Top Key West Private Sightseeing Tours

Key West is famed for its sunsets but the scene in town tends to be crowded. Sidestep the big crowds by getting out onto the water on a private tour. In the company of just your party and the captain, relax as you cruise around the island and the captain points out all the important landmarks.

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.

Paddle through the mangroves, located at the southwest corner of the island, before reaching the salt ponds on this guided kayaking tour. Learn about the history of Key West and South Florida, as well as the local flora and fauna along the way. You also paddle through the Gulf of Mexico and Cow Key Channel as you head to the mangroves.

Visit Fort Zachary Taylor Historic State Park on a tour that introduces you to both the history and natural beauty of Key West. Located on the southwestern tip of the island, the park is a relaxing place to spend a few hours snorkeling, sunbathing, and discovering historical sites. This tour provides an easy way to see more of Key West for those short on time.

Getting out on the water is one of the best ways to explore Key West, but many big tours cram their boats with passengers. This private tour promises an un-crowded experience. Head out onto turquoise water aboard a unique tiki bar boat and look out for marine life such as turtles and dolphins as you cruise to a sandbar where you can swim or just soak up the sun.

This is the only private guided booze cruise in Key West. We provide you with dockside access to three different watering holes on three different keys in Key West. First stop is at The Geiger Key Marina Restaurant. This is a Tiki bar and restaurant located approx. 5 miles north of the City of Key West. Access is gained through a beautiful mangrove inlet. Second stop is located at The Boat House Bar located on Cow Key Channel in the City of Key West. See the sites while enjoying a cold beverage. The third and final stop is The Hogfish Bar & Grill located in the "Old Florida" fishing village of Stock Island. This is the quintessential locals experience that you don't want to miss. Book it today!

Discover the Great Florida Reef while visiting the Florida Keys on this private snorkel excursion. Board a private boat and depart from Big Pine Key towards Looe Key, where you can jump in the water and explore the extensive coral reef system. Snorkel alongside your captain and learn about the various species you encounter such as barracuda, parrotfish, and rays.

Regular boat tours around Key West provide excellent views, but miss the most important view of all: the underwater world beneath the boat. This private glass-bottom boat tour provides the full, 360-degree experience of the waters around Key West. Exclusively for your group, this tour lets you create your own adventure, whether you want to snorkel the reef, explore an offshore island or simply relax on a sandbar.

Swap crowded bus tours for a private and personalized tour of Key West on a comfortable, and unique, tiki bike. Your driver will pedal you around the streets of Old Town and the Historic District to top attractions and places that cannot be reached by bus. You'll also be treated to a slice of famous Kermit's Key lime pie.

Getting out on the water is a must-do in Key West, but big boat tours tend to be crowded. Enjoy a personalized, crowd-free experience on this private cruise. Head into the backcountry of the Florida Keys that larger boats can’t access, then anchor at a sandbar where you can swim in the clear water or relax on a floating raft.

This private tour is ideal if you want to see it all in Key West, but are not a fan of crowded group tours. In the company of just your group and a guide, hit the streets and stroll to all the top attractions, including the Southernmost Point and Mallory Square. Best of all, the tour can be customized to your own interests.

Discover the islands near Key West on this private land-based tour of the Florida Keys. Designed for small groups of up to 12 people, this tour travels along the Overseas Highway, and experience the Seven Mile Bridge, relax on Bahia Honda Beach, and snap photos of endangered Key Deer on Big Pine Key. The guide will offer fun facts and information about the Florida Keys and the islands along the way.

Turn your phone or tablet into a local tour guide with this location-aware audio/multimedia tour! CAR RENTAL/DRIVER ARE NOT INCLUDED. There’s so much to see and do in just one-and-a-half hours of driving between Key West and Marathon. Visit the Keys’ most beautiful state park, tan on a secret nude beach, check out a limestone quarry inhabited by American alligators, spot rare Key deer, find the Keys’ best shrimp pizza, and jump off an abandoned bridge into a cool-water canal. You’ll have historic photos, a map linked to your GPS, plus websites and restaurant menus at your fingertips. Soon after booking, you'll receive a confirmation email with login instructions and a coupon code.

Go sightseeing along the Overseas Highway on a full-day tour from the island of Key West. Discover the wonders of the Florida Keys including the Florida Keys Aquarium Encounters, Bahia Honda State Park, National Key Deer Refuge, and Seven Mile Bridge. Lunch, snacks, entrance fees, and hotel pickup and drop-off are included on this small-group tour with numbers limited to 10 people.

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.

There are plenty of sunset cruise options to choose from in Key West, but most pack guests onto large commercial boats. This private cruise is exclusively for your group, letting you avoid crowds and get the best seats to view the fabulous Key West sunset. You’ll have a tour of Key West harbor and Sunset Key, learn about the area's history and enjoy an unobstructed view of the sun dipping below the horizon.

Historic Homes & Stories of Key West- "2020 WINNER- Best Key West History Tour" Join our award-winning guides for a wonderful, fun, and informative 2 hour stroll through the celebrated Old Town neighborhoods where you'll discover many of the most beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community. We’ll see the exteriors of a variety of beautiful homes and public buildings, each with its own legendary story, notable history, and rich style. There's something for everyone to enjoy on this fascinating look behind the scenes of historic Key West. *Voted Top Tour Guides of North America *Over 20 years experience *Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. We look forward to welcoming you and sharing Old Town Key West with you.

Swap the standard sightseeing tours of Key West for a more personalized experience. This private tour is exclusively for your group and led by a Key West local and unofficial "mayor." As you stroll through the Old Town streets, you'll learn all about the colorful histories and personalities that have shaped Key West.

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Choose to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. We're licensed like a limousine, so you can enjoy your favorite beverages en route. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.

Turn your phone or tablet into a local tour guide! Download this location-aware audio/media tour, then cruise! Nowhere on this tour will the speed limit exceed 35 mph. PLEASE NOTE ELECTRIC CAR, SCOOTER OR BIKE RENTAL IS NOT INCLUDED. Rent from one of the vendors recommended at the beginning of the tour, then sight-see from the comfort of your own car, scooter or bike. Learn about Key West's deep ties to the Bahamas and the city's pivotal role defeating the Confederacy. Discover why 250 Africans are buried by the beach, and the surprising tourist spot that was once the island's "blacks only" beach. Visit the island's first black church. Find the Keys' best conch salad, get a taste of Haitian and Cuban flavors and sample Key Lime pie. Historic photos plus links to restaurant menus and websites rest at your fingertips. Spend one hour or a whole day. Shortly after booking, you'll receive a confirmation email with login instructions and a coupon code.

Turn your phone or tablet into a local tour guide! Download this location-aware audio & multimedia tour to your device. Local knowledge, historic photos, and links to websites and restaurant menus rest at your fingertips. In just an hour of easy walking, learn the history, culture, and cuisine of Key West, never wasting a step. Visit the most important museums and attractions. Discover the island’s best Key lime pie, Cuban cigars, rum mojitos, craft beer, conch ceviche, fish tacos, and handmade sandals. Learn about famous writers, wreckers, and pirates. End with a swim on a popular beach. Perfect for solo travelers and small groups. Sight-see at your own pace, avoid being herded in a big crowd and only linger in the places that truly interest you. Soon after booking, you'll receive an email with a login instructions and a coupon code allowing you to access your tour.

Turn your phone or tablet into a local bike tour guide! Download this location-aware audio/media tour, and as you ride, you'll be alerted to historical and cultural landmarks, ecological facts, scenic side streets, good places to eat and restroom stops. BIKE RENTALS ARE NOT INCLUDED. Use your own bike or rent from one of the vendors suggested at the beginning of the tour. Key West's flat roads are perfect for cycling. The Atlantic side of Key West offers the island's most scenic views and widest streets. Visit 25 points of interest in just one hour of cycling (10 miles,) avoiding heavily-trafficked streets and crowded areas downtown. A one-speed beach cruiser or bike for urban riding works perfectly. You won't be going up hills or off-roading. Sight-see at your own pace, avoid being herded in a crowd and linger only in the places that truly interest you. Soon after booking, you'll receive an email with login instructions and a coupon code allowing you to access your tour.

Drinking and drifting on the ocean is the quintessential Key West experience, but most booze cruises cram their passengers in. Enjoy a far more relaxed and personalized experience on this private tour. You'll have dockside access to three different watering holes in three different parts of Key West, so you can see the sites while enjoying a cold beverage.

Kick back, drop your line in the water and a enjoy a relaxing day in the Florida Keys, trying your hand at a catch that may include sailfish, wahoo, mahi mahi, tuna, snapper, grouper, king mackerel, and shark. This private charter includes exclusive use of a 31-foot (9.5 meter) open fishing boat with shade, instruction for beginners or advanced tips for the pros, and all the equipment you need.