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The Voyage of a Lifetime

What inspired this Couple to sail from their home port of New Hampshire to New Zealand?
Top: The author’s first offshore doublehanded trip aboard this Valiant 40, Chanticleer, took him to the Caribbean.

Top: The author’s first offshore doublehanded trip aboard this Valiant 40, Chanticleer, took him to the Caribbean.

Setting out from Portsmouth, New Hampshire, in 2018, Jeff Bolster and his wife, Molly, hoped to circumnavigate on their Valiant 40. After port-calls in the Caribbean, Panama, Galapagos, French Polynesia, Cook Islands and the Kingdom of Tonga, they were in New Zealand waiting for South Pacific cyclone season to end when Covid-19 broke out, interrupting their voyage. Dealt lemons, they made lemonade, cruising New Zealand’s northern coast for 19 months, until leaving their boat and flying back to the States. Jeff and Molly plan to return to the boat in November 2022. Jeff’s thoughts on pulling off the voyage will appear in a few installments. This is the first.

By the time we untied our snow-covered dock lines in November of 2018, outbound for the South Pacific, we had been dreaming of round-the-world voyaging for a long time. Yet like many people we had careers, children, a mortgage, aging parents—all sorts of reasons to keep imagining it rather than doing it. For 20 years, on two different boats, we made do with summer cruises in New England, a delivery trip up the East Coast, and four dashes to the Caribbean, always squeezed in between work and family obligations. Wonderful in many ways, it was not the fulfillment of our fantasy to live barefoot for years with the sun always setting ahead off the bow, to savor landfalls as towering volcanic islands rose from the sea at dawn, or to sail in the wake of Captain Cook and other storied navigators.

Molly and Jeff Bolster (below) spent decades sailing and cruising before they set off to circle the globe.

Molly and Jeff Bolster (below) spent decades sailing and cruising before they set off to circle the globe.

Suddenly it was now or never. A husband-wife team, ages 64 and 57 at departure, we realized that it was time to go. Put aside the careers. Prep the boat. Shove off while still fit. We expected magic and serenity and satisfaction. We got all three, and more to boot. But we knew there would be challenges with just the two of us, watch-on and watch-off, in a small boat on the deep blue sea. Voyaging requires some strength and stamina. If you really want to go, don’t wait too long.

Prior to setting off  around the world we departed for the Caribbean four times, learning a great deal about sailing doublehanded offshore.

Our vision of circumnavigating embraced the astonishment it sparked, and the earnestness it seemed to demand. Bora Bora? Might we actually sail one day through the pass in its fringing reef and drop our anchor? We thought so, knowing there could be wild nights along the way, hove to with the helm lashed, boat riding like a duck with its head tucked under its wing, as well as languid days eating juicy mangos on tropical islands. We fantasized about voyaging, but ultimately learned that long-distance cruising requires you to go with the flow, to live through higher highs and lower lows. Your wonder at watching Waved Albatrosses nesting in the Galapagos or a Green Flash as the sun sets ahead of your bow wave will be tempered by moments when your marine toilet is indisposed or your engine won’t start, when there is no plumber or mechanic for 1,000 miles.

In Pacific crossroads such as the Galapagos and Tahiti we encountered cruisers whose inspirations differed significantly, as varied as the nations from which they hailed. While we all shared the kinship of voyaging, there were builders whose primary satisfaction had been constructing their boats and installing systems; adventurers whose wanderlust drove them seaward; refugees from the corporate world; and latecomers to cruising determined to have one grand exploit in life. Like us, many had been inspired by cruising narratives. Other than casting off your own dock lines on the voyage of a lifetime, nothing beats a stint as an armchair sailor experiencing those accounts.

Books inspired the author and his wife to set sail.

Books inspired the author and his wife to set sail.

Beginning in childhood my wife and I were irresistibly drawn to voyage narratives, sailing magazines, and seductive images of vessels in the restless sea. Molly fondly remembers trolling her grandfather’s bookshelves, full of circumnavigating authors such as Francis Chichester and Irving and Electa Johnson. I’m still awed by tales such as Joshua Slocum’s heroic Sailing Alone Around the World, his memoir of doing something no one then thought possible. In grade school I fell under the sway of David Putnam’s David Goes to Greenland, recounting how the boy-author sailed north from Long Island Sound in 1926 aboard the famed schooner Effie M. Morrissey. I never imagined that 62 years later Molly and I would sail the old Morrissey from New Bedford to Newfoundland as deckhand and mate. For us, crossing the Pacific culminated decades of desire sparked by the written word, reinforced by coastal cruises and ocean passages.

During our Caribbean jaunts and our voyage to the South Pacific we talked with cruisers on all sorts of boats. Most were sailboats, though capable powerboats are crossing the world’s oceans. Eye-catching FPBs (Functional Power Boats) designed by Steve and Linda Dashew stood out for their vast range, good seakeeping, and array of comforts unimaginable on small sailboats, as well as their stealthy good looks. In New Zealand we spent time with the owner of a Nordhavn 52, a capable trawler. He, too, had crossed from Panama. Powerboaters must have as much confidence in their propulsion engines as sailors have in their rigs. In lonely expanses of distant oceans, search and rescue services are few and far between, or simply unavailable. The self-reliance once assumed to be part of every boater’s repertoire has become relegated to long-distance cruisers, for whom it is often an inspiration.

Repairs are part of the journey.

Repairs are part of the journey.

A capable sailing yacht costs considerably less than most powerboats able to complete similarly ambitious passages. And that’s before the fuel bill. Voyaging is a pay-to-play game. Nevertheless, the cruising community includes the well-to-do and the nearly broke. Cruisers on a shoestring budget are the most resolute DIYers, frequently unable to pay for technical services, but impressively resourceful. We met a few who had ditched promising careers at a young age, bought simple boats, re-fit them, and embarked on the voyage of a lifetime planning to watch every dollar, eat rice and beans, and cut corners constantly. Their inspiration drew on the lure of a simple life.

We occasionally met cruisers who were in way over their heads. A few had been thoroughly chastened, one young skipper nearly falling overboard through negligence, a story he and his wife recounted with horror in the presence of their

Several crews were downright scary, like the Kiwi couple who explained in Tonga that they had bought their big catamaran recently in Tahiti, and that “after we departed, some rope from the top of the mast to the end of the boom broke, and we didn’t know if it was important. We called the broker to ask what it did.” True story. They had sailed 1,600 miles downwind without knowing how to reef their mainsail. The aphorism that God has special providence for fools and drunks came to mind.

Such negligence is rare. With preparation and practice, long voyages are within reach. Buy a suitable boat. Test the waters with coastal trips. Talk to experienced cruisers. Count on the unexpected, because it is always part of the bargain. You’ll need to read technical manuals. But don’t neglect to treat yourself to the lure of classic and contemporary voyage narratives, the song of the sirens. The dreams they spark are likely to propel you on the voyage of a lifetime. 

This article was originally published in the October 2022 issue.



A Slice of Paradise

Sailing to Tonga, a couple encounters one of the last slices of South Pacific paradise


Around The World Under Square Rig

A circumnavigation is the stuff of dreams, the ultimate sailing challenge. Few pull it off.


Bringing Chanticleer Home

As Hurricane Irma stormed toward Tortola with our boat in its crosshairs last year, I mustered every possible shred of hope.


The boy and his raft: A perfect day on the coast of Maine

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Trip of a Lifetime

A family of five tackles distance cruising in a Fleming 65


Lessons for a Lifetime

A new Maritime High School will open nearĀ Seattle with a curriculum designed to inspireĀ a love of boats and boating