Top North America Sailing Trips

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around...

Rise and Shine! There’s no better way to start your day in Newport than sailing past stunning sights while sipping a cool Mimosa aboard the...

Choices for your private occasion in a catamaran different sizes as well as Yachts depending on the amount of people and your experience. Also inclusive...

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory,...

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll...

Sail along the coast, enjoying the refreshing breeze in this exclusive sailing experience. Marvel at the beauty that makes Los Cabos a unique destination and...

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

Embark on the adventure of knowing the Bacalar lagoon. Aboard our ranger 26, the Taan'ik (facing the wind in the Mayan language), we are at...

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...

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment...

If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April...

Why This is a "Must-Do" Experience: Unrivaled Views: Get up close to the Arch and see the diverse marine life, including tropical fish and occasionally...

Enjoy a sailing experience like no other as you cruise Lake Champlain guided entirely by the wind—making every journey unique. Along the way, your captain...

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...

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience,...

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran,...

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see...

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and...