Itinerary check

Question

Feedback appreciated. Trip mid May.

Arriving Saturday 6.30 am. Boston through Tuesday - 3 nights - staying at Beacon Hill

Tuesday pick up car - Salem to Gloucester: explore the area through Thursday (Rockport, Gloucester, Portsmouth, what else -etc ?) - 2 nights at Gloucester hotel

Thursday leave south though Manchester, Plymouth towards Cape Cod and stay in Falmouth hotel for 3 days(one day MV, one Provincetown) - 3 nights

Sunday- Tuesday : Newport - 2 days.

Thank you!

Answer

Your itinerary for mid-May looks great and well-balanced, with a good mix of history, coastal towns, and relaxation. Here are some suggestions and feedback to help you make the most of your trip:

Saturday - Tuesday: Boston (Beacon Hill)

Beacon Hill is an excellent location to stay, with its charming cobblestone streets and proximity to many key attractions. You’ll be able to walk to the Freedom Trail, Boston Common, and enjoy restaurants and cafes in the area. Here are a few things to consider for your time in Boston:

Freedom Trail: Definitely a must-do, with many historical sites along the way. It’s a great way to start your trip and learn more about the city’s history.
Boston Tea Party Museum: Another key historical spot. It’s interactive, so great for all ages.
Newbury Street: For shopping, dining, and people-watching, Newbury Street is the place to go.
Fenway Park: If you’re interested in sports, consider a Fenway Park tour or even catching a game if the Red Sox are in town.

Since you’re staying in Beacon Hill, you'll be within walking distance of many attractions, so be sure to take some time to explore the neighborhood itself. The nearby North End is also great for Italian food, and you might want to check out the Boston Public Market for local goods.

Tuesday - Thursday: Salem to Gloucester

This leg of your trip will let you explore the beautiful Massachusetts coast. Salem and Gloucester are both fantastic spots, and you have a few nearby towns you can explore too:

Salem: Famous for its witch trials history. The Salem Witch Museum and the House of the Seven Gables are key sites to visit. Walk around the town and explore the maritime history.
Gloucester: Famous for its fishing heritage, visit the Fishermen’s Memorial and Cape Ann Museum. The harbor views are lovely.
Rockport: A picturesque town known for its art galleries and beautiful coastal views. Be sure to visit Bearskin Neck and explore the unique shops.
Portsmouth (NH): A charming town just across the border in New Hampshire. The Strawbery Banke Museum, Prescott Park, and the scenic waterfront make for a great visit.
Manchester-by-the-Sea: A lovely small town with great beaches and scenic views of the Atlantic Ocean. It’s a nice stop between Gloucester and Plymouth.

Thursday - Sunday: Cape Cod (Falmouth)

Falmouth is a great base for your time in Cape Cod. You’ll be able to explore the surrounding areas and visit Martha’s Vineyard (MV) and Provincetown:

Martha’s Vineyard (MV): A day trip is perfect for exploring this lovely island. Rent bikes or take a guided tour to see the lighthouses and charming towns like Oak Bluffs and Edgartown.
Provincetown: A must-visit for its lively arts scene, great food, and beautiful beaches. Try the Provincetown Art Association and Museum, and explore the stunning Cape Cod National Seashore.

Also, while in Cape Cod, you might consider taking a scenic drive along Route 6A or visiting the Cape Cod National Seashore for a hike or beach day. The area is beautiful, with plenty of outdoor activities to enjoy.

Sunday - Tuesday: Newport, Rhode Island

Newport is a fantastic final stop on your itinerary. The town is known for its mansions, waterfront views, and colonial history. Here’s what you can do in Newport:

The Mansions: A visit to The Breakers, Marble House, and Rosecliff is a must. These Gilded Age homes are stunning and offer insight into the opulent past of the town.
Cliff Walk: A scenic 3.5-mile path along the ocean with views of the mansions and the coastline. It’s a beautiful way to spend a few hours.
Waterfront Dining: Newport is known for its seafood, and you can’t go wrong with a meal at one of the waterfront restaurants.

This itinerary looks like a perfect mix of history, culture, and beautiful coastal scenery, with a good balance of driving and relaxation. Just be mindful of the driving distances, especially between Cape Cod and Newport. You’ll need to plan for some travel time, but overall, it’s a lovely route with so much to see along the way!

Enjoy your trip!