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2-day trip to Gloucester, Massachusetts Itinerary

Last updated: 2024 Jun 17

Exploring the Coastal Charm

Morning

Start your day with a delicious breakfast at The Sugar Magnolia. Indulge in their famous pancakes and enjoy a cup of freshly brewed coffee. After breakfast, head to Gloucester Harborwalk and take a leisurely stroll along the waterfront. Admire the scenic views of the harbor and watch the fishing boats come and go.

Afternoon

For lunch, visit The Lobster Pool and savor a mouthwatering lobster roll while enjoying the ocean view. Afterward, explore the Cape Ann Museum to learn about the rich history and art of the region. Don't miss the famous Fitz Henry Lane collection.

Evening

As the sun sets, head to Gloucester Schooner Adventure and embark on a sunset sailing excursion. Enjoy the beautiful coastal scenery and feel the ocean breeze as you sail along the coast. Afterward, treat yourself to a seafood dinner at The Gloucester House and savor some fresh local catch.

Bedtime

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Outdoor Adventures and Art

Morning

Start your day with a hike at Ravenswood Park. Explore the beautiful trails and immerse yourself in nature. Afterward, grab a quick snack at Cape Ann Coffee to fuel up for the rest of the day.

Afternoon

Visit Gloucester Beaches and spend the afternoon relaxing on the sandy shores. Take a dip in the Atlantic Ocean and soak up the sun. For lunch, head to The Causeway Restaurant and enjoy some delicious seafood chowder.

Evening

Explore the vibrant art scene of Gloucester by visiting the Rocky Neck Art Colony. Wander through the galleries and admire the works of local artists. For dinner, indulge in Italian cuisine at Tonno, known for its fresh seafood dishes. End the day with a drink at Rhumb Line, a cozy bar with live music performances.

Bedtime

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