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Top Key West Private Sightseeing Tours

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We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

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27 Key West Private Sightseeing Tours | All Key West Tours

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Key West Morning Boat CharterHalf-day Tours

Key West Morning Boat Charter

star-5
Enjoy a morning in the crystal clear water of The Florida Keys National Marine Sanctuary. This private custom charter will take you on an adventure snorkeling at the reef. See marine life in their natural habitat. Sea Turtles, Tropical Fish, Starfish and a living coral reef abound. Your Captain is knowledgeable and will guide you through the experience. You will stop at a tropical sandbar to splash around and see the home for many bird species while encircling the mangroves on your tour. You will also be welcome to Kayak or use the stand-up paddle board! This will help you navigate the sand-bar and have some fun. If fishing is on your bucket list, we can cast the rod and enjoy some near shore fishing. It's your day and you design the activities that you are interested in. No two trips are alike and we can't wait to help you make wonderful memories!
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  • 3 hours
  • Free Cancellation
From
US$248.00
Price varies by group size
From
US$248.00
Price varies by group size

Beach Day in Key West with Picnic LunchBus Tours

Beach Day in Key West with Picnic Lunch

star-5
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.
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  • 3 to 5 hours
  • Free Cancellation
From
US$99.00
From
US$99.00

Booze Cruise Key West Private Charter Half-day Tours

Booze Cruise Key West Private Charter

star-5
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 through a beautiful mangrove inlet. Second stop is located at The Boat House restaurant located on Cow Key Channel and in the city of Key West. See the sites while enjoying a cold beverage. Third and final stop is The Hogfish Bar 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!
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  • 3 hours
  • Free Cancellation
From
US$248.00
Price varies by group size
From
US$248.00
Price varies by group size

Sunset Booze Cruise Key West Private CharterHalf-day Tours

Sunset Booze Cruise Key West Private Charter

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!
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  • 3 hours
  • Free Cancellation
From
US$248.00
Price varies by group size
From
US$248.00
Price varies by group size

Private Sunset Boat Charter Key WestPrivate Sightseeing Tours

Private Sunset Boat Charter Key West

star-5
Enjoy a private 2 hour sunset cruise in Key West with your family and friends. Sit back and relax while your Captain points out all the sites along the way. Enjoy the privacy of a private charter while you take in the gorgeous sunsets that Key West celebrates nightly. Feel free to bring food or beverages of your choice, the cooler is full of ice. Looking forward to seeing you on the dock!
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  • 2 hours
  • Free Cancellation
From
US$200.00
Price varies by group size
From
US$200.00
Price varies by group size

Private 90-Minute Harbor Sailing Charter in Key WestSailing

Private 90-Minute Harbor Sailing Charter in Key West

star-5
Enjoy a morning or afternoon of sailing on this private, 90-minute cruise off the coast of Key West. Spend a relaxing time on board a boat headed to Sunset Key and the Key West National Wildlife Refuge. Led by a captain and mate, pass some of Key West’s top attractions and look for more than 600 species of colorful fish, coral and other sea life.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$314.66
per group
From
US$314.66
per group

Private Key West Sunset SailDay Cruises

Private Key West Sunset Sail

star-4.5
Watch the sun set and the moon rise off the coast of Key West on this private, 2-hour sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a private sailing vessel with a captain and mate. Stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset. Soft drinks are included. A cooler with ice is available to store any beverages brought on board.
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  • 2 hours
  • Free Cancellation
From
US$479.99
per group
From
US$479.99
per group

Private Secret Food Tour of Key WestPrivate Sightseeing Tours

Private Secret Food Tour of Key West

Soak up the charm of the neighborhood's fully-restored, historically significant Victorian, shotgun, and conch-style homes on tree-lined streets. The area's atmosphere makes it easy to lose yourself in the magic of Key West, immersing yourself in the vibe of the Conch Republic. Let our guide entertain you with funny and interesting anecdotes about this beautiful district. 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. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!
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  • 2 hours 30 minutes
From
US$102.70
From
US$102.70

Private Key West History and Culture Rickshaw Experience Private Sightseeing Tours

Private Key West History and Culture Rickshaw Experience

star-5
You will sit and relax on our spacious and comfortable Rickshaw as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience its amazing architecture and historic sites as you learn the rich history, culture, and folklore of our beautiful island of Key West. First-row, Historic, Cultural and Fun, the only VIP experience tour in Key West.
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  • 2 hours
  • Free Cancellation
From
US$189.00
per group
From
US$189.00
per group

Private Looe Key Snorkel from Big Pine KeySnorkeling

Private Looe Key Snorkel from Big Pine Key

star-5
Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef system after the Great Barrier Reef in Australia, and the Palancar Reef in Mexico and Belize. It is a special place for snorkeling.
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  • 3 hours
  • Taking safety measures
From
US$495.00
per group
From
US$495.00
per group
Taking safety measures

2-Hour Private Sunset Cruise around Key WestPrivate Sightseeing Tours

2-Hour Private Sunset Cruise around Key West

star-5
This is the only 2 hour sunset cruise in Key West that provides a private guided tour around the island.Sit back and relax while your Captain points out all the sites along the way. Enjoy the privacy of a private charter. Feel free to bring food or beverages of your choice. Price is $375 TOTAL and includes up to 6 people. Looking forward to seeing you on the dock!
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  • 2 hours
  • Free Cancellation
From
US$200.00
Price varies by group size
From
US$200.00
Price varies by group size

Private Dinghy Drinking Tour through Key West WatersPrivate Sightseeing Tours

Private Dinghy Drinking Tour through Key West Waters

star-5
On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to 5. An experienced licensed boat captain who knows the waters will drive your boat. Dinghies can go through narrow tunnels in the mangrove trees that bigger boats cannot get through. Be ready to duck under branches. We will stop at waterfront bars. 3 or 4 stops depending on your preferences. If your group is larger, we will take additional boats. You can get in the water to swim or wade at any time. You will see lots of fish and sea creatures. Most of our guests bring beer, water or alcoholic beverages along for the tour. We have coolers to keep them chilled.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$65.00
From
US$65.00
Taking safety measures

Marathon Tarpon Fishing CharterNature and Wildlife

Marathon Tarpon Fishing Charter

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant Tarpon! Marathon the hub for fishing in the Florida Keys, great beaches, shopping, fantastic food and home to the largest Tarpon run. View the beautiful waters, all while experiencing the thrill of a chance to catch the silver king, the myth, the legend of the sea the Florida Keys Tarpon. Your trip is guided by our licensed Captain in a modern fish catching Tarpon catching style boat. All the fishing rods and reels, right and left handed and all the tackle you need, as well as all other necessities including safety equipment. Take a deep breathe and lets do this, the Silver King is waiting! Travelers that have enjoyed our fishing charters also have enjoyed The Turtle Hospital, a tour down Seven Mile Bridge or a beautiful sunset at Sombrero Beach.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$717.52
per group
From
US$717.52
per group
Taking safety measures

Marathon Reef Fishing ChartersNature and Wildlife

Marathon Reef Fishing Charters

Sail across the beautiful waters of the Florida Keys for a day of reef fishing. Charter a private boat for up to six people and cast your line as you try to catch Wahoo, Mahi Mahi, Snapper, Grouper, King Mackeral, and more. Tours are suitable for beginner and experienced anglers so everyone can have a good time catching fish and enjoying a beautiful day out on the water.
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  • 4 to 8 hours
  • Free Cancellation
  • Taking safety measures
From
US$772.72
per group
From
US$772.72
per group
Taking safety measures

Kayak Tour of Mangrove Maze from Key WestHalf-day Tours

Kayak Tour of Mangrove Maze from Key West

star-5
On this Tour you will paddle through three different bodies of water; The Gulf of Mexico, Cow Key Channel and into the Mangrove Mazes to get into the Salt ponds of Key West. Our Tour guides will share the History of Key West and South Florida, educate you on the flora and fauna that you may encounter and see throughout the tour and discuss how to become more sustainable in today's world.
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  • 3 hours
  • Free Cancellation
From
US$69.34
From
US$69.34

Rum Runner Bar Boat Tour of Key WestDay Cruises

Rum Runner Bar Boat Tour of Key West

star-3
We are the only floating bar in the island and we take you to places that normal tours do not, 100 year old Shipwreck, Movie boat set of Beach Bum, and we provide swimming if you book the whole boat. You will see Castaway Island a.k.a. Christmas Tree, Sunset Key and the crazy wildlife in, under, and around the waters of Key West.
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  • 1 hour
  • Free Cancellation
From
US$35.00
From
US$35.00

Key West Waterway Cleanup and Environmental Education TourNature and Wildlife

Key West Waterway Cleanup and Environmental Education Tour

star-4
Join the Blue Moon Crew for a day to Beautifying our waterways. Blue Moon Kayak Key West has adopted Cow Key Channel and is always looking for additional help to clean up our local waters. Here is your chance to help make an impact on your vacation by looking closely in the water, in the mangroves, and on the beaches. Everyone can make a difference by spending a little time of their day picking up one - two - three or more pieces of plastic. We will educate you on the different types of debris we find, and how long each takes to decompose in our natural environment, and what impacts they have to our local flora and fauna. Blue Moon Kayak Key West is part of a non-profit Paddle with a Purpose. Portions of this tour proceeds will go directly back to Paddle with a Purpose to help fund larger scale water way clean ups. Note:This is a tour and clean up excursion, but knowledge is the goal and purpose, not distance so it is great for all skill levels.
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  • 2 hours
  • Free Cancellation
From
US$62.50
From
US$62.50

Marathon Backcountry Fishing CharterNature and Wildlife

Marathon Backcountry Fishing Charter

Cruise through mangrove forests and along brackish waters on this Florida backcountry fishing trip. In addition to beautiful scenery, a backcountry fishing trip offers calm waters—perfect for those who are prone to seasickness or nervous about heading out on open ocean. This tour includes all of the instruction and equipment you need for a successful trip looking for bonefish, tarpon, and more.
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  • 4 to 8 minutes
  • Free Cancellation
  • Taking safety measures
From
US$579.54
per group
From
US$579.54
per group
Taking safety measures

Marathon Inshore Fishing CharterNature and Wildlife

Marathon Inshore Fishing Charter

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and fantastic food. View the beautiful scenery, while experiencing the thrill of a chance to catch species such as Yellowtail, Snapper, Permit, Tarpon, Grouper, Barracuda, and Shark. Your tour is guided by a licensed Captain in a modern open fishing style boat with a t-top for shade. All the fishing rods and reels, right and left-handed and all the tackle you need, as well as all other necessities including safety equipment. Booking with confidence on TripAdvisor, it makes this charter an easy, reliable and enjoyable decision. Reserve Today to get hooked up! Travelers that have enjoyed our fishing charters also have enjoyed The Turtle Hospital, a tour down Seven Mile Bridge or a beautiful sunset at Sombrero Beach.
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  • 4 to 8 hours
  • Free Cancellation
  • Taking safety measures
From
US$579.54
per group
From
US$579.54
per group
Taking safety measures

4-Hour Private Florida Keys Tour from Key WestHalf-day Tours

4-Hour Private Florida Keys Tour from Key West

star-5
Keep your eyes free to roam on this tour of the Lower Keys from Key West. Ride in a comfortable van across the Overseas Highway and more than 20 bridges en route to three islands, including stops at Bahia National Park, Blue Hole, and more. This small-group tour is limited to 13 passengers or fewer and includes private audio headsets to ensure you can hear your driver's commentary along the way.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$212.50
Price varies by group size
From
US$212.50
Price varies by group size
Taking safety measures

Marathon Offshore Fishing CharterNature and Wildlife

Marathon Offshore Fishing Charter

star-1
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.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$987.00
per group
From
US$987.00
per group
Taking safety measures

Private Tour of Florida Keys from Key West: 7-Mile Bridge, Beach, and Key DeerDay Trips

Private Tour of Florida Keys from Key West: 7-Mile Bridge, Beach, and Key Deer

star-5
Private, exclusive tour of the islands near Key West. The only land-based tour in the Florida Keys, operating from Key West. Small groups of up to 12 travel in a comfortable customized air-conditioned vehicle along the Overseas Highway. Drivers are professional tour guides who share fun and interesting information about the Florida Keys and the islands we traverse. Experience the iconic 7-Mile Bridge, relax on the world-famous Bahia Honda Beach, and photograph endangered Key Deer on Big Pine Key. Children are welcome. This tour is customizable. You'll love this tour so much, you'll book it again next year!
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
US$294.00
Price varies by group size
From
US$294.00
Price varies by group size
Taking safety measures

Private Southernmost Key West History and Culture Walking TourPrivate Sightseeing Tours

Private Southernmost Key West History and Culture Walking Tour

Join us for the best walking tour in Key West! You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA! Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States. The private tour is the best way to explore Key West and have fun with your own group of friends or family! Book Now and call us to schedule the time that is convenient for you! What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
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  • 2 hours
  • Free Cancellation
From
US$238.55
per group
From
US$238.55
per group

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key WestDay Trips

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

star-5
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.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
US$389.50
Price varies by group size
From
US$389.50
Price varies by group size
Taking safety measures

Experiences Types

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Private Sightseeing Tours in Key West?
Q:
What tours in Key West are taking additional safety precautions?
Q:
What tours in Key West are good for avoiding crowds?

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