Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Speedboat and Snorkeling Adventure in Cancun Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Paddle at Dawn with visit to Cenotes and Islands Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor Sunrise by Paddle or Kayak with Floating Picnic View all Tours with Instant Confirmation →

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 →

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 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

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: 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

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

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

Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu …More

Oahu, USA

4.8 (6)

Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu...

2 hours Free Cancellation

4.8 (6)

from
$92

This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's …More

Halifax, Canada

5.0 (30)

Halifax Summer Breeze Sail

This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's...

2 hours Free Cancellation

5.0 (30)

from
$93

Enjoy the beauty of sailing in the waters of the magical town through a sailboat ride in Velero in Valle de Bravo, crossing the lake …More

5.0 (16)

Private Sailing Tour in Valle de Bravo

Enjoy the beauty of sailing in the waters of the magical town through a sailboat ride in Velero in Valle de Bravo, crossing the lake...

1 hour

5.0 (16)

from
$93

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

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

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