Not all treasure is found on a map.

Many Texans have Key West on their bucket list and rightfully so. It is a small island town at the southernmost point of the US, 90 miles from Cuba, that is filled with history, boating fun, great seafood, and entertaining bar scenes. This is a place where you will relax (as they say, come as you are) but you’re also going to want to stay fairly busy, absorbing all that Key West has to offer.

Margaritaville Beach House Key West, formerly Barbary House Resort, after a $3 million investment, to include enhancements to amenities and design aesthetics, sits across the street from a public beach. With the laid-back casual vibe of Margaritaville, this is a good spot to lay your head in their nautical-themed suites, cool off in the pool and make this your central point for all the fun that you’ll experience in town.

The restaurant and bar area, called Tin Cup Chalice & Chill, is the central spot for dining and enjoying the cool pool water, while the rooms/suites are spacious, filled with much-needed AC and some even have kitchenettes. The two-bedroom suite is ideal for a family if kids are included in the trip.

Take to Two Wheels

After you check in, visit the concierge desk to secure your bike rentals which you will want to keep for the entirety of your visit. Key West is spread out enough that you’re not going to want to walk everywhere you go but vehicles are also unnecessary. The hotel does offer a complimentary shuttle that runs on the hour each hour and drops off at the historic seaport and downtown area.

Island Eye Candy

Sunset Sail

Key West is known for its sunsets so enjoy a sunset sail with Sebago Key West where you can board a catamaran or schooner and enjoy sailing on the water with some new friends and friendly crew members while you enjoy an open bar and live music, ultimately landing some beautiful sunset photos.

Dolphin Watch

Get out on the water for a dolphin watch and snorkel tour with Honest Eco, a local company that strives to give guests natural experiences, telling the backstory of local dolphins and getting you in the water to enjoy beautiful marine life near the coral reef that’s only 7 miles offshore.

Sunset Carnival

Another popular spot to enjoy the sunset is the nightly celebration at Mallory Square that is a free local tradition. This sunset celebration is a carnival where you’ll enjoy street performers, musicians, vendors and, of course, the stunning sunset.

Hemingway Home & More

Visit Ernest Hemingway‘s Home & Museum to enjoy a tour through the beautiful property where you’ll learn all about this bestselling author’s life (1899-1961), including his four marriages and the 60 (some are polydactyl, six-toed) cats that live on property. Hemingway’s estate is the location of the island’s very first swimming pool and also his second story studio where he wrote many of his classics. This Spanish Colonial house sits on a one-acre lot, the largest single family plot in Key West.

With the use of your cruiser bike, make sure that you visit The Truman House which was President Truman’s summer home, Fort Zachary Taylor State Park which has the very best swimming beach on the island, and drive down Duval Street where you’ll see loads of shops and bars including Sloppy Joe’s where it’s a party all day long.

Pro Tip: Visit keywestattractions.org and keywestvacationpass.com for activities and deals on packages. 

Island Dining

On the Water

Half Shell Raw Bar is located right on the water in the Historic Seaport area and is a super casual spot to enjoy fresh seafood – and when they say fresh, they mean it. With a “fresh catch” option on the menu, guests can indulge in a sandwich or entree made with fish caught that same day. Their namesake, though, is their large selection of raw eats. If plain raw oysters are not your speed, the restaurant has a unique BBQ or garlic raw oyster platter. If you want raw seafood but are not fond of mussels, then the restaurant has raw shrimp. Do not be fooled by the name, though, because there is a solid selection of cooked entrees.

Casual Cuban

El Siboney is a casual Cuban restaurant where the locals go, so you know it’s delicious. Owned and operated by a young family, this is where you’re going to enjoy plates of shredded pork and perfectly seasoned shrimp with filling sides of rice and beans. Seafood lovers can choose from a classic selection of island fare like coconut shrimp, grilled Mahi-Mahi and breaded butterfly yellowtail to name a few. If surf is not your favorite, then turn to turf and choose from El Siboney’s beef and pork selections.

Head to Heaven

A trip to Key West is not complete without dining at the famous Blue Heaven. Known for its breakfast, they serve meals all day long at this popular spot in the historic Bahama Village neighborhood. They’re known for their key lime pie, homemade banana bread and hearty brunch enjoyed in an outdoor relaxed atmosphere — with live music if you time it right. The Rooster is a breakfast platter featuring eggs, ham, cheese grits and banana bread. But they’re also well known for their seafood eggs Benedict and shrimp and grits. Guests can enjoy a hearty and unique dinner paired with local brews like Key West Sunset Ale or or Iguana Bait Kolsch.

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Cover photo courtesy Rob O’Neal/Florida Keys News Bureau

Marika Flatt, Outstanding Austin Communicator 2021, is the Travel Editor of Texas Lifestyle Magazine. She began her travel writing career with Austin Woman Magazine when it premiered in the fall of 2002. Now, she can be seen on TV shows across Texas, offering travel tips, in addition to her long-running “Weekend Trip Tip” on NPR’s Texas Standard.