Top North America Sailing Trips

631 Results
JFarwell Sunset Wine and Cheese Yacht Sailing

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved …More

Halifax, Canada

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved...

2 hours 30 minutes Free Cancellation
5.0 (171)
from
$146
Let's Go Sail the York River in Gloucester Point Virginia

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the …More

Likely to Sell Out
Likely to Sell Out

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the...

2 hours 30 minutes Free Cancellation
5.0 (168)
from
$96
Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board …More

Camden, USA

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board...

2 hours Free Cancellation
4.9 (167)
from
$73
Tulum: Snorkeling and Private Sailing Tour

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spectacular view of the Tulum ruins …More

Tulum, Mexico

We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spectacular view of the Tulum ruins...

1 hour 15 minutes Free Cancellation
5.0 (164)
from
$60
Daytime Sailing Along San Diego's Skyline

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor...

2 hours Free Cancellation
5.0 (161)
from
$99
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

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
JFarwell Adventure Yacht Sailing in the Halifax Harbour

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged …More

Halifax, Canada

Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged...

1 hour 30 minutes Free Cancellation
5.0 (159)
from
$80
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hours Free Cancellation
4.9 (157)
from
$69
Marco Island Private Catamaran Sailing Tour

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at …More

Likely to Sell Out
Likely to Sell Out
Naples, USA

It’s your own private sail with Captain Nick, the owner of Easy Breezy Charters. Breezy is a 30-foot Stiletto sailing catamaran with open nets at...

2 hours
5.0 (154)
from
$450
Sailboat tour across the seven colors lagoon in Bacalar

Discover the seven colors lagoon and the most iconics points inside (Chanel of the pirates, cenotes and bird sanctuary) . You will sail and swim …More

Bacalar, Mexico

Discover the seven colors lagoon and the most iconics points inside (Chanel of the pirates, cenotes and bird sanctuary) . You will sail and swim...

3 hours Free Cancellation
5.0 (152)
from
$41
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 …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

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
2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours Free Cancellation
4.8 (142)
from
$130
Waikiki Turtle Snorkeling Adventure(8am)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the...

3 hours Hotel pickup offered Free Cancellation
4.9 (141)
from
$100
Newport Sunset Sail on Schooner Adirondack

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during …More

Newport, USA

Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during...

1 hour 30 minutes
4.8 (140)
from
$74
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, …More

Maui, USA

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours Free Cancellation
5.0 (140)
from
$193
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical …More

Maui, USA

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours Free Cancellation
5.0 (135)
from
$269
El Cielo Cozumel snorkel by Private Boat

Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private …More

Cozumel, Mexico

Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private...

4 hours Free Cancellation
4.8 (133)
from
$625
Mexico City: Xochimilco at sunrise + Breakfast and transportation

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for …More

Mexico City, Mexico

Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for...

5 hours Hotel pickup offered Free Cancellation
5.0 (130)
from
$160
Private Luxury 42ft Sailing with Snorkeling in Los Cabos

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful …More

Likely to Sell Out
Likely to Sell Out
Cabo San Lucas, Mexico

Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful...

3 hours Free Cancellation
5.0 (129)
from
$872
Polynesian Canoe Sunset Sail

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

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (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 (128)
from
$250

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