4-Day Northeast USA Road Trip: Boston to New York City

Day 1: Historic Boston

Boston, Massachusetts, USA on June 8, 2025

8:00am

Breakfast at Tatte Bakery & Cafe

Enjoy a delicious breakfast of pastries and coffee at this popular Boston café known for its rich flavours and charming ambiance. It opens at 7:00am, perfect for an early start.
USD15, 1h

9:30am

Freedom Trail Walking Tour

Follow the 2.5-mile red-brick trail through 16 historic sites in downtown Boston, including Paul Revere's House and the Old North Church, to explore Revolutionary War history.
USD30, 3h

1:00pm

Lunch at Quincy Market

Dine at the bustling Quincy Market food hall rich with diverse cuisines such as New England clam chowder and lobster rolls. Open until 7:00pm.
USD20, 1h

2:30pm

Museum of Fine Arts Boston

Explore one of the most comprehensive art museums in the country with diverse collections spanning ancient to contemporary art. Open 10:00am to 5:00pm on Saturdays.
USD27, 2h

5:00pm

Evening walk at Boston Common

Relax with a stroll through the Boston Common, the oldest city park in the US, perfect for enjoying greenery and evening views.
Free, 1h

7:00pm

Dinner at Union Oyster House

Experience dinner at America’s oldest restaurant offering fresh seafood and classic New England dishes. Usually open till 9:00pm on Saturdays.
USD40, 1.5h
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Day 2: Historic Salem & Portsmouth

Salem, Massachusetts & Portsmouth, New Hampshire, USA on June 9, 2025

7:30am

Breakfast at The Ugly Mug Diner, Salem

Start your day with hearty American breakfast classics in this quirky diner popular among locals. Opens at 7:00am.
USD15, 1h

8:30am

Salem Witch Museum

Learn about the 1692 Salem witch trials and their impact through engaging exhibits. Museum opens at 9:00am daily.
USD15, 1.5h

10:30am

Drive to Portsmouth, NH

A picturesque 45-minute drive north along the coast to Portsmouth, a charming historic seaport town.
USD0, 0h45m

11:15am

Explore Market Square and Strawberry Banke Museum

Visit lively Market Square for shops and cafes, then tour the nearby open-air Strawberry Banke Museum to see restored historic homes. Museum open 10am-5pm.
USD15, 2h

1:30pm

Lunch at The Friendly Toast

Enjoy creative brunch and lunch dishes in a retro-themed restaurant located near Market Square. Open all day from 7:00am.
USD20, 1h

3:00pm

Nubble Lighthouse Visit

Drive to nearby Cape Neddick (30min) and visit the iconic Nubble Lighthouse, one of the most photographed in New England.
Free, 1h

5:00pm

Return to Portsmouth and relax

Spend a relaxed evening enjoying waterfront views or local pubs.
Varies, 2h

7:30pm

Dinner at Jumpin' Jay's Fish Café

Savor fresh seafood and creative dishes in this award-winning Portsmouth restaurant. Reservations recommended. Open till 9pm.
USD45, 1.5h
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Day 3: Coastal Portland

Portland, Maine, USA on June 10, 2025

7:00am

Breakfast at The Holy Donut

Try unique potato-based donuts and fresh coffee at this local favorite bakery. Opens early for morning treat.
USD10, 0h45m

8:00am

Portland Head Light and Fort Williams Park

Visit Maine’s oldest lighthouse with spectacular ocean views and explore the vast coastal park grounds. Open daily, free entry.
Free, 2h

10:30am

Old Port District

Walk through Portland’s historic waterfront district with cobblestone streets, boutiques, and galleries.
Free, 1.5h

12:00pm

Lunch at Eventide Oyster Co.

Treat yourself to fresh oysters and lobster rolls at this trendy seaside eatery. Open noon to 9:00pm.
USD35, 1h

1:30pm

Portland Museum of Art

Explore impressive collections that feature local and international artists. Open 10am-5pm on weekdays.
USD20, 2h

4:00pm

Casco Bay Ferry Ride

Take a short ferry cruise to one of the nearby islands, enjoy sea breeze and scenic views. Ferry schedules vary, check in advance.
USD15, 1.5h

6:30pm

Dinner at Fore Street Restaurant

Fine dining featuring wood-fired dishes with locally sourced ingredients. Open till 10pm. Reservation recommended.
USD50, 1.5h
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Day 4: Big Apple Highlights

New York City, New York, USA on June 11, 2025

7:00am

Breakfast at Ess-a-Bagel

Enjoy fresh, classic New York bagels with a variety of spreads for a true NYC breakfast. Opens at 6:30am.
USD12, 0h45m

8:00am

Central Park Morning Stroll

Walk or bike through the iconic Central Park to soak in the green respite in the heart of the city. Open dawn to dusk.
Free, 1.5h

9:45am

Visit The Metropolitan Museum of Art

Explore one of the world's largest and finest art museums, featuring art from every era and culture. Opens at 10:00am.
USD30, 3h

1:00pm

Lunch at Shake Shack, Midtown

Grab a classic American burger or hot dog from this famous NYC burger chain. Open all day.
USD20, 1h

2:30pm

Walk the High Line

Explore this elevated urban park built on a historic freight rail line with gardens, art installations, and city views. Open 7am to 10pm.
Free, 1.5h

4:30pm

Visit Times Square

Experience the vibrant lights and buzz of Times Square, the iconic NYC landmark that is best seen in late afternoon and evening.
Free, 1h

6:00pm

Dinner at Carmine’s Italian Restaurant

Enjoy family-style Italian dishes in a lively atmosphere. Open till 11pm, perfect for a relaxed finale.
USD50, 1.5h
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