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: Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar Whale Watching Sailboat Tour in San Jose del Cabo Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Chesapeake Bay Private Cruise Key West Christmas Cruise with Live Band and Drinks

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 →

Whale-Watching Pirate Ship Cruise in Los Cabos

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in …More

Cabo San Lucas, Mexico

4.8 (109)

Whale-Watching Pirate Ship Cruise in Los Cabos

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in...

2 hours Free Cancellation

4.8 (109)

from
$99

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

Romantic Dinner in the Spanish Galeon with Sax in Cancun

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner? …More

Punta Sam, Mexico

4.4 (7)

Romantic Dinner in the Spanish Galeon with Sax in Cancun

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner?...

4 hours Hotel pickup offered Free Cancellation

4.4 (7)

from
$99

Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun

If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable …More

Punta Sam, Mexico

4.7 (3)

Enjoy The Spanish Galeon with a Romantic Night Dinner in Cancun

If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (3)

from
$99

Amazing Romantic Dinner In Cancun On A Spanish Galeon

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

Punta Sam, Mexico

5.0 (1)

Amazing Romantic Dinner In Cancun On A Spanish Galeon

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

3 hours Free Cancellation

5.0 (1)

from
$99

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly …More

Santa Monica, USA

4.7 (3)

Marina Del Rey Luxury Yacht Experience

Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly...

1 hour 15 minutes Free Cancellation

4.7 (3)

from
$99

Los Cabos Sunset Cruise: Iconic Views, Group Joy, Food and Drink

What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience travelers dream about. You’ll sail right up to the legendary Arch, …More

Cabo San Lucas, Mexico

5.0 (1)

Los Cabos Sunset Cruise: Iconic Views, Group Joy, Food and Drink

What Makes This Tour Unique? This isn’t just another sunset cruise—it’s the Cabo experience travelers dream about. You’ll sail right up to the legendary Arch,...

2 hours 15 minutes Free Cancellation

5.0 (1)

from
$99

Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

Key West, USA

5.0 (5)

Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$98

Let's Go Sail the York River in Gloucester Point Virginia

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the …More

5.0 (168)

Let's Go Sail the York River in Gloucester Point Virginia

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the...

2 hours 30 minutes Free Cancellation

5.0 (168)

from
$96

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a …More

Fort Lauderdale, USA

5.0 (401)

Fort Lauderdale Sailing Charter

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a...

4 hours Free Cancellation

5.0 (401)

from
$95

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

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

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience …More

Monterey & Carmel, USA

4.8 (62)

Sunset Sailing Cruise in Monterey Bay

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience...

1 hour 30 minutes Free Cancellation

4.8 (62)

from
$95

Public Sunset Sailing Cruise on Lake Champlain

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack …More

Burlington, USA

5.0 (23)

Public Sunset Sailing Cruise on Lake Champlain

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack...

2 hours

5.0 (23)

from
$95

Public Sunset Picnic Boat Cruise on Lake Champlain

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food …More

Burlington, USA

5.0 (7)

Public Sunset Picnic Boat Cruise on Lake Champlain

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food...

2 hours Free Cancellation

5.0 (7)

from
$95

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)

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...

7 hours Free Cancellation

4.6 (72)

from
$94

Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos

Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-seekers with our two exciting options: Option 1: All-Inclusive …More

Playa del Carmen, Mexico

3.9 (65)

Isla Mujeres, Snorkel, Lunch & Pick Up from Cancun to P.Morelos

Prepare for a thrilling day trip to Isla Mujeres from Cancun, tailored for nature lovers and fun-seekers with our two exciting options: Option 1: All-Inclusive...

10 to 11 hours Hotel pickup offered Free Cancellation

3.9 (65)

from
$94