Rent car or take train

Question

Travel from Logan Airport to downtown? We are arriving on Saturday morning to spend the day exploring Boston. The following day, we’ll head to Acadia, stopping in Salem, Portland, and Kennebunkport before returning to Boston to fly out on Thursday morning (spending Wednesday night in Boston again). Should I pick up a rental car when we land and deal with downtown parking, or should I return to the airport on the day of our road trip to pick up the car and then return it the night before our flight?

Answer

For your trip, it really depends on how much convenience you value versus the potential costs and logistics. Both options—picking up a rental car at Logan upon arrival or waiting until you're ready for your road trip—have pros and cons. Let’s break them down to help you decide what will work best for you and your itinerary.

Option 1: Rent a car when you land at Logan Airport

Pros:

Convenience: You’ll have immediate access to your rental car, which can be useful for luggage, exploring the city, or taking short trips in and around Boston. Plus, if you have a lot of bags or need flexibility with timing, having the car right away may be more comfortable.
Flexibility for Day One: Having the car means you can easily explore areas outside of downtown, such as more suburban attractions or spots where public transport may not be ideal. You can also avoid the hassle of returning to the airport on the day of your road trip.
Parking Options: Many hotels in downtown Boston offer valet parking or parking garages, although these can be pricey. If your hotel offers a good deal on parking, it could be worth it for the convenience of having your car on hand.

Cons:

Parking Costs: Parking in downtown Boston can be expensive. Public parking garages may charge up to $40 or more per day, especially in busy areas. Additionally, finding parking on the street can be tricky due to the city’s layout.
Traffic and Navigation: Boston’s streets are narrow and confusing, and traffic, especially on weekends, can be frustrating. The city is known for its difficult driving conditions, and if you’re not familiar with Boston, navigating downtown might be stressful.
Public Transport Alternatives: Boston has a well-connected public transportation system (MBTA, or "the T"), so you could easily get around without a car for the day. The Silver Line bus from Logan Airport goes directly to downtown Boston, making it an easy and affordable option.

Option 2: Rent the car the day you leave for your road trip

Pros:

Avoid Parking Fees in Boston: By not having a car while you’re exploring Boston, you can avoid the high costs of parking and the stress of driving through the city. You’ll also be able to enjoy your time exploring without worrying about where to park your car.
More Relaxed Experience: Boston’s public transport options and walkability make it easy to get around the city without a car. You can use the subway, buses, or even taxis/Uber for a day of sightseeing, which can be far more convenient than having a car in a busy city.
Pick up the car closer to your road trip: If you pick up the rental car only when you're leaving for the road trip, you can avoid the hassle of having to drive in Boston. The rental car companies near Logan Airport are easily accessible and typically offer good pick-up locations.

Cons:

Extra Trip to the Airport: You’ll have to take an Uber, taxi, or public transport to Logan Airport to pick up the car before starting your road trip. This means extra time and cost, as you'll need to go to the airport twice—once when you arrive and once to pick up the car.
Less Flexibility on Day One: Without a car, you may be somewhat limited in where you can explore easily. While public transportation is great, some areas in the suburbs or attractions outside of the city (e.g., Salem or coastal towns) might require a car.

Conclusion:

Both options have their merits, but I would generally recommend renting the car only when you're ready to start your road trip. Here’s why:

Boston’s public transportation system is efficient, and for one day, you can easily get around by subway, walking, or using ride-shares like Uber or Lyft.
Parking costs and traffic in Boston can be frustrating, especially if you’re unfamiliar with the area. By not renting a car right away, you avoid those hassles for your first day.
You'll be saving yourself an additional trip to Logan Airport to return the car the night before your flight. By renting only when you're ready to leave for your road trip, your experience will be much smoother.

However, if you feel that having the car right away would add more convenience and flexibility to your time in the city, especially if you want to do some exploring outside the city, then renting when you land might be the better choice.

Either way, you’ll have a fantastic time in Boston and beyond. Enjoy your trip!