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I’m putting together a Boston plan and expect to use the MBTA a lot mostly Green/Red/Orange to get between Back Bay, Downtown, Cambridge and a couple of evening stops. For someone who doesn’t know the city well, are there any stations or stretches you’d avoid late at night or any lines that feel less comfortable after the crowds thin out? I’m not looking to stereotype neighborhoods, just trying to make smart choices and avoid walking into a sketchy situation by accident. Also, if you have do this instead tips best place to sit which exits feel safer when you switch to a taxi/rideshare, I’d appreciate it.

Great advice about using the number of boats as an indicator! That makes total sense. More options usually means better quality and variety to choose from. The Dry Tortugas sound amazing too. Thanks for the detailed tips and itinerary examples!

If you are staying in Portland, plan on spending time around the Old Port and Commercial Street since it is easy to walk, full of good food, and the waterfront vibe is great. A small rental car also helps if you want a quick coastal drive to places like Cape Elizabeth, and October evenings can feel chilly near the water. For the Boston side, I once used Blue Nile Livery for an early airport pickup and it made the travel day much smoother.