We will be arriving Boston Sept 5th at noon and plan on spending the day on the Old Trolley Tour before departing for our checkin that evening in Brewster. We will have two vehicles and I am wondering what is the best way to handle this..is there parking near one of the trolley stops or is there some way to leave the cars at the airport and take a subway back and forth and then leave from the airport. Which is easier or more economical.
Thank You...Barbie

You can pick up the Trolley Tour at the Aquarium. Since it appears that you are coming into Boston from Logan Airport, the most economical way is to take either the #66 or #67 MBTA bus from the airport terminal that you arrive from to the MBTA Airport stop (blue line). From there, take the blue line inbound to the Aquarium stop (it actually stops on State Street by the Quincy Market). Cross the street to the Aquarium and board the Trolley Tour there (head towards the pier). The cost of the T is $1 per person - the MBTA bus is free, you'll buy $1 tokens for the T at the Airport stop. Then return to the airport the same way, get off at the international terminal as it is only one level, the courtesy shuttle area for car rentals is well marked, and then pick up the courtesy shuttle for your rental car. Courtesy shuttles run frequently, about every 5-7 minutes. This way you avoid paying for parking in Boston.

Note that on the T, there is a stop called State Street, but that is the stop immediately after the Aquarium stop. As an FYI, years ago the Aquarium stop on the T was by the Aquarium.

Just one question, what do you intend to do with your luggage while on the Trolley Tour? If you do decided to rent your cars in advance, there are parking lots near the Aquarium, but the price is fairly steep even on the weekend.

Check out the MBTA website for a map of the MBTA stops.

Thanks so much for some direction. That is a good question about the luggage. Do we lock it in lockers at the airport or take a chance by locking it in the trunks of our cars.
I really didnt think this out real well.
Again thank you...Barbie

Here's a thought. Take the courtesy shuttle from the airport terminal to whichever car rental agency you are using. Fill out the paperwork, and put your luggage in the trunks of the cars. Don't put anything on the seats. Leave the cars at the rental agency - free parking. Take the courtesy shuttle back to the airport - International terminal is the easiest one. Then follow the rest of the directions that I provided earlier to get into Boston and back. You benefit from the free parking, which is basically secure, and a place to store your luggage.

The only thing is that the clock starts ticking on your rental as soon as you sign the rental contract. But then, if you took the cars and parked them somewhere it would be the same thing.

I have had no problems (so far!) just leaving my luggage with the airline ... just not bothering to go get the bags off the carousel. I later retrieve the bags from the airlines' baggage office. I've not done that at Logan, however ... but you might consider using that tactic too.

I am not sure I would just leave luggage at Logan - Logan has very limited baggage control as far as checking luggage claim numbers, etc. In the zillion times I have flown home to Logan I have never had anyone check to make sure my luggage was mine - many other airports at least spot check luggage ownership. I have also seen lots of luggage just sitting around near carousels - even since 9/11. I would worry that that might be the fate of the travelers luggage if he just didn't claim it.

I worried if I could still not (immediately) pick up my checked bags too after 9/11. I decided not to ask, as I was sure the answer would be "No", but each time I've chanced it, the luggage was there. I never have anything of value in them, but it would be an inconvenience. I'd surely ask for compensation of what did get lost, since what's the reason for the claim checks on the bags if airports aren't going to check them? I'm most worried that they'll do a "planned" explosion of my bag if they don't know what's in it. I offer it only as something I've done .... maybe not the best choice for everyone.

My recommendation would be to pick up your luggage, put it in the trunk of your rental cars, and head for the parking garage next to the Aquarium. The Old Town Trolley Tours start near the Aquarium. And, the Aquarium parking garage is just off I-93.

Though the complete trolley route takes only about two hours, you'll probably want to get off at one or more stops to walk around, explore, have some refreshments, shop for souvenirs. The trolleys only run until 5PM.

Late afternoon on a Friday is no time to be going to the airport and back, particularly if your destination is Cape Cod. Much better to pick up your car, already in Boston, and be on your way.

Leaving your luggage at Logan is extremely risky. If you leave it in your rental car, and leave the rental car with the intention of returning in a few hours, you may find that the car has been moved.

You never know what the Cape traffic will be like on a Friday night, or how long it will take to cross either of the bridges. And, the earlier you get yourselves out of Logan on a Friday, the better.

The traffic leaving Boston on a Friday afternoon/evening will be challenging enough without having to go the the airport and back first.

I think djk's plan is very good. But watch out, the last time I used that parking garage, it was VERY expensive. But IMHO worth it in this particular situation.