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Top USA Sailing Trips

Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's …More

Key West, USA

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours Free Cancellation
5.0 (292)
from
$102
Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner …More

Big Island of Hawaii, USA

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner...

1 hour 30 minutes Free Cancellation
4.8 (744)
from
$141
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay …More

Miami, USA

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay...

3 hours 30 minutes Free Cancellation
4.9 (458)
from
$101
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
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 Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), …More

Honolulu, USA

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hours Hotel pickup offered Free Cancellation
4.9 (670)
from
$90
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours Free Cancellation
4.7 (89)
from
$148
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in …More

Maui, USA

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hours Free Cancellation
4.8 (836)
from
$213
2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the …More

Hilton Head Island, USA

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the...

2 hours Free Cancellation
5.0 (121)
from
$485
Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red …More

Big Island of Hawaii, USA

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red...

4 hours 30 minutes Free Cancellation
4.9 (590)
from
$179
Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy …More

Big Island of Hawaii, USA

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy...

3 hours Free Cancellation
4.8 (108)
from
$189
Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are …More

Seattle, USA

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are...

2 hours Free Cancellation
4.9 (218)
from
$60
Happy Hour Sunset Sail on Maui's Luxury Catamaran

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted …More

Maui, USA

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted...

2 hours Free Cancellation
4.9 (101)
from
$169
Catamaran Sailing Cruise in Monterey

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind …More

Likely to Sell Out
Likely to Sell Out
Monterey & Carmel, USA

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind...

1 hour 15 minutes Free Cancellation
4.8 (43)
from
$65
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic …More

Oahu, USA

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes Free Cancellation
4.9 (217)
from
$62
Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as …More

Oahu, USA

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes Free Cancellation
5.0 (276)
from
$51
Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset …More

Key West, USA

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset...

2 hours (approx.) Free Cancellation
5.0 (1,716)
from
$3,499
Escape from the Rock! Cruise around Alcatraz

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an …More

San Francisco, USA

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an...

1 hour 30 minutes Free Cancellation
4.5 (146)
from
$48
2-Hour Sunset Sail on the San Francisco Bay

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step …More

San Francisco, USA

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step...

2 hours Free Cancellation
4.8 (422)
from
$129
Private Sunset and Eco Tour in Destin Up to 18 Guests

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutes Free Cancellation
5.0 (45)
from
$450

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