BOS
Anywhere from Boston
From Boston, winter wishes lean warm, and a fall city trip in the other direction is the interesting one.
These are places with enough of a reason to leave Logan, not a thin list of every airport code we know. Prices are not shown here because a fare without a live source would be a guess.
Orlando
Theme parks, warm water, and a flight that is nonstop from a lot of US cities.
Late January through early May, and again in November, when the parks are cooler and slightly quieter.
Punta Cana
All-inclusive beach time without a packed itinerary.
December through April. June through November is storm season, so travel insurance matters more.
Lisbon
A European city that still fits a careful budget better than many of its neighbors.
April through June and September through October. August is lovely and crowded.
Charleston
A city weekend that can grow a beach day without a second flight.
March through May and October through November. Summer is beautiful and very warm.
London
Museums, parks, and a city that works well without a car.
May, June, and September. Winter is theater weather if you pack a real coat.
Nashville
A city trip with a short flight from much of the country.
April, May, October, and November. Summer is hot and the honky-tonks do not get quieter.