When we travel, I get a little obsessive about planning. I think some may read this and think I’m type A, scheduling everything to the minute, holding to a rigid itinerary type of person, but that’s truly not the case. Writing everything I have to do (make the flight) with most things I might want to do (certain attractions, areas, restaurants) makes the actual travel feel rather effortless. For me, preparation results in relaxation. And next week I go to Boston for the first time!

Things I do before I travel to a new city or country:

Create a color-coded spreadsheet* of key events by day.

Ask people who have been for recommendations on places to eat and things I must do. Ignore many suggestions, but remember the ones that keep coming up from different people, e.g., Mike’s Pastry in Boston for the cannolis. Yes, we will say, “Leave the gun, take the cannolis” at least twice.

Obsess over at least one thing that doesn’t really matter. For our upcoming Boston trip, the obsesssion was about where to pick up and drop off the rental car and what the best deal was on rentals. This took 2 hours, 3 canceled reservations, and resulted in a cost difference of only $30 and a travel difference of only 7 miles.

I often book at least one fancy restaurant meal and do light research on other places to eat in a variety of price ranges. In Italy, this place was Osteria Francescana, the number one rated restaurant in the world. If I eat well and take in some views, any trip seems worth it.

Create a list of items I must pack (chargers, black polka dot dress, red journal, sunglasses, 5 pairs of underwear, book I am currently reading + another book that will be easy to read in airplane, book for Joe in case he forgets).

Download audio guides for any specific walks or tours. This worked very well in Rome — Joe listened to the audio guides and told us the bits about the Colosseum and the Forum that we would find most interesting. This satisfied his need to learn and inform as well as my need not to have to follow a guide in a group.

The spreadsheet includes the following:

Daily itinerary of specific places we have to be, e.g., MacMillan Pier by 10:00 for whale watching tour

Key information (confirmation numbers, addresses and key codes for Airbnb apartment, times of flights)

Costs for tickets, travel, and lodging

Names of public transit stops near lodging

Potential activities by location that we can choose based on weather, mood, travel time. Freedom Trail, Boston Common, North End.  Accademia, Ponte Vecchio, that little sandwich place.

Specific notes and comments, such as, “Steps located near Caffe Vaticano,” or “Chocolate shop and printing studio near Old North Church,” or “TAV Air Side is for passengers who do not need to pass through customs upon arrival in Turkey.”