Origin of a Lifetime Trip


Inspiration comes in many forms. On March 1st, after enjoying the Atlanta Hawks victory over the Dallas Mavericks, my good friend Sam told me about his upcoming trip to Italy. As I listened intently, I was drawn into the deal – round-trip airfare between JFK and Milan, 6-nights hotel accommodations, and 1-week car rental, all for $699 per person. Wow! I always wanted to visit Italy, but knew that a similar trip would be much more expensive than Sam’s deal.

Over the next few days, I explored Sam’s deal in intimate detail, and had several conversations with the tour company. I considered several options, including flying from Atlanta, and extending the trip. Ultimately, I decided to forego the deal – there was about $600 airfare surcharge for extending the trip and flying from Atlanta.

New challenge accepted:

  1. build the trip on my own, around my wedding anniversary
  2. minimize out-of-pocket spend using mostly miles and points
  3. enjoy a mix of sightseeing and relaxation
  4. keep it all a surprise for my wife

Over the next 2-1/2 months, I spent hundreds of hours planning this trip. Hundreds of hours researching options for airfares, hotels, resorts, trains, car rentals, and sightseeing. Hundreds of hours debating which cities to visit, and the number of nights to spend in each. Hundreds of hours speaking with friends who have strong opinions of Italy (all good!), with very specific recommendations for my trip. Hundreds of hours in eager anticipation.

Expectations were high, but will they compare to reality?

You may also like