USA East Coast Itinerary

We spent just under two weeks road tripping along the East Coast of the US, starting in New York City and ending in Boston, with stops in New Hampshire, Maine and Marblehead along the way.

Along the way, you’ll explore vibrant neighbourhoods, drive through stunning landscapes, discover charming coastal towns, and unwind by beautiful lakes.

East Coast Itinerary (Part 1): New York

New York is one of those cities you could visit again and again and still not scratch the surface, but this is a pretty perfect 3-day intro.

Accommodation is very pricey in NYC, so we based ourselves in the Financial District. The hotel wasn’t quite Lemon Stays-worthy, but it’s a great base-easy access to the rest of Manhattan and Brooklyn, and a bit calmer too.

Day 1: Midtown, High Line & West Village

Start the day with a proper NYC bagel at Leon’s Bagels (a few locations across Manhattan- we went to Little Italy). Is it worth the hype? Honestly, it depends what you order- go for the sausage, egg and cheese or a classic lox and you’ll be very happy. Grab a coffee from Urban Backyard opposite.

Then jump on the subway (easiest way to get around) and head to Midtown. Stop at Grand Central Terminal (especially if you’re a Gossip Girl fan like me), then wander down Fifth Avenue, do some shopping if you fancy and walk past the New York Public Library and into Times Square. Not our favourite place, but worth a quick look just to say you’ve been.

Next, head up the Empire State Building- the Manhattan skyline is honestly one of the best in the world and well worth it.

In the afternoon, make your way to Hudson Yards to see the Vessel, then walk the High Line, an old railway turned into an urban park that takes you all the way through Chelsea to the West Village. It’s a must.

For lunch, Chelsea Market has loads of great options, or grab pizza from L’Industrie Pizzeria (West Village) very good…but not quite the best pizza of our trip.

The West Village was our favourite neighbourhood in Manhattan- cool cafés, bars, independent shops and those classic brownstone streets. We went for pre-dinner drinks at Katana Kitten (banging cocktails), then dinner at Fiaschetteria Pistoia (walk-in only). The beef ragu and tiramisu were 10/10 and the staff were so lovely- great first night vibes.

Day 2: Upper West Side, Central Park & East Village

Head to the Upper West Side for breakfast. Zabar’s does a huge classic lox bagel, or for a sit-down option Sarabeth’s is a proper NYC brunch institution.

If you’ve got room (we somehow always do), grab cookies from Levain Bakery or banana pudding from Magnolia Bakery.

Then walk it off in Central Park- we wandered past Bethesda Terrace, Bow Bridge and around the reservoir. After that, pick a museum- the Metropolitan Museum of Art or Guggenheim Museum are both close by.

For lunch, head to Katz’s Delicatessen, a proper NYC institution. You queue at the cutter stations (it looks chaotic but runs so smoothly), and you might even get a taste while you wait. We shared the pastrami sandwich and honestly… one between two was more than enough. It’s huge, and the pastrami is incredible- tender, juicy and packed with flavour.

Because we clearly hadn’t had enough food, we stopped at Sunday Morning for a cinnamon roll (delicious).

In the afternoon, visit the 9/11 Memorial & Museum. It’s incredibly powerful and really well done- we’d recommend it to anyone visiting NYC.

After a pre-dinner chill (needed), head to the East Village, known for its great nightlife. Start with drinks at Sauced (fun vibes, great natural wines), then dinner at La Esquina Brasserie- a cool basement spot with great tacos and margaritas (order the fried plantain).

Day 3: Lower Manhattan & Brooklyn

Start the day closer to home with breakfast at Leo’s Bagels. This felt much more local, full of New Yorkers grabbing breakfast before work, and ended up being our favourite bagels of the trip. The “Whole Shebang” is unreal, packed with Scotia salmon, scallion cream cheese, Bermuda onion, tomatoes, cucumbers and capers.

Walk past Wall Street and the New York Stock Exchange, then head to Whitehall Terminal for the Staten Island Ferry. It’s completely free (yes, free) and gives great views of the Statue of Liberty.

In the afternoon, head to Brooklyn. Start with coffee at 787 Coffee (we tried the piña colada latte-can confirm, banging), then grab lunch at Mo’s General in Williamsburg. This was hands down the best pizza of our trip- the Detroit-style slices and mozzarella sticks were unreal (10/10 cheese pull).

Williamsburg is such a cool neighbourhood- make sure to check out independent stores like Mogutable, Leif and Loaf on Paper.

Then make your way to DUMBO for the classic Washington Street photo, and walk back across the Brooklyn Bridge at sunset- one of the best views in the city.

For your final night, head to the Lower East Side or Chinatown. Around Dimes Square there are loads of great spots like Sunn’s and Cervo’s.

If you’re staying in the Financial District, finish with a nightcap at The Dead Rabbit.

NYC Tips

• Tipping: It’s expected and adds up quickly- factor it in.
• Accommodation: Book early, it’s expensive. Financial District is a great base. An AirBnB in Brooklyn may also be a sensible option. 
• Pace yourself: You’ll do a lot of steps- build in a pre-dinner rest.
• Plan loosely: There’s so much to do, so aim for 1–2 areas a day.
• Transport: Don’t hire a car- the subway is easy and felt safe.

East Coast Itinerary (Part 2): New Hampshire

Day 4: NYC → New Hampshire (Road Trip Begins 🚗)

Now time for the road trip!!

We picked up our hire car from the Financial District, which actually worked really well as it was fairly quiet. We loved our Ford Bronco- highly recommend if you can get one. Also worth downloading QEEQ for good deals (their diamond membership is great if you’ve got more trips planned).

The drive to New Hampshire took around 5 hours, with a very important pit stop at Katz’s Deli in Connecticut. And no… it’s not related to the famous NYC one (we were also confused until the waitress broke the news). But honestly? It was SO good. Huge sandwiches and probably on par with the original (order the club!).

We arrived at the beautiful Follansbee Inn, set right on the edge of Lake Kezar. I’d actually stayed here as a child, so it felt really special to come back. The setting is incredibly peaceful, and the hosts Denis and Kendall are as warm and welcoming as it gets.

That evening, we kept things simple- drove into nearby New London, grabbed takeaway from Pizza Chef of New London and a bottle of wine next door, then headed back to sit by the lake. Sunset, pizza, wine… and even a few shooting stars. Pretty perfect first night.

Day 5: Hiking & Lake Sunapee

Breakfast at the inn deserves its own moment. Denis brings his Louisiana roots into the mix- think fluffy buttermilk biscuits and creative egg dishes with a Cajun twist- while Kendall puts together a beautiful granola and fruit spread. It’s so good we brought home the recipes.

We started the day in Warner, a quintessential New England town. Coffee and something sweet at Cafe One East, followed by a browse of the independent shops like Buttonwood.

Late September is peak fall foliage season here. According to locals, it’s actually the most beautiful time of year to visit with stunning landscapes- vibrant reds, oranges and yellows. We parked at Winslow State Park and hiked up Mount Kearsarge. It’s a manageable hike with panoramic views at the top- 100% worth it but bring a snack for the top. 

Afterwards, we headed to Lake Sunapee, wandered around the harbour and picked up a bottle of wine from Sunapee Cellar & Pantry. The whole place had such a nice vibe- there was even a small beer festival on with live music (shoutout to Nick Bredice and his guitar). The boat trip around the lake is on our list for next time (https://sunapeecruises.com/.

By this point, we were starving (shock), so we followed Denis and Kendall’s recommendation to Wildwood Smokehouse. Top tip: get there when it opens—it sells out fast.

This was hands down the best BBQ of the trip. Order the Wildwood nachos, then the Porky Pig (pulled pork piled high on a roll). Ask for it “the real way” with coleslaw and pickles, and definitely add mac & cheese if you can handle it. Absolutely banging.

Back at the inn, there was live music and (of course) homemade sweet treats from Kendall- brown sugar cinnamon pop tarts included. Not a bad way to end the day.

Day 6: Slow Day by the Lake

After eating our bodyweight in pancakes, we went for a walk- luckily there’s a beautiful 3-mile loop around the lake. You get views of Mount Kearsarge in the distance and some gorgeous New England homes along the way.

One morning we attempted it on a tandem bike… which, as a couple, is a real test of communication skills. Good luck 😅

The rest of the day was all about slowing down- sunbathing on the deck, reading in the hammock, and kayaking out to Blueberry Island for a picnic. Honestly, pretty ideal.

For dinner, there are loads of easy nearby options:

• Little Brother Burger Company
• The Elms Restaurant & Bar
• Flying Goose Brew Pub
• Blue Canoe

(Or just go back to Wildwood Smokehouse… no judgement.)

We ended the day watching the sunset over the lake and oh, it was a good one.

Day 7: New Hampshire Coast & Maine Border

For our final day, we drove out to the New Hampshire coast- completely different feel to inland.

The town of Portsmouth is well worth exploring (you can park at Parrott Avenue). We grabbed a coffee from Elephantine Bakery and wandered around- lots of food spots if you fancy lunch.

Just 5 minutes over the border into Kittery, you’ll find some lovely coastal views. Drive down Pepperrell Road and you’ll come across a few great waterside spots.

We stopped at Frisbee’s Wharf for a cold beer- super chilled vibe, right on the water, and the seafood looked incredible.

This stretch of the trip felt like a complete contrast to NYC- slower, more scenic, and just super chilled. And I have to say, the people in New Hampshire are so lovely… probably because they get to live somewhere so heavenly. 

East Coast Itinerary (Part 4): Maine

Day 8: New Hampshire → Maine (Lobster Roll Heaven 🦞)

After saying our goodbyes to Denis and Kendall (and casually discussing how we’d happily take over the inn one day), we hit the road and headed to Maine.

We based ourselves near York, which is a great spot for exploring southern Maine. On the way, we made a couple of stops- first at Cape Neddick Lighthouse (aka Nubble Lighthouse), then onto Ogunquit Beach for lunch.

Now… lobster rolls. Maine is famous for them (it’s the top producer of cold-water Atlantic lobster), so expectations were high. Our first one at Ogunquit Beach Lobster House absolutely delivered- warm roll, melted butter, packed with sweet lobster meat. Unreal. Pricey? Yes. Worth it? 100%. Even better with a pint of Sea Dog Brewing Company blueberry beer.

We spent a bit of time exploring Ogunquit, a classic coastal town with a really nice vibe. There are loads of shops and food spots, plus the Ogunquit Playhouse and Ogunquit Museum of American Art if you fancy something cultural.

For snacks/coffee, Village Food Market & Cafe is great, and for ice cream you have to go to Big Daddy’s Ice Cream. The Maine Blueberry Pie flavour is a must, but they also had loads of unreal options like S’mores, Banana Chocolate Chip and Almond Butter Crunch.

One thing you have to do here is walk Marginal Way- a 1.25-mile coastal path with amazing views, ending at Perkins Cove. Park at Obed’s lot to make life easy.

At Perkins Cove, there are a few great casual food spots if you fancy something by the water- Barnacle Billy’s is a classic for lobster and drinks, and Footbridge Lobster is another great shout. You can also hop on a Finestkind Scenic Cruises from here (May–October), including a lobstering trip with a real Maine lobsterman, which looked very cool (on our list for next time).

That evening, we went for dinner at Cape Neddick Lobster Pound- a proper classic Maine spot. Waterside setting, big portions, huge menu. We went for seafood pasta and baked haddock (both very good). 

Day 9: Whale Watching & Portland

Maine is one of the best places for whale watching, so we had to do it. From May to October, the waters attract humpback, minke and finback whales.

We booked with Cap’n Fish’s Cruises, departing from Boothbay Harbor. The crew were super knowledgeable, and we were lucky enough to spot two whales (surreal moment), plus harbour porpoise and seals.

Top tip: get a seat on the top deck for the best experience- it fills up fast. The trip lasts a few hours and there’s a small bar onboard, but we brought lunch which worked well.

Boothbay itself is worth more time than we had- Coastal Maine Botanical Gardens are on our list for next time.

On the way back, we stopped in Portland for dinner. It’s a really cool city with loads of independent shops, cafés and a creative vibe. We grabbed a banging burrito from Taco Escobarr, but Terlingua (a BBQ spot) is on our list for next time.

If You Have More Time in Maine…

If we did this again, we’d 100% spend a couple more days further north.

• Acadia National Park: unreal scenery and some of the best hikes on the East Coast. The Beehive Trail comes recommended – short but steep and exposed (not for the faint-hearted), with incredible coastal views
• Bar Harbor: charming base for exploring Acadia
• Camden & Cape Elizabeth: both highly recommended by locals

Maine was such a highlight of the trip- coastal views, incredible seafood, and that laid-back New England charm. Definitely somewhere we’d come back to (mainly for another lobster roll).

East Coast Road Trip Itinerary (Part 4): Marblehead & Boston

Day 10: Maine → Marblehead (Coastal New England Charm)

Next stop: Marblehead.

This is classic coastal New England, full of character, independent cafés, seafood spots and little boutiques. It’s the perfect place to relax, with beautiful beaches and a charming harbour.

We stayed at Harborside Hideaway, a lovely Airbnb guest suite attached to a historic colonial home. The location is spot on in the heart of the old town, and it has all those little personal touches that make it feel homely.

After checking in, we wandered along Fort Beach and up to the seawall for views over the harbour, then drove to Devereux Beach for sunset- such a good spot.

For dinner, we headed into town and ended up at Elia Taverna for fresh, delicious gyros. If you’re after seafood, the Old Town has loads of great options:

• The Barnacle
• Little Harbor Lobster Company
• The Landing
• Maddie’s Sail Loft
• Sea Salt

Day 11: Boston Day Trip

Our mornings in Marblehead started with a trip to Farine Artisanal French Bread for coffee and pastries, such a good spot (you’ll often hear locals ordering in French).

We then had a wander around the independent shops- Maison de Mer and Henry & Co are definitely worth popping into.

When you fancy a change of pace, Boston is just a 30-minute train from Swampscott (quick Uber from Marblehead). This is why Marblehead is such a good base- seaside calm with easy city access.

We loved Boston- great food scene, loads of green space, friendly people, and way more relaxed than NYC.

We caught a Boston Bruins game (they won 🎉), which was such a fun experience. Definitely grab an overpriced beer and a hot dog- it’s all part of the experience.

For dinner, we headed to the North End (Boston’s Little Italy) and ate at Tony & Elaine’s- must book. Mozzarella sticks to start (elite cheese pull), then rigatoni alla vodka (add the chicken cutlet 👀) and spaghetti meatballs. Huge portions, so come hungry.

Before heading back, we stopped at Coogan’s for a nightcap- proper local Irish pub vibes.

Day 12: Boston Stayover

We also spent a night in Boston before flying home, staying in a brownstone on Bay State Road near Fenway Park and the Charles River- a great base (and rare to have parking).

Boston’s neighbourhoods all feel quite different, but the South End was our favourite- artsy, full of character, and packed with amazing food spots.

Lunch was a huge sandwich (get the “Italian”) from Boston Pocket & Deli, eaten in a nearby park. Other good lunch options:

• Flour Bakery + Cafe
• The Buttery
• The Friendly Toast

We spent the afternoon wandering around the beautiful Boston Common and Public Garden, then explored Beacon Hill—think cobbled streets, bookshops and very pretty houses.

We also checked out the Seaport District, which has a more modern feel with waterfront restaurants and summer pop-ups.

Dinner back in the South End was such a highlight. We started with cocktails at Desnuda Cocina & Bar, then headed to The Beehive, which was so good. Live blues music, amazing atmosphere, and standout dishes like whipped ricotta with hot honey and baby back ribs.

We followed the locals post-dinner to Franklin Cafe (open until 2am). It was our last night after all.

Other great South End spots to try:
KAVA Neo-Taverna, Coppa, MIDA, Banyan Bar + Refuge, Kaia, Anchovies, Gigi, The Elephant Walk, Capri, The Shawmut Inn, El Centro, Ilona.

For wine + cheese: Formaggio Kitchen or Neighbourhood Wines.

Day 13: Final Day (Cambridge)

With a late flight, we spent our final morning in Cambridge (easy subway from Boston).

Naturally, we went in search of one last bagel. Bagelsaurus was closed (devastating), so we went to Black Sheep Bagel Cafe instead- the lox bagel was banging.

We wandered around Harvard University (beautiful campus, very impressive) and popped over to MIT, mainly to say we’d been.

Other food spots in Cambridge that came recommended:

• Row 34
• Area Four
• Pammy’s
• Little Donkey

If You Have More Time in Boston…

• Walk the Freedom Trail (2–3 hours)
• Lunch at Quincy Market (lobster mac & cheese or clam chowder in a bread bowl)
• Walk the Boston Harborwalk
• Shop at Newbury Street’s boutiques
• Ferry to the Boston Harbor Islands
• Visit Isabella Stewart Gardner Museum
• Baseball game at Fenway Park 

And just like that… home time.

Such an incredible trip- from the buzz of NYC to quiet lakes, coastal Maine, and finishing in Boston. Also, a very emotional goodbye to our beloved Ford Bronco.