Don’t miss the boat to Martha’s Vineyard

If you want the perfect Martha’s Vineyard vacation, start planning early—really early. Otherwise, as I discovered, you just might miss the boat. Here are some ways to ensure you get the trip of your dreams hassle free, while saving at least enough money for another Black Dog sweatshirt. You’ll be off the ferry and steaming fresh seafood in no time. Quahogs anyone?

Last year, I was completely prepared for my August stay on the Vineyard well in advance, or so I thought.

Getting to the Vineyard

Six weeks before my trip, I scrambled to make a reservation with the Steamship Authority, the single ferry that carries cars, only to get stuck with undesirable departure times. At first, I couldn’t get the days I needed, so I had to sweat out the wait list, which barely came through at the very last minute.

Hoping to correct my mistake this year, I set out to book in mid-February, six whole months in advance, but the same thing happened. That’s when I learned that car reservations for nonresidents opened up January 17 and sold out within weeks for peak times such as weekends and the month of August.

Word of advice: Know your plans and book early. Or, forget the car.

Bringing a car is not only difficult, but also expensive and ultimately unnecessary. While it costs $130 round-trip for the car during the peak summer months, foot passengers never need reservations, and pay fares starting at only $14, depending on the ferry company. For those who need to go the long haul once on the Vineyard, there’s affordable bus service and even taxis. Perhaps the best mode is bicycle, which you can bring on the ferry for about $6 or rent. Taking it slow—pedaling by rolling horse farms, “honor-system” flower stands, and even homespun studios along the new Arts & Artisan trail—is the only way to live in true island style.

Vacation rental

Unfortunately, vacation homes are not exempt from the book-early mentality. According to Abby Rabinovitz, a rental agent at Tea Lane Associates in West Tisbury and Chilmark, “This year has been a hot season and some of the best homes were booked up by January 1.” She says, “If you know your plans in advance, it’s best to start looking in September and October.”

However, if you’re late in the game, don’t despair. “The market is always in flux, where owners are always putting new properties on the market. The early spring can be an especially good time to find deals if your plans are flexible.”

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Rabinovitz continues, “To save some money or get a nicer place, look outside August, the peak month. July, late June, and early September are particularly good times for equally pleasant weather and lower prices.” Or, as she suggests, “Rent a home that’s a bit off the beaten path in places like Aquinnah instead of Chilmark.” I found a hidden cottage in the West Tisbury woods near the airport for only $1,500 per week in August. Comparable places on the island cost between $2,000 and $3,500.

Prices will depend on what features—such as size, quality, and location—you prefer, so it’s best to shop around. Also, as a rule of thumb, homes right on the beach tend to cost more.

Good websites to find rentals include Martha’s Vineyard Online, a comprehensive source dedicated to the Vineyard, as well as multi-destination sites such as VRBO, HomeAway, and CyberRentals, which all allow you to search by town. If you’re having trouble finding availability, try calling a local agent who works directly with multiple property owners.

Affordable activities off the beaten path

Booking transportation or a rental home can make or break a vacation, but what you do on the island can create the best memories. While many congregate in the popular towns of Edgartown, Oak Bluffs, and Vineyard Haven, heading “up island” to the countryside will take you out of the fray. And, you won’t need to plan in advance or spend a thing.

On your way to the Aquinnah Cliffs and Gay Head Lighthouse on the Vineyard’s southwest corner, stop for fried clams at The Bite in Menemsha. This pint-sized fishing village of seafood shanties is one of the best spots to see the sunset, as well as pick up the catch of the day.

The farmers’ market in the restored Grange Hall (Wednesdays and Saturdays, from 9:00 a.m. to noon) is the place to mingle with locals and pick up a few locally-grown provisions for your cookouts. You’ll find stalls selling fresh produce, canned or bottled items like herb-infused oils and vinegars, and even cut flowers and potted plants.

If you want to play in the sand, the marshy beach at Long Point Wildlife Refuge limits visitors, so it feels more secluded ($3 per person June 15 to September 15, free the rest of the year). The surf tends to be a bit rougher than on the other side of the island, but allow the crashing waves to lull you into a state of relaxation. That’s likely why you came to the Vineyard in the first place.

One question remains: Can you visit Martha’s Vineyard for under $500? Yes. Book an affordable vacation rental and share it with friends. Although my home cost $1,500, it was big enough for four, bringing the price down to $375 each. Also, travel on foot or bike as much as possible, and cook your own seafood rather than dining out. Try grilling clams until the shells open, then lightly steam them in a pot with butter, garlic, and fresh herbs—simple, inexpensive, and delicious. As long as you catch the boat, you won’t spend much on having fun.