USA Sailing Trips

375 Results
Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (213)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours Free Cancellation
4.8 (213)
from
$138
Key West Day Sail on Schooner America 2.0 with 2 Drinks

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that …More

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

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

1 hour 30 minutes Free Cancellation
5.0 (212)
from
$82
Sunset Catamaran Sail in Cocoa Beach

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana …More

Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana...

2 hours Free Cancellation
4.9 (206)
from
$56
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
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather …More

Naples, USA

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather...

2 hours 30 minutes Free Cancellation
4.9 (196)
from
$70
Newport Afternoon Sightseeing Sail on Classic Sailboat

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, …More

Newport, USA

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail,...

1 hour 30 minutes
4.9 (196)
from
$61
Boston Harbor Sunset Sail Tour

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon....

2 hours Free Cancellation
4.9 (189)
from
$82
2-Hour Private Sailing Experience in San Diego Bay

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing …More

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

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing...

2 hours Free Cancellation
5.0 (188)
from
$675
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
Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and …More

Maui, USA

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and...

3 hours Free Cancellation
4.8 (174)
from
$169
New York City Sailboat Day Cruise to the Statue of Liberty

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as …More

Likely to Sell Out
Likely to Sell Out
New York City, USA

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as...

1 hour 45 minutes Free Cancellation
4.9 (174)
from
$60
Let's Go Sail the York River in Gloucester Point Virginia

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the …More

Likely to Sell Out
Likely to Sell Out

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the...

2 hours 30 minutes Free Cancellation
5.0 (168)
from
$96
Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board …More

Camden, USA

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board...

2 hours Free Cancellation
4.9 (167)
from
$73
Daytime Sailing Along San Diego's Skyline

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor …More

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

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor...

2 hours Free Cancellation
5.0 (161)
from
$99
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
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hours Free Cancellation
4.9 (157)
from
$69
Marco Island Private Catamaran Sailing Tour

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at …More

Likely to Sell Out
Likely to Sell Out
Naples, USA

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at...

2 hours
5.0 (154)
from
$450
Buccaneer Pirate Cruise in Destin

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger...

90 to 120 minutes Free Cancellation
4.8 (146)
from
$62
2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours Free Cancellation
4.8 (142)
from
$130
Newport Sunset Sail on Schooner Adirondack

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during …More

Newport, USA

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during...

1 hour 30 minutes
4.8 (140)
from
$74
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, …More

Maui, USA

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours Free Cancellation
5.0 (140)
from
$193

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