USA Sailing Trips

377 Results
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: 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
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
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
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
Deluxe Sunset & Day Sail Small Group

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as …More

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

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as...

2 hours 30 minutes Free Cancellation
5.0 (371)
from
$119
2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. …More

Likely to Sell Out
Likely to Sell Out
La Jolla, USA

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail....

2 hours 30 minutes Free Cancellation
5.0 (370)
from
$119
Deluxe Day Sail in San Diego

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego …More

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

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego...

2 hours 30 minutes Free Cancellation
5.0 (82)
from
$119
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat …More

San Diego, USA

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat...

2 hours Free Cancellation
4.9 (204)
from
$119
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your …More

Key West, USA

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hours Free Cancellation
4.9 (119)
from
$119
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on …More

Likely to Sell Out
Likely to Sell Out
La Jolla, USA

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on...

2 hours 30 minutes Free Cancellation
5.0 (114)
from
$119
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
Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a …More

Special Offer
Special Offer
Key West, USA

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...

6 hours (approx.)
4.9 (558)
$125
$120
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes Free Cancellation
4.5 (44)
from
$120
Private Sailing Tour of Bodega Bay

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as …More

Napa & Sonoma, USA

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as...

3 hours Free Cancellation
4.9 (91)
from
$123
Key West Dolphin Watch and Sunset Sail on Catamaran

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of …More

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

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

3 hours Free Cancellation
4.9 (40)
from
$124
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area …More

Panama City Beach, USA

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hours Free Cancellation
5.0 (3)
from
$124
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole …More

Seattle, USA

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole...

2 hours 30 minutes Free Cancellation
5.0 (36)
from
$125
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

San Diego, USA

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation
5.0 (359)
from
$125

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