Top North America Sailing Trips

633 Results
Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in …More

Key West, USA

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
4.9 (14)
from
$127
Small-Group San Diego Sunset Sailing Excursion

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat …More

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

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat...

3 hours Free Cancellation
5.0 (638)
from
$127
Lahaina Maui Sunset Sail on 'Alihilani

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for...

2 hours 30 minutes Free Cancellation
5.0 (226)
from
$127
Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing …More

Maui, USA

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing...

2 hours Free Cancellation
5.0 (46)
from
$127
Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear …More

Likely to Sell Out
Likely to Sell Out
Maui, USA

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear...

2 hours 30 minutes Free Cancellation
4.8 (42)
from
$127
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole …More

Seattle, USA

Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole...

2 hours 30 minutes Free Cancellation
5.0 (36)
from
$125
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

San Diego, USA

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation
5.0 (359)
from
$125
San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

San Diego, USA

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation
5.0 (85)
from
$125
Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky …More

Cabo San Lucas, Mexico

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky...

2 hours 30 minutes Free Cancellation
4.9 (17)
from
$125
Luxury Camden Sailing Experience

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor …More

Camden, USA

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor...

2 hours Free Cancellation
4.9 (17)
from
$125
San Diego Sailing Sunset and Afternoon Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

La Jolla, USA

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation
5.0 (9)
from
$125
Sail Seattle's Iconic Lake Union All Year Around

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to …More

Seattle, USA

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to...

2 hours Free Cancellation
5.0 (2)
from
$125
Romantic Dinner Touring the Nichupté Lagoon in Galeón

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is …More

Cancun, Mexico

Love will fall at the foot of the Nichupté Lagoon, as you discover its most precious secrets aboard the Columbus Romantic Dinner Cruise. This is...

3 hours Free Cancellation
5.0 (1)
from
$125
Dinner and show pirate night Hook in Cancun

Captain Hook’s Cancun tour offers an immersive experience unlike any in the area. More than just a cruise, it’s a dinner-show aboard an authentic 18th …More

Cancun, Mexico

Captain Hook’s Cancun tour offers an immersive experience unlike any in the area. More than just a cruise, it’s a dinner-show aboard an authentic 18th...

3 hours Free Cancellation
5.0 (2)
from
$125
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area …More

Panama City Beach, USA

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hours Free Cancellation
5.0 (3)
from
$124
Key West Dolphin Watch and Sunset Sail on Catamaran

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of …More

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

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

3 hours Free Cancellation
4.9 (40)
from
$124
Private Sailing Tour of Bodega Bay

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as …More

Napa & Sonoma, USA

This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as...

3 hours Free Cancellation
4.9 (91)
from
$123
Vancouver Sailing Tour - Learn the Ropes

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience …More

Vancouver, Canada

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience...

3 hours Free Cancellation
5.0 (2)
from
$121
Private Isla Mujeres Adventure & Free Time

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with …More

Playa del Carmen, Mexico

If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with...

6 hours Hotel pickup offered Free Cancellation
4.9 (9)
from
$120
Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

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 …More

Special Offer
Special Offer
Key West, USA

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...

6 hours (approx.)
4.9 (558)
$125
$120

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