This is my second in a two part series about trip planning and organization. I spend a LOT of time planning out our trips. I’m definitely someone who likes to have things organized and planned, although I do love the unexpected moments that happen on trips.

Choosing a Destination

Deciding where to go is hard, not because I can’t decide, but because of costs. There are LOTS of places I would love to go, but cost is a major factor. So I usually begin by making a list of places we would love to visit then I plug those destinations into the AAA web site to get airfares. This allows me to narrow things down considerably because the airfare is the most expensive part of the trip. If we won’t be flying, then I take into consideration driving time to each destination.

At this point, we don’t really get to choose the timeframe for our trips. We have one child in college and one who will be in high school, so we fit things in around their school schedules (which have completely different breaks and summers). This often means we’re traveling in early August, when everyone else in the world is too. When our kids are older, I look forward to being able to travel in the shoulder seasons (spring and fall) when prices are lower.

Getting Started

Once we have chosen a destination and made plans, I buy Frommer’s and Fodor’s guidebooks for the location. I read them thoroughly and make notes in a notebook of places to go, things to do, places to eat, and things like hours, web site addresses, entrance fees, and any tips the books have offered. Then I start a Word document where I type in all of the information in an organized way, by city or daily location. Once I’ve done this, a schedule of sorts starts to emerge, based on things we’ve booked and the days and hours places are open.

Using the Internet

I look up every web address I’ve written down and print out hours, addresses, and maps if I think they will be helpful. I visit general toursim web sites for each location and look for links to coupons, places I haven’t read about yet and any tips. Next I check out Tripadvisor.com, where I read through the lists of the top attractions and restaurants in each location. If I find something I don’t already have, I add it to my list. I usually look up attractions and restaurants I’ve noted from the guidebooks to see what people are saying about them on Tripadvisor. This has helped me narrow things down a lot.

Maps

This year I’ve added a new trick to my bag. I created a Google map for each city and dropped pins for where we are staying, places to visit, places to eat and where to shop. One problem I often have is that although I compile a lengthy list of restaurants, we invariably end up out and about and starved. We want to eat somewhere close to where we are and it can be difficult to figure out if anything on my list is nearby. The maps I created will be accessed by our phones, so we can pull them up and look for nearby restaurants when needed.

I always carry a paper map because you can never trust you can connect to the internet. Even a GPS sometimes cannot get a satellite (we had the worst time with this in Aruba). Although the guidebooks I buy have maps in them, I frequnetly find that the free maps you pick up at your hotel or at tourism sites are much better, so I always grab those when possible.

Transportation

We feel most comfortable when we can have a car, but when visiting cities, you really can’t because parking is so hard. So I do my research in advance about public transportation. We usually buy a visitor’s pass for subways – usually there is a 3 day pass you can buy that allows you unlimited access. I make sure to have a subway map with me at all times and I make notes about what subway stops are closest to attractions we will visit.

As convenient as public transportation is, sometimes it is more than we can bear to walk blocks to get to the station, wait endlessly for a train, then hoof it again once you get off. So we always have enough cash for a taxi ride, just in case. I usually will write the name and address of our hotel on an index card and then just hand it to the driver in case there is a language barrier.