I have just returned from the best week of sailing around Martha’s Vineyard that I’ve ever experienced. We had good sailing each day, two of which were outstanding and one of which was a red-letter day of sailing. On the second day we sailed from Vineyard Haven down Vineyard Sound past Naushon Island and ended up coasting on light airs to just off Menemsha, which is on the southwest corner of Martha’s Vineyard. The next day the wind picked up in the afternoon and we raised the mainsails and the staysails and headed across Vineyard Sound through Quick’s Hole between Pasque Island and Nashawena Island, in the Elizabeth Islands, and on across the Buzzards Bay to South Dartmouth where we anchored for the night. What was memorable about this sail was that it was all done on a single tack, which was executed getting away from Menemsha. The next day there was too much fog in Buzzards Bay for our “no auxiliary powered” vessel to safely cross over to Vineyard Sound. Buzzards Bay has heavy barge traffic, which makes it dicey for a boat with no radar to venture out into a fog-shrouded sound. So we spent that day sailing close to shore just outside of Clark’s Cove (South Dartmouth, Mass.). The following day dawned with virtually no air movement at all so we stayed another night in the same anchorage, which, to be fair, is quite a pretty area of weather shingled cottages from the early 1900s surrounding a sailboat-infested harbor. The excitement started at 2 a.m. Saturday morning when a front came through with high winds and horizontal rain interlaced with a dramatic display of lightening. We were all awakened at 6 a.m. with a call for all hands on deck to raise the sails and anchor so we could get under way asap. All of us stumbled up on deck to find a complete change in the weather. The violent front that came through in the night dragged in behind it a beautiful crystal clear day with plenty of wind to satisfy or scare any sailor. The wind was out of the NW and blowing a steady 30 knots. We only raised the mainsails and the staysails. We flew across Buzzards Bay at a steady 12 knots and through Quick’s Hole, which is always tricky in a high wind, and came about into Vineyard Sound.The waves in the bay looked to have been 2′-3′, whereas, those in the Sound appeared to a landlubber, such as I, to be 3 feet plus. As we sped up Vineyard Sound the water started coming in over the starboard scuppers and at one point the bow of the yawl boat, which is carried on davits off the stern, was underwater. If you are a thrillseeker, it doesn’t get much better than this. The Shenandoah was about the only craft out that morning, except for some McMansion-sized yachts and the Woods Hole Ferry, which is about the size of an office building. We must have given the people ashore quite a thrill when they looked out their windows as they sipped their first cup of coffee of the day. I certainly would not have given up being aboard that day, but I’d have loved to have seen us from shore……straight out of “Master and Commander”.
The drama happened as we started to wear ship between West and East Chop so we would have a straight shot into Vineyard Haven’s harbor, which is the Shenandoah’s home port. The crew was making no headway in bringing across the mainsail due to the sheer force of the wind, so all passengers on deck jumped in to help. With at least 15 people hauling on the rope we just managed to move the mainsail across. Just as the mainsail was secured there was an explosion like a cannon as a 15-square-foot section of the sail ripped. The torn section was held onto the sail by its outer edge, so it produced a thunder-like noise as it whipped about in the 30-knot wind. Just as this was happening, the first mate yelled that the inner jib was ripping, and it was lowered on Captain Bob Douglas’s orders. As the Shenandoah managed to slide into the lee of West Chop where we anchored close to the East Chop side of the outer harbor, the torn piece of sail came loose and landed in the water about 100 feet away from the ship. Ryan, our superb cook, who is also a strong swimmer, immediately jumped in and dragged it back to where passengers and crew could haul it aboard. Ryan is a college student, not a professional cook, who produced gourmet meals day after day on an old-fashioned coal-burning stove in a galley the size of a large broom closet. This was his last day before heading back to school. His “rescue” of the sail was above and beyond the call of duty, which seems to be the motto for all the crew. Nothing is wasted onboard ships and that goes for usable canvas.
It seems that when we were hauling on the rope to move the mainsail across, the power of the wind was such that the gaff whipped across faster than the boom, thus putting more stress on the canvas then it was able to handle. Something had to give and the canvas sail was weaker than the wooden spars. The excitement at the end of this sail fully demonstrated the vast sailing knowledge and experience and enthusiasm of the captain and his crew, most of whom are teens or just out of their teens. They worked like a well-oiled machine. Like all professionals who want to learn what went wrong, the captain and his crew examined the torn canvas as soon as it was laid out on deck. Calls were immediately made to the sailmaker and the Shenandoah’s people ashore to see if there was a spare mainsail in the sail loft. With the wind steady at 20-25 knots and still gusting to 30, the captain and the crew of the Shenandoah were already getting the ship ready for its next cruise, which started on the following day. Those on board who had been on the Shenandoah many, many times all said that this day would go down in the annals of history of the ship as the best, most exciting day of sailing. I have to say this was the best, most thrilling vacation day I’ve ever experienced. I should be so lucky that another day will even come close to it. It was the end of the week of sailing for the passengers, all of whom were sad to go! – Dick Evans, vice president
Read This Next
Introducing
FX Excursions
FX Excursions offers the chance for once-in-a-lifetime experiences in destinations around the world.
#globility
Insta FeedDaily
Sep 22, 2026Cunard’s “Queen Mary 2” to Undergo Stunning Refurbishment
Cunard recently announced a stunning refurbishment of Queen Mary 2; the ship prepares to enter dry dock on March 31, 2027, as the flagship of the Cunard fleet and the only ship in the world offering regularly scheduled trans-Atlantic crossings between Southampton and New York. The refurbishment will introduce new Grill Suites, an elevated wellness offering, enhanced retail spaces and refreshed guest areas, while preserving the ship’s Art Deco identity. The ship will return to service May 9, 2027.
Sponsored Content
An Adults-Only Resort for All the Milestone Moments
On Saturday, Feb.14, Devossion by Live Aqua celebrated its grand opening, marking a significant milestone for Grupo Posadas and the Live Aqua brand. This adults-only resort focuses on celebration, authentic Mexican experiences and elevated hospitality — perfectly situated in the heart of the Riviera Maya.
Daily
Sep 22, 2026Santa Barbara, California, Delays Autumn with a Second Summer
Experience Santa Barbara’s second summer, when golden hour sunsets, warm evenings and wine season offer a unique Californian take on fall. The destination’s pre-autumn season is perfect for those not yet ready to let go of warm weather just yet.
Daily
Sep 22, 2026Bruce Springsteen Center for American Music Opens in Long Branch, New Jersey
Earlier this year, COOKFOX Architects announced the opening of Bruce Springsteen Center for American Music at Long Branch, New Jersey’s, Monmouth University. This new cultural landmark is dedicated to telling the story of music in this country while celebrating Bruce Springsteen’s work within that tradition. The 30,000-square-foot building houses exhibits about the music of Bruce Springsteen and of other American musical genres; the Springsteen archives; a 240-seat auditorium for concerts, academic lectures and video screenings; and gallery space for changing exhibits.
Sponsored Content
IHG Business Edge: A Smarter Way for Small- and Mid-Sized Businesses to Travel
IHG Business Edge is a complimentary travel program designed to help small- and mid-sized businesses manage travel more efficiently while saving on hotel stays. Members enjoy access to guaranteed discounts, loyalty benefits, and partner offers across IHG Hotels & Resorts’ global portfolio of 7,000-plus hotels in more than 100 countries.
Melt into Mediterranean Charm in Barcelona and Costa Brava
Usually regarded for its Modernist architecture, centuries of artistic influence and polarizing football team, Barcelona has come into its own as a growing tech hub. The capital of Catalonia hosts the annual Mobile World Congress each March, and its Poble Nou neighborhood cradles some of the world’s most recognizable startups like TravelPerk and Typeform.
Seven Seas Prestige to Feature New Spaces
September 2026
Sep 19, 2026Destinations
Sep 18, 2026Choose Your Own Island Vibe in French Polynesia
“We are on small, tiny rocks, isolated in the middle of the largest ocean.” On a nature tour on the atoll of Tetiaroa, my naturalist guide, Thierry Sommers, thus reminded me of the oceanic remoteness of our location in the South Pacific. I was staying at The Brando, a luxurious private island resort that sits a mere 30-minute flight from the main island of Tahiti but still feels gloriously far away from regular civilization.
Sponsored Content
IHG Business Edge: A Smarter Way for Small- and Mid-Sized Businesses to Travel
IHG Business Edge is a complimentary travel program designed to help small- and mid-sized businesses manage travel more efficiently while saving on hotel stays. Members enjoy access to guaranteed discounts, loyalty benefits, and partner offers across IHG Hotels & Resorts’ global portfolio of 7,000-plus hotels in more than 100 countries.
Daily
Sep 18, 2026Downtown Phoenix Welcomes First Upscale Urban Retreat
This month, in Phoenix, Arizona, Pacific Hospitality Group opens Denū Hotel & Spa, the newest hotel property in The Meritage Collection.
ShareThis