The Perfect Honeymoon Road Trip in New England

The best way to see this honeymoon destination: on a road trip

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Despite the number of states that make up New England—which includes Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont—the region is actually quite compact, making it easy to explore a large chunk in a relatively short amount of time. With quaint seaside towns, quiet country roads, a robust craft beer scene, and plentiful delicious, fresh seafood, New England makes for a great road-trip honeymoon destination in the U.S. Whether you decide to tackle the whole area or concentrate on a smaller section, here are some logistical tips for planning the ultimate honeymoon road trip in New England.

Courtesy of Hotel Portsmouth

When to go and how long to stay
As with most vacations, the optimal time to visit will depend on a number of factors, including your budget, tolerance for crowds, and interests. If skiing and snowboarding are must-do activities, you’ll want to visit during the snowy months of November to March; if you’re looking for prime beach and boating season, then your window is June, July, and August. Fall foliage season, when the leaves turn to brilliant colors of red, yellow, and orange, is September and October. And if you’re looking for activities like hiking and fishing, spring and fall are safe bets.

While the temperatures will vary by state (getting colder as you head north) in general, winters in New England are snowy and bitterly cold, while summers highs can reach 80°F.

Prices are generally highest during summer and fall foliage season (ski resorts will be pricier during ski season, of course), and this is when you’ll find the most crowds. If you don’t mind colder temperatures, winter is a great time to avoid the bulk of other tourists, though you’ll find that in smaller towns, tourist service can be lacking in off-season.

Four to five days will give you a basic introduction to the region; you can stay overnight in two to three towns and have some time for day trips. A week will give you a bit more flexibility, and 10-14 days will let you explore a few places in depth or give you the time to go farther off the beaten path.

Courtesy of Hotel Portsmouth

Getting there and traveling between cities
Several airports serve New England so you can choose which best fits your travel plans and budget. If you’re planning to cover a lot of ground, you may want to book an open-jaw ticket (flying into one airport and out of another) to avoid backtracking; however, this may cost more.

Boston Logan International Airport is one of the largest in the Northeast and more airline options may mean lower prices. It’s also pretty centrally located; from Boston it’s less than two hours to Portland (ME) or New Haven (CT), and less than an hour to Providence (RI) or Portsmouth (NH).

Once on the ground, the best way to get around is by car. This will give you the most flexibility to design your own itinerary and stop where and when you want. Roads are paved and well-marked; many highways require tolls, so bring cash or opt to rent a toll pass from the rental company.

Courtesy of Press Hotel

Planning a route and choosing destinations
As with any trip, where to go will depend a lot on what you'd like to do and the time of year. If you want to take in the major cities, you can spend a few days each in Providence, Boston, Portsmouth, and Portland. If you’re all about rugged coastlines, you may want to spend more time in northern Maine, Cape Cod, or Martha’s Vineyard in Massachusetts. Beer-lovers may want to spend more time in Vermont, which boasts more breweries per capita than any other state, or follow the beer trail in Maine or Connecticut. Skiers might head to Stowe or Sugarbush resorts in Vermont, while history buffs may opt for Boston, with day trips to Salem, Concord, and Plymouth.

Depending on your must-visit destinations, you may want to do a progressive road trip, moving from town to town every day or so, or you may want to pick one or two bases at which to stay for several days, and then take day trips to explore outside of that base.

If you’re flying in and out of the same airport, decide if you want to start farthest away and work your way back, or vice versa. This may depend on the timing of your flights; if, for example, you’re flying in and out of Boston and your flight home is very early in the morning, you may want to explore Boston on the final leg of your trip so you don’t have to drive far to the airport on the day of your departure.

Courtesy of Press Hotel

Sample five-day itinerary
For a five-day trip to from Boston to Portland, fly in and out of Boston Logan; pick up a rental car and drive the two hours north to Portland to kick off the trip with an introduction to some of Maine’s best beer at Allagash Brewing, where tours are offered daily. Stay in the beautifully restored Press Hotel, once the home of the city’s Press Herald newspaper (old typewriters and wallpaper with old newspaper headlines nod to its past). Spend the next day exploring the historic town, gorging yourself on buttery lobster rolls. Take a day trip to the charming towns of Ogunquit and Kennebunkport, or visit Cape Elizabeth to check out Portland Head Light.

From Portland, backtrack south to Portsmouth, New Hampshire, and check into the Hotel Portsmouth, where the two-story loft rooms feel like mini-apartments. Explore the main boutiques and design shops of Market Square, stop for a steaming fresh-baked popover from Popovers on the Square, learn about more than 250 years of local history at the Strawberry Banke Museum, and finish the day with cocktails and delicious seafood—including lobster pasta, smoked lobster tail, and, of course, lobster rolls—at hip Row 34.

Enroute back to Boston, stop off in Salem to visit the Salem Witch Museum and dig into some fresh clams and oysters at the Sea Level Oyster Bar. Then check into the sexy XV Beacon hotel in Boston’s historic Beacon Hill neighborhood, where it’ll be hard to tear yourself away from the room’s four-poster bed, gas fireplace, and rain forest–shower. Explore the city’s history on the Boston Freedom Trail, take a beer tour to visit breweries like Harpoon and Samuel Adams, and head to Moo... in the XV Beacon for modernized steakhouse classics—or head to the North End neighborhood for traditional pasta and Italian wines served by candlelight.

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