Find Things to Do in...
Search
Tours & Things to Do

More Great Destinations

Take time to explore tours and activities in these amazing destinations:


Shop With Confidence
  • Low Price Guarantee
  • Only Top Quality Tour and Activity Companies
  • 100% Secure Transactions
  • No Hidden Fees
  • 500,000+ Satisfied Customers
Why Book With Us
  • Save Money:

    Booking ahead will almost always save you money.

  • Save Time:

    You've got better things to do than wait in ticket lines.

  • Get The Tour You Want:

    Booking online means you get first pick of available tours.


Contact Us
Search by Category
Recommended Activities
Advanced Search

Here are your 6 search results for Private & Custom Tours in Key West, United States

Private Sunset Sail with Wine and Cheese

Private Sunset Sail with Wine and Cheese - Key West, Florida

Duration: 2 hours
Location: Key West, Florida

From USD
$350.00

Sunset sailing trips in Key West should be romantic with friends and/or family, and that's why we only offer private sunset sails. Our beautiful sail boat is not rented to anyone else during your sail ... More info ›

Sunset sailing trips in Key West should be romantic with friends and/or family, and that's why we only offer private sunset sails. Our beautiful sail boat is not rented to anyone else during your sail. The beauty of a private sailing charter is that you dictate where and how long we will be sailing, or just leave it up to the Captain to take you to the untouched locations of our reef system.

After booking we will call you to discuss drinks and snacks you wish to have on your private sunset sail.  After we pick you up from your hotel or resort, we whisk you away to your sailboat downtown where you will meet the Captain.   After a brief introduction we will take you and your guests to Key West harbor and all the sites along the beautiful coast.  Wine and cheese laid out and presented during the sail.  If you wish to grab the helm or work the lines the Captain would love to inspire future sailors, or just relax and enjoy the sail.  We sail with the engines shut off unlike many of the "sail charters" in Key west.

Less info

Private Sail with Reef Eco Exploration

Private Sail with Reef Eco Exploration - Key West, Florida

Duration: 4 hours
Location: Key West, Florida

From USD
$599.99

Trip starts out at Galleon Marina for a 4 Hour sail. You will be taken through the National Marine Sanctuary which is home to Dolphins, Loggerhead turtles and flying Mantas and much more ... More info ›

Trip starts out at Galleon Marina for a 4 Hour sail. You will be taken through the National Marine Sanctuary which is home to Dolphins, Loggerhead turtles and flying Mantas and much more. Depending on the wind it takes about an hour to reach the Reef. Private half day sail excursion without the crowds in Key West!

This is one of the most preserved areas in all of Key West. You will travel on a beautiful 33 foot sailboat and be taken to a mooring ball where you may swing or snorkel up to two hours. It all depends on what you'd like to see and do while on the water and how long you wish to stay in that area.  

As a private charter we will customize your trip for your special occasion, for you, or your group. Trips are designed for families or couples and is completely private with no one on board except your group and the Captain.

Less info

Private Key West Sunset Sail

Private Key West Sunset Sail - Key West, Florida

Duration: 2 hours
Location: Key West, Florida

From USD
$370.88

Enjoy an exclusive and intimate sunset cruise on the Java Cat. Departing from the Key West Historic Seaport, your captain sails the surrounding waters with the Key West sunset as the main event ... More info ›

Enjoy an exclusive and intimate sunset cruise on the Java Cat. Departing from the Key West Historic Seaport, your captain sails the surrounding waters with the Key West sunset as the main event. The best value in Key West for a private sunset Key West charter! A group of up to 6 guests can “own the boat” for a fabulous Key West sunset sail.

No trip to Key West is complete until you experience the world famous Key West sunset. And the best place to experience this colorful end of the day is on the Java Cat out on the open water. Your tour sails from Key West's Historic Seaport. As you leave the Seaport, watch all the people lined up on the dock for Mallory Square's Sunset Celebration with its street performers, local musicians, artists and food vendors. Sail on past the Navy Mole with its big ships, luxurious Sunset Key and historic Fort Zachary Taylor. The waters around Key West are teeming with wildlife. Look for dolphins, turtles and jumping fish. Watch Magnificent Frigate birds cavort high overhead while pelicans and ospreys hunt for dinner.

Sit in Java Cat’s comfortable aft-deck under the shaded Bimini top or lay out on the fore-deck trampolines. As the sun descends toward the blue ocean, relax and savor the moment. Feel the sun caress your skin while the balmy salt air tousles your hair. Return from your sunset sail refreshed, with a renewed appreciation for the simple things in life.

Less info

Private 90 Minute Customized Sailing Charter

Private 90 Minute Customized Sailing Charter - Key West, Florida

Duration: Flexible
Location: Key West, Florida

From USD
$294.99

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility ... More info ›

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some friendly dolphins off the bow!

Arriving at the boat, you will be introduced to your Captain and Mate then you'll settle onto the boat for a quick familiarization and safety briefing and anything you may wish to keep in the coolers will be stowed - then you're ready for departure.

Casting off lines you will motor out of the harbor and then the sails will be raised. If you want to assist the crew - you are more than welcome!

Once the sails are set your Captain will shut off the engine and head out into the bright tropical waters surrounding Key West to enjoy the sun, feel the wind lift the boat and explore the rich wildlife preserve that surrounds this beautiful island. You have only to ask if you wish to have a turn at the helm; with many years sailing experience your captain is more than happy to stand by while you feel the power of the wind and enjoy the peace and delight that comes from travel under sail.

With a host of local knowledge at your disposal, your crew will point out areas or objects of interest, and of course they are always on the look out for the frequently-seen turtles and dolphins that inhabit the area, as well as a vast array of seabirds and other wildlife. Sail around Sunset Key and take a look at the Key West's most fantastic National wildlife preserve

As the tour nears its end, you will power back into the harbor and you are free to enjoy the remainder of your day in sunny Key West!

Less info

Booking.com

Private Sunset Sail with Cheese Platter

Private Sunset Sail with Cheese Platter - Key West, Florida

Duration: 2 hours
Location: Key West, Florida

From USD
$394.99

The perfect Key West sunset sail - peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with a free gourmet cheese platter and soft drinks with ice provided for any adult beverages you choose to bring.

Arriving at the sloop, you will be introduced to your Captain and Mate then settle onto the boat for a quick familiarization and safety briefing from the captain while the mate stows anything you may wish to keep in the coolers and prepares the boat for departure.

A short motor out of the harbor brings the boat to a spot where the captain can turn her into the wind and the mate can hoist the sails - aided by any guests who are feeling particularly enthusiastic! After that, the engines will be shut off so you can enjoy the sights and sounds of Key West in peace and tranquility.

As you sail in the best direction for the evening according to the wind, the current and the tide, your crew are happy to highlight points of interest along the way and answer any questions for you, as well as take your photo and serve up your drinks and complimentary cheese platter ... More info ›

The perfect Key West sunset sail - peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with a free gourmet cheese platter and soft drinks with ice provided for any adult beverages you choose to bring.

Arriving at the sloop, you will be introduced to your Captain and Mate then settle onto the boat for a quick familiarization and safety briefing from the captain while the mate stows anything you may wish to keep in the coolers and prepares the boat for departure.

A short motor out of the harbor brings the boat to a spot where the captain can turn her into the wind and the mate can hoist the sails - aided by any guests who are feeling particularly enthusiastic! After that, the engines will be shut off so you can enjoy the sights and sounds of Key West in peace and tranquility.

As you sail in the best direction for the evening according to the wind, the current and the tide, your crew are happy to highlight points of interest along the way and answer any questions for you, as well as take your photo and serve up your drinks and complimentary cheese platter.

As the sun dips beneath the horizon it's the perfect time to enjoy the colorful view, and shortly after dusk you will make your way leisurely back to the harbor so you can continue your evening in Key West.

Less info

Private Afternoon Snorkel with Sunset Sail

Private Afternoon Snorkel with Sunset Sail  - Key West, Florida

Duration: 4 hours
Location: Key West, Florida

From USD
$595.00

Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's amazing natural wildlife with up to five others, before sailing back to shore at sunset.

You will be welcomed on board your charter by your Captain and Mate, who will give you a short safety briefing while any drinks and snacks you've brought along are stowed in the coolers containing your complimentary soft drinks and ice.

Motor out of the harbor, and as soon as you're safely out of the way of the busy shipping lanes you'll hoist sail and continue the rest of the journey with the peaceful sounds of the waves and the breeze all around.

As you sail out to the best reef or sponge garden for your snorkel adventure (according to wind, tide and current on the day), your crew will be happy to answer questions and point out places of interest along the way - they've got some great local knowledge and always love to share Key West's colorful history and characters!

When you reach your snorkeling spot, you'll strike sail and drop anchor. You'll receive your gear and then you're free to explore the ocean or lie on deck and soak up the sun ... More info ›

Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's amazing natural wildlife with up to five others, before sailing back to shore at sunset.

You will be welcomed on board your charter by your Captain and Mate, who will give you a short safety briefing while any drinks and snacks you've brought along are stowed in the coolers containing your complimentary soft drinks and ice.

Motor out of the harbor, and as soon as you're safely out of the way of the busy shipping lanes you'll hoist sail and continue the rest of the journey with the peaceful sounds of the waves and the breeze all around.

As you sail out to the best reef or sponge garden for your snorkel adventure (according to wind, tide and current on the day), your crew will be happy to answer questions and point out places of interest along the way - they've got some great local knowledge and always love to share Key West's colorful history and characters!

When you reach your snorkeling spot, you'll strike sail and drop anchor. You'll receive your gear and then you're free to explore the ocean or lie on deck and soak up the sun. Key West forms part of a large wildlife preserve so you will get to see some of the variety of sponges, corals, fish, crustaceans, starfish, urchins, birds and even maybe a dolphin or two!

With everyone safely back on board you'll make your way toward the harbor through the sunset, past the crowds at Mallory Square's Sunset Celebration and weaving in and out of the many other beautiful boats out to enjoy the evening - it's a great view! Your mate will serve your complimentary cheese platter to enjoy as the sun goes down and as the colors fade from the sky, you'll head back to the dock.

Less info