You have two weeks to spend at your destination. You could plan every day down to the minute filled with activities, dining, car rentals/transportation, and lodging OR you could fly by the seat of your pants and see where the trip takes YOU. Try vacation planning by NOT planning your vacation for a truly exciting trip.
If you want to take a leisurely, non-planned vacation, plan on doing so during non-peak travel times. If you go during peak travel times to your destination you could find yourself without a place to stay, a rental car or sold out venues.
Lodging
It is a good idea to plan the first two nights lodging arrangements ahead of time. This will give you a couple of days to explore the city you first visit and decide where you want to go next. Try booking a room at a vacation rental or bed and breakfast so you can visit with the inn’s owners and get ideas of where you should go next on your vacation.
Transportation
Rental cars are an option in most destinations and allow you to take control and go off the beaten path. The downside is that you need to be good at navigation and map reading. An alternative is public transportation via bus or railway. This allows you to enjoy the scenery or even maximize your time by traveling overnight to your next destination.
Meeting Locals
A successful spontaneous trip will require that you meet locals at their local restaurants and bars. Avoid chain restaurants where you’ll likely mingle with other tourists. Local eateries and pubs will show you the true color of the city and give you an informal way to meet locals and ask them for advice. Strike up a conversation with the bartender. Most locals will be happy and proud to share their favorite things about their city or country.
Activities
Some vacation planning you may need to do ahead of time. You need to determine what it is you are going for and what you want to see when you are there. Once you’ve selected a city, region or country, visit their tourism website to find out more about what there is to do. You will often find maps of the area, information about public transit and current events. Another great resource is your friends and family. Social networking sites like Facebook and travel focused sites, like TripAdvisor.com also have many recommendations from real travelers on vacation planning.