Top Key West Sightseeing Tours - page 3

This self-guided audio tour takes you through the Key West Cemetery, a unique graveyard filled with characters that shaped the island's bohemian past. Join Frank Everhart, a nearly 30-year Key West resident, on a walking tour where you'll uncover the secrets of legendary figures, millionaires, and families. As you stroll among crumbling graves, spot descendants of Cuban cockfighting roosters and sun-bleached iguanas. Hear stories of the 1846 hurricane, the Freemasons, and the USS Maine Memorial, whose victims' deaths sparked the Spanish-American War. The 75-minute tour starts at the main entrance, passing through the Jewish B'Nai Zion Cemetery, where you'll learn to decipher gravestone symbols.

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a half-day adventure aboard our luxurious Manitou Cruise—a spacious, smooth-riding tri-toon with a deluxe swim deck, perfect for soaking up the Key West sun in comfort and style. Guided by one of our licensed, experienced captains, your private charter explores the untouched beauty of Key West’s backcountry—customized to your pace and preferences. Cruise to local sandbars, glide through scenic mangroves, or venture farther to spots like Mud Key, Snipes Point, and the Dolphin Playground, where wild dolphins often play in their natural habitat. Swim, snorkel, relax on remote beaches, or simply enjoy the ride with a drink in hand—it’s your trip, your way. Perfect for families, couples, or small groups seeking a flexible and private escape into the real Key West.

Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to? Stop in his favorite bars for a drink? You are in luck. Our tour will begin at the Florida Keys Historical Military Memorial in Mallory Square and wind our way along storied streets and the favorite haunts of Hemingway himself, until we reach the iconic Hemingway Home and Museum and the towering Key West Lighthouse. You’ll see his bust, his favorite bar, the spot he first lived, where he ate and lived. And you’ll also hear the story of Key West along the way. Go at your own pace, stop anytime for a drink, and continue when you want. The tour never expires.

Set sail for the sunset on your own private evening cruise with a captain to show you some of the most scenic spots around Key West, Florida. Listen as your guide tells you fun facts about the area and its waters, while you soak up views of islands and waterfront mansions. Keep your eyes peeled for marine wildlife like dolphins during this private experience.

Explore beautiful coastlines, wild history, and fascinating wildlife with this self-guided walking tour of Key West. Get to know famed author Ernest Hemingway and the island’s influence on his work. Hear stories of pirates, shipwrecks, and disasters and marvel at lush tropical gardens and coastline. Then stroll along Duval Street, the bustling heart of Key West, and savor the rich culture of this one-of-a-kind island. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Head out into the open waters on this small-group kayaking and snorkeling ecotour adventure. Follow your captain through scenic mangrove tunnels and over calm waters as you make your way to one of the area's most-stunning snorkeling destinations. Learn about local wildlife before taking a dip and get an underwater look. Gear is provided on this tour that's perfect for all levels.

Key West is famous for stunning sunsets, and this dinner cruise offers the perfect way to enjoy them. Savor breathtaking views as the sky transforms, while indulging in a tropical buffet, live music, and incredible vibes. It’s an unforgettable evening on the water. Relax on a luxury catamaran with an open-air sundeck and fully air-conditioned lower cabin. Grab a drink from the open well bar as live tropical music sets the mood. Every moment is filled with beauty, flavor, and celebration as you soak in Key West’s legendary charm. This popular cruise often sells out, so book your spot today! Don’t miss your chance to experience the best of Key West – sunsets, music, and memories await on this unforgettable adventure.

Cruise alongside Key West’s picturesque waterfront in style during this private sunset tour aboard a charactered tiki bar boat. Enjoy BYOB drinks in a floating, thatched bar, complete with private restroom, bluetooth-equipped television and stereo, and padded bar stools. Head past attractions like Sunset Pier, Mallory Square, Wisteria Island, and Trumbo Point, with cruises timed to capture the coastline’s famous sunsets.

Set sail for a full-day escape to the hidden gems off Key West’s coast—where pristine beaches and secluded islands await. Whether you're soaking up the sun, taking in the coastal views, or just unwinding with your group, this experience blends the excitement of the open water with the comfort of premium onboard amenities. Perfect for history lovers and adventure seekers alike, this guided journey offers something for everyone.

Experience two distinct Florida Keys environments in one outing with this snorkel and sandbar combo from Marathon. Visit a protected reef area known for marine life and shallow depths, then continue to a calm sandbar ideal for relaxing and exploring clear waters. This tour balances active snorkeling with downtime, making it a practical choice for confident swimmers who want variety without booking separate excursions.

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch for wildlife throughout the trip such as dolphins, sea turtles, fish, birds, and much more! A cooler filled with ice and bottled water will be provided. Feel free to bring any food or alcoholic beverages.

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through Key West’s backcountry mangrove channels, you get a chance to escape the hustle and bustle of Downtown and discover the true meaning of bliss. Wade through tropical clear blue waters, explore the sandbar on paddleboard, and soak in the picture-perfect setting that this adventure has to offer!

Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat for an easy day out. Whether you’re a beginner or an experienced angler, your captain and crew assist with your fishing skills. Fish for reef species like snapper, grouper, and mackerel. A fishing license and all bait are included, and the boat features restrooms, shaded seating, and a small galley with snacks and drinks for your convenience.

Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.

Get front row seats to a stunning Florida Keys sunset, without the hassle of chartering your own vessel, on this catamaran cruise from Key West. Sip on your choice of wine, sparkling, beer, margaritas, or sangria as you watch the sun go down over the water. As you sail, catch glimpses of the island and marvel at the views from the turquoise water.

Explore Key West through the eyes of a local on a craft cocktail tour that stops at six off–the–beaten–path establishments for drinks and food tastings, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.

Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the docks into some of the most colorful neighborhoods in Key West, pausing to sample locally caught pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere.

Key West’s Old Town is a wonderfully walkable area that’s best enjoyed at a slow and steady pace. Take advantage of free time under the sun while learning about the history of the island during this self-guided audio tour of Old Town. A tour guide narrates this journey up and down the streets, having you stop at attractions like the Little White House and the Lighthouse. You’ll end your walk at Mile 0: the Southernmost Point of the Continental US.

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobstructed view of the surrounding seascape. We will search for our resident Atlantic Bottlenose Dolphins and then head to the best seat in the house to witness a world-famous Key West sunset. Watch as the sky erupts in a spectacle of color from the peaceful vantage point of the water. Organic fruit and filtered water will be provided to keep you refreshed, and you're welcome to bring your own adult beverages to toast to a successful day. Join us for a relaxing and memorable evening that celebrates the serenity of sailing, the wonder of marine life, and the breathtaking beauty of a Key West sunset.

Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.

Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches only accessible by boat, with a flexible itinerary customized just for you. • Watch wild dolphins in their natural habitat • Private eco-friendly tour, just for your group • Cruise Key West’s beautiful backcountry waters • Flexible departure times to fit your schedule • Learn about marine life from a local guide

Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.

Explore the only living coral reef in North America during this snorkeling adventure from Key West. Sail toward the reef on a state-of-the-art catamaran. Receive snorkeling guidance from your crew—ideal for first-time snorkelers. Use of sanitized snorkel gear and reef-safe sunscreen means you don’t need to pack your own, plus cocktails and non-alcoholic drinks are provided after the snorkeling.

Naval history buffs and aspiring pirates alike are guaranteed to have a whale of a time at the Mel Fisher Maritime Museum. Your admission also includes an audio guide, which offers in depth commentary on the museum’s many artifacts. Highlights include the Spanish Treasure Galleons galleries, Slave Ship and Key West African Cemetery exhibits, and relics from the Henrietta Marie. You can even tour the museum's laboratory and see conservation firsthand.