Top North America Sailing Trips

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 →

Snorkel Sail Adventure off Ka'anapali Beach in Maui aboard Gemini

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, …More

Lahaina, USA

5.0 (55)

Snorkel Sail Adventure off Ka'anapali Beach in Maui aboard Gemini

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hours Free Cancellation

5.0 (55)

from
$193

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by …More

San Diego, USA

4.9 (55)

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by...

2 hours 30 minutes Free Cancellation

4.9 (55)

from
$55

The Boat People Cruise Private Harbor Cruises

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an …More

Newport Beach, USA

5.0 (53)

The Boat People Cruise Private Harbor Cruises

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an...

1 hour 30 minutes

5.0 (53)

from
$100

As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out …More

Puerto Escondido, Mexico

4.9 (53)

Chacahua Afternoon Journey

As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out...

5 hours Hotel pickup offered Free Cancellation

4.9 (53)

from
$83

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

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails …More

Big Island of Hawaii, USA

4.8 (51)

Kona Tradewind Catamaran Day Sail

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails...

1 hour 30 minutes Free Cancellation

4.8 (51)

from
$89

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying …More

Halifax, Canada

4.8 (51)

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying...

1 hour 30 minutes Free Cancellation

4.8 (51)

from
$72

Okanagan Lake Sailing Tour from Penticton & Naramata BC

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We …More

Kelowna & Okanagan Valley, Canada

5.0 (51)

Okanagan Lake Sailing Tour from Penticton & Naramata BC

Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We...

4 hours Free Cancellation

5.0 (51)

from
$183

Private Sailing Charter on San Diego Bay

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural …More

San Diego, USA

4.9 (50)

Private Sailing Charter on San Diego Bay

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural...

3 hours Free Cancellation

4.9 (50)

from
$499

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for …More

Key West, USA

4.9 (50)

Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...

2 hours

4.9 (50)

from
$693

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests, …More

Burlington, USA

5.0 (49)

Public Daytime Sailing Cruise

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests,...

2 hours

5.0 (49)

from
$85

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean …More

Santa Monica, USA

4.8 (49)

Private Therapy Sailing Adventure

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean...

2 to 3 hours

4.8 (49)

from
$400

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

Sunset Dolphin Sail Aboard the Daydreams Sailboat

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. …More

Panama City Beach, USA

5.0 (46)

Sunset Dolphin Sail Aboard the Daydreams Sailboat

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island....

2 hours Free Cancellation

5.0 (46)

from
$107

Private Sunset and Eco Tour in Destin Up to 18 Guests

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset …More

Destin, USA

5.0 (45)

Private Sunset and Eco Tour in Destin Up to 18 Guests

Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset...

1 hour 30 minutes Free Cancellation

5.0 (45)

from
$450

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind …More

Monterey & Carmel, USA

4.8 (45)

Catamaran Sailing Cruise in Monterey

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind...

1 hour 15 minutes Free Cancellation

4.8 (45)

from
$65

Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.

WELCOME to Mayan Paradise - Immersive Experience - We are Liz (Curious Biologist), Daniel (Sustainable Velarista - Tips from Mayan Culture), and we will guide …More

Bacalar, Mexico

5.0 (44)

Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.

WELCOME to Mayan Paradise - Immersive Experience - We are Liz (Curious Biologist), Daniel (Sustainable Velarista - Tips from Mayan Culture), and we will guide...

4 hours Free Cancellation

5.0 (44)

from
$193

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a …More

New York City, USA

5.0 (43)

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a...

1 hour Free Cancellation

5.0 (43)

from
$350

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

Spectacular Sunset Sail on San Diego Bay

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas …More

La Jolla, USA

5.0 (41)

Spectacular Sunset Sail on San Diego Bay

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas...

2 hours Free Cancellation

5.0 (41)

from
$150