Key West Tours: 8 Sightseeing Adventures for Different Experiences

Ranked among the best islands in the U.S. by Conde Nast Traveler readers, Key West welcomes visitors to embrace culture and celebrate tropical living. The city has historical charm, Cuban and Carribean culture, and must-see attractions for all ages. Sightseeing offers the best way to see it all, so here are the top Key West tours. Afterwards, pick a favorite.

Top 8 Key West Tours for the Best Sightseeing Options

key west trolley tours sightseeing

Trolley: Hop-On Hop-Off Trolley Tour

Old Town Trolley has provided Key West tours for over 30 years. Trolleys cover the entire city and allow passengers to hop on and off at their leisure. Tickets are valid for a full day, so riders can tour at their own pace.

Each trolley stops at 13 locations and covers over 100 points of interests. While riding, guests will hear stories, learn about the area and get fun facts. A few sites include Southernmost Point, Key West Aquarium, Key West Cemetery and Ernest Hemingway House Museum.

Sunset Cruise: Schooner Spirit of Independence

Sail Key West’s open waters on Spirit of Independence, an 80-foot ship with an 1800s design and custom, modern materials. Guests can book a two-hour sunset cruise that starts at Schooner Wharf bar, passes Sunset Isle and Mallory Square, and ends after the sunset. With admission, guests also receive food and refreshments, and may see dolphins and sea turtles.

key west tour fishing family

Fishing: Key West Fishing Connection

Locally owned and managed Key West Fishing Connection provides guided fishing charters, including nighttime, blue water, reef and wreck, and tarpon and permit. The company welcomes anglers to fish for four, six or eight hours, so visitors can customize their experience.

Depending on time of year, expect to catch black fin tuna, grouper, marlin, sailfish and wahoo. Blue water fishing uses the trolling method and aims to catch migrating species. Reek and wreck options head 6 to 10 miles into the ocean and anchor over a wreck. Key West Fishing Connection caters to groups up to six passengers.

Snorkeling: Wild About Dolphins

Know anyone wild about dolphins? Then book a dolphin-watching trip with Wild About Dolphins, which offers private and shared charters, with half- and full-day options. All ages can embrace adventure as they see coral reefs, mangroves, marine life and dolphins of course!

Each tour offers an in-depth look at dolphins and how they live. Additionally, visitors are welcome to snorkel and swim, and Wild About Dolphins has all the gear ready. The company also provides a light meal, beverages and sunscreen.

key west kayak tours canoe

Kayaking: Danger Charters

With Danger Charters, it’s easy to explore Key West’s backwaters. This company travels where others won’t go. Plan guided Key West tours on kayaks and venture into mangrove islands. Then gear-up and snorkel underwater among fish, rays and wading birds.

Danger Charters provides all equipment including gear, wet suits, kayaks and paddles, snacks, and refreshments. Even better, visitors have the option between morning and afternoon half-day trips and full-day excursions.

Aerial: Key West Seaplane Adventures

Key West is located in the Florida Keys, which consists of 1,700 islands. While water and land tours can only explore a small area, Key West Seaplane Adventures showcases miles of the Keys from a plane.

Flights take passengers due west over Marquesas Islands, National Marine Sanctuary, ship wrecks, Fort Jefferson and Dry Tortugas National Park. Each passenger gets a window seat and headset, so they can learn about the area in a fun way.

key west tours bike rentals

Key Lime Bike Tours

To stay on land, Key Lime Bike Tours offers Key West tours via bicycle throughout the city. Visit the top sites, hidden streets and end at Key West Key Lime Pie Company for a slice of pie. Each tour lasts two to three hours, and helmets, baskets and bottled water are included.

Key West Food Tours

With proximity to Cuba and heavy Cuban culture, dining out in Key West ranks among the top things to do. Key West Food Tours hosts three different options, so travelers can sample everything.

The Southernmost walking tour is the most popular. It stops at five locations, celebrates Cuban and Caribbean influence, and ends with key lime pie. Seafood lover’s have a tour just for them, as they sample six local specialties. A few include fish tacos, lobster mac and cheese, and conch ceviche. The craft cocktail option allows guests to experience an upscale bar crawl and signature cocktails.

After discovering the best Key West tours, learn more about the lower Florida Keys. Then find tips and tricks for snorkeling Florida Keys.