Top Key West Private Sightseeing Tours

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.

Smaller Groups = Better Experience | Get out of the bars and get on the water! Our customizable 4-Hour Key West Boat Adventure allows you to experience the best of Key West! Mix and match to make your day. Options Include- Dolphin Tour, Snorkeling, and Sandbar Experience All charters include a choice of licensed captain. Use may also bring beverages and food to complete your day! **Please note captain fee of $250 are not included in the above price and must be paid to captain direct via cash / cash app on site** **A choice of captain list will be provided on checkout**

Discover the beautiful Florida Keys with a self-guided audio tour! This 100-mile drive stretches from Key Largo, the first island off the Florida coast, all the way out to Key West, the southernmost point in the continental United States. This self-guided driving audio tour allows you to explore & drive the Keys with maximum flexibility and value. After booking, you can check your email before downloading the Tour Guide App by Action, enter your unique password, and access your tour. The preceding steps require good internet/wifi access. Simply follow the audio instructions and the route from there. This is not an entrance ticket. Check opening hours before your visit. New, extra validity — now, it’s yours for an entire year! Use multiple times over multiple trips!

Key West is a wonderfully walkable island that deserves just as much exploration under the moonlight as it does under the sun. Avoid the crowded group tours and opt for this 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.

Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat that can fit up to 60 passengers. Whether you’re a beginner or an experienced fisherman, your captain and crew helps you with your skills. Try to catch snapper, grouper, mackerel, or shark. A license and all bait are included, and restrooms are on board for convenience.

Eat your way around Key West on this food tour with a guide who introduces you to 'mom and pop' eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and, of course, 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.

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.

Explore Key West through the eyes of a local on a craft cocktail tour that stops at five off–the–beaten–path establishments, 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.

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.

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.

Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.

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.

Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Explore the best that Key West has to offer on this narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Select from an unlimited 1- or 2-day pass to suit your schedule.

This 2 Hour Guided Scenic Tour takes you far into the island! It is not only packed with Key West’s main sights but also takes you off the beaten path and more. All the way to beautiful waterfronts, beaches, going through unique and eclectic neighborhoods, from Bahama Village to the Historic Seaport, further North to the White Street Pier, and of course crossing along all the touristic areas. Sit back and enjoy the ride on a comfortable E-pedicab with Your Private Driver and Tour Guide! A wonderful way to relax and soak in the island vibe while learning about the history and culture of Key West. This tour Includes six stops for photo opportunities: at the Little White House, Southernmost Point, Lighthouse, Mile Marker 0, the Grotto, and White Street Pier. But if you wish to stop at other locations, we'll make it work for you!

Explore Key West on your own terms with a self-guided audio tour designed with cyclists in mind. Grab your bike or rent one locally and head out on this 10-mile (16-km) tour, visiting over two dozen points of interest along the way. Start and stop whenever you wish with this self-paced experience.

This 1 Hour Guided Scenic Tour is not only packed with Key West’s main sights but also takes you off the beaten path. We'll go through unique and eclectic neighborhoods, from the Historic Seaport to Bahama Village, crossing along all the touristic areas. Sit back and enjoy the ride on a comfortable E-pedicab with Your Private Driver and Tour Guide! A wonderful way to relax and soak in the island vibe while learning about the history and culture of Key West. This tour Includes four stops for photo opportunities: the Little White House, Southernmost Point, Lighthouse, and Mile Marker 0. But if you wish to stop at other locations, we'll make it work for you!

Embark on a tour around the island of Key West. Your guide will be talking you through many points of interest around the island. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, your captain will find a quiet and private spot to watch the sun drop into the water uninterrupted by other boats, people, or land!

Enjoy a private boat tour experience, without the hassle and costs of renting one yourself, on this half-day tour around Key West. The experience is fully customizable to your group’s interests, and can include relaxing on a sandbar, island hopping, snorkeling, dolphin watching, a sunset cruise or a combination of activities.

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.

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.

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.

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.