Top North America Sailing Trips

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience...

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack...

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food...

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the...

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

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...

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...

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...

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...

Go whale-watching in Cabo San Lucas aboard a real pirate ship called the Bucaneer Queen. Sail the Pacific Ocean and the Sea of Cortez in...

Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is...

Don't wait any longer; this ultimate romance tour will enrich your life forever! Have you run out of ideas to celebrate love with your partner?...

If you are visiting Cancun or Riviera Maya is time to live the most romantic experience sailing on our Columbus cruise, and live an unforgettable...