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45 results | All Key West Tours

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Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
Likely to Sell OutLikely to Sell Out

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

star-4.5
1541
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
From
$79.95

Key West Sunset Champagne Catamaran Cruise
Likely to Sell OutLikely to Sell Out

Key West Sunset Champagne Catamaran Cruise

star-4.5
404
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$59.95
From
$59.95

Shark and Wildlife Viewing Adventure in Key West
Likely to Sell OutLikely to Sell Out

Shark and Wildlife Viewing Adventure in Key West

star-5
1050
Get up close with sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast of Key West. See dolphins, stingrays, turtles and birds and learn about Key West’s waters, and then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat. Bring a camera to capture the excitement as these super predators swarm. Cold drinks, snacks and polarized sunglasses are included on this Key West shark cruise.
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  • 2 hours
  • Free Cancellation
From
$89.00
From
$89.00

Key West Southernmost Food and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Southernmost Food and Cultural Walking Tour

star-5
748
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
From
$88.68

Key West Snorkel and Sunset Sail: Rum n' Reggae
Likely to Sell OutLikely to Sell Out

Key West Snorkel and Sunset Sail: Rum n' Reggae

star-4.5
216
Combine a snorkel session on North America's only living coral reef with a Key West sunset during this catamaran cruise. Listen to lively reggae beats, snorkel using the provided equipment, and watch the sunset with a rum punch in hand.
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  • 3 hours
  • Free Cancellation
From
$64.45
From
$64.45

Half-Day Cruise from Key West with Kayaking and Snorkeling
Likely to Sell OutLikely to Sell Out

Half-Day Cruise from Key West with Kayaking and Snorkeling

star-5
886
Get ready for fun in the sun on this half-day sailing, kayaking and snorkeling adventure off the coast of Key West. Choose from a morning or afternoon excursion and set sail. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.
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  • 4 hours 30 minutes
  • Free Cancellation
From
$106.00
From
$106.00

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings
Likely to Sell OutLikely to Sell Out

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

star-4.5
190
Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$89.95
From
$89.95

Small-Group Key West Sunset Sail with Wine
Likely to Sell OutLikely to Sell Out

Small-Group Key West Sunset Sail with Wine

star-5
631
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
$99.95
From
$99.95

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
Likely to Sell OutLikely to Sell Out

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

star-5
310
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
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  • 2 hours
  • Free Cancellation
From
$99.95
From
$99.95

Key West Wild Dolphin Sail and Shallow-Water Snorkel
Likely to Sell OutLikely to Sell Out

Key West Wild Dolphin Sail and Shallow-Water Snorkel

star-4.5
270
Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.
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  • 4 hours
From
$97.91
From
$97.91

Island Adventure Snorkel Kayak and Tour from Key West
Likely to Sell OutLikely to Sell Out

Island Adventure Snorkel Kayak and Tour from Key West

star-4.5
393
Get access to a remote nature sanctuary, known only to Key West locals, during this island adventure. Choose to paddleboard, kayak, snorkel, or just lounge on the sandbar and take in the natural ambiance. Snack, lunch, and use of snorkel equipment included; wine and beer available after activities.
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  • 4 hours 30 minutes
  • Free Cancellation
From
$139.70
From
$139.70

Adults only Champagne Celebration Sunset Cruise from Key West
Likely to Sell OutLikely to Sell Out

Adults only Champagne Celebration Sunset Cruise from Key West

star-5
447
Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. 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
From
$81.40
From
$81.40

Key West Craft Cocktail Crawl
Likely to Sell OutLikely to Sell Out

Key West Craft Cocktail Crawl

star-5
211
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
From
$93.68

Key West Historic Seaport Food Tasting and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Historic Seaport Food Tasting and Cultural Walking Tour

star-5
340
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
From
$88.68

4-Hour Private Sand Bar Cruise on a Tiki Bar Boat in Key West
Likely to Sell OutLikely to Sell Out

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

star-5
30
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
From
$564.90
per group
From
$564.90
per group

Florida Keys Nature & History Tour from Key West
Likely to Sell OutLikely to Sell Out

Florida Keys Nature & History Tour from Key West

star-5
56
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
From
$102.00
From
$102.00

Hemingway Food and Walking Tour
Likely to Sell OutLikely to Sell Out

Hemingway Food and Walking Tour

star-4.5
47
Follow in the footsteps of Ernest Hemingway during a walking tour that focuses on food, culture, and history. Exploring Key West on foot means that you'll get a more intimate glimpse into the historic area, which is characterized by its charming bars and plethora of museums. Plus, you'll receive personalized attention as you explore in a small group limited to only 15 other travelers.
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  • 2 hours
  • Free Cancellation
From
$89.00
From
$89.00

2-Hour Private Sunset Cruise around Key West

2-Hour Private Sunset Cruise around Key West

star-4.5
36
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
$200.00
Price varies by group size
From
$200.00
Price varies by group size

2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
Likely to Sell OutLikely to Sell Out

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

star-4.5
35
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
From
$456.88
per group
From
$456.88
per group

Private Half-Day Key West Boat Trip
Likely to Sell OutLikely to Sell Out

Private Half-Day Key West Boat Trip

star-5
129
If Key West isn’t a paradise enough, you can up the ante and spend the perfect day on the water with this half-day, customizable private boat trip. Jump on board and let the captain help you make the experience as memorable as possible. Fishing? Snorkeling? Kayaking and sunbathing? You can do it all with equipment provided by the captain. Float on a pool noodle and sip on soda while you enjoy quality time under the sun.
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  • 4 hours
  • Free Cancellation
From
$725.00
per group
From
$725.00
per group

Beach Day in Key West with Picnic Lunch

Beach Day in Key West with Picnic Lunch

star-5
56
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
$125.00
From
$125.00

Private Key West Morning Charter Boat Tour

Private Key West Morning Charter Boat Tour

star-5
32
Exploring the crystal-clear waters of the Florida Keys National Marine Sanctuary is a must-do when visiting the Keys, but big boat tours can feel crowded and rushed. This private snorkeling tour is exclusively for your party and takes you out to the reef to see marine life, as well as a tropical sandbar. You'll also have the chance to paddle board around bird-filled mangroves.
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  • 3 hours
  • Free Cancellation
From
$258.34
Price varies by group size
From
$258.34
Price varies by group size

Corsair 2 Sportfishing Key West
Likely to Sell OutLikely to Sell Out

Corsair 2 Sportfishing Key West

star-5
79
While you’re in Key West, head out on the deep blue waters on this sportfishing charter. The saltwater fishing boat holds up to six anglers, and is rigged with state-of-the-art navigational electronics and safety equipment, outriggers, a fighting chair, a live bait tank, and ice boxes. Plus, it features two private restrooms, a kitchen, flybridge, beds, and air conditioning.
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  • 4 hours
  • Free Cancellation
From
$900.00
per group
From
$900.00
per group

Key West Sushi Sunset Cruise
Likely to Sell OutLikely to Sell Out

Key West Sushi Sunset Cruise

star-4.5
28
Key West is famed for its glorious sunsets but the most popular spots to take them in are usually crowded and noisy. Swap the bustling streets of Key West for the calm of the sea. This sunset cruise lets you see the sun dipping below the horizon while you relax on the deck while enjoying great food and drinks.
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  • 2 hours
  • Free Cancellation
From
$75.00
From
$75.00

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