USA Sailing Trips

Public Daytime Sailing Cruise

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests, …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests,...

2 hours
5.0 (49)
from
$85
2 Hours Private Sailboat Charter in the San Francisco Bay

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the...

2 hours Free Cancellation
4.8 (22)
from
$695
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and …More

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and...

2 hours Free Cancellation
4.8 (175)
from
$60
Newport Sightseeing Day Sailing Experience on Schooner Adirondack

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, …More

Newport, USA

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges,...

1 hour 30 minutes
4.9 (159)
from
$61
Friday Night Firework Cruise in Waikiki

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, …More

Oahu, USA

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline,...

1 hour Free Cancellation
4.8 (35)
from
$70
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
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy,...

1 hour 15 minutes
4.8 (30)
from
$91
Sunset sail Aboard Manakai Catamaran

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a...

1 hour 30 minutes Free Cancellation
5.0 (26)
from
$50
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hours Free Cancellation
5.0 (40)
from
$214
Guided Seattle Sailing Adventure from Bainbridge Island

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we …More

Seattle, USA

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we...

2 hours Free Cancellation
5.0 (86)
from
$360
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
Best Private Luxury Daytime Boat Tour in New York City - 2 Hour

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view …More

New York City, USA

Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view...

2 hours Free Cancellation
5.0 (99)
from
$500
Private Sailing Charter on San Diego Bay

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural …More

San Diego, USA

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural...

3 hours Free Cancellation
4.9 (50)
from
$499
Schooner Eastwind Sunset Sail to see the Maine Coastline

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and …More

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and...

2 hours Free Cancellation
4.8 (77)
from
$75
Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest …More

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest...

2 hours Free Cancellation
4.9 (61)
from
$75
Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people …More

Oahu, USA

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people...

120 to 150 minutes Free Cancellation
5.0 (55)
from
$1,414
Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation
5.0 (40)
from
$599
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
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes Hotel pickup offered Free Cancellation
4.7 (67)
from
$197
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and …More

Newport, USA

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and...

1 hour 30 minutes
4.8 (58)
from
$61
Waikiki Sunset Cruise from Oahu

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point …More

Oahu, USA

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point...

2 hours Free Cancellation
4.8 (76)
from
$45

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