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 →

Tall Ship Silva Sailing Cruise Ft. a Live Musician

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our …More

Halifax, Canada

4.4 (337)

Tall Ship Silva Sailing Cruise Ft. a Live Musician

A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our...

2 hours Free Cancellation

4.4 (337)

from
$47

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot …More

Cabo San Lucas, Mexico

4.6 (299)

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot...

3 hours Free Cancellation

4.6 (299)

from
$199

Cozumel ClearBoat Adventure with Snorkeling

Perfect For Families and Couples! Hope on aboard a unique experience in the only 100% transparent boat in the World. This is definitely a one …More

Cozumel, Mexico

4.4 (296)

Cozumel ClearBoat Adventure with Snorkeling

Perfect For Families and Couples! Hope on aboard a unique experience in the only 100% transparent boat in the World. This is definitely a one...

1 hour 35 minutes Free Cancellation

4.4 (296)

from
$45

Starfish, Stingrays and the Cozumel Turtle Sanctuary Snorkel Tour

People’s Choice- Best snorkeling tour! immerse in a world of Adventure and admire Spectacular marine life on this Cozumel Snorkeling trip. Enjoy 3 of the …More

Cozumel, Mexico

4.5 (277)

Starfish, Stingrays and the Cozumel Turtle Sanctuary Snorkel Tour

People’s Choice- Best snorkeling tour! immerse in a world of Adventure and admire Spectacular marine life on this Cozumel Snorkeling trip. Enjoy 3 of the...

4 hours Free Cancellation

4.5 (277)

from
$59

El Cielo Cozumel Snorkel trip by Catamaran

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head …More

Cozumel, Mexico

4.5 (251)

El Cielo Cozumel Snorkel trip by Catamaran

TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head...

4 hours Free Cancellation

4.5 (251)

from
$95

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

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this …More

Portland, USA

4.6 (242)

Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this...

2 hours Free Cancellation

4.6 (242)

from
$101

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty …More

Honolulu, USA

4.7 (242)

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hours Free Cancellation

4.7 (242)

from
$79

Half-Day Luxury Sailing Experience in Tulum with Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so …More

Tulum, Mexico

4.5 (225)

Half-Day Luxury Sailing Experience in Tulum with Open Bar

This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so...

4 hours Hotel pickup offered Free Cancellation

4.5 (225)

from
$149

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of …More

Cancun, Mexico

4.6 (159)

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club

Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of...

7 hours 30 minutes Free Cancellation

4.6 (159)

from
$89

Escape from the Rock! Cruise around Alcatraz

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an …More

San Francisco, USA

4.5 (146)

Escape from the Rock! Cruise around Alcatraz

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an...

1 hour 30 minutes Free Cancellation

4.5 (146)

from
$48

Luxury Whale Watch Cruise to The Arch Los Cabos

Whale season is from mid-December thru mid-April, you can book this tour all year round but to travel only during the Whale Season (Dec 15 …More

San Jose del Cabo, Mexico

4.7 (137)

Luxury Whale Watch Cruise to The Arch Los Cabos

Whale season is from mid-December thru mid-April, you can book this tour all year round but to travel only during the Whale Season (Dec 15...

2 hours Hotel pickup offered Free Cancellation

4.7 (137)

from
$95

Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Baltimore, USA

4.7 (118)

Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes Free Cancellation

4.7 (118)

from
$65

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to …More

Punta Sam, Mexico

4.7 (108)

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (108)

from
$99

Halifax Sunset Cruise Ft. a Live Musician

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature …More

Halifax, Canada

4.7 (98)

Halifax Sunset Cruise Ft. a Live Musician

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature...

1 hour 30 minutes Free Cancellation

4.7 (98)

from
$43

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Maui, USA

4.7 (90)

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours Free Cancellation

4.7 (90)

from
$148

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service …More

Punta Sam, Mexico

4.7 (88)

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service...

2 hours Hotel pickup offered Free Cancellation

4.7 (88)

from
$89

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA

4.6 (87)

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours Free Cancellation

4.6 (87)

from
$57

Luxury Catamaran tour to Isla Mujeres with transportation from Playa del Carmen

Because it's an amazing place where you can relax in the beautiful Caribbean Sea, we offer you a personal assistance from our incredible crew that …More

Cancun, Mexico

4.6 (72)