Living Aboard in Paradise

This Minnesota couple sold everything, bought a boat and escaped winter for the Caribbean.
Great Harbour Cay in the Berry Islands
Windbird on break in Great Harbour Cay in the Berry Islands, Bahamas. Sam Weigel

It’s a breezy night in the warm gulf stream, and I am wide awake with anticipation. Dawn, my wife and ever-capable mate, is off watch and fast asleep. I brace against the cockpit coaming and stare out into the darkness; starlight defines a wave-tossed horizon. The distant lights of Florida appear every time we crest a big roller, then they disappear in the troughs.

This is an exciting sight after nine days and 1,300 nautical miles at sea, yet it stirs mixed emotions. We’ve spent the past three years cruising the Bahamas and Caribbean aboard Windbird, our Tayana 42, and I don’t want this adventure to end.

Our journey began with a remarkably casual decision. We had been enjoying bareboat charters for a few years and occasionally toyed with the notion of cruising full time. I’d come to dread the long, brutal Minnesota winters and often fantasized about escaping to tropical waters. Dawn was ready for a break from her job as a middle-school math teacher; as an airline pilot, I had an unusual degree of work flexibility during the winter. When I floated the idea of going cruising for a few years, we decided to go for it.

English Harbour in Antigua
Taking in the view of English Harbour in Antigua, as seen from Shirley Heights. Sam Weigel

For the next 12 months, we worked, saved, researched, bought gear and took classes. We sold our house and downsized to an apartment. Dawn quit her job, and I transferred to an airline fleet and base with seasonal flexibility. After looking at a dozen boats, we made an offer on a 42-foot Taiwanese cutter whose previous owners had sailed it around the world. We soon found ourselves the slightly anxious owners of a 34-year-old 15-ton yacht.

Our planned monthlong refit in Charleston, South Carolina, that fall turned into three months of boatyard hell thanks to Hurricane Matthew and our own inexperience with marine contractors. But in early January 2017, we cast off the dock lines and, hearts aflutter, pointed Windbird’s bow south.

Sam Weigel in a hammock aboard his yacht
The author enjoys downtime at Cambridge Cay, Exuma Cays Land and Sea Park. Sam Weigel

Making our way to Fort Lauderdale, Florida, we realized that sailing offshore is far easier and more efficient than motoring down the Intracoastal Waterway. Fortunately, Dawn turned out to enjoy sailing at night and proved a capable watch stander, a skill that allowed us to make several long offshore passages.


Our first overnight crossing of the Gulf Stream was calm, and our morning arrival to the Bahamas’ cerulean waters was exhilarating. A fantastic cruising destination right on America’s doorstep, the Bahamas has enough active weather, tidal anchorages and shifting shallows to hone novice cruisers’ skills. We spent three months exploring the Berry Islands, the Exumas, Long Island, Eleuthera and the Abacos, and fell in love with the country and its friendly people. We also enjoyed becoming part of the tightknit international community of wandering sea nomads. Despite being significantly younger than most cruisers, we formed many close friendships while hiking, snorkeling, sharing potlucks, attending bonfires, and enjoying sunset jam sessions on the beach.

fire built on Sand Dollar Beach, Stocking Island, Bahamas
Fireside on Sand Dollar Beach, Stocking Island, Bahamas. Sam Weigel

Cruising wasn’t the never-ending vacation we’d envisioned, though. It’s a lot of hard work, filled with uncertainty and occasional discomfort. Plans change constantly with the weather and mechanical breakdowns. Chandleries and mechanics are rare in the Out Islands; you find yourself tackling daunting repairs with only the help of a few books, spotty internet and perhaps a sympathetic fellow cruiser. It’s quite rewarding when you succeed, but it’s discouraging when something else breaks the next day.

Tropical cruisers’ long-term plans are largely driven by the inexorable approach of hurricane season. Options are to retreat to the United States, head for the far southern Caribbean, store the boat ashore, or continue to live aboard while being prepared to haul out or run for cover on short notice. We spent summer 2017 on the Chesapeake Bay while upgrading Windbird’s canvas, electrical system and solar panels, and we were grateful to be out of the path of Category 5 monsters Irma and Maria as they dealt a one-two punch to the northeastern Caribbean.

Sam Weigle at the wheel in St. John, US Virgin Islands
At the wheel in St. John, US Virgin Islands. Sam Weigel

That November, we sailed offshore to Abaco, spent several more months in the Bahamas, and then continued down the “thorny path” via Turks and Caicos and the lovely Dominican Republic. After crossing the infamous Mona Passage and cruising the south shore of storm-ravaged Puerto Rico, we spent several months lolling around the battered but still beautiful US and British Virgin Islands before hauling out in a protected Puerto Rican boatyard. Fortunately, it was a quiet storm season for the Caribbean to recover while we visited family and worked full time to rebuild the cruising kitty.

Upon our return to Puerto Rico that fall, we discovered that an undetected deck leak had turned our trusty diesel engine into a rusty hunk of junk. Thus began our biggest project yet: re-powering with a new Yanmar diesel in St. Thomas.

It went surprisingly smoothly, and a month later, we continued on our way down the island chain. The sailing was superb, with most landfalls an easy daysail apart. All the islands are lush and volcanic, yet each has its own unique history, culture and vibe; together they form a brilliant West Indian kaleidoscope.

Paddleboarding in Hog Cay anchorage in the Bahamas
Paddleboarding in Hog Cay anchorage in the Bahamas. Sam Weigel

We particularly liked swashbuckling Antigua, wild Rastafarian Dominica and the cruisers’ paradise of the Grenadines. We spent five beautiful months in the Lesser Antilles before heading to breezy Curaçao for the summer. The ABC Islands would make a convenient jumping-off point to cruise the western Caribbean the following season.

But then our plans changed, which is why tonight, after a long passage from Bonaire, we are almost back to the United States. I curl up in the cockpit and watch the eastern horizon brighten with streaks of deep purple, pink and orange. Majestic swells flash in the sunrise as they sweep under our stern, our sturdy boat digging in and riding each wave as it races by with a melodic hiss.

Yacht cruising from Guadeloupe to Dominica
Cruising from Guadeloupe to Dominica. Sam Weigel

These past three years have given me so many fond memories, but even more, they’ve given us the lifelong skills and the confidence to explore our beautiful watery world. Our time cruising the Bahamas and Caribbean was made possible through a lot of hard work and sacrifice, but these things fade while the results endure. On balance, I have found the cost to be a worthy price of admission.