Sailing on a Five-Masted Ship
Published 12:33pm on 11 Mar 2026
As sailing enthusiasts, we have a wealth of opportunities to sail locally, regionally, and beyond. Our venues to sail vary in wind, climate, comfort, scenery, amenities and companions. In February, my partner Paul and I experienced sailing on a boat I've dreamed about since pre-Covid days: Windstar Cruises' Wind Surf. 
She's 615 feet long with her bowsprit, and 66 feet across her beam. Her five masts are equipped with seven self-furling computer-driven sails, so this was purely a pleasure trip! Although she has capacity for 342 guests, there were only 261, so the ship never felt crowded. Weighing 14,745 gross tons, her speed was not much different than a breezy day on the Columbia—with the sails and engines she maxed out at 15 knots. Wind Surf's masts reach 221 feet tall, when fully out the sails billow at 26,881 square feet. Our eight-night trip covered nearly 1,000 nautical miles.
Wind Surf is dwarfed by Enchantment of the Seas.
Sailing on this ship was different from my experiences sailing in flotillas. Most of our voyages were at night. The stars were brilliant and abundant; one evening a crew member guided us through the different constellations and talked about the historical practice of navigating by the night sky.
Most of our traveling was at night, allowing us to explore several islands, recreational options and cultural features during the day. Our cabin was spacious for a sailing ship, with 188 square feet, ample storage drawers and a private bath. Rather than featuring balconies, most rooms have porthole views. While the meals offered abundant and high-quality choices for any dietary preference, we both managed to lose weight on the trip!
The digital chart display is full-size, and the wheel is small--about one foot in diameter.
Although our excursions to snorkel coral reefs were canceled to protect them from wave damage, we had other opportunities to swim in the sea, ride horses, go cave tubing, and visit ancient ruins. During two days of sailing between Panama and Honduras we read books, attended chef cooking demonstrations and enjoyed live music.
For more tall ship adventures, check out Sail250 in Boston and SAIL4th250 in New York City in June and July. Tall ships are convening from around the world to celebrate our country's heritage. Many of the ships are offering tours or short sails. July 3rd the Class B tall ships sail on the East River, and July 4th the Class A Tall ships sail the Hudson. Many US based ships participating in longer sailings have wait lists. https://sail4th.org/ and https://www.sail250.org/
