here include a couples’ massage, champagne, and daily breakfast with an ocean view at One Duval.

Pier House Resort & Spa

For a B&B feel, The Gardens Hotel is an adults-only spot that offers rooms and suites in a historic home plus cottages with private pools on the lushly landscaped grounds. Luxurious and charming accommodations feature private decks or balconies, marble bathrooms (most with whirlpool tubs), minifridges, Keurig coffeemakers, luxe linens, and robes. This boutique hotel often features live jazz in the gardens and has two heated pools, a pool bar, complimentary breakfast and Wifi, and a self-serve wine gallery,

If you’re traveling with kids, Santa Maria Suites is conveniently located within walking distance of both Old Town attractions and the beach. It has spacious, clean, and contemporary 2-bedroom suites with 2 bathrooms, full kitchens, living rooms with sleeper sofas, laundry facilities, and private balconies or patios. Onsite you’ll find two heated pools, a poolside bar, a Latin restaurant, a fitness center, a nightly happy hour, and 24-hour concierge service.

Set on a private island just minutes away from Key West by boat, Sunset Key Cottages is kid-friendly yet also romantic, so it’s great for either couples or families. It features the famous waterfront restaurant Latitudes, as well as a pool (with bar), spa, and beautiful white-sand beach. Spacious and airy cottages range from 1 to 4 bedrooms and offer separate living areas, kitchens, and private outdoor spaces. One-bedroom cottages only have garden views; you’ll have to upgrade to a 2-bedroom or higher for oceanview and oceanfront options.  Boat transfers are included.

You can also find plenty of Key West vacation rentals on sites like AirBnB and VRBO.

Key West Restaurants

For such a small island, Key West offers a huge variety of delicious dining options. Here are some of the top restaurants in Key West.

Be sure to feast on some Cuban food during your visit. Some of the best Cuban restaurants in Key West are El Siboney, El Meson de Pepe’s, The Original Sandy’s Café, Ana’s Cuban Café, Frita’s Cuban Burgers, Five Brothers Grocery and Sandwich Shop, and Amigo’s Tortilla Bar for fusion Cuban and Mexican.

Of course, there are plenty of seafood options. Half Shell Raw Bar in the Key West Historic Seaport serves delicious fresh seafood including conch ceviche and Key West pink shrimp in a casual waterfront location, where diners can watch the boats come and go.

Schooner Wharf also serves fresh seafood plus all sorts of specialty cocktails in its open-air waterfront setting at the foot of William Street. It also offers live music. DJ’s Clam Shack has been featured on the Food Network’s “Diners and Drive-Ins” and is a casual restaurant serving a wide variety of seafood and sides at reasonable prices.

A bicyclist, followed by his dog, pedals past the Blue Heaven restaurant in Key West, Fla. In the 1930s, author Ernest Hemingway officiated boxing matches at Blue Heaven that is situated in Key West’s historic Bahama Village. Photo by Andy Newman/Florida Keys News Bureau

Blue Heaven is a whimsical restaurant that offers al fresco breakfast, lunch and dinner in a courtyard filled with tropical foliage, as well as indoor dining. There’s live entertainment on the weekends, and while the setting is casual, the food is sophisticated and top notch.

For a romantic and elegant dinner, go to Latitudes Key West. One of the best Key West restaurants on the water, it’s just offshore. Take a short boat ride from the Opal Key Resort & Marina to get to this fine dining restaurant, set on the water on the island of Sunset Key. Be sure to make a reservation and dress up a bit.

Outdoor dining at One Duval, Pier House Resort & Spa Key West

One Duval at Pier House Resort & Spa is another fantastic option for a romantic dinner, offering beautiful water and sunset views as you savor mouthwatering dishes like grouper with crabmeat and Cuban short rib empanadas. You can dine indoors or on the waterfront deck.

Other excellent restaurants in Key West for dinner include Louie’s Backyard, Dinner Bel Mare, La Trattoria, Nine One Five, Santiagos Bodega, Garbo’s Grill, Little Pearl, and Lobster Shack Key West. Great breakfast and lunch spots include Two Friends, Moondog Café, Breakfast Club Too, Hogfish on Stock Island, Sandy’s Café, and The Café (which also serves dinner).

Cuban Coffee Queen serves breakfast, lunch, and smoothies in addition to a wide assortment of coffee including the traditional café con leche, cortadito, and bucci. Try unique offerings like a Cuban Chocolate Mocha, Cuban Carmel coffee, or Turmeric con Leche at either of two locations: downtown and the waterfront. Ana’s Cuban Café also serves breakfast, smoothies, and lunch including excellent Cuban sandwiches and café con leche.

Those with a sweet tooth will love Glazed Donuts, which features handmade glazed doughnuts but also an inventive menu of special types and flavors. (And of course, don’t miss having some authentic local Key Lime Pie at any restaurant you visit. One of the best spots for this is One Duval at Pier House Resort & Spa—their Mile High Key Lime Pie is some of the most delicious you’ll find.)

An aerial photo of Duval St. in Key West, FL. (Rob O’Neal/Florida Keys News Bureau)

Key West Bars

Some of the most famous bars in the U.S. are in Key West. While they may be touristy, they are still worth a stop. 

Of all the Key West bars on Duval Street, Sloppy Joe’s is the most iconic. Famous as the hangout of author Ernest Hemingway (who was good friends and fishing buddies with the owner and is said to have come up with the name), it has been around since the day Prohibition ended.

You’ll find Hemingway memorabilia here as well as a mix of locals and tourists. This bar is also known for its excellent and creative house cocktails and good food, as well as live local music every day (and dancing at night).

Visitors stroll past Sloppy Joe’s Bar on Duval St. Sloppy Joe’s, which was once frequented by Ernest Hemingway, features live entertainment, a classic bar and retail store. (Rob O’Neal/Florida Keys News Bureau)

Also on Duval Street is Jimmy Buffett’s Margaritaville Café. Stop here for—you guessed it—a margarita and enjoy live music as well as food. The Green Parrot is another good spot for live music. For something different on Duval, head to the Little Room Jazz Club and enjoy the romantic atmosphere and sophisticated music.

Set in Old Town, Hog’s Breath Saloon (also located in Destin) is a popular local hangout as well as tourist attraction. In addition to a full range of drinks, you’ll also find a raw bar, food, and live music.

The Sunset Tiki Bar at The Galleon gives you front-row seats to Key West’s famous sunsets in addition to delicious drinks and live music. Another excellent place to toast the sunset is Sunset Pier, located next to Mallory Square and featuring waterfront tables, food, and live music.

Schooners Wharf, located in the Historic Seaport, has an authentic “old Key West” vibe. This casual and laidback spot is perfect for relaxing with a cold beer or cocktail, watching the boats, and listening to live music. It also serves food.

People gather outside Captain Tony’™s Saloon in Key West, Fla. The famous watering hole was the first home of Sloppy Joe’s Bar, where author Ernest Hemingway spent time when he lived and wrote in 1930s Key West. The building that houses the saloon dates back to 1851 and originally served as an icehouse that also doubled as a morgue. FOR EDITORIAL USE ONLY. Photo by Laurence Norah/Florida Keys News Bureau

For a classic local dive bar, visit The Chart Room. Located at The Pier House resort at the foot of Duval Street, this is the site of Jimmy Buffett’s first gig. Another local bar with a long history is Captain Tony’s Saloon, which was the original location of Sloppy Joe’s so it claims Hemingway as a patron as well. Located on Greene Street, this Key West dive bar has live music every day.

An aerial photo of the waters surrounding Key West, Fla., which are protected by the Florida Keys National Marine Sanctuary. The sanctuary includes a 2,900-square-nautical-mile area surrounding the entire Keys island chain and encompassing the continental United States’ only living coral barrier reef. FOR EDITORIAL USE ONLY. Photo by Laurence Norah/Florida Keys News Bureau

How to Get to Key West

It’s easy to fly to Key West, which has its own airport offering direct flights to multiple major U.S. airports, including Miami, Atlanta, Fort Myers, Chicago O’Hare, and Charlotte.

A fun way to get to Key West is by car. The scenic 3-hour drive through the Florida Keys spans about 166 miles from Miami to Key West, taking you alongside some of Florida’s best scenery and offering plenty of places to explore and sightsee throughout the drive.

Another fun way to get to Key West is by ferry. The Key West Express runs between Fort Myers Beach or Marco Island and Key West. The trip generally takes about 3 and a half hours, and the jet powered catamarans have air-conditioned interior space as well as exterior decks and a full-service galley and bar as well as TVs.

An aerial photo of the Key West Historic Seaport. (Rob O’Neal/Florida Keys News Bureau)

Best Time to Visit Key West

Key West has warm weather in the winter, making it a very popular destination for snowbirds and others looking to escape chilly temperatures. This is peak season for Key West, and prices will reflect that—but it can be worth it! Lows are generally in the mid-60s and highs are in the low-to-mid 70s, and there are tons of festivals during the winter months.

In the summer the heat and humidity can be stifling, but there’s usually a breeze and an afternoon thunderstorm to cool things down. Plenty of families come on vacation so it still can be crowded, but prices are lower than winter. June, July, and August are the cheapest times to visit Key West.

The months of June to November are hurricane season, so if you plan to visit Key West during any of those you’ll want to keep an eye on the forecast and be sure to purchase travel insurance. You’ll also want to pack an umbrella and rain gear.

DRY TORTUGAS, Florida Keys — A snorkeler swims along the moat wall at Fort Jefferson in Dry Tortugas National Park. Located 68 miles west of Key West, Fla., in the Gulf of Mexico, the park is made up of seven tiny coral-and-sand islands and visitors can reach it by ferry, seaplane or private boat. The Civil War-era Fort Jefferson, one of the largest masonry structures in the Western Hemisphere, is the remote park’s awe-inspiring centerpiece. (Rob O’Neal/Florida Keys News Bureau)

Spring and fall are excellent times to visit Key West, as temperatures are mild, humidity is lower, crowds are less, and prices are lower. March to May are prime spring months (but avoid spring break if you can), while September to November are the best months in the fall to visit Key West. Fantasy Fest is held in October, so prices and crowds will be much higher then. (Note that this is not a family-friendly event!)

December through April is the dry season, and June through October is the rainy season. Temperatures in Key West range from lows of 65 degrees in January to highs above 90 in August. The average water temperature is about 72 degrees in the winter and 78 degrees or higher in spring, summer, and fall.

Now that you’ve read all about visiting Key West, are you going to plan a trip here? Let us know in the comments!

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