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Honeymoon offers chance at fulfilling sailing dream

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It's sink or swim for landlubber Bill Fink as he charters several boats during his Caribbean honeymoon.

Despite growing up near the shores of Lake Michigan in Chicago, I never was part of the boating scene.

Between the cost, the planning and the weather, sailing seemed like too much of a hassle. But after a lifetime of listening to Jimmy Buffett sing sweet tales of sailing under Caribbean sunsets, sipping on cocktails and stopping at scenic islands, the pull grew stronger than a rip current. At the age of 42, I decided I had to try it.

Knowing I didn't have the nautical chops to master the helm on my own, I decided to charter a boat in the Caribbean. Three boats over three weeks, to be exact, to see what would work best.

The first I tried was a narrow, 39-foot monohull with three passengers and a captain, part of a four-ship sailing "flotilla" through the British Virgin Islands. My second charter was a private, captained 47-foot power boat cruising the same area. For the super-luxury option, I chartered a 46-foot catamaran through the Grenadines, complete with captain and chef.

Just to make things interesting, I did all of this during my honeymoon. As long as I was jumping into one adventure, I might as well try another.

No. 1: Mobile Margaritaville

Ironically enough, my sailing honeymoon began at the Bitter End, a yacht club on Virgin Gorda in the British Virgin Islands. We were joining a group of four boats chartered for 16 people from Sunsail, with captains aboard to guide us.

Joining a sailing charter group has its benefits in managing costs, but unless you show up with your own group or family, you never know if you'll get along with your fellow passengers. That's where the rum comes in. After a couple of rounds of potent rum runners and pain killers, my wife and I became best friends not only with our shipmates, but the other dozen people of the flotilla - and about half the bar, as well.

Staggering back to the boat after a festive night ashore, we retired to our coffin-like cabin on board. Note: the first night of a honeymoon is best not spent in a small, bobbing room with no air conditioning. Fortunately, we awoke the next day to sunshine and cool breezes, which our captains used to launch the group to sea.

Our four boats sailed a spirited race from Virgin Gorda to Jost Van Dyke, the captains shouting instructions for the inept passengers to help with the sail changes.

We cruised into a bay so blue it looked air-brushed, then rode dinghies to a prime snorkeling reef before returning to the boat for beers from the coolers.

We spent the next few days following our captains' suggestions to sail into a variety of scenic coves for exploring, harbors for fine dining and bays for overnight parties with the gathered "yachties." We picked up a few sailing tips along the way and left with some new friends, as well as a greater appreciation for the near infinite possibilities of cruising through the byways of the British Virgin Islands.

No. 2: A pirate turns 42

Captain Jimmy pointed our 474 Powercat toward Anegada, about 15 miles from the tightly grouped British Virgin Islands. We watched sailboats and smaller powerboats fall behind our 47-foot yacht as our captain cranked up the engines and powered us northward into the wind.

The Spanish explorers called Anegada the "drowned island" because, from a distance, the flat island disappears below the waves like a drowning sailor. My wife and I felt more like the king and queen of the seas as we lounged on the wide front deck.

Chartering a Moorings Powercat was like travelling in our own small luxury hotel, with a nice kitchen, air conditioning and roomy cabins. The powerful engines brought us to places the wind couldn't, and Captain Jimmy had the skill to avoid the rocking that buffeted some of the boats around us.

Powerboating lacks some of the adventure of sailing - the challenge of working with the winds on the high seas, for example. But sometimes it's nice just to kick back, relax and have the captain steer your big white floating limo to your next destination.

The experience was definitely a step up from our shared monohull, especially the air conditioning, a critical component during a sweltering July.

We had engine trouble, but a call to a nearby Moorings marina brought repair staff (one with his screwdriver tucked in his dreadlocks). They quickly fixed the problem - a benefit of chartering from a major operator.

While we waited for the boat to be fixed, Jimmy patiently tried teaching me some basic knots. Despite days of practice, he still had to re-do my clumsy efforts to rope the fenders to the deck or the dinghy to shore. But after nearly two weeks at sea, I felt like I was learning some boating basics.

No. 3: Cheese and wine in paradise

The ultimate in charter sailing is the crewed yacht experience.

My wife and I hopped aboard a Moorings 4600 catamaran to meet Mick and Charlotte, the married team comprising our captain, first mate and chef.

A couple for 26 years, they were an inspiration to us newlyweds. Working and living together in harmony on a boat year after year, they made the whole "tying the knot" experience seem as easy as an island breeze. Mick worked the helm while Charlotte cranked up the anchor and checked the sails. Off we went.

The breezes alternated strong and slow in the Grenadines, where we spent four days island hopping. Puttering on small engines into the Tobago Cays, we moored on a buoy and swam with sea turtles. After lazing on a small white sand beach, we climbed back aboard and were met by Charlotte, who was waiting with blended rum punch. She grilled up a freshly caught red snapper in a salsa sauce. Repeat for three meals a day, followed by a "rinse" in bathtub-warm waters, and you have a recipe for a happy honeymoon.

When the wind kicked up one day to 30-knot levels and prevented us from reaching a targeted island, we were fine with the change of direction, riding where the winds blew us, another day in paradise.

Freedom of the seas

After nearly three weeks aboard boats, I'm still pretty much a fumbling idiot as a sailor.

But for a short time, I was able to experience the romantic ideal of sailing the Caribbean. I felt like I was living Jimmy Buffett's lyrics while sipping a margarita shipboard in the waters of one beautiful bay after another, chomping on a coconut and watching the sunset with both wife and friends.

The different sailing charters surprisingly reminded me of my childhood family road trips to Wisconsin. Whether crammed into our station wagon or reclined in a luxury RV, the journey became our destination. My enduring memories are made up of what we saw and experienced along the way.

The flexibility of the open road is a lot like the freedom of the seas.

So grab a few friends, a cooler of ice and a captain, and set sail.

Information for this article was gathered on a research trip sponsored in part by Discover Boating, Sunsail, Moorings, Tourism BVI and Tourism St. Vincent.

Bill Fink is a California-based freelance writer.