CherylAnn Robinson Sailed the Caribbean on a Four-Masted Ship
At a Glance
On my eight-day voyage aboard Star Clippers' Star Flyer through the Pirate Islands, I discovered a sailing experience that blends hands-on participation with genuine luxury. I helped raise sails, watched guests steer the ship, and enjoyed fine dining despite the small galley, all while experiencing authentic Caribbean culture and entertainment under the stars—something entirely different from traditional big-ship cruising.
I had always been curious about sailing ships, those romantic vessels that seem to belong to another era. So when the opportunity came to board the Star Flyer, a four-masted clipper ship sailing through the Caribbean's Pirate Islands, I knew I had to experience it myself. If this type of voyage appealed to me, I reasoned, it would appeal to my clients too. I gathered six other couples and in February we set sail from St. Maarten on what would become one of my most memorable travel experiences.
Our ship held just 170 passengers and 63 crew, a ratio that immediately set the tone for what was to come. We traveled under the wind power of 16 sails (with a backup engine if needed), visiting Anguilla, Virgin Gorda, Jost Van Dyke, Sopers Hole, Norman Island, St. Kitts, and St. Barts. This was not your typical cruise, and from the first morning I understood why.
The Crew Made All the Difference
What I keep telling everyone about is how accommodating the entire crew was, from the captain to the sailors to the support staff. The bridge had an open policy where you could ask any question and receive a thorough explanation. But they went far beyond answering questions. Everyone who wanted could climb to the crow's nest, 45 feet up the main mast. I helped raise the sails myself, pulling on ropes alongside the crew. One gentleman in our group actually steered the vessel for almost two hours. A sailor showed him how to follow the gauges, and then he was in charge. These weren't staged photo opportunities. They were genuine invitations to participate in the sailing of the ship.
I had no idea what to expect when I started this vacation. I knew I was boarding a large sailboat, but I was amazed at the luxury waiting for us. The food was better than what I have had in the dining room of any big ship, and the galley was remarkably small. I still don't know how they managed it. The cabins were a bit smaller than on a large cruise ship but beautifully appointed, with everything we needed. The decor throughout was elegant without feeling stuffy.
Never a Dull Moment
People often ask me if it was boring, being on a sailing ship. It was far from that. The entertainment was different from what you might expect on a mega-liner. We danced to a one-man band one night. Another evening, a steel band was pirated on board from one of the islands. There were informational talks about pirates and the British Virgin Islands, knot-tying lessons, and a talent show. One night we watched movies under the stars, an old film chronicling a sailor's adventure around Cape Horn. When we weren't on a beautiful beach, I could sit and read in the library or enjoy drinks at the bar. I was never at a loss for something to do.
Here's something I never would have guessed: there were miles and miles of rope everywhere on that ship. It had never registered with me how much rope it takes to keep 16 sails working properly. Standing on deck, watching the crew work those lines with practiced efficiency, gave me a new appreciation for the craft of sailing.
Who This Voyage Is Perfect For
A Star Clippers sailing trip works for any age as long as you love the sun, the ocean, beaches, and a touch of luxury. I watched older guests and younger couples alike enjoying themselves equally. If you want spectacular views, fine dining, relaxation, or adventure, every box gets ticked. Many of my clients are beginning to seek more upscale experiences, something different from the usual big ship cruise, and this delivers exactly that.
I should mention that this voyage is not ideal for anyone with mobility issues. There are no elevators, and at most stops guests tender to shore, which can be challenging. My practical advice: pack water shoes for rocky beaches and wet landings, and bring a waterproof case for your phone because you will want underwater photos.
Now that I have sailed on Star Clippers myself, I can paint the full picture for clients considering this experience. I know the pros (and there are many), and I understand exactly who will fall in love with this type of voyage. The combination of hands-on adventure, intimate ship size, and genuine luxury is something I cannot wait to share with travelers who don't even realize this experience exists for them.