Key West, the southernmost gem of Florida, is a tropical haven that beckons travelers with its rich history, vibrant culture, and breathtaking landscapes. From stunning sunsets to lively streets, this island paradise offers a myriad of experiences that cater to every kind of traveler. Here are 8 must-do activities that will make your Key West visit unforgettable:
Visit the Mallory Square Sunset Celebration
Join the lively gathering at Mallory Square every evening at sunset to witness the enchanting sunset. Street performers, local artisans, and stunning ocean views create a unique atmosphere that truly captures the essence of Key West. A celebration that started in the 1960's this is one you should absolutely NOT MISS! For an extra special & romantic evening, check out this private Mallory Square sunset cruise while you enjoy the included snacks and drinks. Another option is to sign up for the Waterfront cocktail walk to Mallory Square - a guided walking tour that will take you by local Key West hot spots to sample food and drinks before arriving at Mallory Square for the sunset celebration!
Duval Street Exploration
No trip to Key West is complete without at least one stroll down the iconic Duval Street, lined with charming boutiques, art galleries, restaurants, and vibrant nightlife. For a fun twist on Duval Street, check out this haunted pub crawl and ghost tour where you'll spend 2-hours checking out the most haunted bars in Key West with a local guide...one of the bars in located in a former morgue! On this tour you'll also learn why Key West was once referred to as Bone Island.
Take a ride on the Conch Tour Train
Hop on this iconic train for a guided tour through the historic streets of Key West. Learn about the island's history, culture, and hidden gems. For under $40.00 per person you'll enjoy an 1.5 hour tour of Key West. You'll see where Hemingway used to hang out, tour Old Town Key West from the Front Street Depot to Mallory Square and everything in between! You can't go wrong with the Conch Tour Train - you'll see all the important sites and can decide which ones you'd like to explore more!
Take a Day Trip to Dry Tortugas National Park
Embark on a day trip to this remote island paradise. Located off the coast of Key West, the Dry Tortugas were discovered by Ponce de Leon in 1513. This area is known for its reefs and its many, many shipwrecks. The Dry Tortugas are also home to Fort Jefferson, a strategic Harbor that was started in 1846 and never completed.
The Dry Tortugas are only accessible by plane or boat. We prefer visiting via a Catamaran Tour vs. a seaplane for a number of reasons. First, it's far cheaper to get to the island via a catamaran. Also, the catamaran tour includes both breakfast and lunch on the boat which is a nice perk as there are no restaurants or services here. You'll have plenty of time to explore both land and water before being returned back to Key West.
Spend a Day Deep Sea Fishing
Florida is the fishing capital of the world so it only makes sense to spend a day fishing the waters around Key West while you're visiting. There are so many options when it comes to fishing charters in the Keys. We'll go over a few to help you make your decision!
Large Fishing Boat: At under $100 per person for a 6 hour fishing trip this is a great option if you'd like to go deep sea fishing on a budget. The boat holds up to 60 passengers but the captain and crew do a great job of spending time with all guests as they fish. The fee includes a fishing license and all bait.
Sportfishing Charters: Corsairs 2 Sportfishing is one of the best on the island. Their fishing boat can hold up to 6 anglers and the boat features two restrooms, a kitchen, flybridge, beds and air conditioning. You'll have the chance to catch mahi mahi, wahoo, tuna & more up to 18 miles off-shore and can choose from a half day, 3/4 day or full day charters. Priced between $900 & $1500 for up to six anglers, it's pricier than the larger group option but is totally worth it!
The Southernmost Point Buoy
Have you even been to Key West if you don't have photos at the Southernmost Point Buoy? We say no! It's an easy walk to the buoy from almost anywhere on the island but you can also use the Hop-On Hop-Off Trolley Tour to get around the city. The trolley visits more than 100 places throughout Key West and with an unlimited day pass available you can get on and off the trolley as many times as you'd like! Priced at about $50 per person for a one-day pass it's a great option for people who may have mobility issues or just don't want to have to walk everywhere in the Florida heat.
Visit the Ernest Hemingway House and Museum
Immerse yourself in literary history at the Hemingway Home. Explore the beautiful gardens and meet the famous six-toed cats that roam the premises. The museum is open daily from 9:00 AM - 5:00 PM and advanced tickets are not needed. They can be purchased at the door for $18.00. The museum is open 365 days a year. Learn even more about Hemingway but adding on the Hemingway Food and Walking Tour where you'll be taken on a 2 hour tour of the real places where Hemingway lived, worked and played including his first apartment in Key West, the bookstore where his first book was sold, and numerous other historical sites. This tour also includes lunch complete with drinks and a slice of authentic Key Lime pie.
Go on a Sunset Catamaran Sail
Key West is known for its sunsets and as a frequent visitor and Florida native I can tell you they are not to be missed! A sunset sail is one of the best ways to see the sunset and there are lots of options depending on the vibe you're looking for. The best news is that you can enjoy one of these sunset sailings for under $100 per person. The Key West Sunset Sail will take you on 2-hour trip on a 70' catamaran. You'll enjoy live music, appetizers, and a full bar. Everything is included in your ticket price except for gratuities. For a more intimate experience you may want to try the Key West Dolphin Watch Sunset Sail. This tour is priced under $100 as well and combines a dolphin watch with the sunset sail. Appetizers and cocktails are included in this sailing as well! If you're looking for something really special, try the Private Key West Sunset Sail. Priced at just under $600 for private groups up to six, you'll explore on a private boat with a captain and first mate. Light snacks and beverages are included on this sunset sailing and a cooler is provided if you want to bring alcoholic beverages. You'll want to book this one well in advance as it is regularly sold out!
There is so much to do in Key West that we can't begin to cover everything in one article but if you're planning a trip please reach out to us anytime - we are a full-service travel agency, certified Florida Vacation Specialists and Florida residents! We'd love the opportunity to help you plan your trip! The best part? Our services are 100% free to our clients! Read how we earn a living here! You can also fill out the form at the bottom of this page and we'll contact you right away.
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