Top USA Sailing Trips

Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Wind & Wine Sunset Sail
59
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running....
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2 Hours (approx.) Instant Confirmation
Best Rate
$85
Details
Best Rate
$85
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sail, Snorkel, Kayak with Sunset Option
31
Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....
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4.5 Hours (approx.)
Best Rate
$80
Details
Best Rate
$80
Details
Key West Morning Mimosa Private Charter
3
This exclusive experience is for 1 to 40 persons as a private charter and includes unlimited pastries, juices, coffee and mimosas for your group!...
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2 Hours (approx.)
Best Rate
$800
Details
Best Rate
$800
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
279
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern...
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2 hours Instant Confirmation
from
$74.95
Details
from
$74.95
Details
San Diego Whale Watching Cruise
133
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...
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4 hours 30 minutes Instant Confirmation
from
$85
Details
from
$85
Details
Four Winds II Molokini Snorkeling Tour from Maalaea Harbor
166
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...
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5 hours
from
$128.24
Details
from
$128.24
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Full-Day Power Adventure: Sailing & Watersports Package
144
This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...
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6 hours Instant Confirmation
from
$184.95
Details
from
$184.95
Details
Afternoon Sail & Snorkel Captain Cook Monument at Kealakekua Bay
22
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you...
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3 hours
from
$82.73
Details
from
$82.73
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Sail Aboard Schooner
20
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...
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2 hours Instant Confirmation
from
$103.20
Details
from
$103.20
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Sunset Champagne Catamaran Cruise
85
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy...
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1 hour 30 minutes Instant Confirmation
from
$51.95
Details
from
$51.95
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Dolphin Watch
123
Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...
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6 hours Instant Confirmation
from
$124.95
Details
from
$124.95
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Na Pali Coast Kauai Snorkel and Sail
60
Sail the majestic Na Pali Coast and witness its beauty with 4,000-foot cliffs, cascading waterfalls, sea caves, secluded beaches, dolphins, turtles and breathtaking scenery. You...
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5 hours Instant Confirmation
from
$192.50
Details
from
$192.50
Details
Deluxe Sail & Snorkel Captain Cook Monument at Kealakekua Bay
7
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument"...
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4 hours 30 minutes
from
$141.82
Details
from
$141.82
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Sunset Sail with Live Music and Open Bar from Ka’anapali Beach
5
Exclusive to Sea Maui, it's the only sail that departs Ka'anapali beach 3 times a week with awesome LIVE music on board. It's sunset sailing...
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2 hours Instant Confirmation
from
$91.90
Details
from
$91.90
Details
Adults only Champagne Celebration Sunset Cruise from Key West
129
Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included...
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2 hours Instant Confirmation
from
$81.40
Details
from
$81.40
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
12pm Turtle Canyon Snorkel Adventure
14
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful...
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2 hours 30 minutes Instant Confirmation
from
$87.18
Details
from
$87.18
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Leila Na Pali Sunset Dinner Sail
4
Sail the legendary Na Pali Coast aboard Leila, a 50-foot Kauai-made sailing catamaran and witness the beauty of 4000-foot cliffs, cascading waterfalls, sea caves, secluded beaches,...
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4 hours 30 minutes Instant Confirmation
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$149.50
Details
from
$149.50
Details
Pau Hana Sunset Cruise with the Whales
6
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and...
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2 hours Instant Confirmation
from
$139
Details
from
$139
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
43
Picture the perfect Key West sunset, as you sail and sit on the deck of a romantic two-masted schooner. With the wind blowing in your...
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2 hours Instant Confirmation
from
$79.95
Details
from
$79.95
Details
Turtle Snorkeling Adventure
9
**Turtle Canyon Snorkel Adventure** Turtle Canyon Snorkel Adventure with three schedules to choose from (8am, 11pm and 2:00pm). Get ready to explore and be greeted...
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2 hours Instant Confirmation
from
$76.20
Details
from
$76.20
Details
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Waikiki Sunset Cocktail Sail with Open Bar
15
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one...
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1 hour 30 minutes Instant Confirmation
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$65.39
Details
from
$65.39
Details