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Bermuda: Destination Cruising Off The Beaten Track


Often a stopping-off point for those headed to the Mediterranean, many cruisers forget that Bermuda’s beautiful, well-manicured islands are a destination in their own right.

Bermuda has sent out its siren call to sailors and cruisers for centuries, most often as a brief reprovisioning point for ships crossing the Atlantic or traveling to and from the Caribbean. The island is a safe haven from the perils of ocean crossing, but it’s also a civilized landfall made up of protected harbors, deepwater coves and bays, pink beaches, manicured golf courses, iconic white-roofed cottages bathed in colorful flowers, and some darned good rum.

Despite the fact that Bermuda is centered amid a deceptive fringing reef that has sunk ships relentlessly for 400 years, its cruising potential—replete with scuba-diving opportunities and countless attractions ashore—caused my husband, Ron, and I to decide it would make a perfect destination in itself. After Ron announced his intent to retire, we spent the next eight months planning and preparing for a visit to this idyllic island aboard our Krogen 58, Equinox.

Over the centuries, ships have gratefully approached this strategic bit of rock with heady visions of landfall, only to be stopped short by the treacherous and thorny nest of reefs festooning its waters. Vertical walls of limestone and coral jut up from the depths to barely brush the water’s surface, some as far as 8 miles from shore. Since Bermuda’s founding in 1609—itself the result of a shipwreck—these reefs have ripped open the hulls of hundreds of ships, catching not only the inexperienced and unwary but also seasoned captains.

As a diver, Bermuda’s reefs and wrecks were attractive to me, but as a mariner, the reefs made me apprehensive about our passage. I tried to reassure myself that it was better to be concerned, rather than complacent, about our cruising abilities.

While many a vessel with varying number of crew has made the passage to Bermuda, we did so with just the two of us aboard, and it was our farthest passage offshore to date. We had cruised the Atlantic Seaboard and crossed to the Bahamas several times, but being a mere 90 or even 150 miles offshore paled in comparison to the idea of heading directly away from the States to reach a pinprick in the Atlantic 650 miles distant. Tales of dangerous sudden squalls, high winds, and unrelenting ocean swells gave us pause for thought, even though we knew Equinox was built for such a challenge. Stoutly made, she had adequate fuel capacity, and we had the nerve to give the journey a try. For us, this would be destination cruising of a different order.


Much to our surprise, during the planning stages of our trip, we found no real cruising guides for Bermuda. The closest we could find was a thin pamphlet issued by Bermuda’s Department of Tourism that was aimed at private yachts. Two of its 24 pages merely listed the various British Admiralty Hydrographic Office charts needed for the approach to the island, as well as the purveyors of those charts. Before the pilotage and harbor entrance notes, the pamphlet provided information about communications and the distress, urgency, and safety frequencies used—not very comforting. It also included a listing of approach beacons and light signals around the island, as well as some terse information about customs and immigration clearance procedures. Only under “Miscellaneous Information” were there any facts about dockage and marinas. Bermuda and its cruising anchorages remained shrouded in mystery. Even our Internet searches provided only general knowledge about anchorages and facilities in St. George’s and Hamilton.

We had purchased Equinox specifically with the rigors of offshore cruising in mind and spent two years shaking down the boat and becoming familiar with her systems. With this trip looming, we revisited everything and ensured that all major systems were inspected, checked, and tuned for the voyage. Bermuda’s reefs and their dangerous reputation—coupled with the fact that it was hurricane season—meant that acquiring insurance for the trip was a bit more of a challenge than originally anticipated. After many conversations with our broker and armed with persistence, diligence, and the patience to complete reams of official paperwork, we finally secured a good policy that would allow us to stay in Bermuda for nearly six weeks, well into August.

With that hurdle overcome, we focused on provisioning and final maintenance checks in preparation for the voyage itself. We also watched the weather with intensity. At the end of June, with Ron newly retired, we made our way down the Chesapeake from Baltimore. After a brief wait for a good weather window, we turned Equinox’s bow toward Bermuda.

Two days later, with landfall still more than 35 hours away, we heard Bermuda Harbour Radio (call sign “VBR”) on VHF 16 for the first time, hailing a sailboat that was approaching the island. Bermuda Harbour Radio diligently tracks all incoming and outgoing vessels, confirming their identities and course headings before clearing each to enter or exit St. George’s Harbour through the narrow Town Cut. Hearing Harbour Radio’s polite and very proper greeting to the other vessel made the prospect of landfall real and quite welcome. Stories of sailors finding this landmark came to mind; I vividly imagined their rush of gratitude at the reprieve from the constant demands of being at sea—and their misery at being brought up short by the island’s reefs.

Nowadays, though, with Bermuda Harbour Radio and its modern tracking technology keeping a watchful eye out for mariners, it’s reassuring to know they will contact you if you’re heading afoul and will “virtually” escort you around the reefs. We contacted them the next morning, about 30 miles out, to confirm our arrival.

Seeing Bermuda—actually, seeing any land—after three and a half days at sea was a treat. It would have been more of a relief, though, had it not been for the reefs. We brought Equinox in carefully from the north and east to give ourselves a healthy distance from the North Rock and then the Northeast Breaker beacons. After skirting Kitchen Shoals, we arrived uneventfully in the midst of some of the nastiest weather Bermuda had seen that summer: pouring rain and high winds. The radar was just plain ugly. (I don’t know how sailors do it in such conditions; I must admit, we loved being snug in our pilothouse.) Although not under blazing sunshine as we’d imagined, our entrance through Town Cut and into St. George’s Harbour was just as welcome. We tied up at Ordnance Island to clear customs and immigration in the monsoon-like downpour, less than artfully attired in our dripping foul-weather gear.


Bermuda is British in its love of bureaucracy. We discovered that while customs allows visiting vessels to stay up to six months, immigration typically only grants visas for the crew for 21 days. A visit to the Government House in downtown Hamilton was in order so we could apply for a visa extension. (A good explanation as to the reason also was required.) Visa extension applications are only accepted between 9 a.m. and noon, so be aware of that, or you’ll have to return another day during proper hours. We found this out the hard way but did manage to secure an extension for the duration of our stay, almost five weeks.

Prior to our arrival, our biggest decision had been where to stay. All foreign yachts must clear in at St. George’s, so that was our starting point. Most visiting vessels stay a day or so to explore the quaint town, which offers several wharves and marinas for dockage. Boats can dock alongside a wharf or pier on a first-come, first-served basis by simply contacting the St. George’s dockmaster on VHF 14. It’s just as easy to use the anchorage at Powder Hole, on the opposite side of the harbor.

St. George’s is worth exploring. Many of the town’s old stone buildings are still in use as stores, restaurants, and museums along the main thoroughfare and waterfront. The original models and drawings of these buildings were brought over from England, and the resulting Bermudian architecture hasn’t varied much in 400 years. The capital of Bermuda until 1815, St. George’s served as a base for Confederate blockade runners during the U.S. Civil War. Today, the island nation’s prosperity is evident in its tidy streets and well-kept homes, providing a safe and secure dream destination for visiting boaters.

Most cruisers don’t stay long in St. George’s; instead, they head back out Town Cut and travel north and west along the well-charted ferry channel to the western end of the island to either the Royal Dockyard or Hamilton, Bermuda’s capital and largest city. While good docking facilities are available at Dockyard Marina, it’s rather far from most amenities, requiring a dinghy or ferry ride to Hamilton. Berths in Hamilton are restricted to yacht club slips, boatyards, marinas, and a few moorings, but being within walking distance of the downtown area and its history, nightlife, and many restaurants and shops is the reason the majority of boats stay there. The Royal Bermuda Yacht Club and the Royal Hamilton Amateur Dinghy Club both are venerated institutions, and while they welcome visiting yachts, space can be limited, especially during well-known events such as the Newport Bermuda Race and the Royal Bermuda Yacht Club Anniversary Regatta.

We had loosely planned on staying in the urban anchorage at St. George’s and then moving to a slip in Hamilton, but we weren’t totally enamored of either choice because we wanted to get off the beaten path. Luckily for us, good friends who live in Bermuda provided a third alternative that delighted us to no end: Castle Harbour. After we cleared in with customs, our buddy Warren climbed aboard and guided us back out to the Atlantic and along Bermuda’s south shore to Castle Roads, the original entrance to Castle Harbour. Castle Harbour is a huge natural harbor that was once an important anchorage, providing an access route to St. George’s. The harbor was used by sailing ships during the 17th and 18th centuries until the loss of HMS Cerberus on the rocks just outside the entrance convinced the Admiralty to forbid its use as an anchorage.

Castle Roads is seldom used today, except by small pleasure boats, and we were well aware that it’s not marked as an anchorage on the charts. Entering the Roads from seaward, there are no buoys or day marks to warn of the extensive coral reefs, so without local knowledge, we never would have attempted to enter this area. With Warren as our pilot and Ron at the helm, I held my breath as we threaded our way through the reefs in heaving seas, watching waves crash and break on the base of rocky islands at the entrance. Once safely inside the Roads, the wide expanse of Castle Harbour opened to reveal a secret gem of an anchorage: steep, green hillsides dotted with homes sporting the ubiquitous Bermudian white roofs, all nearly half-hidden by lush flowering foliage reaching down to the harbor’s azure seas. Equinox had plenty of water beneath her keel—depths averaged 40 feet—and with Warren’s knowledge about the few day marks on the larger reefs inside the harbor, we navigated to a breathtaking cove near our friends’ home on the east side of Tucker’s Town peninsula, on Bermuda’s Main Island. This is what cruising is all about: seeing parts of a country that few visitors ever get to experience.


We were enchanted with our protected anchorage. With its proximity to public dinghy docks, it was a perfect home base from which to explore and experience Bermuda’s gracious hospitality—from day trips in our dinghy, Eclipse, to dives on the southern reefs and wrecks to “pedal bike” rides along immaculate roads through scenic villages. We visited Bermuda’s museums, aquarium, and zoo, and several of its historic forts.

Happily, opportunities for exploring secluded beaches and remote islands abounded, since the archipelago consists of approximately 123 islands. We discovered that simply compiling a list of Bermuda’s islands is complicated, since many islands are referred to by more than one name, and place names often are repeated. Take “St. George’s,” for example, which can refer to one of four places: the town, the island, the parish, or the harbor. No matter the name, we enjoyed each spot we visited.

A favorite area to explore was the pair of large islands at the entrance to Castle Harbour: namely, Castle Island and Charles Island. These islands are the site of historically important colonial fortifications, some dating from as early as 1612, all originally built to protect the Castle Roads channel and its harbor. Considered the keystone of Bermuda’s defense, Castle Island contains no fewer than three separate forts, including a large fortress known as King’s Castle. The island is now a nature reserve and is open to the public under strict regulation to protect its population of tropicbirds and skinks. Swimming and snorkeling are allowed in the adjacent waters, and there are a few small mooring balls for day use. We spent many an afternoon watching the native “longtails”—white-tailed tropicbirds—swoop and dive as we floated in the warm turquoise waters.

Along with its numerous islands, Bermuda has many inlets, sounds, and lagoons, only a fraction of which we managed to explore. From our anchorage in Castle Harbour, we threaded our dinghy under the low causeway bridge at the north side and meandered through the ever-present coral heads and reefs punctuating the north lagoon of the Main Island to Harrington Sound. The sound’s only access is through the rapids at Flatt’s Inlet, under the fixed, 8-foot-high Flatt’s Bridge. At slack water the entrance isn’t so remarkable, but the constant tidal flows between the ocean and sound cause 3- to 4-knot rapids in the narrow inlet at midtide. Because the bridge is fixed, there’s no tender; instead, there’s a stop light affixed to each side to regulate the flow of boat traffic. With its many bays, caves, cliffs, and coves (although not many beaches), Harrington Sound is gorgeous for fishing, swimming, snorkeling, sunfish sailing, and kayaking. Eagle rays are abundant, and we saw many of them feeding on the indigenous calico clams found there.

Best of all, we often ended our days of exploration by wining and dining with our friends, with their family and friends, or with newly met friends, either at their houses or on board Equinox—one of the many advantages of cruising aboard one’s home. We took it upon ourselves to sample the local cuisine as much as possible, garnering recommendations about restaurants and tiny eateries to find the best Bermuda fish chowder. A spicy tomato-based chowder, this national dish tastes best with a dollop of Gosling’s Black Seal Rum and a dash of Outerbridge’s Sherry Pepper sauce added tableside, per local custom. We also were taught the absolute necessity of pairing the chowder with a Dark ’n’ Stormy, the local beverage of choice, composed of ginger beer (a peppery ginger soda that puts American ginger ale to shame) mixed with—you guessed it—Gosling’s Black Seal Rum. Between the Dark ’n’ Stormies and the common rum swizzles, we discovered firsthand where Bermuda’s rum-stained reputation comes from.


The culmination of any summer visit to Bermuda is the national holiday of Cup Match, held on the Thursday and Friday before the first Monday in August. Cup Match is a two-day cricket match between the St. George’s and Somerset Cricket Clubs, and it virtually shuts down the nation. Those who aren’t at the match listen to it on the radio while taking to the water in droves: out in boats, or camping by the hundreds on the pink-sand beaches. Cup Match also has historical significance; Thursday marks Emancipation Day, which ended slavery in 1834, and Friday is Somers’ Day, which commemorates Sir George Somers, a British admiral and privateer whose wreck on the eastern reefs gave birth to Bermuda’s first settlement.

Our holiday weekend’s festivities were capped with Bermuda’s annual Non-Mariners Race on Sunday afternoon. A Bermuda tradition for more than 30 years, the object of this “boat race” is to bang together a few pieces of wood or other “non-mariner” objects (in the original race, it was baby buggies) and attempt to row or sail your craft across Mangrove Bay in Somerset to the Sandys Boat Club wharf. From what we could tell, the purpose of the day is to forgo the usual Bermudian adherence to propriety and enjoy a day of complete silliness, as the object is to sink in the most outrageous way possible.

We arrived in Mangrove Bay aboard Eclipse to find an amazing array of rafted-up boats, barges, canoes, and all manner of watercraft. Strung together in groups of two to 20, most vessels had flags flying, music blaring, and drinks flowing. There was a starting line for the race somewhere, but I doubt anyone saw it among the hundreds of anchored vessels, jet skis cruising about, and inflatable rafts and kayaks bumping along amid a very courteous yet ragtag assembly of inebriated mariners and non-mariners alike. As far as the race itself, each shabbily constructed craft typically had a theme, many of which reflected a local political scandal that we non-natives were blissfully unaware of.

We joined right in the festivities, rafting up with Justified, a 45-foot Bertram sportsfisherman belonging to our barrister friend, Justin, and clambered aboard to help him anchor amid the chaos and tight space. There was a lovely spread of food and drink aboard, as Justin was hosting Bermuda’s governor, Sir Richard Hugh Turton Gozney, and his family, along with the commodore of the Royal Bermuda Yacht Club, Ralph Richardson, whose boat was rafted to Justified’s port side. We had no idea we would be hobnobbing with the Bermuda’s high society, but, hey—it’s a small island. We never did see the actual race, but the following was reported in Bermuda’s daily newspaper, The Royal Gazette: “Non-winners of the race were undeclared and difficult to determine, with several floats toppling over simultaneously, but one undeclared winner may have also captured a non-title.” Clearly, the event was a success.

A day before our departure, after we’d filled up with the duty-free fuel that was available once we had cleared out in St. George’s (the town), Ron and I hiked to Fort George, on the highest point on St. George’s (the island), for a private tour of Bermuda Harbour Radio. One of the gracious Bermudians whom we had met and become friends with was Scott Simmons, the chief radio officer for BHR. Scott had arranged to show us the inner workings of the lookout station, an amazing juxtaposition of old and new. Atop a very steep hill, inside a three-century-old fort, and across a three-story-deep dry moat lies the high-tech radar and radio installation of Bermuda Harbour Radio. From the building’s windows you can see the entire archipelago and the web of waterways stretching to the west.

Before demonstrating the workings of the radar-tracking computers and radio workstations that the station uses to communicate with all inbound and outbound ships, Scott introduced us to Tom and Peter, the technicians on duty. I recognized their voices—we had heard or spoken to each over the VHF when we had first made landfall in Bermuda. The courtesy and dedication of the radio technicians is very impressive, and seeing them in action was a real treat. As any sailor or cruiser who enters Bermuda by ship for the first time can attest, there is nothing better than hearing the calm, welcoming voice of Bermuda Harbour Radio after days at sea. As timing would have it, we witnessed the arrival of the cruise ship Norwegian Dawn as she squeezed her way into St. George’s (the harbor), and listened to the radio direction of the technicians sitting beside us.

Leaving Bermuda was difficult, and our parting was filled with heartfelt goodbyes. The island had totally captivated us with its gorgeous scenery, flower-scented evening air, tiny whistling frogs singing in the foliage, fascinating 400-year history, and, most importantly, wonderful people. Cruising on one’s own boat opens horizons to new friendships, and we were no exception. Our Bermudian friends were incredibly generous, going out of their way to help us whenever we needed assistance of any kind, whether it was finding transportation to town or locating a repairman, and even leaving freshly grown vegetables on our aft cockpit table.

While others might use “The Rock” as a transit point, Bermuda is a gem of a cruising destination, and a rare one indeed.