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 →

Boat to Isla Espíritu Santo and Balandra

Nothing with sea lions and get to know Espíritu Santo Island and Balandra from another perspective accompanied by MARINE BIOLOGISTS guides on a super comfortable …More

La Paz, Mexico

4.9 (31)

Boat to Isla Espíritu Santo and Balandra

Nothing with sea lions and get to know Espíritu Santo Island and Balandra from another perspective accompanied by MARINE BIOLOGISTS guides on a super comfortable...

6 hours 30 minutes Free Cancellation

4.9 (31)

from
$143

This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's …More

Halifax, Canada

5.0 (30)

Halifax Summer Breeze Sail

This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's...

2 hours Free Cancellation

5.0 (30)

from
$93

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, …More

Chicago, USA

4.8 (30)

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy,...

1 hour 15 minutes

4.8 (30)

from
$91

Private Afternoon Harbor Cruise on Kismet for parties up to 20

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history …More

Charleston, USA

5.0 (30)

Private Afternoon Harbor Cruise on Kismet for parties up to 20

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history...

2 hours Free Cancellation

5.0 (30)

from
$1,549

Private Charleston Harbor Catamaran Sail

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a …More

Mount Pleasant, USA

5.0 (30)

Private Charleston Harbor Catamaran Sail

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a...

2 hours 30 minutes Free Cancellation

5.0 (30)

from
$950

Best Private Luxury Sunset Boat Tour in New York City - 2 Hour

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on …More

New York City, USA

5.0 (29)

Best Private Luxury Sunset Boat Tour in New York City - 2 Hour

Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on...

2 hours Free Cancellation

5.0 (29)

from
$600

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations …More

Maui, USA

4.9 (29)

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations...

2 hours Free Cancellation

4.9 (29)

from
$110

4-Hour Private Fishing Charter in the Riviera Maya

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully …More

Playa del Carmen, Mexico

5.0 (29)

4-Hour Private Fishing Charter in the Riviera Maya

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully...

4 hours

5.0 (29)

from
$750

Baltimore Evening Sail on the Summer Wind

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful …More

Baltimore, USA

5.0 (28)

Baltimore Evening Sail on the Summer Wind

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful...

1 hour 30 minutes Free Cancellation

5.0 (28)

from
$75

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA

5.0 (28)

Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours Free Cancellation

5.0 (28)

from
$170

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush …More

Bacalar, Mexico

4.8 (28)

Tour Sailing boat 4 Hours

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush...

4 hours Free Cancellation

4.8 (28)

from
$36

Cabo Private Sunset Sailing with Open Bar and Appetizers

Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personalized service and a relaxed atmosphere designed for comfort and exclusivity. The …More

Cabo San Lucas, Mexico

4.9 (27)

Cabo Private Sunset Sailing with Open Bar and Appetizers

Unlike crowded sightseeing boats, you will enjoy a private luxury sailboat experience with personalized service and a relaxed atmosphere designed for comfort and exclusivity. The...

2 hours 30 minutes Free Cancellation

4.9 (27)

from
$999

Private Sunset Sailing Cruise with Drinks in Puerto Vallarta

On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains …More

Puerto Vallarta, Mexico

5.0 (27)

Private Sunset Sailing Cruise with Drinks in Puerto Vallarta

On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains...

3 hours 30 minutes

5.0 (27)

from
$853

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a …More

Oahu, USA

5.0 (26)

Sunset sail Aboard Manakai Catamaran

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a...

1 hour 30 minutes Free Cancellation

5.0 (26)

from
$50

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

Vancouver Island, Canada

4.8 (26)

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...

4 hours Free Cancellation

4.8 (26)

from
$132

South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have …More

Oahu, USA

4.8 (26)

South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutes Free Cancellation

4.8 (26)

from
$48

Private Luxury Sunset Sail 39Ft Catamaran in Cozumel – 3 Hours

This is more than a sunset cruise it's a completely private evening aboard a spacious 39 foot Lagoon catamaran. Unlike shared sunset tours, your boat …More

Cozumel, Mexico

5.0 (26)

Private Luxury Sunset Sail 39Ft Catamaran in Cozumel – 3 Hours

This is more than a sunset cruise it's a completely private evening aboard a spacious 39 foot Lagoon catamaran. Unlike shared sunset tours, your boat...

3 hours Free Cancellation

5.0 (26)

from
$1,600

Discover with us the breathtaking lagoon of the seven colors. We tell you the true stories of the Pirates of the Caribbean. Learn more about …More

Bacalar, Mexico

5.0 (26)

Sail away! Hobie Cat Tour Bacalar

Discover with us the breathtaking lagoon of the seven colors. We tell you the true stories of the Pirates of the Caribbean. Learn more about...

3 hours Free Cancellation

5.0 (26)

from
$83

Luxury Sunset Sail on Serendipity Catamaran in Charleston

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local …More

Charleston, USA

5.0 (26)

Luxury Sunset Sail on Serendipity Catamaran in Charleston

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local...

2 hours Free Cancellation

5.0 (26)

from
$150