Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 676 Sailing Trips activities in North America. Sort by Popularity. - Page 7Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Polynesian Canoe Sunset Sail
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North America
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Superb118 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Shallow Water Snorkeling and Dolphin Watching in Key West
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Shallow Water Snorkeling and Dolphin Watching in Key West
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North America
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Superb432 reviews4.6
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....
Pau Hana Sunset Cruise with the Whales
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More

Pau Hana Sunset Cruise with the Whales
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North America
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Superb45 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Sunset Sail Cruise in Key West
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North America
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Superb211 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More
Private Tour

Private Boat Tour Adventure in Miami Celeb Homes, Snorkeling, Fun
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North America
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Superb52 reviews4.8
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....
Private Tour
Sunset Sail on Historic Schooner in Key West
Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I return, Bea and I will sail around the world!" Step foot on the gorgeous teak... More
Private Tour

Sunset Sail on Historic Schooner in Key West
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North America
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Superb95 reviews4.8
Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then ....
Private Tour
Evening Colors Sunset Sail Tour in Seattle
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More
Private Tour

Evening Colors Sunset Sail Tour in Seattle
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North America
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Superb416 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Private Tour
Key West Sunset Snorkel with Unlimited Draft Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
Private Tour

Key West Sunset Snorkel with Unlimited Draft Beer & Wine
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North America
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Superb114 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Private Tour
Panama City Beach Sunset Sail on The Footloose Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More
Private Tour

Panama City Beach Sunset Sail on The Footloose Catamaran
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North America
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Superb387 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour
12pm Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
Private Tour

12pm Turtle Canyon Snorkel Adventure
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North America
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Superb265 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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
Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More
Private Tour

Small Group Waikiki Sunset Sailing Tour
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North America
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Superb86 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Private Tour
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More
Private Tour

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....
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North America
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Superb63 reviews4.7
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....
Private Tour
Boston Harbor Sunset Sail Tour
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More
Private Tour

Boston Harbor Sunset Sail Tour
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North America
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Superb62 reviews4.7
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Private Tour
2hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
Private Tour

2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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North America
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Superb48 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
Private Tour
Sailing Tour through the Laguna de los Siete Colores
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More
Private Tour

Sailing Tour through the Laguna de los Siete Colores
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North America
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Superb1,289 reviews5
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....
Private Tour
Portland Tall Ship Cruise on Casco Bay
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More
Private Tour

Portland Tall Ship Cruise on Casco Bay
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North America
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Exellent222 reviews4.5
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Private Tour
Sailing Tour through the Lagoon of the 7 Colors
Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee you excellent attention and service from our crew. Disconnect from the world ... More
Private Tour

Sailing Tour through the Lagoon of the 7 Colors
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North America
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Superb977 reviews4.9
Sail with people who share your passion for adventure! You will explore fascinating places along the....
Private Tour
Private boat for 6 hours with snorkeling & beaches in Puerto 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 best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make this rese... More
Private Tour

Private boat for 6 hours with snorkeling & beaches in Puerto Vall....
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North America
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Superb1 review5
Sail on a private trip aboard our 26-foot boat. Ideal for up to 8 passengers. We are sure that with ....
Private Tour
BYOB Waikiki Sunset Swim and Diamond Head Sailing
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
Private Tour

BYOB Waikiki Sunset Swim and Diamond Head Sailing
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North America
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Superb143 reviews5
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Private Tour