For the Boston part, relying on public transportation is the best idea and its pretty easy to get around. But there is no reason to stay at an airport hotel. Were you thinking of that for budget reasons? You should stay right in downtown Boston somewhere, then head to the airport on your final day.

Staying at the airport (or in Harvard Square or Brookline) will add at least an hour round trip to anything you want to do.

P-town is at the far end of the Cape, and if you want to see a lot, you will be better off in the middle.

You can do day trips to Nantucket from Hyannis, most cheaply and reliably on the Steamship Authority Fast Ferry. You should not need a reservation on a weekday in October if it is after Columbus Day.

To go to the Vineyard, you will want to be at the west end of the Cape, Sandwich or Bourne or Falmouth or Woodsa Hole, because commuter traffic on the Cape is moderately heavy before 9:30 AM. You will have a choice of Steamship ferries to the Vineyard; Oak Bluffs is a better arrival point than Vineyard Haven.

P-town is another good day trip, unless you want to be part of the large gay social scene, which is somewhat reduced in the shoulder season.

Many things in the Cape and Islands are now open until Thanksgiving, and during the week are quiet enough that I might not even make hotel reservations. Lots of the tourists traps will be closed, fortunately. Route 6A is best for antiques and arts.

Do not plan to be in Boston the weekend of October 20-21 unless you love rowing. It is the Head of the Charles regatta with crews from around the world taking over the river, the hotels, and the restaurants. If you do like athletic events, it is a great one.

I would not stay at an airport hotel in Boston as a base. It's inconvenient. You may consider hotels in the Seaport/Waterfront area. Those hotels are in close proximity to the airport (2 stops on the Silver Line) but also closer to the city for sightseeing.

Once again, the suddenness of replies is amazing!!!We were thinking of staying at or near the airport because of the rental car. I have read driving in Boston is a disaster so why pay for a rental car that just sits for 2 days? We MUST have the rental car for the first part of the trip, the non-Boston part. Any advice on this? Also, what "middle town" along the Cape would be the best base camp for what we want to do? Thanks for any additionl advice!!!!

so return the rental car and take mass transit or a cab to your hotel in downtown. You can return the car at the airport, or maybe even at a downtown site, depending on the company (there are some rental car offices that are not too difficult to get to from the highway, and then you can easily get to a T stop).

I'm not really a Cape expert, but I would think PTown would be one of the nicer towns to stay in off-season. Though it is surely less convenient for touring around the whole island. You could also take a look at Chatham or Wellfleet, which are very nice places on the outer cape and a bit more convenient for getting to Hyannis for the ferry. There are plenty of nice places to walk, in the National seashore. Also, the Wellfleet Bay Audobon Wildlife sanctuary is very pretty and has some nice trails, particularly if oyu are interested in birds.
http://www.massaudubon.org/Nature_Connection/Sanctuaries/Wellfleet/index.php

Yes, drop the car at the airport when you return from the Cape (easy exit for Logan Airport from the Expressway, clear directions for rental car returns at the end of the tunnel.
Take the Silver Line bus or the Blue Line subway or the water taxi to Rowe's Wharf ( a spectacular way to enter the city). Ask your hotel for their recommendations, though they may well be on their website.

What sort of accomodation do you want: bed and breakfast/inn, standard motor hotel (Holiday Inn or Hampton), resort, or a cottage/condominium? And how much do you want to pay?

china_cat, Provincetown in an interesting place and has an interesting setting (the dunes etc) but it is one of those towns that had an industrial waterfront and has been trying with only minor success to make it attractive. It is entirely different from Chatham, for example. All those famous writers and artists summered there because is was cheap, not beautiful. It is also at the end of US 6, a very dangerous section of US 6. Again, a great day trip, perhaps a great place to spend the summer, but not a good location in my mind to use to tour.

You do NOT have to return the car at the airport. All car rental companies allow you to choose a different drop-off site. AFter you find a hotel in downtown Boston, check for the nearest car rental location and pick that as your drop-off spot. Most companies do not charge extra as long as the return is in the same city/area.

It's a lot easier to drop off the car in downtown than the airport. If you drop off at the airport, you're talking about spending at least 90+ minutes extra b/c you have to take the car rental shuttle back to the airport terminals, then take mass transit from the airport into the city (all with luggage in tow...)

Commercial Street in Provincetown is funky, fun, and very atmospheric. Chatham's Main Street is the same: Just more upscale. Both towns have a vibrant year round population but things will have slowed down a bit, that's for sure.

Five days on the Cape in October: Hmmmm. I think I'd stay in Sandwich, Chatham, Harwichport, Orleans, or Provincetown.

What do you hope to experience on the Cape?

P-Town, Bowsprit: Fun, yes. Attractive, no. Atmospheric in October? Perhaps, esp on the weekend.

Agree strongly with your recommendations in order, though if I wanted to go to the Vineyard for a day trip, I might split my time between Sandwich and Orleans or Chatham. The thought of some poor soul looking at the map, seeing Route 28 to be a fairly direct route between the Outer Cape and Woods Hole and then actually trying to drive it in time for an early ferry horrifies me.

Thanks for the great advice on Boston!! I am still torn over the Cape Cod portion, though, and am leaning toward staying in Hyannis which is where the traditional and fast ferries depart for Nantucket and Marthas's Vineyard. Hyannis is also are where the Elegant Dinner Train departs. Has anyone taken this?.What is everyone's impression of Hyannis? We only have 4 days for the Cape which is hardly long by any means and at least one, if not 2, would be full days spent at Nantucket and/or the Vineyard. Is there enough to see in those 2 locations to hold our interest?In answer to what do we wish to do, we'd like to spend some time beach strolling and perhaps enjoying an artsy feel to a community. I've read in the AAA Tour book for Massachusetts , in the section specific to Hyannis, that there is a "nearby beach" (Craigville Beach) that is quite popular. True?Where exactly is this, in Hyannis?This is difficult!

Hyannis is the business center of Cape Cod and the least definitive of the traditional and much more charming Cape experience. Don't base yourselves there; you'll be missing out on the best of the Cape. Really.

Also, the Dinner Train is truly dismal. Avoid.

Why not drive another 30 minutes toward Chatham, arguably one of the most beautiful Cape towns, and take the high speed ferry out of Saquatucket Harbor in Harwichport to Nantucket?

btw: This is the first time I've ever known anyone to consider Provincetown less than beautiful. I'm not sure where that's coming from exactly....

Well, I can tell you that it is not from any anti-gay sentiment, if that is your implication. You will note that in my original response above, I suggested that the OP might want to stay there if s/he were interested in the gay social scene. I detect no hint of snark in that.

I would agree that it is funky, fun, and has an interesting history, but like many working fishing villages that have become mostly tourist destinations, it does not, unlike Key West, Savannah, Charleston, Easton, MD, Stonington, CT, or Portsmouth, NH, have to my mind much visual charm. I am talking about the town, not the seashore. Ditto Vineyard Haven and Gloucester, but not Marblehead. Your mileage may vary,

I never 'imply' but your particular assumption didn't cross my mind. Sorry if I wasn't clear and left room for an incorrect assumption.

We will have to agree to disagree here re. the charm of downtown Provincetown. I think it is one of the lovliest towns on Cape Cod along with Falmouth, Sandwich, Brewster, Chatham, Wellfleet, etc.

My mileage does indeed vary, it would seem. That's ok; the world would be a boring place if we all agreed.