Top North America Sailing Trips

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 →

Los Cabos Seasonal Whale Watch and Snorkel Tour

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the …More

San Jose del Cabo, Mexico

4.9 (19)

Los Cabos Seasonal Whale Watch and Snorkel Tour

Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the...

4 hours Hotel pickup offered Free Cancellation

4.9 (19)

from
$239

Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a …More

Miami, USA

5.0 (19)

Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a...

3 hours Free Cancellation

5.0 (19)

from
$899

6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and Stromatolites.

Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modify the route to discover areas far from tourism. 6 …More

Bacalar, Mexico

5.0 (19)

6hrs of Sailing in Bacalar Lagoon: discover Cenotes, Islands and Stromatolites.

Ideal for adventurers and sailing lovers! Explore the most emblematic points of the lagoon, or modify the route to discover areas far from tourism. 6...

6 hours Free Cancellation

5.0 (19)

from
$468

Experience Oceanside Sailing with Whales and dolphins!

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the …More

Carlsbad, USA

5.0 (18)

Experience Oceanside Sailing with Whales and dolphins!

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the...

2 hours Free Cancellation

5.0 (18)

from
$150

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

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA

5.0 (18)

Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours Free Cancellation

5.0 (18)

from
$180

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from …More

Oahu, USA

4.9 (18)

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hours Free Cancellation

4.9 (18)

from
$70

JFarwell Private Yacht Wine & Cheese Sunset Sail

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine …More

Halifax, Canada

4.9 (18)

JFarwell Private Yacht Wine & Cheese Sunset Sail

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine...

2 hours 30 minutes Free Cancellation

4.9 (18)

from
$146

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

Private Catamaran Ride in Los Cabos Food and Bar Outdoors

Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail in front of the Cabo San Lucas Arch while enjoying open bar …More

Cabo San Lucas, Mexico

5.0 (18)

Private Catamaran Ride in Los Cabos Food and Bar Outdoors

Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail in front of the Cabo San Lucas Arch while enjoying open bar...

3 hours Free Cancellation

5.0 (18)

from
$1,687

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Oahu, USA

5.0 (17)

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours Free Cancellation

5.0 (17)

from
$300

2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel …More

5.0 (17)

2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel...

2 hours Free Cancellation

5.0 (17)

from
$245

Cabo Private Catamaran: Arch, Sea Lions and Beach for Up to 12

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Cortez. Our well-trained bilingual crew will …More

Cabo San Lucas, Mexico

5.0 (17)

Cabo Private Catamaran: Arch, Sea Lions and Beach for Up to 12

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Cortez. Our well-trained bilingual crew will...

3 hours 30 minutes Free Cancellation

5.0 (17)

from
$840

Clear Boat to Cabo Lands End, The Arch and more

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take …More

Cabo San Lucas, Mexico

4.9 (17)

Clear Boat to Cabo Lands End, The Arch and more

Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take...

1 hour Free Cancellation

4.9 (17)

from
$39

Slow Sailing Bacalar Experience with snack and drinks

Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered mainly by the wind. By choosing to sail, you help …More

Bacalar, Mexico

4.9 (17)

Slow Sailing Bacalar Experience with snack and drinks

Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered mainly by the wind. By choosing to sail, you help...

3 hours Free Cancellation

4.9 (17)

from
$37

Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky …More

Cabo San Lucas, Mexico

4.9 (17)

Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales

Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky...

2 hours 30 minutes Free Cancellation

4.9 (17)

from
$125

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor …More

Camden, USA

4.9 (17)

Luxury Camden Sailing Experience

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor...

2 hours Free Cancellation

4.9 (17)

from
$125

Private Luxury Adventure Tours in Cabo San Lucas

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2 …More

Cabo San Lucas, Mexico

4.9 (16)

Private Luxury Adventure Tours in Cabo San Lucas

Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2...

2 hours Hotel pickup offered Free Cancellation

4.9 (16)

from
$149

Whale Watching with Lunch and transportation included

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of …More

Cabo San Lucas, Mexico

4.8 (16)

Whale Watching with Lunch and transportation included

Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of...

3 hours Hotel pickup offered Free Cancellation

4.8 (16)

from
$110