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3 Days in Gloucester Massachusetts Itinerary

Last updated: 2024 Jun 14

Exploring Cape Ann

Morning

Start your day with a hearty breakfast at Sugar Magnolias, a local favorite known for its delicious pancakes and friendly atmosphere. After breakfast, embark on the Gloucester Scenic Cape Ann & Rockport Self-Driving Tour, which will take you through the picturesque landscapes of Cape Ann and Rockport. This tour is perfect for getting acquainted with the area's natural beauty and charming towns.

Afternoon

For lunch, head to The Gloucester House Restaurant, where you can enjoy fresh seafood with a view of the harbor. After lunch, visit the Cape Ann Museum to explore its extensive collection of art and artifacts that tell the story of Gloucester's rich maritime history.

Evening

In the evening, dine at Passports Restaurant, known for its eclectic menu and cozy ambiance. After dinner, take a leisurely stroll along Stacy Boulevard to enjoy the scenic views of Gloucester Harbor.

Bedtime

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Gloucester Scenic Cape Ann & Rockport Self-Driving Tour
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Art and History Immersion

Morning

Begin your day with breakfast at Mamie's Kitchen & Market. Following breakfast, visit Hammond Castle Museum to explore this medieval-style castle built by inventor John Hays Hammond Jr., offering stunning views of the Atlantic Ocean.

Afternoon

For lunch, try Latitude 43 for a modern twist on classic New England cuisine. In the afternoon, visit Rocky Neck Art Colony to discover one of America's oldest working art colonies and browse through various galleries showcasing local artists' work.

Evening

Enjoy dinner at The Franklin Cape Ann before heading to Gloucester Stage Company for an evening performance. This local theater offers a range of productions from contemporary plays to classic dramas.

Bedtime

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Outdoor Adventures and Relaxation

Morning

Start your day with breakfast at Two Sisters Coffee Shop. Afterward, head to Good Harbor Beach for some relaxation or a refreshing swim in one of Gloucester's most popular beaches.

Afternoon

Grab lunch at Seaport Grille located on the waterfront offering delicious seafood dishes. In the afternoon take a whale watching tour from Seven Seas Whale Watch which offers an unforgettable experience observing these magnificent creatures in their natural habitat.

Evening

Conclude your trip with dinner at 1606 Restaurant & Bar located in Beauport Hotel offering upscale dining with stunning ocean views.

Bedtime

Find amazing hotels in Gloucester, Massachusetts, USA.