Boston
The weather is probably the biggest variable for Boston visits. Come prepared for variety, and you’ll outsmart Mother Nature. Check the sports schedules if you have a nearby reservation. When the home teams are playing in town, traffic around their venues can come to a standstill. (The Boston−New York sports team rivalry is legendary. Do not, under any circumstances, wear clothing with a New York team’s logo!) The waterfront can be breezy, so even in summer, a wrap or light jacket is a good idea. Depending on where you’re staying, you can probably leave the car at home. Public transportation and cabs will be at your service (and Boston drivers are notoriously aggressive!). If time permits you to travel beyond the 617, you can rent a car to explore the mountains, beaches, or historical sites.