Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Speedboat and Snorkeling Adventure in Cancun Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Paddle at Dawn with visit to Cenotes and Islands Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor Sunrise by Paddle or Kayak with Floating Picnic View all Tours with Instant Confirmation →

Q: Got any more North America trip ideas?

We sure do. Check out our curated lists of hand-picked North America Tours. Top 10 North America 2026 Senior-friendly tours North America The best tours and activities for culture lovers in North America Top Day Trips from North America Things to do in North America this summer View all North America Trip Ideas →

Q: What are the most popular styles of Tours and Activities in North America?

Based on our sales data over the past year, the most popular styles of tours and activities in North America are: North America Luxury & Special Occasions North America Luxury Tours North America Tours & Sightseeing North America Kid Friendly North America Cruises, Sailing & Water Tours View all tour styles in North America →

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

5.0 (359)

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...

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

5.0 (85)

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...

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

4.9 (17)

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...

2 hours 30 minutes 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

5.0 (9)

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...

2 hours 30 minutes Free Cancellation

5.0 (9)

from
$125

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

4.9 (17)

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...

2 hours Free Cancellation

4.9 (17)

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

5.0 (2)

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...

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

5.0 (1)

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...

3 hours Free Cancellation

5.0 (1)

from
$125

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

Maui, USA

5.0 (226)

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...

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

5.0 (46)

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...

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

Maui, USA

4.8 (42)

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...

2 hours 30 minutes Free Cancellation

4.8 (42)

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

San Diego, USA

5.0 (638)

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...

3 hours Free Cancellation

5.0 (638)

from
$127

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

Key West, USA

4.9 (1,704)

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...

2 hours Free Cancellation

4.9 (1,704)

from
$127

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

4.9 (14)

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...

3 hours

4.9 (14)

from
$127

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

4.8 (422)

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...

2 hours Free Cancellation

4.8 (422)

from
$129

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views …More

San Francisco, USA

4.9 (52)

Golden Gate Bridge Sailing Tour

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views...

2 hours Free Cancellation

4.9 (52)

from
$129

Isla Mujeres Platinum by Albatros Catamarans

The Platinum Tour is unique because it offers an unparalleled experience of luxury, adventure, and relaxation in the Mexican Caribbean. What sets it apart is …More

Cancun, Mexico

4.4 (245)

Isla Mujeres Platinum by Albatros Catamarans

The Platinum Tour is unique because it offers an unparalleled experience of luxury, adventure, and relaxation in the Mexican Caribbean. What sets it apart is...

7 hours Free Cancellation

4.4 (245)

from
$129

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily …More

Cancun, Mexico

4.0 (10)

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily...

7 hours Hotel pickup offered Free Cancellation

4.0 (10)

from
$129

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. …More

Oahu, USA

4.8 (142)

2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours Free Cancellation

4.8 (142)

from
$130

2.5 hr Sailboat Tour aboard Orion's Child

Cool Shore Excursions Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. …More

Fort Myers, USA

5.0 (93)

2.5 hr Sailboat Tour aboard Orion's Child

Cool Shore Excursions Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel....

2 hours 30 minutes Free Cancellation

5.0 (93)

from
$130

4-Hour Sailing Adventure on The Strait of Juan de Fuca

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water …More