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You are here: Home / 101 Things to Do in Key West, Florida

The tropical island of Key West, population 26,000, is the last tiny isle on an archipelago that stretches over 110-miles/181 kilometers south from the northernmost isle of Key Largo close to the south Florida mainland. Often referred to as the “first island of the Caribbean” this two by four-mile plot of paradise is actually closer to Cuba (just 90 miles away) than it is to Miami, Florida. The archipelago is mainly linked together by a series of bridges commonly called the Overseas Highway or Highway 1. As a former resident of Key West, author and photographer Gary Sikorski shares a selection of his favorite places to go and things to do, based on his book, 101 Things to do in Key West.

Key-West-Schooner-Hindu

Number 1
Schooner Hindu is an historic, spectacularly-appointed, majestic tall ship built in 1925. It has been exquisitely restored with massive sails catching the wind for a breathtaking ride. Their peaceful and relaxing Morning Mimosa Cruise includes locally-made pastries, freshly-brewed Cuban coffee, and bottomless mimosas. The elegant schooner and her extremely friendly crew also offer a popular sunset sail. Key West Bight Marina, http://sailschoonerhindu.com.

Key-West-Key-Lime-Pie

Number 3
Key Limes just don’t seem to travel well – so for authentic, tart Key Lime flavor, you absolutely must have a slice of Key Lime pie while in Key West. And the best pie on the island is found at the famous yellow and green shop on the corner of Elizabeth and Greene Streets. Kermit’s has mastered everything that’s Key Lime including: cookies, salsa, chutney, taffy, jelly beans, olive oil, soaps, shampoos, and of course, Key Lime Pie! Tip: The piece de resistance is their chocolate-covered Key Lime pie on a stick. Kermit’s Key West Key Lime Pie Shoppe, www.keylimeshop.com.

Key-West-Sand-Sculpture

Number 8
Sand-Isle bills itself as makers of the “coolest sand sculptures on planet earth”, and after walking by the unbelievable works of art that line the beach behind the Casa Marina, I’d have to agree! Marianne and Chris, the husband and wife team that started Sand-Isle, have quite a reputation for creating imaginative and remarkable sand sculptures all around the world. Join their two-and-a-half-hour workshop and learn the techniques that have helped them construct extraordinary sand creations for major corporations, international competitions and popular television shows. Sand-Isle Sand Sculptures, www.sandisle.com/sand-sculpting-101.

Key-West-Art-Museum

Number 13
A wonderful collection specifically focusing on the island and assembled by the Key West Art & Historical Society can be found inside the historic four-story Customs House, an architectural marvel that originally housed the island’s customs office, postal service and district courts. The seven galleries found throughout the imposing building feature exhibits recalling when the island was first settled, the establishment of the Flagler Overseas Railway, WW II memorabilia, a salute to Ernest Hemingway, along with plenty of local artwork and interesting island artifacts. Some interesting sculptures surround the building, so make sure you walk around the exterior. Key West Museum of Art & History, www.kwahs.org.

Key-West-Old-Town-Trolley

Number 16
Will you be in Key West for just a short period of time and want to see the whole shebang? Then jump aboard the friendly orange and green Old Town Trolley. The informative and sometimes humorous tour covers a lot of ground, and eventually passes virtually every major sight-seeing attraction on the island. There are thirteen stops along the winding route, and you can hop off at any point, explore the area, and then hop back on when another trolley passes by. Tip: Your ticket is valid for the entire day – so long breaks are just fine. Old Town Trolley Tours, www.trolleytours.com/key-west.

Key-West-Key-Deer

Number 22
When traveling US Highway 1 either to or from Key West, you’ll pass through Big Pine Key, renowned as the home of the cute, miniature Key Deer. Standing just over two feet tall, this endangered subspecies of the white-tailed deer is only found in this area of the Florida Keys. Just drive by and you are bound to see them foraging near the roadside, especially around sunset when they are most active. Take a few minutes and detour out to the National Key Deer Refuge for a better chance of seeing the adorable animals. Tip: DO NOT speed through Big Pine. The endangered deer frequently cross the road which is thankfully heavily patrolled! Endangered Key Deer, Big Pine Key, www.fws.gov/refuge/National_Key_Deer_Refuge.

Key-West-Kayaking

Number 31
Grab a paddle and join Mitch Hollingsworth on an informative, scenically-captivating kayaking trip through the calm, blue-green waters of the remote regions of the Lower Keys’ back country, an area of hundreds of enchanting mangrove islands accessible only by small boats. Mitch will guide you through a winding maze of serene canopied canals bordered by a canvas of densely tangled mangrove tree roots, while he shares his extensive knowledge of the vast mangrove eco-system. You’ll also have encounters with tropical fish, crabs, turtles, and aquatic birds foraging for food. Red Mangrove Kayaking, www.redmangrovekayaking.com.

Key-West-Fort-Zachary-Taylor

Number 35
Besides boasting the best beach on the island, the other reason to venture inside the fifty-four-acre historic Fort Zachary Taylor State Park is the massive Civil War-era fortress known to locals as “Fort Zach”. Built in the mid-1880s, the thick-walled red brick and concrete stronghold displays the largest (and extremely impressive!) collection of Civil War-era cannons in the United States. Climb up and walk around the fort’s roof for a nice view of the Atlantic. Tip: The fort does offer a guided tour once a day — check ahead for the time. Fort Zachary Taylor, www.floridastateparks.org/park/Fort-Taylor.

Key-West-Maritime-Museum

Number 39
Located right next to the Eco-Discovery Center on the Truman Waterfront, the massively impressive USCGC Ingham is the only Coast Guard battleship afloat today to receive two presidential unit citations for extraordinary heroism in action against an armed enemy. Retired from military use in 1988 after fifty-two years of service, the vessel is a time capsule of that era; with everything left on board from interesting communication equipment to old cigarette packs. Tip: Board the ship for their sunset happy hour (with great views!) held every Friday and Saturday. U.S. Coast Guard Cutter Ingham Maritime Museum, www.uscgcingham.org.

Key-West-Hot-Sauces

Number 51
Be prepared to let your taste buds sizzle! Peppers of Key West is stocked wall-to-wall with over a thousand flavors of hot sauces from around the world, with various degrees of heat ranging from mild to brutally spicy. Hot sauce, barbeque sauce, salsa, jerk sauces, and marinades abound. They even have a glass case filled with ultra-rare limited edition sauces. Belly-up to their tasting bar that’s colorfully lined with over 120 different tiny bottles of sauces ready to be sampled. Tip: The shop doesn’t sell beverages, so if you’re going to sample, bring your own water or better yet beer! Peppers of Key West, www.peppersofkeywest.com.

Key-West-Hemingway-Museum

Number 70
The Ernest Hemingway Home & Museum is quite possibly the most acclaimed attraction on the island. It was in this very house where the famed author, from his pool-side office, wrote several of his most famous books. The home was extensively remodeled by Ernest and his wife Pauline, who resided here from 1931-1939. Some of the family’s actual furnishings on are display, along with memorabilia, photographs, paintings, and first editions of Hemingway’s works. The place is usually very crowded with international tourists – and descendants of Hemingway’s beloved and famed six-toed cats! Ernest Hemingway Home & Museum, www.hemingwayhome.com.

101 things to do in Key West, Florida.101 Things to do in Key West, Published by Schiffer Publishing (2018)
152 pages, 316 color images; Hardcover, US$29.99; ISBN: 978-0-7643-5476-2 Discover the spectacular island paradise of Key West through this insider photographic traveler’s guide. Join Gary Sikorski as he tours this popular destination town and uncovers where to dine on the best local seafood or even share a freshly picked coconut. Through his camera lens experience the thrill of the world-famous Sunset Celebration at Mallory Square or sail the Atlantic Ocean in search of sharks. Using the detailed map explore the alleys of historic Old Town or the exclusive shops and lively bars along Duval Street. Adventure seekers can ride along on a tropical bike tour or kayak through the exotic Florida mangroves.
For more information about Florida Keys Tourism, visit www.fla-keys.com.
Another Florida article in our Travel Article Library: learn about Northeast Florida’s historic accommodations and sumptuous breakfasts in a feature article spotlighting St. Augustine and Amelia Island.

Gary J. Sikorski is a freelance photographer who has traveled extensively and photographed virtually every country in Western Europe, as well as parts of South America, Mexico, the Caribbean, and Hawaii. The Key West book is Gary’s third photographic guide. He has also published 101 Things to Do in Martha’s Vineyard (2015) and 101 Things to Do in Rhode Island (2016).

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