Top Key West Sightseeing Tours in 2026

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.

One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service being set to premium standards! We offer a more intimate experience with less crowded excursions for the comfort of all of our guests.

Some big boat tours in the Florida Keys can feel crowded and impersonal. This private tour instead offers a personalized and customizable experience of the Lower Keys. Where you go and what you do is largely up to you, whether it's snorkeling, kayaking, dolphin-watching or simply chilling out on the water.

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp when in season, offering an authentic taste of the Keys. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups looking to unwind while taking in panoramic views of the surrounding waters. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, helping ensure the best possible experience on the water. Your confirmed departure time will be reflected in your booking confirmation.

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.

Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key West sunset - hues of orange, pink and purple. Sip on ice-cold beverages prepared by your friendly crew while the warm sea breeze carries the sounds of island music and laughter. The atmosphere is relaxed and festive, perfect for making new friends or sharing moments with loved ones. Expect a laid-back and enjoyable trip while unwinding with a refreshing beverage from the bar. As the last sliver of sun disappears below the water, watch for the green flash, an enchanting touch of magic. Sail back to Key West Harbor under the star-filled sky, creating a Key West memory to last a lifetime.

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.

The best way to experience Key West is by getting out on the water, but with so many tours available, it can be hard to choose. This tour company has decades of experience of guiding visitors on jet skis through the waters they know so well and giving everyone plenty of time to let loose on the waves.

Take in rare birds–eye views of Key West on a parasailing adventure over Smathers Beach. With a range of departure times offered throughout the day, this tour is a popular, flexible choice for families. Your guide, who ensures that the small group has a personalized experience, takes photos and videos available for purchase after the trip.

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.

Discover the natural beauty of Key West on our 2-Hour Guided Clear Kayak Eco Tour. Paddle through crystal-clear waters in a completely transparent bottom kayak, giving you a unique view of tropical fish, seagrass beds, and vibrant marine life beneath you. Along the way, your guide will share fascinating insights into the local ecosystem and hidden gems of the Florida Keys. Perfect for couples, families, and adventurers looking to experience Key West like never before.

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.

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.

Go parasailing above the emerald waters of Key West for a thrilling 1-hour tour that provides sweeping views of Florida’s southernmost city and its surroundings. Head out in a 12-passenger state-of-the-art parasailing boat out to the ocean, then your guide secures you into a double or triple-person parasailing device for a ride that gently lifts off and glides above the water, all without getting wet.

Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and delicious key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.

Explore the streets of Key West on this guided small-group walking tour. As you wander through Old Town, discover the history and culture of the island, which includes tales of shipwrecks, cigar manufacturing, and treasure hunting. Stop at popular attractions such as the Ernest Hemingway Home and Museum, the Southernmost Point, and Audubon House & Tropical Gardens.

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

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.

Experience the best that Key West has to offer with this combination tour that includes a dolphin watch, snorkeling, and a view of the island’s famous sunset. Spot dolphins in their natural habitat in the Florida Keys National Marine Sanctuary and snorkel in the blue waters surrounding Key West during this family-friendly excursion. The tour departs from the Key West Historic Seaport at 201 William St, near South Beach on Duval Street.

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.

Get a different perspective of Key West and visit some lively local spots at the same time during this haunted pub crawl tour. Take a journey through the streets of Key West as your guide regales you with scary stories. From eerie tales of possessed dolls to creepy encounters with the macabre, enjoy the entertainment as you visit various landmarks.

Key West is rich in spooky history but you need a local's insight to fill you in. This walking tour is focused on the island city's hauntings and ghost tales. As you visit notable spots such as St. Paul's Episcopal Church and the Audubon House and Tropical Gardens, your guide will shed light on prominent figures and the dark history of Key West.

Set sail along Key West's coast on a relaxing catamaran cruise combining dolphin watching with a front-row view of the island's famous sunset. Glide across the water aboard a spacious sailing catamaran, with wide-open views of the surrounding seascape and opportunities to spot Atlantic bottlenose dolphins along the way. With fresh fruit and water provided, and space to bring your own drinks, this is a laid-back way to spend an evening on the water.

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.