Okay! here are my suggestions out of the places I've been:
Italy: aaaaaamazing trip, there is so much history and culture and beautiful people packed into a country barely the size of california...I can't even name my favorite city, because I LOVED it all. Besides the more "well-known cities", Torino was beautiful....with tons to do without all the chaos of larger cities. Also, Ischia...beautiful mountains & beaches.
I love tropical places, my favorites (so far) are Bermuda, Aruba, St. Thomas, and Cozumel (just dont drink the water in Mexico!) Overall, i prefer the Eastern Carribean to the Western or Southern. I think the Eastern islands have the most beautiful beaches.
About Bermuda: DEFINATLY cruise....food is super expensive there...a burger & fries is like 15 bucks..plus what I like about cruising to Bermuda is that you're in one port for the full amount of time you are there...there are only two "at sea" days.
Aruba's beaches are beautiful but it is all desert terrain outside the beach... also, it's not a real "hot-spot" it's more couples oriented it seemed (which would have been fine, had I gone AFTER I was married!)
Toronto, Canada: ton's of Italian people...(highest Italian population outside of Italy) therefore: great italian restaurants! lots of good shopping & of course, Niagra Falls.
Onto the U.S.
(Besides NYC which is the greatest city in the world...haha)
Boston, MA: it is so quaint with tons of cool little shops. Places to hit: Faneuil Hall, Quincy Market, Boston Science Museum, Boston Aquarium.
SanFranciso, CA: Fisherman's Wharf
Baltimore,MD: Little Italy, Baltimore Aquarium
Palm Springs, FL: City Place: tons of ritzy stores for mostly window shopping, but a lot of fun and tons of night-life.
Grand Canyon, AZ-The Grand Canyon! so breathtaking.