The SDSA adopts a new Bermuda strategy to the Caribbean and the Azores
by Bennett Kashdan and Ronna Benjamin
Whether you are contemplating your first offshore passage or are a veteran of ocean crossings, joining a rally can offer an appealing combination of camaraderie, shared experience, and logistical support. While every skipper ultimately remains responsible for the safety of vessels and crew, organized rallies can help turn distant cruising dreams into achievable plans.
For East Coast sailors headed south each fall, few topics generate more dockside debate than the best departure strategy. Should you leave from the Chesapeake Bay or from New England? Should Bermuda be part of the plan, or merely a weather-dependent option?
When the first Salty Dawg Rally departed Hampton, Virginia, in 2011, the route to the British Virgin Islands was envisioned as a non-stop passage. Today, the Salty Dawg Sailing Association offers organized departures from both Hampton and Newport, Rhode Island, and Bermuda has assumed a much more prominent role in rally planning.
What has changed over the past fifteen years is not the Atlantic Ocean itself, but the tools available to those crossing it. Advances in weather forecasting, routing software, and satellite communications have transformed offshore decision-making. With Starlink and other emerging connectivity options, crews can remain informed throughout a passage in ways that were unimaginable only a decade ago. Modern weather routing allows skippers greater flexibility to adapt to changing conditions and, in many cases, make informed course changes while underway rather than relying solely on forecasts downloaded before departure.
The impact of these advances has been evident during both past two fall SDSA Caribbean Rallies. In 2024, weather patterns encouraged many southbound boats departing Hampton to make Bermuda a planned stopover. In 2025, limited weather windows out of Newport led many New England boats to sail first to the Chesapeake before beginning their offshore passage south. Such strategic adjustments, once difficult to coordinate, have become far more practical with today’s communications and forecasting capabilities.
For many sailors, Bermuda—known affectionately as “The Rock”—has become far more than an emergency refuge. It remains a proven safe haven when weather or mechanical issues dictate an unscheduled stop, but it is increasingly viewed as a destination in its own right. The island welcomes organized rallies and races, waives many of its normal cruising and entry fees for participants, and offers attractive duty-free fueling options. As a result, some rally crews now plan a Bermuda stop from the outset, using the island for crew changes, vessel preparation, or simply a well-earned break in the passage.
That said, Bermuda’s appeal should not obscure the realities of the late-fall North Atlantic. Conditions can change quickly, and prudent skippers generally avoid lingering. For most southbound crews, two or three days ashore provides sufficient time to rest, refuel, reprovision, and enjoy the island before taking advantage of the next favorable weather window.
The spring migration north presents a markedly different experience. More settled weather patterns, warming temperatures, and the gradual retreat of winter systems often allow crews greater flexibility in their schedules. Rather than a brief tactical stop, Bermuda can become a genuine cruising destination where sailors pause to explore the island, reconnect with friends, and prepare for a final leg back to the U.S. East Coast or across the Atlantic to the Azores and Europe. Many of the 2026 SDSA Azores rally participants spent most of May in Bermuda and loved it!
Hooked on Bermuda
So, what awaits sailors who choose to stop and stay in Bermuda?
For most cruisers arriving from the Caribbean or preparing for an Atlantic crossing, the answer begins in St. George’s Harbor. After days offshore, the protected anchorage feels like an enormous exhale. Once the anchor is down and the boat secured, one of Bermuda’s greatest strengths quickly becomes apparent: so much of the island is accessible directly from the harbor.
The Town of St. George’s, a UNESCO World Heritage Site, is compact, colorful, and easy to explore on foot. From the dinghy dock, cruisers can wander narrow lanes lined with historic stone buildings. Cruisers will find pubs at which they can try the local Swizzle or Dark & Stormy, restaurants at which they can order a traditional Bermuda fish sandwich on raisin bread, an ice cream parlor, a new brewery, and an abundance of small shops. Tobacco Bay, one of Bermuda’s most beautiful swimming holes, is a short walk from town.
The only unwelcome surprise for cruisers may be Bermuda’s prices, which can produce a bit of sticker shock. On the other hand, one can’t help but notice how clean the island is and how friendly and helpful the locals are.
Those willing to venture beyond St. Georges will find an island that is remarkably easy to explore by public bus, scooter, bicycle (electric or push), or ferry. Buses are easy to navigate and access- there is a bus stop right in the middle of St Geroge’s across from the Tourism office. Highlights include the city of Hamilton, the Crystal Caves and Swizzle Inn, the Royal Naval Dockyard, the many rail trails, and the spectacular beaches of the South Shore.
Some cruisers choose to move their boats to Hamilton Harbour, with easy access to excellent restaurants, provisioning opportunities, and a front-row seat to the island’s world-renowned sailing scene. Bermuda hosted the 35th America’s Cup in 2017 and, in May, 2026, SailGP racing on the Great Sound further cementing the island’s reputation as one of the premier sailing venues in the world.
Salty Dawg Azores Rally
In May 2026 Bermuda proved to be the perfect starting point for the thirteen sailboats participating in the SDSA rally to the Azores. Rally participants had casual meet ups to get to know one another at the brewery, on excursions to Hamilton, at beach barbeques. We helped one another with boat repairs and parts and talked about the weather incessantly.
Planned activities for rally members included a rum tasting sponsored by Goslings Rum at Bermuda Yacht Services (thanks to Mark Soares and Goslings), a chicken dinner at the Dinghy Club, and a farewell dinner at the White Horse Tavern.
Finding a weather window around the planned departure date of June 1 in between complicated fronts that blow east over Bermuda is challenging. On an SDSA rally, and with the help of Chris Parker’s MWXC, each captain is encouraged to make an individual decision regarding the most prudent day to depart. This spring all thirteen boats weighed anchor within a few days of each other, and all arrived safely in Horta, experiencing the thrill of doing a transatlantic crossing in the company of others.
For many offshore sailors, Bermuda begins as a practical stop dictated by weather, routing, or rally schedules. But it rarely remains just a waypoint. More often, it becomes one of the most memorable destinations of the voyage. Whether sailing from Newport or the Chesapeake, southbound to the Caribbean, northbound towards home or eastbound to Europe, “The Rock” remains one of the enduring highlights of any sailor’s offshore experience.
