A 12-Day Guide to Exploring New England’s Best Stops

Vermont’s Quiet Luxury

There’s something about New England that doesn’t try too hard to impress and still does. Maybe it’s the mix of storied streets and rugged coastlines. Maybe it’s how you can eat oysters in Maine, hike through Vermont forests, and sip vintage wine in Rhode Island, all in the same week. For travelers who like their itineraries curated, not crowded, this region offers the kind of slow-burning magic that stays with you long after the bags are unpacked.

If you’re carving out 12 days to explore, this road trip weaves through iconic cities, remote retreats, and seaside towns with just the right balance of indulgence and discovery. Here’s how to do it right.

Days 1–2: Start Strong in Boston, Massachusetts
Boston isn’t just your entry point; it’s a city that deserves its own spotlight. From the leafy paths of Beacon Hill to the waterfront buzz of Seaport, the city layers history and innovation like few others. Start at Raffles Boston for understated luxury and skyline views that remind you why you booked this trip.

Wander the cobblestones of the Freedom Trail, swing by the Isabella Stewart Gardner Museum, then unwind with oysters at Neptune in the North End or a martini at Grill 23. Boston doesn’t show off but it knows exactly what it’s doing.

Days 3–5: Slow Down on Nantucket
When the mainland starts to feel loud, Nantucket offers an elegant hush. Board a ferry (or charter a seaplane, if you’re that kind of traveler) and arrive in a place where time slows and style stays classic. The cobblestone streets. The hydrangea-lined cottages. The scent of salt and sunscreen in the air.

Check into The White Elephant; it’s as effortless as it is iconic. Mornings are for wandering the Whaling Museum or lounging at Steps Beach. Afternoons? You’re drinking champagne at CRU, eating lobster rolls at Galley Beach, or reading something indulgent with your toes in the sand.

Boston, Massachusetts

Days 6–7: Channel East Coast Elegance in Watch Hill, Rhode Island
Rhode Island is often overlooked, and that’s precisely its charm. Especially when you’re headed to Watch Hill. This isn’t just a beach town; it’s where classic Americana meets white-glove service. Your stay? Ocean House. Think: sweeping verandas, curated wine tastings, private beach walks, and staff who somehow always remember your name.

On the drive in, pause at Newport to tour the Gilded Age mansions, or at least wander The Breakers for a Gatsby moment. Back in Watch Hill, dinner at COAST is a masterclass in restraint and refinement. The kind of place where the sunset feels personally scheduled.

Days 8–9: Retreat Into Vermont’s Quiet Luxury
Vermont is New England’s exhale. And Barnard is where that breath deepens. Rolling hills, birch forests, and the kind of silence that reminds you to check in with yourself. Twin Farms is your hideaway here, an all-inclusive, adults-only escape that somehow feels both indulgent and intimate.

Days are unhurried: paddleboarding on the private lake, cycling through autumn foliage, and reading by the fire with local cheese and a vintage red. Dinner isn’t just served; it’s staged as a multi-course experience tailored to your palate, not a preset menu.

And if you need civilization? Woodstock is nearby, with general stores that stock both maple syrup and cashmere.

Days 10–11: Eat Your Way Through Portland, Maine
Portland is Maine’s most delicious contradiction: rugged coastlines meet cutting-edge cuisine. The vibe is casual, but the standards are sky-high. You’ll check into Blind Tiger, a boutique stay where every detail feels handpicked because it is.

Start with coffee from Tandem Bakery, then take your pick: hike Fort Williams Park for a view of the Portland Head Light, or just head straight for the oysters at Eventide. For dinner, Twelve is your best bet helmed by an Eleven Madison Park alum, it’s where Maine ingredients go haute. Portland isn’t trying to impress you. It just does.

Day 12: Circle Back or Stay Still
Your last day can go two ways. You can slowly make your way back through the Maine coast, maybe stop at Kennebunkport for a last lobster roll, or let the day pass slowly, spa robe on, book in hand. Either way, don’t rush it. Trips like this aren’t meant to be checked off. They’re meant to linger.

Conclusion
This isn’t a whirlwind. It’s not designed to leave you dizzy. It’s 12 days that flow from one perfectly placed moment to the next. Cities that don’t shout. Hotels that understand stillness. Meals that don’t rush the check. If that sounds like your kind of luxury, then New England isn’t just a stop. It’s a reset.