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Top USA Sailing Trips

376 Results
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes …More

Panama City Beach, USA

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes...

3 hours Free Cancellation
4.9 (5,049)
from
$52
Key West Sunset Sail with Live Music, Champagne,  Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran …More

Key West, USA

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) Free Cancellation
4.8 (3,830)
from
$80
Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge. …More

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

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.) Free Cancellation
4.9 (2,738)
from
$105
Key West Backcountry Safari

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness. …More

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

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.) Free Cancellation
4.9 (2,738)
from
$105
San Diego Whale Watching Cruise

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we …More

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

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we...

4 hours Free Cancellation
4.8 (2,470)
from
$85
Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with...

2 hours Free Cancellation
4.9 (2,417)
from
$90
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in …More

Panama City Beach, USA

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in...

2 hours Free Cancellation
4.9 (2,096)
from
$42
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Shore Excursions's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from …More

Oahu, USA

Experience one Cool Shore Excursions's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from...

2 hours Free Cancellation
4.9 (1,795)
from
$50
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island …More

Oahu, USA

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island...

2 hours 30 minutes Free Cancellation
4.8 (1,757)
from
$90
Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Shore Excursions for over a decade. In our opinion, this is the best …More

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

Wind & Wine has been the #1 rated sunset sail on Cool Shore Excursions for over a decade. In our opinion, this is the best...

2 hours (approx.) Free Cancellation
5.0 (1,716)
$115
$99
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
Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and …More

Key West, USA

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...

2 hours (approx.) Free Cancellation
4.9 (1,702)
from
$100
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key …More

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

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours Free Cancellation
4.9 (1,702)
from
$127
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look …More

Kauai, USA

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look...

5 hours Free Cancellation
4.8 (1,559)
from
$223
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along …More

Fort Lauderdale, USA

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along...

1 hour Free Cancellation
4.9 (1,532)
from
$35
Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either...

2 hours Free Cancellation
4.8 (1,464)
from
$81
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for …More

Oahu, USA

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for...

2 hours Free Cancellation
4.9 (1,012)
from
$55
Sunset Sail in Key West with Beverages Included

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention …More

Key West, USA

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

1 hour 30 minutes Free Cancellation
4.9 (982)
from
$79
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne …More

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

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours
4.9 (977)
from
$109
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for …More

Oahu, USA

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...

2 hours 30 minutes Free Cancellation
4.8 (953)
from
$85

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