My wife will certainly differ from me on some of these. She has a much larger vacationing resume. I tend to be a homebody, but these places would get me to leave the comfort and familiarity of home.

1. Maui – The wife and I went to Maui on our honeymoon. This has to be the most beautiful place on earth. Even the touristy stuff is fun. If you drive the Road to Hana, you’ll see some terrific scenery. The weather is wonderful, and the locals are even better.
2. London – I tend to be a big anglophile. From the pubs to the comedy, I love British culture. I spent a week in London, and had a great time. I even tolerated the incessant rain. One highlight from the trip was seeing Agatha Christie’s Mouse Trap. I highly recommend you see it.
3. Montauk, NY (Gurney’s Inn) – We celebrated our recent fourth anniversary here. Montauk is on northern Long Island. We stayed at Gurney’s Inn. The people were very friendly. My wife even wrote an article about our trip to get there from Nashville, TN. It seems they don’t get many southerners up there. You can read it here.
4. Chicago – I was only there for a day, but I had a blast. We flew up, caught a Cubs game and had some deep dish pizza. I look forward to going back as there is much more to do there.
5. Jane Munsell’s House (Millington, TN) – As I stated before, I am a big homebody, and I get homesick a lot. Ms. Munsell is the mother of one our closest friends, Scott Munsell. She is an awesome host, and I didn’t want to leave. I’m sure you have someone in your life like that.