Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 693 Sailing Trips activities in North America. Sort by Popularity. - Page 7New York City Sunset Jazz Sail aboard Clipper City
Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantage point of the harbor. Order a drink from our full bar as we raise canvas and leave Manhattan behind as the melodies of live jazz ... More

New York City Sunset Jazz Sail aboard Clipper City
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North America
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Exellent102 reviews4.4
Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantag....
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

Key West Sunset Snorkel with Unlimited Draft Beer & Wine
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North America
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Superb124 reviews4.6
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Come Sailing with us at Navy Pier: Sail Beautiful 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: Sail Beautiful Lake Michigan
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North America
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Superb60 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
New York City Sailboat Day Cruise to the Statue of Liberty
Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides a... More
Private Tour

New York City Sailboat Day Cruise to the Statue of Liberty
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North America
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Superb126 reviews4.9
Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted sc....
Private Tour
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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North America
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Superb138 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Tour
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 your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailbo... More
Private Tour

Newport Sunset Sail on Schooner Adirondack
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North America
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Superb40 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Private Tour
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 in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More
Private Tour

JFarwell Sunset Wine and Cheese Yacht Sailing
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North America
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Superb121 reviews4.9
Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....
Private Tour
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 marine life. Then, head to a secluded sandbank—a hidden gem pe... More
Private Tour

HipHop Catamaran Party from Cancun to Isla Mujeres
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North America
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Very Good6 reviews3.8
Unlike other tours, we combine adventure, relaxation, and an unforgettable party vibe. Start by snor....
Private Tour
El Cielo Reef Snorkeling tour by Catamaran
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More
Private Tour

El Cielo Reef Snorkeling tour by Catamaran
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North America
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Exellent274 reviews4.4
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....
Private Tour
Seattle Sailing Experience BYOB
This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are perfectly at home on Puget Sound. Sit back and relax as our trained crew hoist the sails and turn... More
Private Tour

Seattle Sailing Experience BYOB
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North America
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Superb92 reviews5
This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to ra....
Private Tour
4-Hour St. Pete Pier to Egmont Key Experience by Ferry
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More
Private Tour

4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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North America
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Superb291 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
Private Tour
FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More
Private Tour

FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
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North America
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Good11 reviews3.4
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....
Private Tour
Luxury Snorkel Adventure in Cabo
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More
Private Tour

Luxury Snorkel Adventure in Cabo
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North America
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Superb41 reviews4.8
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....
Private Tour
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 and fill up the whole boat!). Sit back, relax and enjoy the com... More
Private Tour

Small-Group San Diego Afternoon Sailing Excursion
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North America
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Superb504 reviews5
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
Private Tour
Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More
Private Tour

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb108 reviews4.9
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....
Private Tour
Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More
Private Tour

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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North America
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Superb302 reviews4.7
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
Private Tour
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More
Private Tour

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
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North America
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Superb177 reviews5
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....
Private Tour
9am 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

9am Turtle Canyon Snorkel Adventure
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North America
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Superb254 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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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Superb226 reviews4.6
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Private Tour
Newport Sunset Sail on Classic Sailboat
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More
Private Tour

Newport Sunset Sail on Classic Sailboat
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North America
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Superb21 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour