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Windjamming—on a on a Caribbean barefoot cruise - Windjammer Barefoot Cruises


A week in the Caribbean spent on board a 67-year-old sailing vessel was the perfect way to take a lesson in relaxation and to celebrate a 40th birthday.

Making plans and getting there

In October 2001, unwilling to let the events of September 11 hold us captive, my husband, John, and I narrowed down our destination to Paris or the Caribbean. We took into account the weather, the pace, the language barrier and the distance. Considering that John's birthday was in January, we opted to escape the winter chill for the warm Caribbean waters.

We both have a love for the sea--John for the ships and I for what lies beneath? We contacted Windjammer Barefoot Cruises and selected the S/V Flying Cloud for its 5-day itinerary that would take us throughout the British Virgin Islands.

After a couple of connecting flights from the West Coast, we arrived in Tortola under the cover of darkness. We took a cab to the Road Town Harbour waterfront and waited for the launch to ferry us to our home for the week. The Flying Cloud was at anchor in the middle of the harbor, a quick 5-minute boat ride from the dock.


We were ushered aboard and our bags were taken immediately to our cabin. After taking care of the preliminary paperwork, we went to the top deck to enjoy the first of a number of nights under the Caribbean stars.

Most of the other passengers arrived earlier in the day and had already turned in for the night.

S/V Flying Cloud

The Flying Cloud is a 208-foot privateer that was built in 1935 as a training cadet ship for the French Navy. Originally named "Oisseau des Isles" (Bird of the Isles), she was renamed the "Ave de Tahiti" for her service during WWII and was credited with sinking two Japanese submarines. She joined the Windjammer fleet in 1968 and homeports in Tortola, BVI.

There are accommodations for 66 passengers and a crew of 28. The cabins aren't spacious, but they are adequate, and each has a private--albeit small--bathroom. There is no reason to pack an entire wardrobe, just a few light shirts, shorts, bathing suit, towel and a light jacket for when the trade winds pick up. Leave the formal attire and jewels at home; there's no reason to dress up while on board. We had one suitcase and a large duffel (with my dive gear) along with a carry-on and a camera bag--it all fit nicely underneath the bunk.

Yes, I did say bunk. Unless you've booked the honeymoon suite, you won't be sharing a bed with your mate; the twin-sized bed was cozy for one. Our cabin had a porthole window above the top bunk with a brass cover that was braced open, so we had to be careful not to bump our heads.

There were cubbies in which to put our clothes, so we didn't have to live out of the suitcase, and the ship didn't rock too much, so our stuff stayed put. The towel rack and hooks were adequate to hang other items, and the bathroom had a place to store sundries.

There were three decks. The lower deck had passenger cabins; the upper deck also had passenger cabins and the dining saloon, which did double duty as the Seachest (ship's store) between lunch and dinner. The top deck, or quarter deck, is where passengers spent most of their time on board, perhaps because of its proximity to the bar.

There were no deck chairs; instead, the teak storage compartments along the gunwales provided adequate seating, and mats were available to provide padding for an afternoon snooze.

Life aboard ship

Each morning we were awakened by the sound of a ringing bell in the hallway and a beautiful voice singing, "Rice and shine, darlin's; it's breakfast time."

Breakfast was served between 7:30 and 8:30 and varied on a daily basis. We had a choice of a hot entree or a cold breakfast buffet. There was always a selection of fresh fruit, a different fruit juice daily and fresh baked bread. Coffee and tea were available in the galley all day long.

For early risers, Bloody Marys, coffee and pastries were served at 6 a.m.--ideal to enjoy on the top deck and watch the night turn into day.

One daily event that I especially enjoyed was story time. After breakfast, at about 9, all the passengers gathered on the top deck for the daily briefing from Captain Max. The gathering started out with Captain Max shouting, "Good morning, everybody." To which the proper response was a loud and firm, "Good morning, Captain, Sir!" If he was pleased with our response he ordered Rodney, the bartender, to bring up more rum.

After the formalities, Captain Max would provide a brief and entertaining history of the island we would be visiting that particular day, along with the folklore that went along with it. We also learned about the day's activities, the lunch location (whether on board or on the beach), launch times ashore and, most importantly, the time of the final launch. We were tested on that final detail, since missing the last launch meant a delay in setting sail. It also was when we made our choice for dinner entree by a show of hands.

Each evening around 5 was swizzle time, the Windjammer version of "happy hour." Complimentary rum swizzles flowed freely for those who wanted to partake, and there was no shortage of rum, but virgin swizzles also were available. There also was a variety of appetizers served--never a shortage of the tasty snacks.

Dinner was served each evening at 6:30 and because there were only 30 passengers aboard there was only one dinner seating. Dinner, as with everything else aboard a Windjammer cruise, was casual...very casual. A T-shirt and shorts were appropriate dinner attire and, for the most part, I don't think I ever wore shoes! It was, after all, a barefoot cruise.

The evening entertainment varied. One night we enjoyed crab races on the top deck. The hermit crabs wore numbers on their shells, and eager passengers placed bets on a favorite to win. We walked away with a whopping $6! This was not high-stakes gambling.

Veteran Windjammers were prepared for the "Seahunt," scavenger hunt and "beauty" contest that took place on another evening. For the so-called "beauty" contest, each team needed to select one member who exemplified grace, beauty and talent to represent the team in the Miss Windjammer 2002 pageant. The catch? The team member needed to be a man! My husband, John, was reluctantly willing to undergo the transformation into a glitzy, glamorous beauty--not an easy task.

Each contestant demonstrated a great sense of humor and allowed the rest of the passengers to envy their stylish transformation and incredible displays of talent. The contest also segued into the evening's costume party that allowed passengers to transform themselves into their alter egos.

Island hopping

We sailed at noon on the first day, but on proceeding days our anchorage was usually set by the time we awoke.

Before we sailed from Tortola, those who wished could take the optional island tour for $20 per person. None of the other islands we would visit offered much in the way of shopping, so John and I opted to stay in Road Town for that reason.

Road Town is quite centralized, so it's not necessary to get a taxi. Local shops are plentiful and we found that two hours was enough time to purchase the necessary souvenirs. We also made arrangements for an island tour when we disembarked at the end of the week with a local taxi driver I had met on a previous visit.

Once all the passengers were back aboard, the launch was raised and secured, the anchor was pulled up and the Flying Cloud was ready to set sail. It was customary to play "Amazing Grace" as the sails were raised; over the loudspeakers blared a Scottish bagpiper's rendition of this beautiful song while the canvas sails were unfurled into the wind. Passengers were encouraged to help raise the heavy sails of this 3-masted schooner.

It was an incredible sight to watch each sail as it was hoisted hand over hand from a crumpled pile of canvas. Foot by foot, the sails climbed about 75 feet up the masts. Once the sails were secured, we were "jamming"... windjamming, that is!

In our case, windjamming was an oxymoron. Sure, we were sailing with only the power of the wind, but jamming we were not. I'd equate it with comfortably gliding through the water. These ships were not built for speed and, since I wasn't in a hurry to get anywhere, I just sat back and began my lesson in relaxation.

Our course was set for Salt Island, a small bump in the Sir Francis Drake Channel perhaps best known as the final resting place of the RMS Rhone, a Royal Mail Steamer that sank during a hurricane in 1867.

Our anchorage was in a small cove, far enough offshore to be too far to reach by swimming. It was here that one passenger was made to walk the plank because she missed the final launch and delayed our sailing. The plank once was a diving board, but it broke quite a while ago and it's now used as the plank--after all, you can't have a pirate ship in the Caribbean without a plank.

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