Key West Escapade: A 4-Day Island Adventure

You will arrive in Key West, Florida, driving the Ocean Highway from Miami or flying into the Key West Airport (EYW). If you arrive by plane, you can get an Uber to your hotel. But you could also use the Southernmost Golf Carts, which will deliver your golf cart to the airport.

You will check Into the Opal Resort and Spa. This is one of Key West's most luxurious hotels and offers many amenities.

After check-in, you will have a dinner reservation at Sunset Key at Latitudes. At Latitudes, you can have it all. Fine dining, your own private beach and some of the most amazing views of the sunset. Make sure when at Latitudes, ask to sit on the patio and enjoy a key lime pie martini.

After you take the ferry back to Key West after dinner, you will want to walk over to Duval Street for some amazing nightlife. Since it is your first night, you should check out Captain Tony's Saloon. Captain Tony's was the favorite watering hole of legends like Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein and Jimmy Buffet. Pull up a barstool, crack open a cold one or enjoy Captain Tony's punch and enjoy your first night.

After a fun night out on Duval Street, you will want to wake up and have breakfast at the famous Blue Heaven Cafe. This locally-owned restaurant provides hungry visitors with great breakfast, lunch or brunch options. Step into the backyard and see roaming cats and chickens while listening to some of the freshest Key West sounds. Blue Heaven is known for their Bacon, Lobster and Tomato (BLT) Benedict, freshly baked bread, freshly baked banana bread and many other local favorites. Make sure you save room for the famous Blue Heaven Key Lime Pie. This pie is one of the best on the island and is famous for looking like the top of a rooster.

Once you finish brunch, you can check out some of the amazing shops on and off Duval. Check out an art gallery such as the Wyland Gallery. If clothes are what you are looking for, make sure you stop into Vignette Key West.

After picking up some souvenirs, you will want to head to Dante's Pool Bar. This is a great place on the water to check out and beat the Florida heat. Dante's is a crystal-clear swimming pool warmed by a cascading waterfall. You can grab a cocktail and enjoy this amazing pool featuring local DJs.

Time for Happy Hour! After visiting Dante's, head next door to one of the island's best daily happy hours. Half Shell Raw Bar has been voted the number one raw bar in Key West for 2023. Half Shell serves up a daily happy hour from 4 pm to 6 pm, where you can get half-priced drinks and appetizers. Grab some local oysters or stone crab claws (when in season) and eat them raw! You won't want to miss out on this local dining location.

When Happy Hour is finished, you will want to walk over to Mallory Square for the evening's sunset festival. Mallory Square celebrates the sunset each evening by having music, food, street performers, shopping and some of the best views of the amazing sunset we get each night. No matter where you stand in Mallory Square, you will surely get a great view of the sunset and feel the way the locals do.

When it's time for dinner, you will want to walk up Duval Street to Nine One Five. This new restaurant is currently ranked as one of the top eateries on the island. They serve small plates and one of the best lobster ravioli ever. To drink, make sure you sip on the Salted Carmel Martini! Here's a fun local tip: Head upstairs to be able to sit on the balcony. The tables upstairs are first-come, first served, with no reservation needed.

After dinner, if you still have energy, pop into a bar for local music or visit the famous Sloppy Joe's Bar. This iconic bar has been around since 1933 and has had celebrities, presidents, and fishermen stop in for local music and a cold glass of beer. Sloppy Joe’s bartenders’ welcome patrons at virtually all hours of the day or night. The satisfyingly large drinks and casual atmosphere guarantees that something exciting is always about to happen at Sloppy Joe’s Bar.

On the third day of your vacation, you will want to wake up late from all those long nights on Duval Street. When it is time for brunch, make sure you check out Bagatelle. Bagatelle serves brunch seven days a week, and you can choose to eat inside or on the deck outside. The menu is full of local delights, from spiny lobster mac and cheese to glazed bacon! Make sure you get a mimosa or two here, as all the cocktails are made with freshly squeezed juices.

After brunch, you will want to change into your bathing suites, heading out on Sebago Watersports Snorkel and Dolphin Tour. Did you know that Key West is home to one of the best reefs on the planet? Located about seven miles off the shore, you will find one of the largest and best reefs. Sebago Watersports will take you out to snorkel on this amazing reef, where you can spot amazing colorful fish and local sea life. Once you are finished snorkeling, Sebago will hunt for the amazing bottlenose dolphins that live in our local waters. It's estimated about 300 dolphins call Key West home, and with the help of Sebago's captains, they will find them and create a great way to see these majestic creatures.

Once you finish your sail, you will want to return to the hotel to prepare dinner. When it's time to eat, check out A& B Lobster House. A&B has been offering fine dining since 1947 and has some of the freshest seafood in town. While sitting on the dock, you can enjoy that beautiful Key West sunset while enjoying a seafood tower with snow crab claws, Key West pink shrimp, fresh gulf oysters, little neck clams and many other local delights. I recommend the surf and turf when it is time for the main course. You will enjoy a 6 oz filet and a spiny lobster tail. This is one of the best dinners on the island and a great place to unwind after a long day.

After dinner, if you are in the mood for even more Key Lime Pie, visit Kermit's Key Lime Pie bakery. They serve traditional Key Lime Pie and Key Lime Pie on a stick dipped in chocolate.

On your fourth and final day in Key West, you will want to wake up and grab some coffee at the famous Cuban Queen Coffee. These are some of the best coffees you will have. Make sure to get a Cafe Con Leche with sugar. You can get your coffee cold or hot (I recommend hot), and they also serve some amazing Cuban breakfast sandwiches, pressed juices and entrees. Grab some coffee beans to take home with you after your trip. You can't come to Key West, Florida, and not try some delicious Cuban cuisine.

Before heading to the airport or starting the drive back to Miami, check out some of the amazing museums or parks Key West offers. You could visit the Butterfly Rainforest or Truman's Little White House. If you would rather hit the beach, check out Fort Zachary Taylor State Park, which has a small fee to enter, but a great beach to enjoy. If you have a late-night flight, you can even go out to the Dry Tortugas National Park, where you will need to take a boat or plane to get there.

For one last meal in Key West before heading out, stop by The Conch Republic Grill to get some delicious seafood. This place has amazing oysters and great grouper sandwiches, and it is a great final place to eat before leaving our wonderful island.