re: Possible 10 year Anniversary trip to Italy

I’m not a fan of packages or travel agents, but you need to determine your own comfort level with detailed travel planning. Italy is a very diverse country—deciding where to go & how to spend your time is the first decision to make. You can’t plan much of anything until you do some research and decide on your priorities: do you want city, country, landscapes/scenery, art, religious pilgrimage stuff, wine, food, outdoor activities, etc.

Also, I think it’s a sweet idea to do some planning without her knowledge, but please don’t do all of it. Maybe buy a bottle of Italian wine, write up a note that you’re springing for a trip to Italy, and give it to her....because it would be a shame to buy plane tickets or book specific cities to find out once you tell her that she really wanted to see Venice, or would have preferred Pompeii to walking in Cinque Terre, or only wants to do cities.....make the planning a joint exercise, you’ll both enjoy the trip more that way.