Returning from our sailboat cruise to Florida represented both the end ─ and the beginning ─ of a boating dream. When the trip was finally over, we docked Santorini at our local marina, giving our beautiful old sailboat a much-deserved rest. She had served us well, keeping us safe from the clutches of many on-the-water mishaps.
But as we transferred the mountains of boat gear back to our car, and prepared to resume land life, we realized that the past six months had given us a taste of a drastically different Lifestyle. We realized that we loved the cruising life’s freedom and flexibility, and we wanted more of it.
However, we agreed that a 30-foot sailboat was entirely too cramped for my 6’ 2” husband ─ and unable to provide the creature comforts we wanted. Our solution: Sell the house and find a bigger, better-equipped boat that could handle Poseidon’s wind and weather vagaries.

We knew we’d need a much bigger sailboat to enjoy the space and amenities we wanted. We also knew our budget would be horrified by that sailboat’s price tag. So we turned our attention to trawlers ─ but definitely not shrimping trawlers.
A modern recreational trawler typically has a roomy, functional layout with many amenities. And except for the high-end vessels designed for well-heeled buyers, most trawlers (especially older ones) have decent fuel Economy and a reasonable price tag.
As luck would have it, I was working as a receptionist at an upscale Annapolis, Maryland yacht brokerage. Although I knew all the yacht brokers, some probably wouldn’t understand our boat search goals. However, Keith was cut from a different cloth. Although he often sold high-end racer/cruiser sailboats, Keith appreciated diamond-in-the-rough vessels that just needed the right owner to make them shine.

And that’s how we met Holiday. One day, this 46-foot blue aluminum trawler was trucked into our brokerage and parked just outside the office door. I quickly grabbed the listing and called my husband, eager to schedule a showing. Notice I didn’t call Holiday a yacht ─ that would have insulted her. This salty-looking vessel’s high bow and no-nonsense profile meant Holiday was built for functionality. In fact, Holiday was built in a Massachusetts commercial shipyard.
From the office window, I could see Holiday’s roomy (and covered) back deck, offering a pleasant spot to relax during rainy weather. The covered side walkways would help us navigate the decks in blustery sea conditions. The wide-open front deck offered plenty of room to work with anchoring gear. Everything about this vessel meant business.

Inside, Holiday’s roomy main salon (living room) had enough space for two IKEA lounge chairs, built-in bookshelves, and a worktable. The galley (kitchen) offered multiple kitchen cabinets, space for a small butcher-block cabinet, and a propane stove/oven combination. The steering station was just a few steps away.
Below, a single master stateroom (bedroom) offered room for a walk-around queen bed. The built-in drawer storage, plus two decent-sized hanging lockers, gave us storage we only dreamed of aboard 30-foot Santorini. Holiday’s functional bathroom (head), including the roomy enclosed shower, was another good selling point.
Holiday even had a real engine room! My electrical engineer (and seasoned boat refitter) husband couldn’t wait to redesign the space to accommodate new equipment and banish the past owner’s clutter. If the main level’s living space was largely my domain, the imposing engine room belonged to Mark.

Following Keith’s well-managed negotiations, plus a survey and sea trial, we signed on the dotted line and officially purchased our next boat. Knowing that we’d live on this salty vessel for at least several years, we gave her the name Holiday. We always wanted to view our liveaboard lifestyle as an extended holiday.
After our “new” boat received a fresh coat of bottom paint, we hired an artist to hand-letter a striking gold “Holiday” on both sides of the vessel’s bow. Now outfitted with a proper boat name, Holiday was ready for her launch date.
On that epic day, we watched the big, lumbering Travelift retrieve Holiday from land storage and move her down to the marina’s launch bay. The operation went flawlessly, with a smooth splashdown and no leaks.
Once in the water, we christened our new home with a bottle of good champagne. We also offered libations to the gods of the wind and the sea. Most tradition-minded boat owners follow this protocol ─ for a good reason. These deities are easily miffed, and they could make your life aboard a miserable experience.

Embarking on our liveaboard lifestyle wasn’t as easy as it sounds. Mark had a hefty list of planned equipment upgrades, and those were best done before we actually moved aboard. So we moved Holiday to cheap land storage while Mark worked on the boat on nights and weekends.
To throw a wrench in the works, our house sold much faster than anticipated. And because each boat equipment upgrade triggered at least one “while we’re at it” project, Mark wasn’t sure when Holiday would be habitable.
So we briefly moved to an Annapolis apartment ─ and that’s a period we’d like to forget. Our ground-floor apartment met our needs and had sufficient room for all our “stuff” (the rest was in storage). But we were in limbo, and we felt like two caged rats.
Finally, Holiday was ready to welcome her new captain and crew. We moved the boat into her Annapolis slip adjacent to two big, high-dollar cruising sailboats. We can’t imagine what those owners thought of our rugged-looking trawler, but they were always friendly.
We kept Holiday in that slip for over five years, watching the Back Creek boat traffic while we held down jobs and dreamed of the day we could “go south for the winter.” In the early 2000s, we finally realized that dream ─ but more about that in a future installment.