I need some assistance please. I'm all over the place. I join the others who will be traveling from NY to Boston or the Cape this coming fall.
However, I'm printing out much information about hotels and the city and places to go and eat. But, I just don't know exactly where to begin to organize myself. I always like to give myself leeway for emergencies or anything else that could come up. But, I'm at a loss.
How DO YOU begin to prepare your itinerary when you have no SET idea as to what hotels you are staying at, the dates, just a vague idea? Thanks. I'm 61, female and traveling alone.

You have the skeleton in place. Now pick the dates. Next plan where you want to stay for the first night. Then research that area. Plan what you want to see, where the best restaurants are etc. Keep on trucking.
Have fun,
Another 61 years old female.

First the obvious - where to go; find as many sites on the web (or in past years, pull as many books from the library as I could carry) and read, read, read; make a list of what are my top items; check a map to see what is physically feasible time and driving wise; make up a (flexible) daily agenda, contact the hotel or B&B, and buy travel tickets. Use your computer as much as possible; saves those "phone tag" games. I find that I enjoy the planning almost as much as the trip itself and sometimes begin nearly a year ahead. I started back in 1960 when my friend and I did a month in Europe as two young women; I planned; she followed. We had a memorable trip with lots of time for those wonderful tidbits that just happen. Make sure you keep in mind that museums are closed on Mondays and any other peculiarities that might spoil your day's plan. And always have a small backup so if you aren't enjoying the original plan, you can go on to something else. I have to admit as far as meals I just wing it; I prefer for this to be the economy portion of any vacation. Have a wonderful trip.

As noted before, the first step is to READ about the place your visiting. Start by getting a book WITHOUT a tourist slant; one that gives a sense of what makes the place tick. Insight Guides are not a bad place to start; although there are usually better books on any a place, IG's are written for just about anywhere.

Then decide FOR YOURSELF what it is you hope to accomplish on the trip. Museums? Nightlife? Shopping? Dining? Cultural diversity? Relaxation?

Then grab some tourists books and try to find out where you are most likely to find what you're looking for. Read more than one, noting the biases of the author (some books are written for travellers on a shoestring, others to more upscale visitors). Then pick the places you think are the ones you want to visit.

For each place, write down (1) where it's located, (2) when it's open, and/or the best time to visit, and (3) how badly you want to visit. Group these places geographically, so you can visit as many as possible with a minimum of travel time. Within these georgraphic subsets, try to find a best day to visit (or NOT visit). Pretty soon you'll a list of things to visit on specific days (a museum that's open late on Tuesdays means you'll want to visit the sights around that museum on Tuesday, finishing with that museum).

Then make some judgements. You probably won't be able to visit everything on your list, so make a prioritized list. Decide which things to skip if one high priority item takes more time than you expected, or which things to add if the opposite occurs.

Pretty soon you'll have a list of things to visit on specific days. That's called an itinerary!!

Suggestion: leave at least one day to just wander through a town, just breathing in the cultural atmosphere with no thought of actually seeing anything. Some of the favorite things I've seen have occurred on those days!!

Oh my! I'm so touched by the outpouring of wonderful information. Sometimes it's the most obvious things, right? I felt quite "all over the place" and you have all helped me tremendously. Thank you, thank you, thank you!!