13 days in Massachusetts Itinerary

13 days in Massachusetts Itinerary

Created using Inspirock Massachusetts travel route builder

Make it your trip
Fly to Logan International Airport, Drive to Eastham
— 4 nights
Taxi to Ocean Street Terminal, Hyannis, MA, Ferry to Nantucket
— 4 nights
Oak Bluffs, Martha's Vineyard
— 2 nights
— 2 nights
Drive to Logan International Airport, Fly to San Miguel de Allende



— 4 nights
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Visit Coast Guard Beach and Crosby Landing Beach for some beach relaxation. Popular historic sites such as Chatham Marconi Maritime Center and Fort Hill Rural Historic District are in your itinerary. Next up on the itinerary: tour the pleasant surroundings at Skaket Beach, kick back and relax at Marconi Beach, appreciate the extensive heritage of Wellfleet Bay Wildlife Sanctuary, and take a tour by water with Boat Tours & Water Sports.

To find other places to visit, photos, more things to do, and more tourist information, use the Eastham trip itinerary planner.

San Miguel de Allende, Mexico to Eastham is an approximately 14-hour combination of flight and car. You can also do a combination of flight and car. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Traveling from San Miguel de Allende in July, plan for somewhat warmer nights in Eastham, with lows around 21°C. Wrap up your sightseeing on the 16th (Fri) early enough to travel to Nantucket.

Things to do in Eastham

Outdoors · Parks · Beaches · Historic Sites

Side Trips


— 4 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Step out of the city life by going to Jetties Beach and Surfside Beach. Explore hidden gems such as Cisco Beach and St Paul's Episcopal Church. Next up on the itinerary: see the interesting displays at Whaling Museum, take an in-depth tour of Nantucket Shipwreck & Lifesaving Museum, enjoy the sea views from Brant Point Lighthouse, and see what you can catch with a fishing tour.

Discover how to plan a Nantucket trip in just a few steps with Inspirock's itinerary builder.

Traveling by combination of taxi and ferry from Eastham to Nantucket takes 2.5 hours. Alternatively, you can do a combination of bus and ferry. Expect a daytime high around 28°C in July, and nighttime lows around 20°C. Wrap up your sightseeing on the 20th (Tue) early enough to ride a ferry to Oak Bluffs.

Things to do in Nantucket

Outdoors · Beaches · Parks · Historic Sites

Oak Bluffs, Martha's Vineyard

— 2 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 21st (Wed): enjoy the sea views from Gay Head Lighthouse, then enjoy the sand and surf at Menemsha Public Beach, and then take in the dramatic natural features at Aquinnah Cliffs. Here are some ideas for day two: wander the streets of Martha's Vineyard Camp meeting Association (MVCMA), then don't miss a visit to Flying Horses Carousel, then enjoy the sand and surf at Joseph Sylvia State Beach, and finally enjoy the sand and surf at Katama Beach/ South Beach.

To find more things to do, maps, where to stay, and other tourist information, you can read our Oak Bluffs tour itinerary planner.

Ride a ferry from Nantucket to Oak Bluffs in 2 hours. July in Oak Bluffs sees daily highs of 30°C and lows of 20°C at night. Cap off your sightseeing on the 22nd (Thu) early enough to catch the flight to Concord.

Things to do in Oak Bluffs

Parks · Beaches · Outdoors · Historic Sites

Side Trips


— 2 nights
Concord is a town in Middlesex County, Massachusetts, in the United States. Start off your visit on the 23rd (Fri): explore the different monuments and memorials at Sleepy Hollow Cemetery, explore the activities along Walden Pond State Reservation, then steep yourself in history at Louisa May Alcott's Orchard House, and finally stroll through Minute Man National Historical Park.

To find other places to visit, ratings, where to stay, and other tourist information, use the Concord trip itinerary planning app.

You can fly from Oak Bluffs to Concord in 2.5 hours. Other options are to do a combination of ferry and car; or do a combination of ferry, taxi, and train. In July in Concord, expect temperatures between 34°C during the day and 19°C at night. You'll have a few hours on the 24th (Sat) to wrap things up before traveling home.

Things to do in Concord

Historic Sites · Parks · Nature · Museums

Massachusetts travel guide

History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.