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Top USA Sailing Trips

376 Results
Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way …More

Maui, USA

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours Free Cancellation
4.9 (90)
from
$119
Small-Group San Diego Afternoon Sailing Excursion

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends...

3 hours Free Cancellation
5.0 (568)
from
$116
Sailboat Cruise on Chesapeake Bay

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered …More

Likely to Sell Out
Likely to Sell Out

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered...

2 hours 30 minutes Free Cancellation
5.0 (40)
from
$116
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay …More

Likely to Sell Out
Likely to Sell Out
Pensacola, USA

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay...

2 hours Free Cancellation
5.0 (73)
from
$114
Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in …More

Chicago, USA

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in...

1 hour 30 minutes
4.8 (24)
from
$114
Maui: Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours Free Cancellation
4.8 (85)
from
$112
Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations...

2 hours Free Cancellation
4.9 (29)
from
$110
Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours Free Cancellation
4.5 (2)
from
$110
Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours Free Cancellation
4.9 (103)
from
$110
4-Hour Fort Lauderdale Sailing Charter

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have …More

Fort Lauderdale, USA

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have...

4 hours Free Cancellation
4.9 (323)
from
$110
Key West Schooner Backcountry Eco-Tour

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure! …More

Key West, USA

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...

5 hours (approx.) Free Cancellation
4.9 (216)
from
$110
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes Free Cancellation
4.5 (50)
from
$110
Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes Free Cancellation
4.8 (384)
from
$109
Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hours Free Cancellation
4.9 (283)
from
$109
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours
4.9 (977)
from
$109
Shallow Water Snorkeling and Dolphin Watching in Key West

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours
4.8 (438)
from
$109
Champagne Dolphin Sail and Reef Snorkel

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with...

3 hours
5.0 (10)
from
$109
Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. …More

Key West, USA

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass....

8 hours Free Cancellation
4.7 (19)
from
$107
Sunset Dolphin Sail Aboard the Daydreams Sailboat

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. …More

Panama City Beach, USA

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island....

2 hours Free Cancellation
5.0 (46)
from
$107
Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge. …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.) Free Cancellation
4.9 (2,739)
from
$105

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