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: Pirate Ship by Day Private Luxury Sunset Sail in San Jose del Cabo Marina Private Boat Snorkeling & Beach: 5 Hours + 1 Free in Vallarta Sunset Cruise Tequila Tasting Sailing Charter around Vancouver Harbour Private Tour

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 →

St. Augustine Live Music Sail with Drinks & Sunset Option

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, …More

St Augustine, USA

4.8 (420)

St. Augustine Live Music Sail with Drinks & Sunset Option

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised,...

1 hour 45 minutes Free Cancellation

4.8 (420)

from
$66

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from …More

San Francisco, USA

4.9 (660)

San Francisco Bay Sailing Cruise

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from...

1 hour 30 minutes Free Cancellation

4.9 (660)

from
$65

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. …More

Cozumel, Mexico

4.5 (1,362)

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs

Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip....

4 hours Free Cancellation

4.5 (1,362)

from
$65

Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Baltimore, USA

4.7 (118)

Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes Free Cancellation

4.7 (118)

from
$65

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind …More

Monterey & Carmel, USA

4.8 (45)

Catamaran Sailing Cruise in Monterey

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind...

1 hour 15 minutes Free Cancellation

4.8 (45)

from
$65

Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the …More

Baltimore, USA

4.9 (72)

Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the...

1 hour 30 minutes Free Cancellation

4.9 (72)

from
$65

Baltimore Inner Harbor Sail on the Unforgettable

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Baltimore, USA

4.8 (25)

Baltimore Inner Harbor Sail on the Unforgettable

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes Free Cancellation

4.8 (25)

from
$65

Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide …More

Oahu, USA

5.0 (4)

Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide...

2 hours Free Cancellation

5.0 (4)

from
$65

HipHop Catamaran Party from Cancun to Isla Mujeres

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant …More

Cancun, Mexico

3.8 (18)

HipHop Catamaran Party from Cancun to Isla Mujeres

Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snorkeling in one of the Caribbean's top reefs, surrounded by vibrant...

8 hours Hotel pickup offered Free Cancellation

3.8 (18)

from
$65

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel (depends on weather) and spend …More

Cancun, Mexico

3.0 (4)

Catamaran and Snorkel in Isla Mujeres

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel (depends on weather) and spend...

7 hours Free Cancellation

3.0 (4)

from
$65

Suncoast Sailing's Day Sailing Experience!

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just …More

St Petersburg, USA

4.9 (118)

Suncoast Sailing's Day Sailing Experience!

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just...

2 hours 30 minutes Free Cancellation

4.9 (118)

from
$65

Windjammer Classic Day Sail from Camden, Maine

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations …More

Camden, USA

4.8 (461)

Windjammer Classic Day Sail from Camden, Maine

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations...

2 hours Free Cancellation

4.8 (461)

from
$65

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s …More

4.5 (41)

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s...

2 hours Free Cancellation

4.5 (41)

from
$65

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the …More

Mount Pleasant, USA

4.9 (101)

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the...

2 hours Free Cancellation

4.9 (101)

from
$63

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, …More

Mount Pleasant, USA

5.0 (11)

Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran,...

2 hours Free Cancellation

5.0 (11)

from
$63

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger …More

Destin, USA

4.8 (146)

Buccaneer Pirate Cruise in Destin

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger...

90 to 120 minutes Free Cancellation

4.8 (146)

from
$62

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic …More

Oahu, USA

4.9 (218)

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes Free Cancellation

4.9 (218)

from
$62

Newport Afternoon Sightseeing Sail on Classic Sailboat

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, …More

Newport, USA

4.9 (196)

Newport Afternoon Sightseeing Sail on Classic Sailboat

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail,...

1 hour 30 minutes

4.9 (196)

from
$61

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, …More

Newport, USA

4.9 (159)

Newport Sightseeing Day Sailing Experience on Schooner Adirondack

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges,...

1 hour 30 minutes

4.9 (159)

from
$61

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and …More

Newport, USA

4.8 (58)

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and...

1 hour 30 minutes

4.8 (58)

from
$61