Explore Sea and Air Options to the Tony Vineyard
Fly There in a Flash
Flying is certainly the quickest way to get from Boston to Martha's Vineyard, though it won't fit every family's budget. A direct flight takes only about 40 minutes, taking you to Martha's Vineyard Airport in the middle of the island. Your only commercial carrier of choice from Boston, however, is the regional Cape Air. While it schedules multiple flights per day, expect to pay what you'd pay for a standard medium-haul domestic flight on a major carrier. The cost will add up for a large family. If you have a lot of luggage, the cost will be even more, as Cape Air allows only one free checked bag per passenger. Cape Air's fleet is mostly nine-seater Cessna 402s, so nervous flyers who dislike small planes will have to get over that for a little less than an hour. However, your family will practically have the plane to itself. Larger carriers, including JetBlue, Delta and American Airlines, also serve Martha's Vineyard Airport, but with no flights out of Boston.
Bring the Family Car
While you can't drive to Martha's Vineyard, there is one way to get the family car to the island: the Steamship Authority ferry service (1 Cowdry Rd., Woods Hole, MA). The ferry operates year-round from Woods Hole on Cape Cod, about an 80-mile drive from Boston. From there, it's a 40-minute ride to Martha's Vineyard. You'll pay a fairly hefty charge to get your car aboard, as well as a small fee per family member, but having your car can be a lifesaver if you want to explore the full island without shuffling your children around on buses or dragging them along on long walks. You should reserve the slot for your car on your ferry well in advance, especially if traveling during the busy June-through-August period, as space is limited. Also, be aware that finding parking can be a challenge once you're on Martha's Vineyard. The Steamship Authority docks in Vineyard Haven all year and also in Oak Bluffs from mid-May through mid-October.
Other Aquatic Options
Several other ferry operators offer seasonal service to Martha's Vineyard, but none of them are in Boston, so you'll still need an extra mode of transportation. In the same vicinity as the Steamship Authority, you can take the Island Queen (75 Falmouth Heights Rd., Falmouth, MA) from Falmouth to Oak Bluffs, the Falmouth-Edgartown Ferry (278 Scranton Ave., Falmouth, MA) or Hy-line Cruises (220 Ocean St., Hyannis, MA) from Hyannis to Oak Bluffs. If you prefer to avoid Cape Cod traffic, take the SeaStreak from New Bedford (49 State Pier, New Bedford, MA) or the Martha's Vineyard Fast Ferry from North Kingston, RI (1347 Roger Williams Way, North Kingston, RI), both of which dock in Oak Bluffs. None of these services transports cars, but you can always rent a car in Martha's Vineyard if you need one. Distance-wise, all of these are about 60 or 70 miles from Boston and all have parking nearby. If you prefer to leave the car at home altogether, you can catch shuttle services or a bus from Boston to any of the ferries or the seasonal CapeFlyer train service to Cape Cod. This could be a hassle, however, if you're traveling with small kids and a lot of luggage. As with the Steamship Authority, it's a good idea to buy your ferry tickets in advance, especially in the summer.
Keeping Up Appearances
You'll be rubbing shoulders with the affluent on Martha's Vineyard, so why not arrive there with your family on a private jet? It's actually not as ridiculous as it sounds. As the private aviation industry catches up to the technology age, numerous companies—Victor, PrivateFly and Magellan Jets, to name a few—are consolidating searches for private aviation operators. You might luck out and have your trip coincide with an "empty leg" trip—when someone charters a jet somewhere but doesn't need an immediate return trip, meaning the jet would offer seats at a discount because it would otherwise be flying back empty. Even if that's the case, this will certainly be your most expensive option by far. You also could charter a boat from Cape Cod, though that would be much more expensive than ferry service and would not save much time.