Top North America Sailing Trips

Q: What are the best options for North America Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best North America Sailing Trips are: Private Sailboat Charter from San Pedro: Port of Los Angeles Cabo Sunset Tour with Dinner and Open Bar Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People Private Sailing Charters in Halifax Harbour Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Q: What are the best kid-friendly options for North America Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly North America Sailing Trips are: 3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya 4th of July Fireworks on Clipper City Tall Ship #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson The Nāpali Coast Snorkel Excursion Pirate Ship by Day View all kid-friendly Tours →

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Private Luxury Yacht Charter aboard Tu Enamorado Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp Luxury Yacht 58 ft for up to 20 people 4 hrs Private Cruise Swim with Dolphin Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs View all Tours with Instant Confirmation →

Q: I need a ride! Which North America Sailing Trips have Hotel Pickup?

No problem. These North America Sailing Trips include Hotel Pickup: Private Cruise Swim with Dolphin Private Romantic Sailing Sunset Experience Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Private Luxury Sunset Sail in San Jose del Cabo Marina Private Luxury Yacht Charter with Snorkeling in Los Cabos View all Tours with Hotel Pickup →

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 →

Excursion to Reefs in a transparent boat from Cancun

It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine life, in addition, the colors …More

Cancun, Mexico

4.3 (8)

Excursion to Reefs in a transparent boat from Cancun

It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine life, in addition, the colors...

1 hour 15 minutes Free Cancellation

4.3 (8)

from
$52

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as …More

Oahu, USA

5.0 (279)

Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes Free Cancellation

5.0 (279)

from
$51

Shared Snorkeling Tour Playa El Cielo in Cozumel

We offer a tour with all security measures Our Guides are fully certified Visits to the Palancar reefs, Arrecife Colombia, as well as the visit …More

Cozumel, Mexico

4.9 (125)

Shared Snorkeling Tour Playa El Cielo in Cozumel

We offer a tour with all security measures Our Guides are fully certified Visits to the Palancar reefs, Arrecife Colombia, as well as the visit...

4 hours Free Cancellation

4.9 (125)

from
$51

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide …More

Cocoa Beach, USA

4.9 (244)

Dolphin Adventure Sail in Cocoa Beach

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide...

2 hours Free Cancellation

4.9 (244)

from
$51

Rise and Shine! There’s no better way to start your day in Newport than sailing past stunning sights while sipping a cool Mimosa aboard the …More

Newport, USA

5.0 (15)

Schooner Aquidneck Morning Mimosa Sail

Rise and Shine! There’s no better way to start your day in Newport than sailing past stunning sights while sipping a cool Mimosa aboard the...

1 hour 40 minutes Free Cancellation

5.0 (15)

from
$50

Catamaran Sailing to Isla Mujeres From Cancun

Discover the Mexican Caribbean aboard a luxury catamaran, with premium service, personalized attention and spectacular scenery. At Oceanix Nauticos, we take you to explore the …More

Cancun, Mexico

4.5 (6)

Catamaran Sailing to Isla Mujeres From Cancun

Discover the Mexican Caribbean aboard a luxury catamaran, with premium service, personalized attention and spectacular scenery. At Oceanix Nauticos, we take you to explore the...

5 hours Free Cancellation

4.5 (6)

from
$50

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Shore Excursions's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from …More

Oahu, USA

4.9 (1,799)

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Shore Excursions's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from...

2 hours Free Cancellation

4.9 (1,799)

from
$50

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far …More

Oahu, USA

4.9 (264)

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours Free Cancellation

4.9 (264)

from
$50

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

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

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk …More

Hilton Head Island, USA

4.9 (720)

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk...

1 hour 30 minutes Free Cancellation

4.9 (720)

from
$48

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

Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the …More

Oahu, USA

4.8 (600)

Waikiki Sunset Cruise: 2-Hour Catamaran & Swim Adventure in Oahu

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...

2 hours Free Cancellation

4.8 (600)

from
$47

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

Group Tour in Lagoon of Bacalar with snacks and drinks

Meet your guide at the meeting point and board the boat. Set sail and enjoy the views of the lagoon. See the shorelines, cenotes, birds, …More

Bacalar, Mexico

5.0 (1)

Group Tour in Lagoon of Bacalar with snacks and drinks

Meet your guide at the meeting point and board the boat. Set sail and enjoy the views of the lagoon. See the shorelines, cenotes, birds,...

3 hours Free Cancellation

5.0 (1)

from
$47

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

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, …More

Oahu, USA

4.9 (257)

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes Free Cancellation

4.9 (257)

from
$45

Sailing Tour through the Laguna de los Siete Colores

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical …More

Bacalar, Mexico

5.0 (1,108)

Sailing Tour through the Laguna de los Siete Colores

Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical...

3 hours Free Cancellation

5.0 (1,108)

from
$45

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

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point …More

Oahu, USA

4.8 (76)

Waikiki Sunset Cruise from Oahu

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point...

2 hours Free Cancellation

4.8 (76)

from
$45