New Orleans is the city of jazz and you can hear music all day long in the French Quarter. People are friendly, the food is amazing - try the beignets at Café du Monde :) I fell in love with this city and I can't wait to go back. If you are not a city person, don't worry it doesn't feel like it and you have access to the bayou and the plantations from NOLA.
Boonsboro, Maryland, United States
Nashville is the city of country music. If you can have a seat, go to the Bluebird cafe, they have nice open mic nights. There are so many things to do and see in Nashville, you will have the choice. Nashville is a city to live not a city to visit. Take the time to live at the same pace as the people who live there and enjoy!
Boonsboro is the one of the cities I never went to but as a fan of Nora Roberts' books I have read about it a lot. It sounds like a great city to relax, have a good pizza and stop by the bookstore to meet one of my favorite author. This stop will be a nice one after visiting two big cities.
Boston....I don't know where to begin....First, you can go see a Celtics game or a Bruins game. The food is amazing, try the lobster roll. Walk through the city, visit the baseball field and Harvard. The campus is beautiful, the architecture is amazing and you can feel the atmosphere....
Last stop of my road trip will be Portland. I really like the sea and the city close to it. The atmosphere is different from other cities and you can relax really easily. I think I could stay there forever...