You need a vacation, and trips are sometimes expensive. Fortunately, you can find lots of services to plan your vacation that won't cost you a dime.
For starters, as you're deciding how to reach your destination, use the BeFrugal Fly or Drive Calculator to estimate the cost and time required to complete your trip by airplane or by car, so you can determine which mode of transportation is better.
Once you've made plans, TripIt and WorldMate are two Web services that will organize your itineraries so that you stay on schedule. Entering itineraries is easy: Both services simply ask you to forward the confirmation email message from each airline or hotel, and then they input your schedule automatically.
When you arrive at your destination and you find yourself in need of a connection, try Hotspotr, a Web tool that can help you find Wi-Fi in public places in the United States (and in some areas internationally). Other users report where they found Wi-Fi, and whether it's free; as we went to press, 3794 cities had recorded Wi-Fi spots. Just looking for some food? Foursquare (for Android, BlackBerry, and iOS) is an old app now, but its new Explore feature lets you search by keyword for areas around a city, and if you're new to a place it's a great alternative to Yelp for finding what locals (and visitors) like.