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 →

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you! …More

Cancun, Mexico

4.7 (68)

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure

Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you!...

5 hours Free Cancellation

4.7 (68)

from
$60

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA

4.7 (67)

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (67)

from
$197

Miami Private Yacht Celebration Cruise with Captain

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is …More

Miami, USA

4.7 (52)

Miami Private Yacht Celebration Cruise with Captain

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is...

4 hours Free Cancellation

4.7 (52)

from
$799

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA

4.5 (50)

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes Free Cancellation

4.5 (50)

from
$110

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp

Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres …More

Cancun, Mexico

4.7 (46)

Private Catamaran from Cancun to Isla Mujeres | For up to 40 pp

Enjoy a day sailing through the Caribbean Sea aboard on a 46 ft Catamaran. Decide if you want to go on a trip to Isla Mujeres...

4 to 7 hours Free Cancellation

4.7 (46)

from
$2,231

Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun

Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectacular day in the crystal-clear waters of the Mexican …More

Cancun, Mexico

4.4 (46)

Trimaran La Lupita,Sail Away to Isla Mujeres from Cancun

Sail away through Caribbean waters with the best crew in Cancun aboard "La Lupita.¨ Enjoy a spectacular day in the crystal-clear waters of the Mexican...

7 hours Free Cancellation

4.4 (46)

from
$60

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the …More

Oahu, USA

4.5 (44)

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes Free Cancellation

4.5 (44)

from
$120

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s …More

4.5 (41)

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s...

2 hours Free Cancellation

4.5 (41)

from
$65

Romantic Sunset Dinner Cruising Experience

Sail away on Cancun's only romantic dinner cruise, a magnificent way to pamper your loved one or to enjoy a classy supper with your friends. …More

Cancun, Mexico

4.5 (38)

Romantic Sunset Dinner Cruising Experience

Sail away on Cancun's only romantic dinner cruise, a magnificent way to pamper your loved one or to enjoy a classy supper with your friends....

3 hours Free Cancellation

4.5 (38)

from
$100

Pirate Ship Premium Dinner Cruise with Show

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing …More

Puerto Vallarta, Mexico

4.7 (31)

Pirate Ship Premium Dinner Cruise with Show

While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing...

4 hours Free Cancellation

4.7 (31)

from
$181

Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE!

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring …More

Oahu, USA

4.7 (30)

Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE!

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hour Free Cancellation

4.7 (30)

from
$60

Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp

Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop …More

Cancun, Mexico

4.6 (28)

Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp

Experience the Caribbean like never before with our sophisticated seafarer guiding you through its pristine waters. During this tour, you will have one snorkel stop...

4 hours Free Cancellation

4.6 (28)

from
$5,290

Isla Mujeres by Xcaret All Inclusive Catamaran Cruise

Experience Isla Mujeres the Xcaret way on a luxurious catamaran tour across the Caribbean Sea. Start your day snorkeling at the vibrant El Meco reef, …More

Punta Sam, Mexico

4.7 (25)

Isla Mujeres by Xcaret All Inclusive Catamaran Cruise

Experience Isla Mujeres the Xcaret way on a luxurious catamaran tour across the Caribbean Sea. Start your day snorkeling at the vibrant El Meco reef,...

7 hours Hotel pickup offered Free Cancellation

4.7 (25)

from
$119

Romantic Dinner on a Spanish Galeon in Cancun

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is …More

Punta Sam, Mexico

4.4 (22)

Romantic Dinner on a Spanish Galeon in Cancun

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.4 (22)

from
$99

The Finest Private Yacht Experience in Cabo

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some …More

Cabo San Lucas, Mexico

4.7 (22)

The Finest Private Yacht Experience in Cabo

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some...

3 hours Free Cancellation

4.7 (22)

from
$740

Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursion, departing from Puerto Vallarta. Even those without experience …More

Puerto Vallarta, Mexico

4.4 (21)

Hidden Beach - Marietas Islands

Spend the day exploring and enjoying the marine life of the Marietas Islands on this 5-hour excursion, departing from Puerto Vallarta. Even those without experience...

5 hours

4.4 (21)

from
$205

Pirate Ship Show and Dinner, Premium Openbar in Cozumel

5:30 pm First pirate show and dinner tour in Cozumel with more than 15 years of giving joy, excitement and delicious dinners to visitors and …More

Cozumel, Mexico

4.7 (19)

Pirate Ship Show and Dinner, Premium Openbar in Cozumel

5:30 pm First pirate show and dinner tour in Cozumel with more than 15 years of giving joy, excitement and delicious dinners to visitors and...

3 hours 30 minutes Free Cancellation

4.7 (19)

from
$90

Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. …More

Key West, USA

4.7 (19)

Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass....

8 hours Free Cancellation

4.7 (19)

from
$107

Catamaran in Cozumel with snorkeling at El Cielo and open Bar

Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard with open arms—and an open bar. Margaritas, beer, soft drinks, …More

Cozumel, Mexico

4.7 (17)

Catamaran in Cozumel with snorkeling at El Cielo and open Bar

Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard with open arms—and an open bar. Margaritas, beer, soft drinks,...

5 hours Free Cancellation

4.7 (17)

from
$39

Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager to explore the basics of sailing. Guided by experienced instructors on our …More

Toronto, Canada

4.7 (15)

3hr Discover Sailing Adventure

Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager to explore the basics of sailing. Guided by experienced instructors on our...

3 hours Free Cancellation

4.7 (15)

from
$197