What to Pack to Travel
You won't need any exotic gear for New England, but you do have some packing decisions to make.
Pack lightly if you sail aboard a Maine windjammer.
Dress & Fashion
You'll want at least one fairly nice outfit of the dress or jacket-and-tie variety for special evenings in fancy restaurants. Few establishments enforce a strict dress code anymore, but you should be prepared nonetheless.
Newport RI has numerous restaurants requiring jacket-and-tie/dress, and the Ritz-Carlton in Boston also enforces the dress code.
Rain can come at any time of year. A small umbrella is minimal rain gear in summer; in other seasons a raincoat is necessary as well.
Summer days can get very hot and muggy, so cool cotton clothing is best, but have a sweater or jacket for cool evenings, cruises, and whale-watching expeditions.
In spring and autumn moderately warm clothing, including sweater and windbreaker, is essential.
In winter, be prepared for freezing weather and snow. Full woolens and foul weather gear are required.
Other Items
If you take prescription medicines regularly, bring a supply of the medicine, not a prescription for it.
Doctors are licensed by state, and their prescriptions are not accepted in any state except the one in which they are licensed. In other words, a prescription from a California doctor will not be accepted in Connecticut.
Other handy items might include a pair of binoculars and a flashlight.