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 →

Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer

Welcome to the super combo tour, the best activity in Mexico and the Caribbean. You will start the trip in the town of Puerto Morelos. …More

Punta Sam, Mexico

5.0 (2)

Super Combo ATV in Cancun with Zipline, Snorkel, Cenote, transfer

Welcome to the super combo tour, the best activity in Mexico and the Caribbean. You will start the trip in the town of Puerto Morelos....

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$110

San Diego Wild Life Sailing Adventure Private

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon. …More

San Diego, USA

5.0 (2)

San Diego Wild Life Sailing Adventure Private

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon....

4 hours Free Cancellation

5.0 (2)

from
$503

Dinner and show pirate night Hook in Cancun

Captain Hook’s Cancun tour offers an immersive experience unlike any in the area. More than just a cruise, it’s a dinner-show aboard an authentic 18th …More

Cancun, Mexico

5.0 (2)

Dinner and show pirate night Hook in Cancun

Captain Hook’s Cancun tour offers an immersive experience unlike any in the area. More than just a cruise, it’s a dinner-show aboard an authentic 18th...

3 hours Free Cancellation

5.0 (2)

from
$125

Private Sunset Sail of NYC Skyline and Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your …More

Jersey City, USA

5.0 (2)

Private Sunset Sail of NYC Skyline and Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your...

2 hours Free Cancellation

5.0 (2)

from
$800

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of …More

San Jose del Cabo, Mexico

5.0 (2)

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of...

2 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$135

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and …More

Puerto Vallarta, Mexico

5.0 (2)

Pirate Ship by Day

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and...

6 hours

5.0 (2)

from
$280

Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the …More

Puerto Vallarta, Mexico

5.0 (2)

Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta

Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with us you will know the...

6 hours

5.0 (2)

from
$935

Sailing Charter around Vancouver Harbour Private Tour

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and …More

Vancouver, Canada

5.0 (2)

Sailing Charter around Vancouver Harbour Private Tour

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and...

6 hours Free Cancellation

5.0 (2)

from
$2,342

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and …More

Long Island, USA

5.0 (2)

Oyster Bay Two Hour Sailing Experience

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and...

2 hours Free Cancellation

5.0 (2)

from
$650

Vancouver Sailing Tour - Learn the Ropes

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience …More

Vancouver, Canada

5.0 (2)

Vancouver Sailing Tour - Learn the Ropes

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience...

3 hours Free Cancellation

5.0 (2)

from
$121

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them …More

Maui, USA

5.0 (2)

Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them...

2 hours Free Cancellation

5.0 (2)

from
$164

Sail Seattle's Iconic Lake Union All Year Around

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to …More

Seattle, USA

5.0 (2)

Sail Seattle's Iconic Lake Union All Year Around

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to...

2 hours Free Cancellation

5.0 (2)

from
$125

Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, …More

San Diego, USA

5.0 (2)

Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines,...

2 hours

5.0 (2)

from
$800

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque …More

Kennebunkport, USA

5.0 (2)

Relaxing Saco River Public Sunset Sail

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque...

2 hours Free Cancellation

5.0 (2)

from
$149

Private Sailing Charters on La Vie Dansante

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht …More

Daytona Beach, USA

5.0 (2)

Private Sailing Charters on La Vie Dansante

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht...

3 hours Free Cancellation

5.0 (2)

from
$800

Private Sailing Charters: Island Adventures and Sunset Cruises

Set sail on a private charter with Water Music Charters, offering an unforgettable experience along Folly Beach and Charleston's vibrant waters. With over 25 years …More

Folly Beach, USA

5.0 (2)

Private Sailing Charters: Island Adventures and Sunset Cruises

Set sail on a private charter with Water Music Charters, offering an unforgettable experience along Folly Beach and Charleston's vibrant waters. With over 25 years...

2 hours Free Cancellation

5.0 (2)

from
$350

Maui: Catamaran Sunset Whale Watch with Cocktails

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets …More

Maui, USA

5.0 (2)

Maui: Catamaran Sunset Whale Watch with Cocktails

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets...

2 hours Free Cancellation

5.0 (2)

from
$189

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone …More

5.0 (2)

Sunset Sailboat Cruise on Winyah Bay

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone...

2 hours Free Cancellation

5.0 (2)

from
$145

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

Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply …More

Destin, USA

5.0 (1)

Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply...

3 hours

5.0 (1)

from
$79