Top Key West Private Sightseeing Tours - page 2

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.

Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk. This self-guided adventure immerses you in the rich tapestry of island life where writers like Ernest Hemingway and Tennessee Williams found their muse. Navigate through charming streets, lively bars, and historic neighborhoods that showcase the unique blend of Caribbean, Cuban, and Conch cultures. As you stroll at your own pace, engaging audio narratives reveal tales of resilience, creativity, and community that define this iconic island. Discover the essence of Key West, where every corner invites you to pause, reflect, and connect with its storied past.

Download GuideAlong’s self-guided audio tour bundle to make the most of your Eastern USA road trips. As you drive, hear stories play automatically as you explore scenic drives, national parks, lakeshores, and historic parks. This is the ultimate collection of 14 iconic destinations, including Acadia, Blue Ridge Parkway, Catskills, Florida Keys, Great Smoky Mountains, Lake Superior, Outer Banks, Shenandoah, and Vermont’s Route 100. A memorable adventure awaits on America's iconic roads. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. Stories, tips, and directions play automatically based on your location Travel at your own pace Tour offline using GPS. No cell service or WiFi is needed Suggested itineraries for half, full, or multi-day use Buy once, use forever! No expiry, includes free updates Like having a tour guide along for the drive Purchase one bundle per vehicle.

Ideal for travelers short on time, this private tour covers the best of Key West in one day from Marathon. Highlights include stops at the Hemingway House, Mile Marker Zero, and Mallory Square at sunset. Enjoy roughly three hours of free time to explore at your own pace. Upgrade to include a sunset sail, dinner cruise, or other Key West attractions.

Join me, a true seventh-generation local captain for a personalized Key West adventure on my private boat. Spend the day exploring the stunning turquoise waters and hidden islands of the Florida Keys, with opportunities to snorkel, search for dolphins, visit a sandbar, enjoy light fishing, or simply relax and take in one of Key West’s world-famous sunsets. Every trip is fully private and tailored to what you want to experience — whether it’s adventure, leisure, or a bit of both. Departing conveniently from Garrison Bight Marina, your journey promises incredible views, local insight, and unforgettable memories on the water.

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.

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.

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.

This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll cruise up the bay side and back down the ocean side (or vice versa). Learn the history of the bridges and the Flagler Railway, and see mangroves and beaches. A great way to see the keys!

Journey through Key West's history on this self-guided adventure featuring swashbuckling pirate legends and maritime mysteries. Your smartphone transforms a regular walk into an epic quest, with historical puzzles, fascinating stories, and clever challenges at every stop. Each location brings history to life — from ancient landmarks to hidden historical details you'd walk right past without the app. Solve challenges to unlock the next chapter of Key West's story. This 1–2 hour private adventure runs 24/7. No guide needed — just your smartphone and a sense of curiosity. Available in 5+ languages.

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.

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.

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the sky transforms into a vibrant canvas of colors, providing an unforgettable backdrop for your evening. Bring your favorite beverages to toast the day's end in a romantic and relaxing atmosphere. Capture unique photo opportunities with breathtaking reflections in the water, making this experience perfect for couples or anyone looking to unwind after a day of exploration. - Enjoy a serene 2-hour cruise on the tranquil waters of the Florida Keys - Front-row seat to a spectacular sunset with unobstructed views - Bring your own beverages for a personal touch during the cruise - Perfect for couples or those seeking a relaxing escape after sightseeing

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.

Key West is a wonderfully walkable island that deserves just as much exploration under the moonlight as it does under the sun. Avoid crowded group tours with this private self-guided ghost tour. Using your smartphone, you’ll explore Key West’s allegedly haunted sites and hear their grizzly histories. Go at your own pace, taking breaks or visiting other Key West attractions as you continue your adventure.

Combining the fun of a tiki bar with the serenity of being out alone at sea, this private tiki boat experience gives you the best of both. Reserved exclusively for your group, your captain will take you around Key West waters. Bring your own snacks and drinks to party under the covered bar or relax on the floating mat with a cocktail in hand.

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while soaking in the sun and taking in stunning views of luxurious homes and coastal landscapes. Keep your eyes peeled for dolphins, sea turtles, and tropical seabirds as you glide over the crystal-clear waters. You can choose between a scenic harbor cruise or an island swim stop at a sandy beach for a refreshing dip in the turquoise sea. This is the perfect way to create unforgettable memories in paradise. - Enjoy a leisurely 1.5-hour cruise on a tiki bar boat - Spot local wildlife, including dolphins and sea turtles - Customize your cruise with a scenic harbor tour or beach swim - Knowledgeable Captain shares local history and fun facts

You may have heard the island of Key West called many different things – America’s Caribbean Island, Margaritaville or The Conch Republic. But you know what we locals call it? Paradise!! And I bet by the end of our tour you will agree with me. Go at your own pace. This is a smartphone guided tour that uses GPS to direct you step by step on a hands free adventure.

Key West is filled with rich and spooky history, but ghost tours often lose some of their haunting atmosphere when guests are crowded together in a group. This private walking tour is exclusively for your party so you'll enjoy your guide's undivided attention as they lead you to at least five haunted mansions and two haunted bars.

This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands that make up the Backcountry and Great White Heron National Wildlife Refuge. We will slow down and look for marine life and birdlife. Maybe see a turtle or dolphin. We will take you through "Skinny Water" and look for starfish, rays and sharks. It's a fun adventure not to be missed when visiting the Keys.

Your tour/shuttle can go anywhere between For Lauderdale Florida and Key West! As you check out you'll have the chance to let us know where you're hoping to travel to. We'll come and pick you up and drop you off wherever is convenient for you. Reach out to us if you want us to supply a cooler with any beverages on your tour. Must have at least one adult in your party. The van holds a Maximum of 14 passenger.( Price includes up to 14 Passengers)

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings that celebrate the island’s unique mix of Cuban, Caribbean, and Floridian influences. Start with a refreshing iced coffee before biting into golden, crispy conch fritters—a true island classic. Savor authentic Cuban cuisine that reflects Key West’s cultural heritage, then indulge in rich chocolate-covered Key lime pie, the city’s most famous dessert. Along the way, your guide will share stories of pirates, poets, and island life, bringing the history and charm of Key West to life. To end, you’ll taste our exclusive Secret Dish, a surprise that makes the experience truly unforgettable. This is Key West beyond the postcard—an authentic taste of its food, culture, and soul. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience.

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s Episcopal Church, where we will share stories of its haunted past and the intriguing legend of Robert the Doll. Next, visit The Artist House, where we will delve into the bizarre true story of Carl and Elena, followed by Dean-Lopez Funeral Home and Crowne Plaza Key West-La Concha, which have a dark and chilling past. At Marrero’s Guest Mansion, explore the eerie story of Enriquetta and other ghostly legends associated with this haunted yet historic mansion. Moving on to 322 Duval St, uncover the mysteries of Captain Watlington’s Haunted House and share bone-chilling stories of the haunted past and present of Key West. Our journey concludes at the Audubon House & Tropical Gardens and the infamous Capt Tony’s Saloon, discovering their dark histories and encounters with the paranormal.

Key West is famous as mainland America's Caribbean resort town. Here, time slows down as the island vibes take over. But there is more to this island than umbrella drinks and warm breezes. Key West has an incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships and crews along the Great Florida Reef a few miles offshore, to the creation of the micro-state known as the Conch Republic. While in Key West, you will want to visit many of the sites that make the island distinct such as the Key West Lighthouse, the Hemingway House, the Little White House, and Southernmost Point. On this tour, you will visit all of these and more, stopping for refreshments along the way at many of the island's signature restaurants and bars. You will hear stories of some of the island's more famous residents along with some lesser-known tales that have given Key West its unique place in American culture and history.