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 →

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, …More

San Diego, USA

5.0 (1)

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers,...

2 hours

5.0 (1)

from
$800

6-Night Private Charter in Lake Clark National Park

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

5.0 (1)

6-Night Private Charter in Lake Clark National Park

Spend six nights and seven days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

7 days

5.0 (1)

from
$30,769

3-Night Private Charter in Lake Clark National Park

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group …More

5.0 (1)

3-Night Private Charter in Lake Clark National Park

Spend three nights and four days exploring Lake Clark National Park aboard Odyssey, our 50-foot sailing catamaran, with the yacht reserved for your private group...

4 days

5.0 (1)

from
$20,513

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with …More

Oahu, USA

5.0 (1)

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with...

2 hours Free Cancellation

5.0 (1)

from
$1,500

Sunset Sailing Tour of San Diego Bay up to 6 Guests

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers …More

San Diego, USA

5.0 (1)

Sunset Sailing Tour of San Diego Bay up to 6 Guests

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers...

2 hours

5.0 (1)

from
$800

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and …More

Oahu, USA

4.7 (2,102)

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

2 to 3 hours Free Cancellation

4.7 (2,102)

from
$170

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. …More

Cozumel, Mexico

4.5 (1,362)

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip....

4 hours Free Cancellation

4.5 (1,362)

from
$59

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never …More

Oahu, USA

4.7 (1,265)

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours Free Cancellation

4.7 (1,265)

from
$47

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall …More

Charleston, USA

4.6 (858)

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall...

1 hour 30 minutes Free Cancellation

4.6 (858)

from
$56

Key West Reef Morning Snorkeling with Breakfast and Mimosas

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light …More

Key West, USA

4.7 (694)

Key West Reef Morning Snorkeling with Breakfast and Mimosas

Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...

3 hours Free Cancellation

4.7 (694)

from
$54

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off …More

San Diego, USA

4.6 (681)

San Diego Whale Watching Cruise

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off...

3 hours 30 minutes Free Cancellation

4.6 (681)

from
$54

Pirate Ship Sunset Dinner and Show in Los Cabos

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that …More

Cabo San Lucas, Mexico

4.4 (681)

Pirate Ship Sunset Dinner and Show in Los Cabos

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that...

2 hours Free Cancellation

4.4 (681)

from
$99

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, …More

Toronto, Canada

4.4 (668)

Toronto Tall Ship Boat Cruise

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat,...

2 hours Free Cancellation

4.4 (668)

from
$37

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by …More

Hilton Head Island, USA

4.7 (564)

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by...

1 hour 30 minutes Free Cancellation

4.7 (564)

from
$55

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such …More

San Diego, USA

4.6 (549)

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such...

1 hour 30 minutes Free Cancellation

4.6 (549)

from
$38

Key West Afternoon Reef Snorkeling with Open Bar

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key …More

Key West, USA

4.6 (463)

Key West Afternoon Reef Snorkeling with Open Bar

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key...

3 hours Free Cancellation

4.6 (463)

from
$59

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • …More

Key West, USA

4.6 (432)

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hours Free Cancellation

4.6 (432)

from
$77

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious …More

Tulum, Mexico

4.7 (407)

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious...

2 hours Hotel pickup offered Free Cancellation

4.7 (407)

from
$89

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, …More

San Francisco, USA

4.6 (388)

San Francisco Bay Cruise

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island,...

1 hour Free Cancellation

4.6 (388)

from
$39

The Cool Shore ExcursionsDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous …More

Key West, USA

4.7 (345)

Key West Dolphin and Snorkel Experience

The Cool Shore ExcursionsDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous...

3 hours Free Cancellation

4.7 (345)

from
$70