Exploring the Beauty of New England: A 3-Day Itinerary

Day 1: Historic Boston

Boston, Massachusetts

8:00 AM

Breakfast at Flour Bakery

Start your day with a delicious breakfast of homemade pastries and fresh coffee at Flour Bakery, a local favorite.
Take the subway (T) to South End.
USD20, 1 hour

9:30 AM

Freedom Trail Walk

Embark on the iconic Freedom Trail that leads you through Boston's historical landmarks, from Boston Common to the North End.
Follow the red brick path; it’s a walkable 2.5 miles.
FREE, 3 hours

12:30 PM

Lunch at Quinlan's

Enjoy a cozy lunch at Quinlan’s, known for its fresh seafood and traditional New England fare.
Short walk from the end of the Freedom Trail.
USD25, 1 hour

2:00 PM

Explore the Boston Tea Party Ships & Museum

Dive into Boston’s rebellious history at the interactive Boston Tea Party Ships & Museum.
Walk to the waterfront (20 minutes).
USD30, 2 hours

4:30 PM

Visit the Boston Public Garden

Take a leisurely stroll through the beautiful Boston Public Garden, home to iconic swan boats.
Walk back towards Boston Common.
FREE, 1 hour

6:00 PM

Dinner at The Capital Grille

Savor a superb dinner featuring dry-aged steak and an extensive wine list in a classy setting.
Short taxi or T ride or a 10-minute walk.
USD75, 2 hours

8:30 PM

Evening Walk along the Waterfront

Wrap up Day 1 with a scenic walk along the waterfront, enjoying the views of the harbor.
Walk back to the harbor area.
FREE, 1 hour
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Day 2: Charming Portsmouth

Portsmouth, New Hampshire

8:00 AM

Breakfast at The Friendly Toast

Indulge in a hearty breakfast with quirky decor and extensive menus at The Friendly Toast.
Drive from Boston to Portsmouth.
USD20, 1 hour

9:30 AM

Explore Strawbery Banke Museum

Step back in time at this outdoor history museum showcasing the history of Portsmouth throughout the centuries.
Walk from the café; it’s a 10-minute walk.
USD15, 2 hours

12:00 PM

Lunch at Flatbread Company

Enjoy wood-fired pizzas at this local favorite, known for their organic ingredients.
Short walk from the museum.
USD25, 1 hour

1:30 PM

Visit Prescott Park

Relax at Prescott Park, where you can enjoy beautiful gardens and the riverside views.
Walk next door to Prescott Park.
FREE, 1.5 hours

3:00 PM

Catch a ferry to Isles of Shoals

Enjoy a scenic ferry ride to the Isles of Shoals, known for their natural beauty and historic charm.
Walk to the ferry terminal.
USD40, 4 hours (including ferry ride)

7:00 PM

Dinner at The Ocean Grill

Dine at The Ocean Grill, where you’ll relish fresh seafood with a stunning view of the sunset over the water.
Return ferry trip to Portsmouth and walk to the restaurant.
USD60, 2 hours
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Day 3: Seaside Portland

Portland, Maine

8:00 AM

Breakfast at Becky’s Diner

Start your day at this beloved local diner famous for its hearty breakfasts and jovial atmosphere.
Drive from Portsmouth to Portland (50 minutes).
USD15, 1 hour

9:30 AM

Visit Portland Head Light

Marvel at the stunning Portland Head Light, one of the most photographed lighthouses in America.
Drive to Fort Williams Park (10 minutes).
FREE, 1 hour

11:00 AM

Explore the Old Port

Wander through the charming streets of the Old Port, filled with shops, galleries, and quaint architecture.
Drive back to the downtown area.
FREE, 2 hours

1:00 PM

Lunch at Eventide Oyster Co.

Taste award-winning oysters and delightful seafood at this popular eatery known for its fresh menu.
Short walk to the restaurant.
USD35, 1.5 hours

2:30 PM

Take a Casco Bay Cruise

Enjoy a scenic cruise around the beautiful Casco Bay and its islands.
Walk to the cruise terminal.
USD30, 2.5 hours

5:00 PM

Dinner at Street & Co.

Soothe your palate with exquisite seafood dishes at Street & Co., known for its intimate ambiance.
Walk back to the Old Port for dinner.
USD60, 2 hours

7:30 PM

Evening at the Eastern Promenade

Wind down your trip with an evening at the Eastern Promenade, offering stunning views of the sunset over the bay.
Short drive or walk to the promenade.
FREE, 1 hour
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