Shermans Travel » United States » Massachusetts » Itineraries
Massachusetts Itineraries
Long Weekend
Dedicate 3 days to exploring Boston, then head down to the South Shore for a day of whale-watching.One Week
Give yourself 3 days to explore Boston before traveling to the South Shore for another 2 days. End with 2 days in Cape Cod.Two Weeks
Spend 3 days exploring Boston and 2 apiece visiting the South Shore and Cape Cod. Spend your second week relaxing on Martha’s Vineyard, or head west for a day at Old Sturbridge Village, 2 days in Northampton, and 4 days in the Berkshires.Massachusetts Advice
Hand-Picked Massachusetts Deals
Our Experts save you money with travel deals and advice
During the fall and spring, Mediterranean cruise travelers can find not only good deals, but also sublime weather and sightseeing conditions.
Zach Custer Travel Deal Expert
Sign up for the Top 25 Newsletter
to get exclusive weekly deals