Key West
Sightseeing Tours

Enter your dates to find available activities

Our most recommended Key West Sightseeing Tours

Key West: 2-Hour Sunset Sail on Schooner America 2.0

1. Key West: 2-Hour Sunset Sail on Schooner America 2.0

Take in the vibrant colors of Key West's fabulous sunset as you glide through the waters on one of the finest boats in the Key West Schooner Fleet. Watch the sun fade into the horizon and the stars emerge into the deep blue sky. America 2.0 features teak decks, mahogany-trimmings, and 3,600 square feet of canvas! Sit back and relax while she plies effortlessly through the crystal-clear waters off Key West, heading towards the horizon for the quintessential Florida sunset experience! Some of the sights on this sailing adventure include a view of Fort Zachary Taylor from the water, and views of the famed Sand Key Reef, Mallory Square, and Sunset Pier. Keep your eyes peeled for wildlife such as dolphins, sea turtles, and water birds – and for the famous Key West "Green Flash" at sunset. Bring your family or friends and join the courteous and professional crew for this sunset sail that completes the Key West experience in comfort and elegance.

...
Key West Full-Day Tour by Motor Coach Bus from Miami

2. Key West Full-Day Tour by Motor Coach Bus from Miami

This full-day tour to Key West from Miami starts with a 4-hour drive across 43 bridges and 31 islands to America's “Caribbean Islands,” the Florida Keys. The string of islands and islets, bordered by the Atlantic Ocean and the Gulf of Mexico, leads to Key West, the only frost-free city in the continental United States! Once in Key West, experience a Caribbean atmosphere complete with friendly street artists, lively outdoor cafés, and alfresco restaurants. Spend some time exploring Key West on your own. Book lovers might like to visit Ernest Hemingway’s House to see the former home of the famous author. Or, if you prefer, you can go to the southernmost point of the continental United States at the famous "90 miles to Cuba" Monument. Explore museums, such as the Mel Fisher Museum, the Light House Museum, or Ripley's Believe It Or Not Museum (tickets not included). Feel the pulse of Key West at Mallory Square next to the cruise ship port. You may also choose to add one of our most popular adventure activities, such as a snorkeling trip to see tropical fish, a ride in a glass-bottom boat, or the hop-on and hop-off sightseeing trolley bus (tickets not included in the price). Depart Key West at 5:30 PM for the drive back over the bridges and islands.

...
Ghosts & Gravestones Tour of Key West

3. Ghosts & Gravestones Tour of Key West

Many find Key West a strange place during the day; but after the sun sets, the restless souls of the island’s frightful past begin to stir. On this 1-hour ghost tour, you will hear all-but-forgotten tales as you travel the dark and narrow streets of the Old Town. Pass 19th-century wooden houses that hold secret stories of former inhabitants; stories so tragic and chilling, you’ll soon see why Key West was named one of the top 10 most haunted cities in America. Your Ghost Host will add a pinch of humor to Key West's dark side with tales of deathly love, tragic endings, scores to settle, wrongs to right and ghastly folk - some so strange it will be hard to believe they’re true…

...
Miami: Day Trip to Key West with Optional Snorkeling

4. Miami: Day Trip to Key West with Optional Snorkeling

Start your day on an air-conditioned bus from Miami Beach to Key West with a 4-hour drive. Watch as your tour guide points out the famous 31 Caribbean Islands along the drive known as the Florida Keys. Cross 43 bridges as you travel through the Keys to Key West. See the Atlantic Ocean and the Gulf of Mexico while driving by the coastline. Key West is the most southern point of the USA and only 90 miles from Cuba. Once you arrive in Key West, get 6 hours to explore the island at a leisurely pace. You can enjoy water activities, go on a hop-on trolly, stroll the artistic streets, or sit at outdoor cafes. Key West is the home of Ernest Hemingway, and you can visit his former residence. Nearby the cruise port, you can visit Mallory square for shopping. You may also choose to add one of the most popular adventure activities such as hop on hop off tour or the Conch Tour Train, Key West Aquarium, Key West Shipwreck Museum, Sails to Rails Museum, or the Truman Little White House. Make your way back from Key West to Miami Beach at 5:00 PM.

...
From Miami: Key West Full-Day Trip with Transfer

5. From Miami: Key West Full-Day Trip with Transfer

Experience the southernmost city in the USA by land and sea. Explore the many sights, shops, and restaurants in Key West. Soak in the Caribbean feel of the city and take a glass-bottom boat ride over the third largest reef in the world. Enjoy a pickup at your accommodation in Miami Beach in the morning and head towards Key Largo. Go further to Key West over 42 islands and the magnificent Overseas Highway 1, one of the most spectacular roads in the USA. The route crosses many bridges including the Seven Mile Bridge. Reach Key West before noon and enjoy some free time to explore the city on your own. The tranquil Caribbean town was once the adopted home of the famous writer Ernest Hemingway.

...
Key West Conch Train Tour

6. Key West Conch Train Tour

Climb aboard Key West’s conch train for a 90-minute sightseeing tour of the tropical paradise. The train departs from Front Street Depot and loops through the Old Town to end back behind the Depot at Mallory Square. Stock up on ice cream and homemade fudge at the Depot to eat on board during your tour. You can jump off at Truval Village to visit the Ernest Hemingway Home and Museum, Key West Lighthouse, Southernmost Point, and Key West Butterfly and Nature Conservatory. Climb to the top of the observation tower at Key West Shipwreck and Treasures Museum. Travel back in time to the days of hand-rolled cigars at Mallory Square. And stroll through the Cayo Hueso y Habana Historeum. Back on the conch train, learn about Key West characters, such as Mel Fisher, whose lifelong search for 2 sunken Spanish galleons finally turned up treasure worth USD 450 million. Jump off to enjoy great shopping on Duval Street, and fine dining at restaurants such as Hog's Breath Saloon, Jimmy Buffet's Margaritaville or the Hard Rock Café.

...
Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

7. Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

Meet your guide for the night, a world-class drag queen, at the award-winning lounge, Aqua Bar and Nightclub at 711 Duval St. in Key West. Grab a cocktail and mingle with your fellow crawlers as you await the ring of the ‘bitch bell’ to announce the kick-off of the tour. First, follow your guide through the vibrant streets of Key West and prepare to sing and dance your way through the city as you learn how to party like a true queen. Now you know how to behave like a queen it's time to be treated like one too — skip to the front of the line at every bar and pub along the crawl. Then, spend the night at a number of Key West's best bars and clubs, drink delicious and reasonably priced cocktails, laugh with your fellow crawlers, dance like a queen, and experience how the other half lives. Enjoy a fun-filled tour that's perfect for bachelorette parties, birthdays, and other memorable events.

...
Key West Beachside Parasailing

8. Key West Beachside Parasailing

Board the parasailing boat from Smather's Beach. Get strapped into the harness on the aft of the parasailing boat then slowly rise into the air under a beautiful red, white, and blue parasail. Get an unobstructed panoramic view of Key West from over 300 feet in the air. Slowly sink down for a cooling dip in the waters before you rise high above Key West again. Get reeled back onto the aft deck of the boat following your memorable high flying adventure.

...
From Miami: Key West Full-Day Trip with Parasailing and Transfer

9. From Miami: Key West Full-Day Trip with Parasailing and Transfer

Leave Miami for the sandy beaches and relaxed vibe of Key West. Following hotel pickup, head to the unique hotspot where your adventure awaits. Parasailing should be on the top of your list of activities to do in Key West because of the sensational flight and the great views. First, float on a tropical breeze in a state-of-the-art parasail launch boat and glide above emerald waters. Then soar like a bird and look for dolphins below you. See brightly colored birds fly past, and marvel at the majesty of the Florida Keys landscape. Once you touch back down on land, take the opportunity to shop and check out local restaurants. After a full day, head back to Miami where you’ll be dropped back at your accommodation.

...
Key West: Bone Island Haunted Pub Crawl

10. Key West: Bone Island Haunted Pub Crawl

"Cayo Hueso" in Key West, as it was originally named, translates to "Bone Key" or "Bone Island". On this haunted pub crawl you will experience why Key West is consistently ranked as one of the top five most-haunted cities in America. Crawl along as you delve into some of the more spirited pubs of Old Town. You'll discover Key West's history of cursed treasure, voodoo, murder, suicide, haunted mansions, unexplained deaths, and more. Your professional "ghost host" will introduce you to the darkest side of Bone Island, and after 3 haunted pubs you will be issued a souvenir t-shirt before being released into the night.

...

Other Sightseeing Options in Key West

Want to discover all there is to do in Key West? Click here for a full list.

What people are saying about Key West

Overall rating

4.0 / 5

based on 239 reviews

Awesome for new & experienced riders! Jake & crew were very friendly, fun, patient & professional. Thank you for an excellent ride! I would highly recommend!!! A few things: -Directions to jet ski office is confusing with address given & on Google maps. As you turn right off main rd., "lot 1" with valet parking will be immediately to left. Around the left side of that lot is where office & jet skiing are. Park at closest store. - Only 16+ can drive their own jet ski (but my 15 yo very active son had a blast being on the back!) - Bring towel & wear fitted sunglasses to keep wind out of eyes when riding (it's windy!)

Incredible sunset cruise! The crew were the best, ensured we had plenty to drink (wine, beer or champagne) and fresh delicious snack plates (veggies & dip, crackers & cheese, followed up with shrimp and sauce. Plenty of personal space given current Covid concerns. Bathrooms were easily accessible and very clean. Highly recommend!

The boat is stunning, the crew are warm and welcoming and the service is impeccable - a great addition to any trip to Key West!

As advertised!. Great hard working crew on the Sunset Cruise on 12-29-21. Highly recommended.

Bruce was the best tour guide. Very informative and entertaining.