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 Luxury Sunset Sail 39Ft Catamaran in Cozumel – 3 Hours Kona Afternoon Snorkel to Captain Cook Monument Polynesian Canoe Day Sail Golden Hour Escape: Private Sunset Sail in Coastal Maine Isla Mujeres Platinum by Albatros Catamarans

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 →

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the …More

Oahu, USA

4.5 (44)

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes Free Cancellation

4.5 (44)

from
$120

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as …More

San Diego, USA

5.0 (371)

Deluxe Sunset & Day Sail Small Group

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as...

2 hours 30 minutes Free Cancellation

5.0 (371)

from
$119

2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. …More

La Jolla, USA

5.0 (370)

2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail....

2 hours 30 minutes Free Cancellation

5.0 (370)

from
$119

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego …More

San Diego, USA

5.0 (82)

Deluxe Day Sail in San Diego

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego...

2 hours 30 minutes Free Cancellation

5.0 (82)

from
$119

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat …More

San Diego, USA

4.9 (204)

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat...

2 hours Free Cancellation

4.9 (204)

from
$119

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your …More

Key West, USA

4.9 (119)

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hours Free Cancellation

4.9 (119)

from
$119

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on …More

La Jolla, USA

5.0 (114)

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on...

2 hours 30 minutes Free Cancellation

5.0 (114)

from
$119

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way …More

Maui, USA

4.9 (90)

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours Free Cancellation

4.9 (90)

from
$119

Isla Mujeres by Xcaret All Inclusive Catamaran Cruise

Experience Isla Mujeres the Xcaret way on a luxurious catamaran tour across the Caribbean Sea. Start your day snorkeling at the vibrant El Meco reef, …More

Punta Sam, Mexico

4.7 (25)

Isla Mujeres by Xcaret All Inclusive Catamaran Cruise

Experience Isla Mujeres the Xcaret way on a luxurious catamaran tour across the Caribbean Sea. Start your day snorkeling at the vibrant El Meco reef,...

7 hours Hotel pickup offered Free Cancellation

4.7 (25)

from
$119

Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After …More

San Jose del Cabo, Mexico

5.0 (1)

Los Cabos Sunset Sailing Adventure

Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After...

2 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$119

Pirates Sunset Cruise at the Cabo San Lucas Arch

You'll love visiting the Arch of Cabo San Lucas! - Experience breathtaking views of the stunning sunset where the Sea of Cortez meets the Pacific …More

Cabo San Lucas, Mexico

3.5 (2)

Pirates Sunset Cruise at the Cabo San Lucas Arch

You'll love visiting the Arch of Cabo San Lucas! - Experience breathtaking views of the stunning sunset where the Sea of Cortez meets the Pacific...

2 hours Free Cancellation

3.5 (2)

from
$119

Small-Group San Diego Afternoon Sailing Excursion

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends …More

San Diego, USA

5.0 (568)

Small-Group San Diego Afternoon Sailing Excursion

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends...

3 hours Free Cancellation

5.0 (568)

from
$116

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered …More

5.0 (40)

Sailboat Cruise on Chesapeake Bay

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered...

2 hours 30 minutes Free Cancellation

5.0 (40)

from
$116

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought …More

Cabo San Lucas, Mexico

5.0 (3)

Sunset Cruise Tequila Tasting

Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought...

2 hours Free Cancellation

5.0 (3)

from
$115

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay …More

Pensacola, USA

5.0 (73)

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay...

2 hours Free Cancellation

5.0 (73)

from
$114

Vancouver Sailing Experience on a 50 Foot Sailboat

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for …More

Vancouver, Canada

5.0 (111)

Vancouver Sailing Experience on a 50 Foot Sailboat

I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for...

2 hours 30 minutes Free Cancellation

5.0 (111)

from
$114

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in …More

Chicago, USA

4.8 (24)

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in...

1 hour 30 minutes

4.8 (24)

from
$114

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and …More

Cabo San Lucas, Mexico

4.9 (3,661)

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and...

4 hours Hotel pickup offered Free Cancellation

4.9 (3,661)

from
$112

Romantic Sunset Dinner Cruise in Cancun with Open Bar

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner. …More

Cancun, Mexico

4.5 (14)

Romantic Sunset Dinner Cruise in Cancun with Open Bar

Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner....

2 hours 30 minutes Free Cancellation

4.5 (14)

from
$112

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA

4.8 (85)

Maui: Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours Free Cancellation

4.8 (85)

from
$112