Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 753 Sailing Trips activities in North America. Sort by Popularity. - Page 34Land’s End Sunset Cruise – Open Bar & Tacos Included
Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, with approximately 40 minutes spent at each captivating point along the route. As you glide through the stunning landscapes of Cab... More
Land’s End Sunset Cruise – Open Bar & Tacos Included
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North America
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Superb1 review5
Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....
Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar
Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded group tours, this 2-hour cruise is exclusive to your party, giving you space to relax, celebrate, and enjoy the views in privacy. Sai... More
Private Tour
Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar
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North America
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Superb1 review5
Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded grou....
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
Private Tour
Ultimate Miami Boat Party with Free Open Bar & Live DJ
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North America
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Superb1 review5
Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience.....
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
Likely to Sell Out Waikiki private Day Tour and Sunset sail for couples
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North America
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Superb17 reviews5
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....
Private Tour
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More
Private Tour
Likely to Sell Out Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
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North America
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Superb1 review5
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become par....
Private Tour
Private Luxury Yacht in Miami
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s top destinations—Haulover Sandbar, Oleta River State Park, Biscayne Bay & Sands Key, and Raccoon Island—in style! This sleek 3... More
Private Tour
Likely to Sell Out Private Luxury Yacht in Miami
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North America
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Superb1 review5
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s ....
Private Tour
Jungle Tour
This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through Nichupte Lagoon and snorkel in the El Angel coral reef. Choose to take the driver’s seat or ride shotgun in a 2-seat speedboat a... More
Private Tour
Likely to Sell Out Jungle Tour
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North America
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Superb1 review5
This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through ....
Private Tour
Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic of the Mexican Caribbean, snorkeling in Isla Mujeres and Cancun's ... More
Private Tour
Likely to Sell Out Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....
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North America
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Superb1 review5
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....
Private Tour
3 Hours Private Afternoon Sail in Saint Petersburg
A private 42' Bali 4.2 catamaran charter for up to 6 people, featuring a custom route for cruising and sailing. Enjoy a comfortable trip with cushioned seating, shaded areas, music, and soft drinks. Tailor your day with optional a... More
Private Tour
Likely to Sell Out 3 Hours Private Afternoon Sail in Saint Petersburg
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North America
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Superb1 review5
A private 42' Bali 4.2 catamaran charter for up to 6 people, featuring a custom route for cruising a....
Private Tour
San Diego Private Yacht Charter on a Classic Sailboat 6 Guests
Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is a classic 41-ft Friendship sloop skippered by a USCG-licensed captain with 55 years of sailing exp... More
Private Tour
Likely to Sell Out San Diego Private Yacht Charter on a Classic Sailboat 6 Guests
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North America
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Superb4 reviews5
Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Ph....
Private Tour
Midmorning Whale Watch from Lahaina Harbor
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More
Private Tour
Likely to Sell Out Midmorning Whale Watch from Lahaina Harbor
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North America
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Good3 reviews3.3
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise
Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on board sound system with Tiki-Oki, and the friendliest most fun captains around. You'll be sure to have... More
Private Tour
Likely to Sell Out Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise
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North America
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Superb2 reviews5
Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, b....
Private Tour
Private Sailboat Charter from San Pedro: Port of Los Angeles
Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis (39ft) sailing yacht, perfect for couples or small groups looking for a memorable out... More
Private Tour
Likely to Sell Out Private Sailboat Charter from San Pedro: Port of Los Angeles
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North America
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Superb2 reviews5
Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a su....
Private Tour
Luxury Yacht 58 ft for up to 20 people 4 hrs
Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de Banderas. You will enjoy every moment and every place in this tropical paradise. L... More
Private Tour
Likely to Sell Out Luxury Yacht 58 ft for up to 20 people 4 hrs
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North America
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Superb2 reviews5
Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard ....
Private Tour
Cabo San Lucas Luxury Yacht to El Arco with Snorkeling Stop
Set sail from the lively Marina Cabo San Lucas aboard your private 45ft luxury yacht, perfect for up to 8 guests. A friendly crew welcomes you with a safety briefing before you glide past the stunning El Arco and Lover’s Beach. ... More
Private Tour
Likely to Sell Out Cabo San Lucas Luxury Yacht to El Arco with Snorkeling Stop
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North America
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Superb2 reviews5
Set sail from the lively Marina Cabo San Lucas aboard your private 45ft luxury yacht, perfect for up....
Private Tour
Original Cruisin Tikis Snorkeling Safari
The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart of Destin Harbor while you soak in the scenery and the good vibes... More
Private Tour
Likely to Sell Out Original Cruisin Tikis Snorkeling Safari
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North America
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Superb2 reviews5
The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your ....
Private Tour
JFarwell Sip & Sail aboard the Reverie
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More
Private Tour
Likely to Sell Out JFarwell Sip & Sail aboard the Reverie
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North America
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Superb19 reviews5
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....
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
Likely to Sell Out Private Afternoon Snorkel with Sunset Sail in Key West
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North America
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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
Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours
Enjoy an unforgettable day at sea with our exclusive 9-hour luxury yacht tour in Cancun. This full-day experience offers the perfect combination of relaxation, comfort, and first-class service. As the day winds down, guests will b... More
Private Tour
Likely to Sell Out Luxury 40' Van Dutch Private Yacht Experience – Cancun 4 Hours
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North America
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Superb22 reviews4.8
Enjoy an unforgettable day at sea with our exclusive 9-hour luxury yacht tour in Cancun. This full-d....
Private Tour
Cabo San Lucas Private Custom Snorkel or Sunset Adventure
First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew will make sure that you have a drink in your hand within minutes. You will get to see the world famous Arch, Lover's Beach, Divorce... More
Private Tour
Likely to Sell Out Cabo San Lucas Private Custom Snorkel or Sunset Adventure
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North America
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Superb1 review5
First, you meet on the dock to meet the best crew that Cabo has! You will get boarded and the crew w....
Private Tour