See the Best of Massachusetts: A 4-Day Itinerary

Massachusetts is home to some of America's most significant history and stunning coastal views, making it a fantastic destination for relaxation and exploration. Whether you want to plant your toes in the sand or visit historic sites, The Bay State has it all. Here's how to make the most of a four-day visit.

Day 1: Explore Cape Cod National Seashore

Kick off your trip by driving along US-6 to the Cape Cod National Seashore, where breathtaking views of the Atlantic Ocean await. This picturesque area features six beautiful beaches and offers various activities:

• Relax at the Beach: Choose a beach to unwind, or try to visit them all!
• Outdoor Adventures: For the adventurous, enjoy eleven hiking trails, ocean kayaking, and biking. With a permit, you can even drive off-road on certain beaches.

Race Point Beach, located at the tip of the peninsula near Provincetown, is a must-visit. Spend time by the water or explore the nearby Race Point Lighthouse for stunning views of Cape Cod Bay.

After a day of adventure, dine at The Lobster Pot in Provincetown, a local favorite known for its fresh seafood. Be sure to try the lobster ravioli alfredo and Tim's Clam Chowder.

Day 2: Visit Martha's Vineyard

On day two, head to Martha's Vineyard, one of Massachusetts' top destinations. To reach the island, take the ferry, and make a reservation in advance if you plan to bring your car.

Martha's Vineyard Beaches

With 19 beaches, the island offers plenty of options. For a serene experience, visit Oak Bluffs Town Beach, known for its calm waters and welcoming atmosphere.

Martha's Vineyard Dining

Enjoy the local culinary scene with no chain restaurants in sight. Try ArtCliff Diner for its famous poblano hash, Bill Smith's Martha's Vineyard Clambake Co. for a traditional clam bake, and indulge at Ben and Bill's Chocolate Emporium for a delightful ice cream treat.

Martha's Vineyard Activities

If you're seeking adventure, consider biking around the island, hiking the numerous trails, or renting a stand-up paddleboard or kayak. There's something for everyone!

Day 3: Discover Plymouth

No visit to Massachusetts is complete without exploring Plymouth, the historic site where pilgrims settled in 1620. Start at Plymouth Rock at Pilgrim Memorial State Park, where you can learn about this iconic piece of Americana.

Next, visit the Mayflower II, a full-scale replica of the ship that carried the pilgrims to North America. Tours are popular, so buy tickets in advance!

Wrap up your day at Tavern on the Wharf, a laid-back eatery offering some of Plymouth's best local fare with a scenic view of Plymouth Harbor.

Day 4: Experience Boston

On your final day, make your way to Boston, a city rich in history and culture. Here are a few must-see attractions:

Fenway Park Tour

Start your day with a historic tour of Fenway Park, a must for sports fans. Tickets start at $27 per adult.

Isabella Stewart Gardner Museum

Next, visit the Isabella Stewart Gardner Museum, a unique art gallery featured in the Netflix series "This Is a Robbery." Don't miss the unforgettable atrium!

Samuel Adams Brewery

After exploring, head to Samuel Adams Brewery for a refreshing pint. Join a brewery tour that includes lunch or dinner, perfect for beer enthusiasts.

Dinner in the North End

End your trip in the North End, Boston's oldest neighborhood, known for its Italian restaurants and historic sites. Dine at Carmelina's, one of the best Italian spots in the area.

Where to Stay in Massachusetts

Massachusetts offers several popular resorts near your itinerary highlights. Whether you want to stay at Sun Retreats Dennis Port by the ocean, Sun Retreats Cape Cod nestled in the woods, or Sun Retreats Peters Pond for outdoor recreation, you'll find a perfect spot.

Make a reservation today, as site and cabin rentals are filling up fast!

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