Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 416 Sailing Trips activities in USA. Sort by Popularity. - Page 20Chesapeake Bay Private Cruise
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hul... More
Private Tour

Chesapeake Bay Private Cruise
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USA
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Exellent7 reviews4.4
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guy....
Private Tour
Private Charter Snorkel Sail Adventure off Kaanapali Beach
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘H... More
Private Tour

Private Charter Snorkel Sail Adventure off Kaanapali Beach
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USA
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Exellent7 reviews4.4
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
Private Tour
Private Swim and Sail Charter (Kewalo Harbor)
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). This experience is customization in its duration and activity *Viewing marine life is not guaranteed but we do... More
Private Tour

Private Swim and Sail Charter (Kewalo Harbor)
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USA
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Exellent7 reviews4.4
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....
Private Tour
Private Sunset Sail for Two
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More
Private Tour

Private Sunset Sail for Two
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USA
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Superb5 reviews5
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....
Private Tour
Akialoa Mā’alaea Sunset Sail
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More
Private Tour

Akialoa Mā’alaea Sunset Sail
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USA
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Superb5 reviews5
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....
Private Tour
Private Sailing Trip on Monterey Bay
Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline, soak in the vibrant wildlife, and enjoy the serene ocean atmosphe... More
Private Tour

Private Sailing Trip on Monterey Bay
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USA
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Superb5 reviews5
Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experienc....
Private Tour
Miami Sunset Sail with Premium Wine Tasting on a Luxury Sailboat
This is an intimate, open-air experience where time slows and every sip is savored. Guided by a seasoned wine connoisseur, you’ll explore the art of tasting, paired with a curated cheese and charcuterie board. Set aboard a 40-fo... More
Private Tour

Miami Sunset Sail with Premium Wine Tasting on a Luxury Sailboat
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USA
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Superb1 review5
This is an intimate, open-air experience where time slows and every sip is savored. Guided by a seas....
Private Tour
Private Long Island Sound Sailing Experience
Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast un... More
Private Tour

Private Long Island Sound Sailing Experience
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USA
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Superb1 review5
Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled ....
Private Tour
Sunset Sail in the Gulf of Mexico for up to 6 Guests
Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the sun dips below the horizon. For two and a half hours, enjoy the stunning views along Fort ... More
Private Tour

Sunset Sail in the Gulf of Mexico for up to 6 Guests
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USA
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Superb1 review5
Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the roman....
Private Tour
Themed and Special Event Cruise in Chesapeake Bay
This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversa... More
Private Tour

Themed and Special Event Cruise in Chesapeake Bay
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USA
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Superb1 review5
This cruise is a unique way to celebrate that special event in your life while cruising on your very....
Private Tour
San Diego Classic Sail Charter Private 3-Hour Experience
Enjoy the breathtaking San Diego coastline with our Classic Sail Charter, perfect for up to 6 guests. This 3-hour private sailing adventure offers the ideal blend of relaxation and exploration, with opportunities to see whales and... More
Private Tour

San Diego Classic Sail Charter Private 3-Hour Experience
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USA
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Superb1 review5
Enjoy the breathtaking San Diego coastline with our Classic Sail Charter, perfect for up to 6 guests....
Private Tour

Ultimate Miami Boat Party with Free Open Bar & Live DJ
Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience. This 3-hour Miami booze cruise offers a unique nightclub atmosphere on the water, complete with a FREE open bar serving unlimited... More
Free Cancellation
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Ultimate Miami Boat Party with Free Open Bar & Live DJ
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USA
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Superb1 review5
Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience.....
Free Cancellation
Private Tour
(Saving 13% )
Full Day and Sunset 9 Hour Private Catamaran in St. Pete
The ultimate 9-hour day: island-hopping to Egmont Key, Fort De Soto & Pass-a-Grille with time to swim, snorkel, paddle and lounge—then finish with a private golden-hour sail. Your group (up to 6) enjoys a 42’ Bali 4.2 with cap... More
Private Tour

Full Day and Sunset 9 Hour Private Catamaran in St. Pete
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USA
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Superb1 review5
The ultimate 9-hour day: island-hopping to Egmont Key, Fort De Soto & Pass-a-Grille with time to swi....
Private Tour
Private Luxury Sailboat Charters of Honolulu
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. While aboard this fully renovated 41' vessel, view the most treasured maritime life and landscapes of Oahu on a Day Sail and create gr... More
Private Tour

Private Luxury Sailboat Charters of Honolulu
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USA
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Superb1 review5
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. Whil....
Private Tour
Waikiki private Day Tour and Sunset sail for couples
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More
Private Tour

Waikiki private Day Tour and Sunset sail for couples
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USA
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Superb16 reviews5
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....
Private Tour
Half Day Sunset Catamaran Adventure
Escape the crowds aboard a private luxury catamaran! Sail through Tampa Bay to hidden islands like Egmont Key and Fort De Soto then end your day with a beautiful sunset. Swim, snorkel, and relax on floating mats while your captain... More
Private Tour

Half Day Sunset Catamaran Adventure
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USA
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Superb16 reviews5
Escape the crowds aboard a private luxury catamaran! Sail through Tampa Bay to hidden islands like E....
Private Tour
Private Afternoon Snorkel with Sunset Sail in Key West
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More
Private Tour

Private Afternoon Snorkel with Sunset Sail in Key West
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USA
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Superb4 reviews5
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....
Private Tour
Haunted Yacht Tour of San Diego Bay
Explore the mysterious waters of San Diego Bay on a haunted yacht tour that blends history with ghostly tales. This chilling adventure takes you past iconic landmarks like the USS Midway and Star of India, all while you enjoy the ... More
Private Tour

Haunted Yacht Tour of San Diego Bay
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USA
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Superb4 reviews5
Explore the mysterious waters of San Diego Bay on a haunted yacht tour that blends history with ghos....
Private Tour
Private Cruise Swim with Dolphin
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild Dolphins at the West Coast of Oahu. Learning about the ecosystem of wil... More
Private Tour

Private Cruise Swim with Dolphin
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USA
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Superb4 reviews5
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....
Private Tour
Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us. Our sa... More
Private Tour

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guest....
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USA
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Good2 reviews3.5
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San D....
Private Tour