While it’s been a crazy year – especially for travelers, The Florida Keys and Key West are a tropical destination that Americans can travel to safely and in a socially distanced way. With its plethora of outdoor adventures, al fresco dining, warm weather, and a mask mandate, you can rest assured that Key West and the Florida Keys are the perfect place for a 2020 or 2021 getaway. From our stay at the Perry Hotel in Key West through the Lower Keys, Big Pine, and Key Largo, you won’t want to miss a moment of this tropical paradise.

About Key West

Key West is the southernmost tip of the Continental U.S. located only 90 miles north of Cuba. Bordered by both the Atlantic Ocean and the Gulf of Mexico, Key West has soothing tropical breezes and the highest average temperature in the U.S., which makes it the perfect year-round escape.

How To Get To Key West

While many choose to drive the beautiful Overseas Highway from Miami to Key West and others opt to cruise in, we flew directly from the New York City area right into Key West International Airport. For all of you looking to escape the winter cold, we’ve got great news: you can fly directly to paradise. There are direct flights from several U.S. gateway cities.

Activities in Key West

While Key West is surrounded by beautiful turquoise waters, there aren’t many beaches. Days in Key West are best spent on the water or exploring downtown.

Ernest Hemingway Home: As a writer and longtime Hemingway fan, we absolutely loved visiting the Ernest Hemingway Home & Museum. Hemingway spent a decade in Key West, drinking Rum Runners and writing some of his most prolific novels.

Sailing with Blue Sail Charters: The best way to experience Key West is on the water. Whether you want to sail, snorkel, paddle, or all of the above, Blue Sail Charters is the premier place to experience paradise. Accredited by the American Sailing Association, these lavish boats are perfect for day charters out to the surrounding sandbars or on a multi-day journey out to Dry Tortugas National Park.

Paddle Yoga with Lazy Dog Key West: Paddleboarding and kayaking around the mangroves of Key West is a soothing and tranquil way to absorb the unadulterated beauty of the region. We decided to step things up on a notch and try our hands at paddle yoga with Lazy Dog Key West. In the early morning light, our guide took us out on the peaceful waters of Key West where we surrendered to the silence of our surroundings and traveled inward, repeating mantras of gratitude while flowing through our practice on the water.


Where to Eat in Key West

  • Blue Heaven Key West: Blue Heaven was one of our favorite restaurants in all of Key West – not just because of the food, but because of the experience. With al fresco dining, live music, and arguably the best key lime pie in all of Key West, it’s an absolute must for Sunday Brunch!
  • Hogfish Bar & Grill: Key West is home to some of the freshest and most delicious seafood in the entire world. The Hogfish Bar & Grill is home to the local delicacy, hogfish. This diver-caught fish is flavorful and is best enjoyed as fish & chips or on its “killer” hogfish sandwich.

Grouper at Matt’s Stock Island

  • First Flight: We definitely had a bit of a #fangirl and #fanboy moment when we entered First Flight. This restaurant and Brewery is in one of the area’s most historical buildings – the birthplace of Pan American World Airways. This is the same building where Pan-Am’s first airplane tickets were sold. Today, it’s a delicious brewery and restaurant that serves incredibly fresh and local food in a romantic outdoor setting.
  • Matt’s Stock Island: Located at the beautiful Perry Hotel on Stock Island, Matt’s Stock Island serves American coastal comfort food with a beautiful view of the Stock Island harbor. We highly recommend ordering the grouper gnudi, which was one of our favorite meals we’ve ever consumed.

Key Largo to Big Pine & The Lower Keys

While Key West may be the most well-known of all the Florida Keys, there are around 120 miles of beautiful tropical islands in between. From Key Largo to Big Pine & The Lower Keys, you won’t want to miss this unforgettable piece of paradise.

Activities in Key Largo to Big Pine & The Lower Keys

  • Bahia Honda State Park:  While the Florida Keys are home to some of the most beautiful waters in the United States, there are few white sand beaches. Bahia Honda State Park is home to pristine white sand beaches and crystal-clear waters – perfect for swimming and snorkeling. The beaches run along both the Atlantic Ocean and the Gulf of Mexico.
  • Clear tandem kayaking: While kayaking around the Florida Keys is a common watersport, the team at Get Up and Go Florida Keys put a new twist on an old Florida favorite: the clear tandem kayak. Located on Sugarloaf Key, the clear tandem kayak allows you to kayak alongside mangroves and over pristine waters, all with gorgeous glass-bottomed views of the marine life.
  • Paddleboarding: There are a surplus of places to hire paddleboards to enjoy the calm waters of the Atlantic Ocean and the Gulf of Mexico. While staying at Baker’s Cay Resort, we were able to utilize the hotels in-house paddleboards (and other non-motorized water sports) absolutely free.

Where to Eat

The Hungry Tarpon, Islamorada: The Hungry Tarpon is laidback barefoot dining at its finest. Located right on Robbie’s Marina, there is a mixture of food vendors, a restaurant, bar, outdoor shops, and of course – tarpon feeding. We highly recommend ordering the grouper sandwich and lobster tail.

Calusa at Baker’s Cay Resort, Key Largo: This delicious restaurant is located at Baker’s Cay Resort. You can dine indoors or al fresco and nosh on fresh seafood with a hint of New Orleans flavors.

The Key Largo Conch House, Key Largo: One of our favorite local restaurants was the Key Largo Conch House in Key Largo. Relaxed and unpretentious, this indoor and outdoor restaurant serves up delicious conch fritters, amazing salads, and fresh seafood.

The Raw Bar at the Postcard Inn, Islamorada: The Raw Bar sits 25 feet above the Atlantic Ocean and is one of the best sunset spots in all of the Florida Keys and perhaps the entire United States. As the sun sets over the Florida Keys, this adults-only bar and restaurant has one of the most jaw-droppingly stunning views that truly took our breath away.

Islamorada Brewery & Distillery, Islamorada: Located at mile marker 82.2, The Islamorada Brewery & Distillery serves up delicious beers and cocktails in a brightly colored indoor tasting room and outdoor lawn setting. We highly recommend ordering the Frozen Eggnog Cocktail and the Mermaid Magic Color-Changing Limeaid.


Enjoying an al fresco night out at Baker’s Cay Resort


Unparalleled sunset views at The Raw Bar