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Top Key West Private Sightseeing Tours

Private Sightseeing Tours

57 results

Key West, Florida

2-Hour Private Sunset Cruise around Key West

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.

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2 hours
Free Cancellation

from

$150.00

Price varies by group size

Key West, Florida

4-Hour Private Sand Bar Cruise on a Tiki Bar Boat in Key West

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.

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4 hours
Free Cancellation

4-Hour Private Cruise to a Sand Bar on a Boat in Key West

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.

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4 hours
Free Cancellation

from

$495.00

per group

Likely to Sell Out

Key West, Florida

Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

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.

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2 hours 30 minutes
Free Cancellation

Kayak Tour of Mangrove Maze from Key West

104

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.

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3 hours
Free Cancellation

from

$75.00

Key West, Florida

Gulfstream Fishing - Key West

232

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.

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6 hours
Free Cancellation

from

$76.97

Likely to Sell Out

Key West, Florida

Key West Southernmost Food and Cultural Walking Tour

982

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.

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3 hours
Free Cancellation

from

$88.68

Likely to Sell Out

Key West, Florida

Key West Sunset Dinner Cruise with Tropical Buffet Dinner

895

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.

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2 hours
Free Cancellation

from

$92.95

Likely to Sell Out

Key West, Florida

Key West Craft Cocktail Crawl

304

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.

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3 hours
Free Cancellation

from

$93.68

Likely to Sell Out

Key West, Florida

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

2,092

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.

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2 hours
Free Cancellation

from

$79.95

Likely to Sell Out

Key West, Florida

Key West Historic Seaport Food Tasting and Cultural Walking Tour

421

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 fish tacos, Key West 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, and group size is limited to 12 people to ensure personal service from your guide.

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3 hours
Free Cancellation

from

$88.68

Key West, Florida

Guided Bicycle Tour of Old Town Key West

1,813

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.

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2 hours 30 minutes
Free Cancellation

from

$54.00

Key West, Florida

Key West Mangrove Kayak Eco Tour

1,301

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.

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2 hours
Free Cancellation

from

$60.00

Likely to Sell Out

Key West, Florida

Small-Group Key West Sunset Sail with Wine

842

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.

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2 hours
Free Cancellation

from

$128.89

Key Largo, Florida

Florida Key West Self-Driving Tour (Overseas Highway, 7 Mile Bridge)

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. Here's how it works: Within 30 min, we'll send you two things: a unique password and an app. Download the app, enter password, & download tour. Start at the first stop and follow the instructions! Stick to our route and speed limit for the best experience. No expiration — the tour is available from the minute you book until forever! Recommended: purchase one tour per car. Everyone can listen together! This is not an entrance ticket to the Keys or attractions in the Keys. Check opening hours before your visit.

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1 hour
Free Cancellation

Key West's Self Guided Ghost Walking Tours Smartphone Navigated on WalknTours

Go at your own pace and schedule. You'll see Key West's most haunted spots and hear their ghostly stories on spooky solo walking tour on the WalknTours App. 1 purchase works on 2 smartphones. BOGO! Avoid large tour groups. Hear every word. Optionally read the dialogue. Once you unlock the tour it does not expire and can be taken anytime. This offers spooky narration, theatrically crafted and music infused tour you can take anytime. Contactless and social distance friendly. It's recommended to listen on headphones or earbuds. Also you can Listen on a bluetooth speakers or your phone speaker. What makes this tour special? -The spooky narrator is one of a kind. -This is not a fact dumping tour. It's a spooky adventure. -Go anytime. Go at your own pace -Great bang for your buck. Get the adventure for a fraction of the price of other tours.

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30 minutes
Free Cancellation

from

$6.50

Key West, Florida

Key West’s Old Town Treasures: A Self-Guided Audio Tour

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.

Key West Sunset Bite, Sip & Stroll Audio Tour

Make your way to Key West with a smartphone and you’ll have all you need to discover the island’s best foods. This tour is self-guided through your smartphone. Simply follow the instructions that lead you to places like Mallory Square and the Key West Turtle Museum. Photos and audio recordings are available on your phone, as well as happy hour menus for the best restaurants. Pause the tour whenever you want to savor the flavors of Key West.

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35 minutes

from

$9.99

Likely to Sell Out

Key West, Florida

2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West

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.

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2 hours
Free Cancellation

Custom Charters with a Local Captain

These Tours are unique because they are offered by a seventh generation local who knows the waters and can take you to places other people can’t. This completely custom and private tour so start Band end times are charla e upon guests request. You will have a great day on the water looking at dolphins snorkeling going to sandbars swimming and taking in the beautiful scenery.

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3 hours 30 minutes
Free Cancellation

from

$249.00

Price varies by group size

Likely to Sell Out

Key West, Florida

PRIVATE Key West Haunted History Walking Tour

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.

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2 hours 50 minutes
Free Cancellation

from

$137.50

Price varies by group size

Key West, Florida

Bike Key West Beaches and Back Roads Audio 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 busy streets and crowded areas downtown. A one-speed beach cruiser or urban bike works perfectly. You won't be going up hills or off-roading. To book, choose any future date. Shortly after booking, you'll receive a confirmation email/"ticket" from Viator with login instructions and a coupon code. You can take the tour anytime once you have your unique coupon code.

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1 hour 10 minutes

from

$9.99

Likely to Sell Out

Key West, Florida

Luxury Sailing Catamaran - Private Charters, Owner-Operated

Soaking up the sun and scenery while sailing the coastline is a must-do when visiting Key West. If you would prefer to avoid the big, crowded boat tours, opt for this private catamaran charter, which is exclusively for your group of up to six people. You can bring your own food and cocktails onto the boat to create your own personalized experience.

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3 hours
Free Cancellation

PRIVATE Welcome to Key West Walking Tour

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.

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2 hours 55 minutes
Free Cancellation

from

$137.50

Price varies by group size

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Q:What are the best Private Sightseeing Tours in Key West?

The best Private Sightseeing Tours in Key West according to Viator travelers are:

Q:What Private Sightseeing Tours in Key West are 1 hour or less?

Private Sightseeing Tours in Key West that are 1 hour or less are:

Q:What Private Sightseeing Tours in Key West are taking additional safety precautions?

These Key West experiences are providing additional COVID-19 safety measures:

Q:What Private Sightseeing Tours in Key West are good for avoiding crowds?

These hidden gems in Key West may have limited interaction with crowds:

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Top Key West Private Sightseeing Tours

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Time of Day

Duration

Price

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57 results

2-Hour Private Sunset Cruise around Key West

4-Hour Private Sand Bar Cruise on a Tiki Bar Boat in Key West

4-Hour Private Cruise to a Sand Bar on a Boat in Key West

Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

Kayak Tour of Mangrove Maze from Key West

Gulfstream Fishing - Key West

Key West Southernmost Food and Cultural Walking Tour

Key West Sunset Dinner Cruise with Tropical Buffet Dinner

Key West Craft Cocktail Crawl

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

Key West Historic Seaport Food Tasting and Cultural Walking Tour

Guided Bicycle Tour of Old Town Key West

Key West Mangrove Kayak Eco Tour

Small-Group Key West Sunset Sail with Wine

Florida Key West Self-Driving Tour (Overseas Highway, 7 Mile Bridge)

Key West's Self Guided Ghost Walking Tours Smartphone Navigated on WalknTours

Key West’s Old Town Treasures: A Self-Guided Audio Tour

Key West Sunset Bite, Sip & Stroll Audio Tour

2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West

Custom Charters with a Local Captain

PRIVATE Key West Haunted History Walking Tour

Bike Key West Beaches and Back Roads Audio Tour

Luxury Sailing Catamaran - Private Charters, Owner-Operated

PRIVATE Welcome to Key West Walking Tour

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