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: 2.5 hr Sailboat Tour aboard Orion's Child Private sailing tour of Bacalar Lagoon Private Sailboat + Captain for a Day Experience Sunset & Dolphin Sightseeing Sail Aboard the Lazy Daze Catamaran Private Hilton Head Sunset Sailing Tour with Dolphin Watching

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 →

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

Bacalar Private Sailing Boat Tour with Pick up

Discover the beauty of Bacalar’s Lagoon of Seven Colors on an unforgettable private sailing adventure, with convenient hotel pick-up and drop-off included. Explore some of …More

Bacalar, Mexico

5.0 (35)

Bacalar Private Sailing Boat Tour with Pick up

Discover the beauty of Bacalar’s Lagoon of Seven Colors on an unforgettable private sailing adventure, with convenient hotel pick-up and drop-off included. Explore some of...

3 hours Hotel pickup offered Free Cancellation

5.0 (35)

from
$204

Private sunrise sailboat with breakfast on board

A unique activity in Bacalar that you won't find with anyone else. Enjoy an incredible breakfast at dawn, guided by a team of professionals who …More

Bacalar, Mexico

5.0 (57)

Private sunrise sailboat with breakfast on board

A unique activity in Bacalar that you won't find with anyone else. Enjoy an incredible breakfast at dawn, guided by a team of professionals who...

3 hours 15 minutes Free Cancellation

5.0 (57)

from
$200

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

Private Eco-Tour on a Recreational Catamaran with Kayaks Included

Sailing Fun! Enjoy an easy and relaxing ride through the most beautiful places in the lagoon aboard a recreational catamaran. During this tour, you will …More

Bacalar, Mexico

5.0 (57)

Private Eco-Tour on a Recreational Catamaran with Kayaks Included

Sailing Fun! Enjoy an easy and relaxing ride through the most beautiful places in the lagoon aboard a recreational catamaran. During this tour, you will...

3 hours Free Cancellation

5.0 (57)

from
$199

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to …More

St Augustine, USA

4.8 (8)

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to...

2 hours Free Cancellation

4.8 (8)

from
$199

Sunset Sailing Cruise on San Diego Bay | Champagne Included

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group …More

San Diego, USA

5.0 (1)

Sunset Sailing Cruise on San Diego Bay | Champagne Included

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$199

Adults Only Luxury- Cabo San Lucas Romantic Sunset Sail

Finding the perfect sunset cruise in Los Cabos can be overwhelming. This experience is designed to be your easy choice, offering the perfect blend of …More

San Jose del Cabo, Mexico

3.0 (1)

Adults Only Luxury- Cabo San Lucas Romantic Sunset Sail

Finding the perfect sunset cruise in Los Cabos can be overwhelming. This experience is designed to be your easy choice, offering the perfect blend of...

3 hours Hotel pickup offered

3.0 (1)

from
$199

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

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

Snorkel Sail Adventure off Ka'anapali Beach in Maui aboard Gemini

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, …More

Lahaina, USA

5.0 (55)

Snorkel Sail Adventure off Ka'anapali Beach in Maui aboard Gemini

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hours Free Cancellation

5.0 (55)

from
$193

Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People

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

5.0 (1)

Tour Sailing 4 Hours Private Magic Bacalar Up to 7 People

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

5.0 (1)

from
$193

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, …More

Maui, USA

5.0 (141)

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours Free Cancellation

5.0 (141)

from
$193

Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.

WELCOME to Mayan Paradise - Immersive Experience - We are Liz (Curious Biologist), Daniel (Sustainable Velarista - Tips from Mayan Culture), and we will guide …More

Bacalar, Mexico

5.0 (44)

Sail 4hr in the most SECRET Spot of Bacalar and Beach Club.

WELCOME to Mayan Paradise - Immersive Experience - We are Liz (Curious Biologist), Daniel (Sustainable Velarista - Tips from Mayan Culture), and we will guide...

4 hours Free Cancellation

5.0 (44)

from
$193

Private sailing tour in the seven colors lagoon in Bacalar

You will enjoy a wonderful tour visiting the highlights of the Bacalar Lagoon. Harnessing the power of nature, you will navigate to the Pirates' Channel, …More

Bacalar, Mexico

4.9 (21)

Private sailing tour in the seven colors lagoon in Bacalar

You will enjoy a wonderful tour visiting the highlights of the Bacalar Lagoon. Harnessing the power of nature, you will navigate to the Pirates' Channel,...

3 hours Free Cancellation

4.9 (21)

from
$193

Private Tour: Bacalar Lagoon Tour Sailboat or Pontoon Adventure

Experience the stunning Bacalar Lagoon like never before with my exclusive private tour. Whether you choose the elegance of a sailboat or the comfort of …More

Costa Maya, Mexico

5.0 (4)

Private Tour: Bacalar Lagoon Tour Sailboat or Pontoon Adventure

Experience the stunning Bacalar Lagoon like never before with my exclusive private tour. Whether you choose the elegance of a sailboat or the comfort of...

5 hours Free Cancellation

5.0 (4)

from
$190

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our …More

Big Island of Hawaii, USA

5.0 (713)

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our...

4 hours Free Cancellation

5.0 (713)

from
$189

Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy …More

Big Island of Hawaii, USA

4.8 (109)

Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy...

3 hours Free Cancellation

4.8 (109)

from
$189