13 days in Greater Boston, Nantucket & Yarmouth Itinerary

13 days in Greater Boston, Nantucket & Yarmouth Itinerary

Created using Inspirock Massachusetts tour planner
Make it your trip
— 4 nights
Drive to Hyannis, MA, Ferry to Nantucket
— 4 nights
West Yarmouth
— 4 nights
Drive to Logan International Airport, Fly to Orlando


Boston — 4 nights

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Your day by day itinerary now includes Boston Ballet, Boston Symphony Orchestra and Four-Handed Illusions: An Intimate Evening of Laughs & Wonder. Change things up with a short trip to Dolphin & Whale Watching in Gloucester (about 50 minutes away). There's lots more to do: explore the world behind art at Museum of Fine Arts, stroll around Rose Kennedy Greenway, wander the streets of North End, and browse the different shops at Faneuil Hall Marketplace.

For maps, more things to do, and other tourist information, read our Boston online trip itinerary builder.

Orlando to Boston is an approximately 4.5-hour flight. You can also drive; or take a train. When traveling from Orlando in May, plan for colder days in Boston, with highs around 67°F, while nights are a bit cooler with lows around 50°F. Finish your sightseeing early on the 4th (Sat) to allow enough time to fly to Nantucket.
Nightlife · Tours · Outdoors · Wildlife
Side Trip

Nantucket — 4 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Your day by day itinerary now includes Theatre Workshop of Nantucket. Next up on the itinerary: see the interesting displays at Whaling Museum, enjoy the sea views from Sankaty Head Lighthouse, brush up on your knowledge of spirits at Cisco Brewers, and take an in-depth tour of Nantucket Shipwreck & Lifesaving Museum.

To find where to stay, traveler tips, other places to visit, and other tourist information, read Nantucket road trip planner.

You can fly from Boston to Nantucket in 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. Traveling from Boston in June, you will find days in Nantucket are a bit cooler (69°F), and nights are about the same (57°F). Finish up your sightseeing early on the 8th (Wed) so you can go by car to West Yarmouth.
Outdoors · Beaches · Parks · Historic Sites

West Yarmouth — 4 nights

West Yarmouth is a census-designated place (CDP) in the town of Yarmouth in Barnstable County, Massachusetts, United States. Explore West Yarmouth's surroundings by going to Cape Cod Canal (in Buzzards Bay) and Plymouth (Plimoth Patuxet, Plymouth Rock, &more). There's lots more to do: get curious at Sandwich Glass Museum, steep yourself in history at Edward Gorey House, see majestic marine mammals with Hyannis Whale Watcher Cruises, and kick back and relax at Seagull Beach.

For maps, other places to visit, more things to do, and tourist information, read West Yarmouth online sightseeing planner.

Traveling by car from Nantucket to West Yarmouth takes 2.5 hours. June in West Yarmouth sees daily highs of 73°F and lows of 58°F at night. Finish up your sightseeing early on the 12th (Sun) so you can travel back home.
Museums · Outdoors · Tours · Wildlife
Side Trips

Yarmouth travel guide

Beaches · Mini Golf · Specialty Museums
Yarmouth is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. The population was 23,793 at the 2010 census.The town is made up of three major villages: South Yarmouth, West Yarmouth, and Yarmouth Port.HistoryWampanoag originsPrior to European colonization, Yarmouth was inhabited by the Wampanoag, an Algonquian people. In the Wôpanâak language the area was called "Mattacheese". Wampanoag tribes living in Yarmouth at the time of European settlement included the Pawkunnawkuts on both sides of the lower Bass River, the Hokanums in what is now northeastern Yarmouth, and the Cummaquids in what is now western Yarmouth.Plymouth Colony settlementYarmouth was organized and incorporated as part of the Plymouth Colony on September 3, 1639, following a settlement led by John Crowe (later Crowell), Thomas Howes and Anthony Thacher, and is, together with Sandwich, the oldest town on Cape Cod. Yarmouth originally included what is now the town of Dennis, which was incorporated as a separate community on June 19, 1793. Yarmouth is named after Great Yarmouth, a town in the county of Norfolk, on the east coast of England, which is itself at the mouth of the River Yare.