Key West is known for its white sand beaches and aura of complete paradise. Closer to Cuba than Miami, this city boasts a rich local culture.

There are so many things to do in Key West, you’re guaranteed to never be bored. Grab a bike and join us.

A Day on the Water

Snorkeling

snorkeling in key west
Photo courtesy of Jakob Owens

Perhaps the most popular activity is snorkeling, which you can do with a charter to visit sites offshore, or by yourself right off the beach. Choose from an all-day snorkel tour or split your day with some time on a kayak. Book a tour with Fun in the Sun to try your hand at fishing, spearfishing, or lobstering while you’re at it!

Scuba Diving

man scuba diving in key west
Photo courtesy of Anurag Harishchandrakar

For the adventurous looking to journey to deeper depths, Key West has much to offer trained scuba divers, or those willing to learn. Through charter companies such as Seaduction Key West and Lost Reef Adventures, you can reserve your spot aboard a spacious ship and dive at two different reefs for an hour at a time. Whether you dive at Sambos Reef, Joe’s Tug, Sand Key, or Cayman Salvor (an impressive 187-foot coast guard shipwreck), you’ll see vibrant fish living around the colorful coral castles that make up the Florida Reef.

Pro-tip: Plan your snorkeling and diving excursions as early as possible in your trip so you don’t miss out.

Sailing

boat sailing in key west
Photo courtesy of F S

A trip to Key West is likely to inspire the inner sailor. If you’re not quite up to snuff, the good news is you can learn with the help of Sunset Sail Key West. Choose from a day trip, a sunset sail, or an overnight excursion and learn to captain your own vessel under the supervision of a trained guide.

Beach Day

sandy beach at Key West, Florida
Key West, Florida | Photo courtesy of Joshua Adelman

No need to book a tour for fun if you want to stick close to home. The beach at Fort Zachary Taylor State Park offers some of the best waters on Key West. Community grills make this a great place to have a picnic and spend an afternoon with family and friends. Softer sands and volleyball pits can be found at Smathers Beach.

Key West Culture & History

Hemingway Home

The beauty of Key West has inspired people for centuries, including the great American writer Ernest Hemingway. Visit the Hemingway Home and Museum to learn about the writer’s life, see the old Spanish chest upon which he wrote some of his most famous novels while residing in Key West in the 1930s, and take pictures with the six-toed cats that are said to have descended from his own.

Audubon House

Audubon House in key west
Audubon House | Photo courtesy of David

Another building to visit is the Audubon House & Tropical Gardens, which offers insight into 19th-century life. You’ll see fine furnishings, traditional clothing from the era, and original hand-painted lithographs from the famous naturalist John James Audubon. Tour this magnificent estate, built by Captain Geiger for his family using his profits from salvaging shipwrecks off the Florida Reef. Marvelous gardens filled with orchids, bromeliads, and tropical palms are the perfect setting for a romantic wedding, too!

Mallory Square

sword performer at Mallory Square
Entertainment at Mallory Square | Photo courtesy of photo-gator

Rent a bike and head over to Mallory Square to catch the sunset celebration that takes place every night. Year after year, this daily celebration remains one of the most popular things to do in Key West, and for good reason—a crowd of flame jugglers, sword swallowers, tightrope walkers, an exotic bird show, and more keep onlookers enthralled until the spotlight performance of the tropical sunset! Be sure to get here at least 30 minutes before sunset to see it all.

Restaurants & Food in Key West

A necessity to a great island vacation is indulging in delicious food. Whether you’re looking for a quiet place to have a romantic dinner or just to snag a quick lunch, the restaurants in Key West do not disappoint.

Tacos & Burgers

Garbo's Grill taco truck
Garbo’s Grill | Photo courtesy of Steve

Visit Garbo’s Grill when you’re in the mood for tacos or burgers—their Korean BBQ and fish tacos are highly spoken of, and their Umami burger is great for anyone with an appetite. Bien offers Caribbean/Latino cuisine at a reasonable price for any families with picky eaters.

Seafood

A grass hut with a sign of Hogfish Bar and Grill.
Hogfish Bar and Grill | Photo courtesy of Janelle

More inclined toward seafood? No problem! Head to Eaton Street Seafood Market in Old Town for lobster rolls and buy some fresh fish to take home and cook later. On pleasant evenings, dine on lobster mac & cheese, steak, and mahi-mahi on the patio at The Flaming Buoy, or dine with the locals while appreciating live music and a laid-back atmosphere at Hogfish Bar & Grill.

Cuban Food

With a location so close to Cuba, it’s no surprise that authentic Cuban cuisine has a presence in Key West. Visit Fisherman’s Cafe for Cuban breakfast sandwiches, lobster enchiladas, and some of the crispiest sweet potato fries you’ve ever tasted while looking out on the bay. The best Cuban sandwiches on the island are rumored to be at the family-operated grocery/deli, 5 Brothers. Fresh bread is made daily and the ham is shaved per order. Get here early to pick up some fresh guava pastries before they run out, and be sure to get some Cuban coffee to wash down all the delicious food!

Featured photo courtesy of MBandman

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Author: Kit Kingstad

When not writing about incredible vacation destinations for Vacasa, Kit can be found exploring every corner of his home state of Oregon. Other adventures include backpacking solo through Southeast Asia, scuba diving in the Caribbean, and one of his favorite trips to date: touring the Western states with his puppy, Nyma, in a campervan.