8 days in Greater Boston, Provincetown & Falmouth Itinerary

Boston is known for historic sites, museums, and parks. Your trip includes some of its best attractions: explore the world behind art at Museum of Fine Arts, admire the natural beauty at Boston Public Garden, appreciate the history behind New England Holocaust Memorial, and engage your brain at Museum of Science.

To see reviews, where to stay, traveler tips, and tourist information, read Boston road trip planning tool.

Chicago to Boston is an approximately 4-hour flight. You can also drive; or take a bus. You'll lose 1 hour traveling from Chicago to Boston due to the time zone difference. April in Boston sees daily highs of 56°F and lows of 40°F at night. Finish up your sightseeing early on the 14th (Fri) so you can catch the flight to Provincetown.

Start off your visit on the 15th (Sat): tour the pleasant surroundings at Race Point Beach, learn more about the world around you at Sea Space Marine Discovery Center, appreciate the history behind Pilgrim Monument & Provincetown Museum, then take a leisurely stroll along MacMillan Wharf, and finally see majestic marine mammals with a dolphin and whale watching tour. On the 16th (Sun), you'll have a packed day of sightseeing: explore the wealth of natural beauty at Cape Cod National Seashore.

To see maps, reviews, traveler tips, and more tourist information, you can read our Provincetown route site.

Traveling by car from Boston to Provincetown takes 2.5 hours. Alternatively, you can fly; or ride a ferry; or drive. When traveling from Boston in April, plan for a bit cooler days and about the same nights in Provincetown: temperatures range from 51°F by day to 39°F at night. Finish up your sightseeing early on the 16th (Sun) so you can go by car to Falmouth.

Change things up with these side-trips from Falmouth: Lizzie Borden House (in Fall River) and Plymouth (Plimoth Patuxet Museums, Plymouth Rock, &more).

To find maps, photos, traveler tips, and tourist information, use the Falmouth tour itinerary planner.

You can drive from Provincetown to Falmouth in 2 hours. Other options are to drive; or take a bus. April in Falmouth sees daily highs of 54°F and lows of 36°F at night. Finish your sightseeing early on the 19th (Wed) to allow enough time to fly back home.