We Left the Boat Behind… Was This View Worth It? - The Lazy Geckos Ep. 367

With deteriorating autumn weather churning the North Atlantic and seasonal cruising windows closing down, Jeremiah and Brittany Gowl of Lazy Gecko Sailing & Adventures made the tactical call to pause their offshore itinerary. Mooring their Antares 44i catamaran, SV Calypso, securely at the dock, the cruising family packed their sea bags into a rented van to launch an overland expedition north toward Maine. Swapping ocean swells for asphalt highways, the crew embarked on a land-based travel chapter to explore coastal waterways, historic anchorages, and regional landmarks from a fresh terrestrial vantage point.

Cruising full-time with young children demands constant logistical agility, whether calculating tricky tidal currents through ocean inlets or managing spontaneous road trips. Joined by their children, Graham and Bryn, Jeremiah and Brittany charted a course through the American Northeast, balancing historic architecture against the unpredictable friction of family travel. Their inaugural leg brought them directly into New York’s lower Hudson Valley, establishing a contrasting rhythm between high-end architectural sanctuaries and the quick problem-solving required when reservations fall through.

Fort Hill Sanctuary: The Abbey Inn and Hudson River Overlook

The crew’s first major destination was The Abbey Inn & Spa, perched high on the bluffs of Fort Hill in Peekskill, New York. The landmark property holds deep regional roots, originally constructed in 1902 as a convent and chapel for the Episcopal Sisters of Saint Mary. Decades earlier during the American Revolution, the high promontory served as a critical lookout post utilized by General George Washington to monitor British naval movements along the Hudson River corridor. After the nuns vacated the convent in 2003, developer Martin Ginsburg spearheaded a massive historical restoration that culminated in the property reopening in 2020 as a luxury boutique retreat.

Arriving on a quiet weekday, the family found themselves virtually the sole guests on site, giving the children free rein to explore the cloistered courtyards and manicured stone grounds. The dramatic stone architecture and hilltop presence immediately evoked European fortresses, creating a striking contrast to the fiberglass bulkheads and compact layouts of life aboard a cruising catamaran.

Garden Wanderings and Cruising Memories on the Hudson

Stepping out into the landscaped courtyard gardens, the crew paused to take family photographs against the backdrop of the restored brick convent and chapel. Young Graham quickly gravitated toward the Japanese koi pond, watching massive ornamental carp glide beneath the surface and enthusiastically dubbing the water lily pads “floaties.” The peaceful courtyard offered a welcome break from the long highway miles up from Florida, giving the children space to burn energy while their parents surveyed the expansive river vistas below.

Gazing down at the broad waters of the Hudson stirred familiar sailing memories for Jeremiah and Brittany. Several seasons earlier, the crew had anchored Calypso directly beside the Statue of Liberty in New York Harbor, patiently waiting for the churning tidal currents to reverse in the East River before timing a breathtaking dawn run north up the Hudson. Spotting sailing sloops and motor yachts resting on swinging moorings along the Peekskill shoreline reinforced their bond with the water, even while traveling by van.

The hotel stay delivered domestic luxuries rarely found aboard a voyaging boat, highlighted by plush bathrobes, a multi-jet waterfall shower, and panoramic river views. Following an afternoon of exploration, the family indulged in room service burgers and fries before dining at Apropos Restaurant, savoring grilled octopus, steak, and artisan cocktails. The morning concluded with Brittany taking a quiet shoreline walk along the waterfront park and Metro-North railway trestles, soaking in the misty river scenery before packing the van for the next leg.

The Glamping Cancellation and the Scramble in Mystic

No extended road trip unfolds without logistical friction, and the Gowls soon faced an abrupt detour on their northward journey. The family had pre-booked a unique glamping destination featuring geodesic domes nestled in the woods. However, on the morning of their scheduled arrival, an unexpected email arrived from the property operators stating a strict, non-negotiable rule: no children under the age of thirteen were permitted on the premises due to liability concerns regarding on-site streams and creeks.

Brittany immediately placed a phone call to the property managers to negotiate an exception. She explained that their children were seasoned full-time cruisers who had lived their lives afloat, possessing advanced water safety instincts far beyond their years. Despite her reasoning, the operators held firmly to their insurance policy and issued a prompt cancellation refund. Suddenly without overnight accommodations, the family had to regroup and engineer a fast backup plan.

Recalling a scenic recommendation from a channel viewer, Jeremiah and Brittany charted a detour east to Mystic, Connecticut. After checking into a local Hilton to reorganize their luggage and work through route options, the family headed out for a restorative breakfast at Popover cafe. The children devoured stacks of French toast and fresh bagels, giving the adults time to evaluate northern lodging options and secure reservations for their next leg into northern New England.

Historic Grandeur at the Omni Mount Washington Resort

With a single night to bridge before their confirmed reservations in Maine, the crew secured rooms at the colossal Omni Mount Washington Resort and Spa in Bretton Woods, New Hampshire. Erected in 1902 through the dedicated labor of 250 Italian artisans, the grand Spanish Renaissance hotel stands as a monumental mountain retreat beneath the peaks of the Presidential Range. The sheer scale of the historic property provided an entirely different architectural experience from the boutique quiet of the Hudson Valley.

While Jeremiah wrangled Graham and Bryn in the expansive public verandas, Brittany handled the registration desk. Entering their European-style quarters revealed antique woodwork, multi-chambered layouts, and distinctly vintage infrastructure, including exposed industrial pipes overhead that Brittany jokingly compared to the lower decks of the Titanic. The vintage elevator proved famously minuscule, barely squeezing the family and luggage into its compact cage.

Navigating the rambling corridors in search of the vintage ice machine, Jeremiah checked in with the children to see how they were adjusting to life off the boat. When asked if they missed Calypso, both Graham and Bryn readily admitted longing for their familiar floating home, confirming that no luxury hotel can replace the comfort of a family cruiser. The chapter wrapped up with anticipation building for their upcoming explorations, including a tour of the resort’s historic prohibition speakeasy tucked away in the subterranean stone cave on Level LL.

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