Top North America Sailing Trips

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,...

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...

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay...

Sail away on Cancun's only romantic dinner cruise, a magnificent way to pamper your loved one or to enjoy a classy supper with your friends....

Adults-Only Atmosphere Unlike typical family catamaran tours, this is exclusively for adults, creating a relaxed yet lively vibe perfect for couples, friends, and groups looking...

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the...

Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an...

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking...

Wind & Wine has been the #1 rated sunset sail on Cool Shore Excursions for over a decade. In our opinion, this is the best...

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from...

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with...

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that...

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...

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor...

Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to...

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium...

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate...