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Scenic New England Road Trip: From Boston to Bar Harbor Itinerary

Last updated: 2024 Jun 14

Historic Beginnings in Boston

Morning

Start your day with a classic Boston breakfast at Mike's City Diner, known for its delicious pancakes and omelets. After breakfast, take a leisurely walk along the Freedom Trail, immersing yourself in the rich history of the city.

Afternoon

For lunch, enjoy a lobster roll at James Hook & Co, a local favorite. Afterward, visit the iconic Fenway Park, home of the Boston Red Sox. Take a guided tour of the stadium and learn about its storied past.

Evening

Conclude your day with a seafood feast at Union Oyster House, the oldest restaurant in the United States. Indulge in fresh oysters and clam chowder, savoring the flavors of New England.

Bedtime

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Exploring the Charms of Portland

Morning

Enjoy a scenic drive to Portland, Maine, and have a hearty breakfast at Becky's Diner, a local institution known for its lobster stew. After breakfast, take a walk around the historic Old Port district, with its cobblestone streets and waterfront views.

Afternoon

For lunch, head to Eventide Oyster Co. and try their famous brown butter lobster roll. Afterward, visit the Portland Head Light, a picturesque lighthouse perched on the rocky coast. Take in the stunning ocean views and learn about the lighthouse's history.

Evening

Dine at Street & Co. for a fine dining experience, featuring the best of Maine's seafood. After dinner, take a sunset cruise around Casco Bay, enjoying the sea breeze and the sight of the Portland skyline.

Bedtime

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Welcome to Bar Harbor

Morning

Start your day with a leisurely breakfast at Cafe This Way, known for its cozy atmosphere and delicious blueberry pancakes. After breakfast, take a stroll along the Shore Path, a scenic trail that offers stunning views of the coastline.

Afternoon

For lunch, enjoy a lobster bucatini at Havana, a unique blend of Cuban and Maine flavors. Afterward, explore the shops and galleries in downtown Bar Harbor, picking up some local souvenirs.

Evening

Dine at Galyn's Restaurant, a Bar Harbor institution known for its seafood and steaks. After dinner, take a ghost tour of the town, learning about its haunted history and mysterious legends.

Bedtime

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