Top North America Sailing Trips

632 Results
Romantic Sunset Dinner Cruise in Cancun with Open Bar

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner. …More

Likely to Sell Out
Likely to Sell Out
Cancun, Mexico

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner....

2 hours 30 minutes Free Cancellation
4.5 (14)
from
$112
Private Fishing & Snorkeling Boat Charter (Up to 12 pax)

Set sail on the ultimate private marine adventure departing from Nuevo Vallarta! Perfect for families or friend groups (1 to 12 passengers), your party will …More

Puerto Vallarta, Mexico

Set sail on the ultimate private marine adventure departing from Nuevo Vallarta! Perfect for families or friend groups (1 to 12 passengers), your party will...

5 hours Free Cancellation
4.4 (14)
from
$1,219
New York Fall Foliage Sail up the Hudson River

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson …More

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

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson...

3 hours 30 minutes Free Cancellation
4.6 (11)
from
$143
Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to …More

Mount Pleasant, USA

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to...

2 hours Free Cancellation
4.7 (11)
from
$56
Sunset in Private Sailboat 4 hrs up to 15 pax

Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other important event. You will receive the best service where you will see …More

Puerto Vallarta, Mexico

Sail around the bay, celebrating your birthday, bachelorette party, anniversary or any other important event. You will receive the best service where you will see...

3 hours
4.6 (11)
from
$3,295
Snorkeling Adventure in Isla Mujeres

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world …More

Punta Sam, Mexico

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world...

8 to 9 hours Hotel pickup offered Free Cancellation
4.3 (10)
from
$59
Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to …More

Oahu, USA

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutes Free Cancellation
4.6 (10)
from
$85
Discovering Isla Mujeres on a Double Decker Catamaran

Start your day with a hotel pickup or directly at the marina, then head out to open sea through the spectacular mangrove channels. The bar …More

Likely to Sell Out
Likely to Sell Out
Cancun, Mexico

Start your day with a hotel pickup or directly at the marina, then head out to open sea through the spectacular mangrove channels. The bar...

7 hours Free Cancellation
4.3 (9)
from
$79
LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and …More

Likely to Sell Out
Likely to Sell Out
Long Beach, USA

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and...

1 hour
4.6 (8)
from
$255
Romantic Dinner in the Spanish Galeon with Sax in Cancun

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? …More

Likely to Sell Out
Likely to Sell Out
Punta Sam, Mexico

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner?...

4 hours Hotel pickup offered Free Cancellation
4.4 (7)
from
$99
Sunset Sail on the Black Pearl

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point …More

Sandusky, USA

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point...

2 hours Free Cancellation
4.4 (7)
from
$595
Tall Ship Adventure aboard the Schooner Californian with General Admission

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984 …More

San Diego, USA

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984...

4 hours
4.3 (6)
from
$85
Reef Snorkel adventure in Puerto Morelos With Transport & Lunch

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a must activity in Cancun. You will visit one of the …More

Punta Sam, Mexico

Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a must activity in Cancun. You will visit one of the...

5 hours Hotel pickup offered Free Cancellation
4.5 (6)
from
$44
Sailing Snorkel Adventure

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value. …More

Cabo San Lucas, Mexico

Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sailing Boat Adventure is unbeatable Value....

4 hours Free Cancellation
4.5 (6)
from
$149
Catamaran Sailing to Isla Mujeres From Cancun

Discover the Mexican Caribbean aboard a luxury catamaran, with premium service, personalized attention and spectacular scenery. At Oceanix Nauticos, we take you to explore the …More

Cancun, Mexico

Discover the Mexican Caribbean aboard a luxury catamaran, with premium service, personalized attention and spectacular scenery. At Oceanix Nauticos, we take you to explore the...

5 hours Free Cancellation
4.5 (6)
from
$50
2 Islands in 1 Day: Contoy & Isla Mujeres, Snorkeling + Open Bar

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single …More

Cancun, Mexico

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single...

8 hours Free Cancellation
4.3 (6)
from
$76
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
90 Minute Sailing Tour of Portland

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate …More

Portland, USA

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate...

1 hour 30 minutes Free Cancellation
4.5 (4)
from
$99
Crystal Boat Tour with Snorkeling and Drinks in Cozumel

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first …More

Cozumel, Mexico

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first...

1 hour 30 minutes Free Cancellation
4.5 (4)
from
$55
Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun

If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable …More

Likely to Sell Out
Likely to Sell Out
Punta Sam, Mexico

If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable...

2 hours 30 minutes Hotel pickup offered Free Cancellation
4.7 (3)
from
$99

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