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 →

San Salvador Spanish Galleon Adventure Day Sail with General Admission

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. …More

San Diego, USA

4.1 (7)

San Salvador Spanish Galleon Adventure Day Sail with General Admission

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon....

4 hours

4.1 (7)

from
$85

Sail To Isla Mujeres By Catamaran Buffet And Drinks Included

Escape to paradise on this all-inclusive catamaran tour to Isla Mujeres, one of the Caribbean's most beautiful destinations. Sail across crystal-clear waters, enjoy unlimited drinks …More

Punta Sam, Mexico

3.0 (1)

Sail To Isla Mujeres By Catamaran Buffet And Drinks Included

Escape to paradise on this all-inclusive catamaran tour to Isla Mujeres, one of the Caribbean's most beautiful destinations. Sail across crystal-clear waters, enjoy unlimited drinks...

8 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$85

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

Discover the perfect Caribbean getaway on this all-inclusive catamaran adventure from Cancun to Isla Mujeres. Dive into an unforgettable snorkeling experience at the beautiful El …More

Punta Sam, Mexico

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

Discover the perfect Caribbean getaway on this all-inclusive catamaran adventure from Cancun to Isla Mujeres. Dive into an unforgettable snorkeling experience at the beautiful El...

8 hours Hotel pickup offered Free Cancellation

from
$85

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to …More

Oahu, USA

4.6 (10)

Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutes Free Cancellation

4.6 (10)

from
$85

Evening Colors Sunset Sail Tour in Seattle

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut …More

Seattle, USA

4.9 (726)

Evening Colors Sunset Sail Tour in Seattle

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut...

2 hours Free Cancellation

4.9 (726)

from
$88

Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy …More

Key West, USA

5.0 (5)

Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy...

1 hour 45 minutes Free Cancellation

5.0 (5)

from
$89

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or …More

Key West, USA

5.0 (10)

Key West Nighttime Full Moon Sail

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or...

1 hour 30 minutes Free Cancellation

5.0 (10)

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

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service …More

Punta Sam, Mexico

4.7 (88)

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service...

2 hours Hotel pickup offered Free Cancellation

4.7 (88)

from
$89

Isla Mujeres Plus by Albatros Catamarans

Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise …More

Cancun, Mexico

4.0 (211)

Isla Mujeres Plus by Albatros Catamarans

Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise...

7 hours Free Cancellation

4.0 (211)

from
$89

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while …More

Long Island, USA

5.0 (18)

Sunset Sail Aboard the Liberty Clipper

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while...

2 hours Free Cancellation

5.0 (18)

from
$89

Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the …More

Cancun, Mexico

5.0 (1)

Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the...

7 hours Free Cancellation

5.0 (1)

from
$89

Cabo Sunset Tour with Dinner and Open Bar

If you are in Cabo wanting to make memories that last a lifetime then this is the one for you. Watch the sunset as it …More

Cabo San Lucas, Mexico

5.0 (1)

Cabo Sunset Tour with Dinner and Open Bar

If you are in Cabo wanting to make memories that last a lifetime then this is the one for you. Watch the sunset as it...

2 hours 15 minutes Free Cancellation

5.0 (1)

from
$89

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

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

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