Summer Aboard a Boat: The Cheaper Version of a Vacation Home With Way Better Views

Oleese's salon.
The salon of Oleese, a Hinkley yacht turned summer home for its owners. Jonathan Russo

There are many sayings about home—“home is where the heart is” and “home is where you hang your hat” are just among they many idioms emblazoned signs sold at Hallmark stores across the country. But how loose are you prepared to get with definitions? Because for anyone who is fine with adopting a land-free approach to their housing situation, we have some options with stunning harbor views that could cost you as little as five figures.

David Doody, General Manager at Brewer Capri Marina in Port Washington, N.Y., will easily sell you on the idea making your vacation home seaworthy: “The advantages of living aboard a boat are many. For starters, you always have waterfront. We have over 300 slips. They all come with a water view.”

Another advantage is flexibility. Tired of Montauk? Put the boat in Greenport, Martha’s Vineyard, an inland lake or anyplace on the Maine coast. Admittedly, it may function best as a warm-weather-only option.

That’s what Brooklyn’s Peter Ferguson does. He and his girlfriend Jenna Flora summer on Valfreyja a 47-foot sailboat moored in Dering Harbor on Shelter Island, N.Y. “We don’t want a house. We’re in our own world out here and when we want a change of scenery, we set sail to Block Island or another beautiful harbor.”

Valfreyja at sunset.
Valfreyja at sunset. Jonathan Russo

One of the big decisions in buying a boat is power or sail? The advantages of sail are obvious; you can pick up and go using only the wind, while experiencing the beauty of the voyage. Fuel costs for a power boat can be substantial. Sailboats are the original eco-choice.

The disadvantage is you can only go when there is wind and sailboats have smaller interior space than a same length powerboat. And, the latter are more commodious, “The comfort factor is greater. Often there are multiple levels for living and the feeling of openness is always greater,” Doody said.

Peter Ferguson aboard Valfreyja.
Peter Ferguson aboard Valfreyja. Jonathan Russo

Brad Roaman, a real estate investor, designer and former professional photographer, lives aboard his custom Hinckley 50 Oleese powerboat in Sag Harbor. From his beautifully designed and appointed main salon (living room) he has a magnificent view of the Sag Bridge, boats, and waters beyond. A feeling of nautical serenity pervades. Brad grew up living in marinas. “I could live in a house if I wanted but I love waking up and going to sleep looking at the light on the water.” He added, “I custom built this boat, so the space reflects who I am.”

Oleese, a custom Hinckley 50.
Oleese, a custom Hinckley 50. Jonathan Russo

The depressed market for used boats is another plus. A live-aboard could cost under $50,000. Of course, it’s easy to spend millions on a mega-yacht but, for under six figures you can buy something nice. New York real estate agent Isaac Halpern did just that. A year ago, he bought a Bristol 35-foot sailboat, the Ida G, as a second home. Moored in a harbor on the east end of Long Island he said he “loves being on the boat. The trick is minimalism; do not clutter your boat…but a good bar area is essential.” He also sails her to new destinations. “This year we are going to head up to Maine.”

And compared to land-based real estate boats are a bargainthere  are no annual taxes, for example. But maintenance costs and either a slip, which is a fixed spot at a marina dock, or mooring, a fixed anchor in the water away from a dock, all add up.

“Annual maintenance of 10 percent of the boat’s cost can be expected,” said Connor Needham, customer service manager and third-generation owner at Coecles Harbor Marina in Shelter Island. “If you buy something that needs a lot of repair, it will be much higher.  He advised, “Always have a boat professionally surveyed before purchase so you know what you’re getting into.”

Oleese's galley.
Oleese’s galley. Jonathan Russo

Boats also depreciate, so do not consider this purchase a smart investment. The fiberglass hull might last forever, but non-structural components like engines, electronics, plumbing and canvas often need costly upgrading.

Ellen and Dennis Clark live-aboard temporarily while they are between houses. According to Ellen, “Our architect was late in getting us plans for our new house so we had nowhere to live after we sold our house, and the rental lease expired. So, we decided to move onto our 38-foot sailboat. Everyone told us we would kill each other and hate moving our life into basically a large closet. But it’s not so. We’re having a great time. It is a new and exciting experience.”

Oleese's V-berth.
Oleese’s V-berth. Jonathan Russo

Ellen’s friends have a point. Living aboard is not for everyone. It’s often cramped. Closets and storage are minimal. Cooking is like camping out, and to exit most sailboat beds requires real dexterity. You need a Hygee or KonMari attitude towards possessions. A rainy day can be a trial for anyone with claustrophobia, unless like Ferguson, you “love it when it rains.”

It also helps to be handy. Everyone interviewed is mechanically inclined and can do routine maintenance. Calling highly paid marine mechanics to fix everything can get expensive fast.

Even if it’s not a long-term plan for everyone, living aboard is a good way to figure out exactly where you want to summer. Having the flexibility to experience different places and getting to know the community from the water side can make for a nice life. Summer Aboard a Boat: The Cheaper Version of a Vacation Home With Way Better Views