Nantucket: To get a real feel for the island, take a boat trip along its coastline. Shearwater Excursions’ harbor tours take you past yachts, lighthouses, and extremely fancy waterfront real estate, capping off the experience with a scoop of island-made ice cream. 

White Mountains: Skiing is a must in winter, but if you’re visiting at a balmier time of year, hike Copper Mountain’s Coppermine Trail. You’ll meander through ferns and thick forest until you reach Bridal Veil Falls, a 35-foot waterfall and scenic picnicking spot.  

Boston: History is around every corner in Boston, but to gain a real understanding of its role in America’s founding, book a guided tour of the Freedom Trail. You’ll learn about Paul Revere’s Ride, the Boston Massacre, and other seminal events. 

Vermont: Visiting the factory of Ben & Jerry’s in Waterbury is a New England rite of passage (for the non-lactose-intolerant, at least). Get a tour of everybody’s favorite woke ice cream maker and gorge yourself on flavors both classic and contemporary — we’re partial to the new Netflix & Chilll’d.

Nantucket: You can’t swing a lobster without hitting delicious seafood on this island, but locals swear by the fish sandwiches at Straight Wharf Fish Store, tucked behind the restaurant of the same name (on the wharf of the same name). Grab a lobster roll or freshly sautéed swordfish sandwich and devour them at a picnic table on the dock — extra napkins required!

White Mountains: Schilling Beer Company, housed in an 18th-century mill overlooking the Ammonoosuc River in the town of Littleton, N.H., offers exactly what you’ll crave after a day in the mountains: wood-fired pizzas, thick-cut fries, bratwurst, and a selection of European-style beers (Belgian ales, Czech pilsners, German lagers), all brewed on the premises.

Boston: The line starts forming outside Neptune Oyster well before 11 a.m. opening time — and let’s be honest, you won’t be the only out-of-towner waiting in it. But the cramped North End destination has earned its reputation for textbook New England style shellfish and seafood: a juicy lobster roll, the rich smoked bluefish johnnycake, and the best selection of bivalves in Boston.

Vermont: Polished comfort food that celebrates the best produce from Vermont’s wholesome farms shapes the menu at Butch & Babe’s in Burlington. Fill up on potato rolls stuffed with “smash burger” or falafel, tempura cauliflower with housemade pickles, and caramel apple cream pie.

Nantucket: Bodega is a home design and interiors store with a beautifully edited selection of new and vintage items, from artworks and throws to little decorative items like potted cacti and Moroccan tassels. 

White Mountains: The Brick Store, in Bath, N.H., isn’t any old general store — it’s the oldest continuously operated general store in the U.S., dating back to the early 1790s. Pick up a sandwich and some homemade fudge and eat it on the porch — a favorite haunt of presidential candidates on the campaign trail. 

Boston: The ultimate in-the-know shopping experience in Boston is Bodega. No relation to the Nantucket boutique, this is a secret sneaker and streetwear shop hidden at the back of an unassuming convenience store off Massachusetts Avenue. Just ask the guy behind the counter to let you in. 

Vermont: Shop for a quintessential piece of Vermont attire (and all-around closet staple), the plaid shirt, at the Vermont Flannel Company. The shirts — not to mention blankets, ponchos, and PJ’s — are hand-cut and hand-sewn in a gajillion color combinations. 

Nantucket: If you come to Nantucket and don’t Instagram a lighthouse, did you actually come to Nantucket? We recommend spending a day at Great Point, an idyllic nature preserve with a lighthouse dating to 1784. It’s located on the northernmost point of the island, one of the quietest areas. 

White Mountains: Terrain like this lends itself to adventure sports. At DirtVentures, you can explore trails by ATV in the summer or snowmobile in the winter, both led by instructors who tailor the session to your ability and comfort level. 

Boston: A short boat ride from Downtown Boston you’ll find Boston Harbor Islands National Recreation Area, a group of islands containing a Civil War–era fort and historic lighthouses, walking trails, and tide pools. It’s a lovely, relaxing place to spend a day. 

Vermont: If you haven’t joined the baking trend yet, get yourself to Brot Bakehouse School & Kitchen in Burlington, where the owners teach visitors how to bake delicious sourdough loaves using heirloom grain varieties — or croissants, if that’s more your style.