Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 11Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More

Sailing on Historic Schooner Yacht in Salem, MA
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North America
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Superb124 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
2 hours - Private Sunset Sail along Historic Bay Front
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More
Private Tour

2 hours - Private Sunset Sail along Historic Bay Front
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North America
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Superb27 reviews4.9
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....
Private Tour
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 to make for a peaceful and exciting cruise on the bay. On the way out of t... More
Private Tour

Catamaran Sailing Cruise in Monterey
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North America
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Superb11 reviews4.9
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....
Private Tour
Mexico City: Xochimilco at sunrise + Breakfast and transportation
Xochimilco is a protected nature reserve unique in the world, full of history and tradition, where the ancient Aztecs once sailed, harvested and lived Explore Xochimilco in a different way: in a cayuco where a local person will pa... More
Private Tour

Mexico City: Xochimilco at sunrise + Breakfast and transportation
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North America
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Superb70 reviews5
Xochimilco is a protected nature reserve unique in the world, full of history and tradition, where t....
Private Tour
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 to be as hands on with the sailing process as they would... More
Private Tour

JFarwell Adventure Yacht Sailing in the Halifax Harbour
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North America
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Superb122 reviews4.9
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
Private Tour
Private Kelowna Sailing Cruise on Okanagan Lake
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More
Private Tour

Private Kelowna Sailing Cruise on Okanagan Lake
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North America
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Superb32 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
Private Tour

Tour Isla Mujeres excursion in Collective Transparent Boat
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North America
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Superb38 reviews4.9
We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our ....
Private Tour
Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More
Private Tour

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
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North America
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Superb24 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More
Private Tour

Schooner Applejack Sunset Sail Tour in Boothbay Harbor
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North America
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Superb19 reviews4.9
Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
Private Tour
Halifax Summer Breeze Sail
This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's Island, Pier 21, Point Pleasant Park, and more. This laid-back sail is designed for you to en... More
Private Tour

Halifax Summer Breeze Sail
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North America
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Superb11 reviews5
This two-hour sail allows you to soak in the sights along the coastline so close to our urban center....
Private Tour
1.5-Hour San Francisco Bay Sailing Tour
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More
Private Tour

1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb377 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
Private Tour
New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise
Relax on a comfortable, shaded 2-hour Intracoastal Waterway Sightseeing Cruise aboard Motunui, a 50-ft open breeze catamaran with cushioned seating, tables, and deck-level restrooms. Enjoy a fully narrated tour showcasing Palm Bea... More
Private Tour

New Historic Palm Beach Sightseeing on Motunui Catamaran Cruise
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North America
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Superb377 reviews4.8
Relax on a comfortable, shaded 2-hour Intracoastal Waterway Sightseeing Cruise aboard Motunui, a 50-....
Private Tour
Suncoast Sailing's Day Sailing Experience!
Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More
Private Tour

Suncoast Sailing's Day Sailing Experience!
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North America
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Superb101 reviews4.9
Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....
Private Tour
Key West Sailing & Snorkeling: A Reef Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More
Private Tour

Key West Sailing & Snorkeling: A Reef Adventure
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North America
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Superb129 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Private Tour
Deluxe Turtle Snorkeling Escapade at Waikiki
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
Private Tour

Deluxe Turtle Snorkeling Escapade at Waikiki
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North America
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Superb5 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
JFarwell Moonlight Yacht Cruise from Halifax Waterfront
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More
Private Tour

JFarwell Moonlight Yacht Cruise from Halifax Waterfront
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North America
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Superb36 reviews4.8
Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....
Private Tour
Private Catamaran Sunset Sail in Waikiki
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More
Private Tour

Private Catamaran Sunset Sail in Waikiki
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North America
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Superb6 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More
Private Tour

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
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North America
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Superb513 reviews5
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....
Private Tour
Private Family Catamaran From Isla Mujeres
Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all day when you can do it in less time? Affordable Private Catamaran, avoid crowded vessels Half-day fun catamaran, with a guided sn... More
Private Tour

Private Family Catamaran From Isla Mujeres
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North America
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Superb513 reviews5
Enjoy our “Lite Sailing Charters” Sail through the wonderful Bay of Isla Mujeres! Why invest all....
Private Tour
Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More
Private Tour

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
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North America
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Superb28 reviews5
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....
Private Tour