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 Sailing Charter: Up to 24 Passengers Private Luxury Catamaran Cancun to Isla Mujeres | For up to 30 pp Private Sunset Tour in Marina La Cruz by Yacht LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl Afternoon Ali'i Adventure

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 →

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, …More

Chicago, USA

4.8 (30)

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy,...

1 hour 15 minutes

4.8 (30)

from
$91

New York Sunset Schooner Cruise on the Hudson River

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known …More

New York City, USA

4.9 (224)

New York Sunset Schooner Cruise on the Hudson River

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known...

2 hours Free Cancellation

4.9 (224)

from
$90

New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic …More

New York City, USA

4.9 (75)

New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic...

2 hours Free Cancellation

4.9 (75)

from
$90

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA

4.8 (62)

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour Free Cancellation

4.8 (62)

from
$90

Cabo San Lucas Sunset Sailing Shared Cruise

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San …More

Cabo San Lucas, Mexico

4.9 (799)

Cabo San Lucas Sunset Sailing Shared Cruise

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San...

2 hours Free Cancellation

4.9 (799)

from
$90

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), …More

Honolulu, USA

4.9 (693)

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

3 hours Free Cancellation

4.9 (693)

from
$90

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin …More

Cabo San Lucas, Mexico

5.0 (815)

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin...

3 hours Free Cancellation

5.0 (815)

from
$90

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

Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with …More

Oahu, USA

4.9 (2,419)

Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with...

2 hours Free Cancellation

4.9 (2,419)

from
$90

Adults Only Party Cruise to Isla Mujeres Free one-way pickup

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful …More

Cancun, Mexico

4.0 (177)

Adults Only Party Cruise to Isla Mujeres Free one-way pickup

Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful...

7 hours Hotel pickup offered Free Cancellation

4.0 (177)

from
$90

Full-Day Sailing Isla Mujeres with complimentary Transportation

Set sail on a fun-filled 7-hour adventure along the beautiful Cancun coast, perfect for the whole family! Your exciting day starts with complimentary transportation from …More

Cancun, Mexico

3.0 (3)

Full-Day Sailing Isla Mujeres with complimentary Transportation

Set sail on a fun-filled 7-hour adventure along the beautiful Cancun coast, perfect for the whole family! Your exciting day starts with complimentary transportation from...

7 hours Hotel pickup offered Free Cancellation

3.0 (3)

from
$90

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines …More

Key West, USA

4.8 (750)

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...

2 hours 30 minutes (approx.) Free Cancellation

4.8 (750)

from
$90

Tiki Pub Glow Party Cruise (Adults only)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic …More

Fort Myers, USA

4.9 (18)

Tiki Pub Glow Party Cruise (Adults only)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic...

2 hours Free Cancellation

4.9 (18)

from
$90

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island …More

Oahu, USA

4.8 (1,757)

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island...

2 hours 30 minutes Free Cancellation

4.8 (1,757)

from
$90

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk. …More

Wilmington, USA

5.0 (218)

Sailing Charters in Wilmington

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk....

2 hours Free Cancellation

5.0 (218)

from
$89

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party …More

Fort Myers, USA

4.9 (59)

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party...

3 hours Free Cancellation

4.9 (59)

from
$89

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails …More

Big Island of Hawaii, USA

4.8 (51)

Kona Tradewind Catamaran Day Sail

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails...

1 hour 30 minutes Free Cancellation

4.8 (51)

from
$89

Original Cruisin Tikis Snorkeling Safari

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart …More

Destin, USA

5.0 (1)

Original Cruisin Tikis Snorkeling Safari

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart...

3 hours

5.0 (1)

from
$89

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious …More

Tulum, Mexico

4.7 (407)

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious...

2 hours Hotel pickup offered Free Cancellation

4.7 (407)

from
$89

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