Cape Cod – Nantucket – Newport – Vermont – Portland – Boston
New England is loved for its timeless charm – a region where coastal villages, historic cities, and rolling forests come together in a way that feels both deeply American and quietly romantic. It’s a place of seasons and stories: sandy beaches in summer, golden maple forests in autumn, cozy firesides in winter, and fresh blooms in spring. From lobster shacks to ivy-covered universities, it’s a destination that balances natural beauty, history, and authenticity like few others.
Our two-week journey through the region took us from Boston’s skyline to Cape Cod’s beaches, the windswept island of Nantucket, the Gilded Age streets of Newport, and the mountain calm of Vermont, before ending in the creative coastal city of Portland, Maine. It was the perfect mix of coastal energy and countryside serenity – a road trip that felt like stepping into a postcard, one drive at a time.
One tip right away: for any American road trip, rent a bigger car. It makes life much easier when you’re moving every few days – especially if you have larger luggage. Having the space to load and unload without rearranging everything each morning adds a surprising amount of comfort and calm to a trip like this.
Cape Cod – Where the Road Meets the Sea
Stay: Sandwich Inn & Suites ($253)
We landed in Boston in the afternoon, picked up the car, and drove straight down to Cape Cod, around 90 minutes south. For our first two nights, we stayed at the Sandwich Inn & Suites, a lovely, relaxed inn that felt instantly welcoming after the long flight.
Our first meal set the tone for the trip: lobster rolls at Sesuit Harbor Café. It’s one of those perfect summer spots – casual picnic tables right by the water, great atmosphere, and simple food done right.
During our stay, we explored Chatham, one of the Cape’s most charming small towns. Make sure to also visit Grey Beach and walk all the way out to the viewpoint – the scenery is stunning, especially in the late afternoon light.
Dinner at Fishermen’s View is another must if you stay around the sandwich area, with great seafood and harbor views (at the time we visited the view was slightly obstructed by some construction).
Coffee tip: Snowy Owl Coffee Roasters in Sandwich quickly became my favorite café on the Cape. Lighthouse Keepers Coffee and Nirvana Coffee are also worth a stop if you’re nearby.
(Optional detour) On your way out, walk the Sandwich Boardwalk or visit the Heritage Museums & Gardens – peaceful, beautifully maintained, and quintessentially Cape Cod.
Nantucket – The Island Escape
Stay: Cliff Lodge ($782 total)
On Day 3, we left the Cape behind and headed to Hyannis, where all ferries to Nantucket and Martha’s Vineyard depart.
We stopped at Craigville Beach on the way – a beautiful stretch of sand that’s great for a morning walk or a quick swim. From there, we boarded the high-speed ferry to Nantucket (around 1 hour). There’s also a slower car ferry, but unless you’re staying longer, skip it – bringing a car costs about $365 each way, and parking in Hyannis is easy with the Steamship Authority lot nearby.
If you’re feeling adventurous, Cape Air flies tiny Cessna planes from Hyannis – a unique way to arrive if you’re not afraid of small aircraft.
We stayed at Cliff Lodge, a small BnB in Nantucket Town. It’s charming but compact – our room was about 7 sqm and cost around $380 per night, so prepare for island prices.
Getting around is easy: the island buses are free, and Ubers work fine for shorter trips.
Our favorite experiences:
- The Sconset Bluff Walk to Sankaty Head Lighthouse – one of the most beautiful trails in New England.
- Cisco Brewers, a lively outdoor brewery that’s part beer garden, part community hangout, with multiple food options.
- Cru, a chic restaurant in the harbor serving a top-tier lobster roll (and a great burger).
- A stroll to Brant Point Lighthouse – just 15 minutes from town and picture-perfect at sunset.
For casual eats, try Gemelle Pizza, Born & Bread, or Surfside Taco. Nantucket is great for a little shopping too, with a mix of boutique stores and cozy cafés.
It’s worth mentioning: the crime rate on both Cape Cod and Nantucket is practically zero, which adds to the relaxed feel.
Newport, Rhode Island – Coastal Elegance in One Night
Stay: B&B in Portsmouth ($190)
After two island days, we drove to Newport, Rhode Island, for a one-night stopover. Newport is beautiful but compact – one day is perfect to see the highlights.
We had dinner at Newport Lobster Shack, a no-frills seafood spot by the docks, and the next morning stopped at The Nitro Bar for great coffee and pastries.
Spend the afternoon walking the famous Cliff Walk and driving along Ocean Avenue – the route passes some of America’s most impressive historic mansions.
End the day at Brenton Point State Park, where locals gather to watch the sun dip into the ocean. It’s one of those places that perfectly captures New England’s coastal magic.
If you have extra time, visit The Breakers, the opulent Vanderbilt mansion that gives Newport its nickname: “America’s First Resort.”
Vermont – Maple Syrup and Mountain Calm
Stay: Cozy Capital Stay, Montpelier ($259 total)
From Rhode Island, we headed inland toward Vermont – trading ocean air for mountain views and rolling countryside.
Our base was Montpelier, the smallest capital city in the U.S. (and honestly, one of the most underwhelming). But the surroundings more than make up for it.
We spent two nights exploring nearby towns like Stowe and Woodstock, and both were absolutely charming.
What to do in Vermont:
- Visit the original Ben & Jerry’s Factory in Waterbury – fun, nostalgic, and surprisingly interesting.
- Have dinner at American Flatbread in Stowe – cozy, lively, and delicious pizza.
- Go apple picking at Whitman Brook Orchard – some of the kindest people we met on the trip.
- Stop at Sugarbush Farms to see how maple syrup is made. You can walk through the forest and watch the tapping process up close.
- Grab coffee at Birchgrove Baking or a grilled cheese at The Meltdown Tap Room in Barre.
- Stop by Bragg Farm for souvenirs and maple syrup tastings.
Our favorite moment came at sunset in Barre, watching the hills glow golden – a hidden gem we’d never heard of before. Vermont might be quiet, but it’s quietly magical.
Portland, Maine – Small City, Big Flavor
Stay: Morrill Mansion Inn (€426 / $460)
From Vermont, we drove east toward Portland, stopping in North Conway, New Hampshire, for coffee and outlet shopping.
Portland is small but packed with great food and a relaxed, coastal vibe. Two nights felt perfect.
What to eat and do:
- Breakfast at Becky’s Diner – classic American comfort food by the water.
- Bagels from Forage Market or pastries at Tandem Coffee & Bakery.
- Visit the iconic Portland Head Light, then grab a lobster roll from Bite into Maine, the shack in the park.
- Dinner at Ocotillo.
- Visit the L.L.Bean Flagship Store in Freeport — it’s open 24/7 and surprisingly worth the detour.
- Drive through Cape Elizabeth for postcard views of the Maine coastline.
If you have time, stop at Standard Baking Co. for something sweet before leaving town.
Boston – A Grand Finale
Stay: Kimpton Marlowe Hotel ($1.187)
We ended our road trip in Boston, returning the car as soon as we arrived – parking costs can reach $50 a day, and the city is best explored on foot or by public transport.
What to see and do:
- Visit Harvard and MIT – both campuses are open and beautiful for walks.
- Walk the Freedom Trail through the city’s historic heart.
- Visit Fenway Park if you’re a baseball fan.
- Plane spotters should head to Castle Island / Fort Independence, right near the airport.
- Explore the modern Seaport District – great restaurants, shops, and waterfront views.
- Coffee stops: Blue Bottle, Popup Bagels, and Tatte Bakery.
- Dinner at Geppetto, a warm and stylish Italian spot near our hotel.
Hotels here are expensive, but Boston’s mix of history, culture, and atmosphere made it a perfect finale to our New England loop.
And for the flight home? Let’s just say it ended on a high note – in Lufthansa First Class on the A340-600 (read our full review here).
Final Thoughts
Two weeks in New England is the perfect balance of variety and relaxation.
You’ll drive through small fishing towns, vibrant cities, and endless forests – and eat more lobster rolls than you thought possible.
Every stop had its own rhythm: Cape Cod for summer evenings by the sea, Nantucket for quiet luxury, Vermont for fall colors and farm charm, Portland for creative food, and Boston for a dose of urban energy.
It’s a trip that feels distinctly American – honest, diverse, and full of heart.
And yes, we’d do it again tomorrow.
