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Top USA Sailing Trips

376 Results
Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty …More

Honolulu, USA

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hours Free Cancellation
4.7 (242)
from
$79
Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • …More

Key West, USA

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hours Free Cancellation
4.6 (432)
from
$77
Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha …More

Mount Pleasant, USA

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha...

2 hours Free Cancellation
5.0 (10)
from
$76
Baltimore Evening Sail on the Summer Wind

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful …More

Baltimore, USA

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful...

1 hour 30 minutes Free Cancellation
5.0 (28)
from
$75
Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes Free Cancellation
4.9 (58)
from
$75
Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes Free Cancellation
5.0 (5)
from
$75
Baltimore Harbor Evening Sail on the Unforgettable

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city …More

Baltimore, USA

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city...

1 hour 30 minutes Free Cancellation
4.6 (5)
from
$75
Baltimore Harbor Moonlight Sail on the Summer Wind

Find your own slice of paradise on this 1.5-hour moonlight sail around Baltimore Harbor. Listen to music inspired by the Caribbean as you enjoy the …More

Baltimore, USA

Find your own slice of paradise on this 1.5-hour moonlight sail around Baltimore Harbor. Listen to music inspired by the Caribbean as you enjoy the...

1 hour 30 minutes Free Cancellation
5.0 (3)
from
$75
Windjammer Classic Sunset Sail from Camden, Maine

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. …More

Camden, USA

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience....

2 hours Free Cancellation
4.9 (514)
from
$75
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
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
Newport Sunset Sail on Classic Sailboat

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on …More

Newport, USA

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on...

1 hour 30 minutes
4.8 (57)
from
$74
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
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutes Free Cancellation
4.9 (322)
from
$73
St Augustine Nights of Lights Viewing Boat with Live Music

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset …More

St Augustine, USA

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset...

1 hour 45 minutes (Approx.) Free Cancellation
4.9 (64)
from
$72
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises. …More

Bar Harbor, USA

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises....

2 hours Free Cancellation
4.2 (730)
from
$70
Southwest Florida Sunset Sail

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The …More

Fort Myers, USA

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The...

2 hours Free Cancellation
5.0 (509)
from
$70
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
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from …More

Oahu, USA

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hours Free Cancellation
4.9 (18)
from
$70

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