I usually write my travel tip blog posts retrospectively; I carefully think about why I did, what I liked, didn’t like, would do differently, etc. But I have a different idea this time around: what if I write posts as I was going along in the planning process so you could see how all that unfolded in “real-time”?’
Plane Ticket Process
So there are two parts of trip planning that Will is in charge of, not that he’s not capable, I just enjoy planning vacations. The things he is in charge of planning are renting cars & buying plane tickets; I want nothing to do with either. This is basically how this trip’s plane ticket-buying process went:
- I told Will I was dying to go back to Siena and Assisi to share those places with him
- He asked if I want him to put a flight watch on his many plane apps
- I said yes
- I randomly asked him over the next few months how prices were looking
- Finally one day 2 weeks ago he says tickets are good and asks if he should buy them
- I say “YES!!!”
- DONE.
That is a literal play-by-play of pretty much every time we plan a trip. 🙂 After Will bought the tickets he sent me the flight itinerary so I can start planning our days from here. Funny fact about this upcoming trip: Will didn’t realized he bought our return tickets with an overnight layover in Copenhagen, so we are coming back a full 24 hours later than intended. We’re not changing the tickets though because we go the tickets for cheap (that’s probably why) and we normally try to come back on a Saturday so we have this kind of flex time on Sunday if needed…it’s needed now!
Read more: How to Plan a 2-Week Trip: Part 1
Daydreaming Process
This is literally the best part about trip planning! I get to daydream every free mental moment I have on what I want to do, see, eat, experience. I usually jump in between daydreaming and planning for the following month after buying tickets as it slowly shifts to more planning. In this phase I try to get a feel for the type of trip we want to go on because that changes everything in the planning stage. Here’s what I’ve cooked up for this trip so far:
- We’re going in winter time so that means less crowds but also less sunlight and earlier closing times, which means it will be a slower trip
- We want to stay out of major cities most of the time (i.e. Florence, Rome) and focus on Assisi & Siena
- We want to spend time just driving to little towns and out-of-the-way locations = rental car is a must
- We want to spend some quiet time together, just the two of us; our last few trips have been family trips, which are lovely, but we want something different this time
- We want to have time to stroll the cities and towns we visit
P.S. The daydreaming phase also includes healthy amounts of Pinterest 🙂 I call it research.
Planning Process
I am a recovering type-A planner. I still make plans, lots of them, but I am better about leaving room for surprises and unplanned adventures. However, maximizing spending time at UNESCO World Heritage Sites is still an absolute must for me soooo that is also #1 on my planning list. Once I figured out where we are going I immediately google what UNESCO has in the area. Here’s what’s on the radar for this trip:
- Assisi
- Pienza
- Siena
- San Gimignano
- Val d’Orcia
- Etruscan Necropolises of Cerveteri and Tarquinia
- Medici Villas & Gardens (maybeeeee, if I can squeeze it in)
In addition to UNESCO, I am also going through all my travel books and I keep a running list of things they recommend.
Read more: How to Plan a 2-Week Trip: Part 2
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Food Journeys of a Lifetime: 500 Extraordinary Places to Eat Around the Globe
- Top 10 historic food shops: Antico Pizzicheria de Miccoli, Siena
- Campo dei Fiori, Rome
- Eat: Carciofi alla Romana (Roman artichokes)
- Tuscans Noble Food Tradition: Bistecca alla Fiorentina, Ribollita, Focaccia & Schiacciata bread, Pappardelle alle Lepre, Vin Santo, Crostini di Povertà, Trippa alla Fiorentina
- Top ten extreme restaurants: Fortezza Medicea, Volterra
- Sangiovese in Tuscany
- Top 10 places to enjoy cafe society: Rome, Italy
Sacred Places of a Lifetime: 500 of the World’s Most Peaceful and Powerful Destinations
- Top 10 mosaic interiors: Santa Maria Maggiore, Rome
- Abbazia di San Galgano
- Basilica of St. Francis, Assisi
- Chapel of the Stigmata, la Verna
Secret Journeys of a Lifetime: 500 of the World’s Best Hidden Travel Gems
- Pienza
- Top 10 sculpture parks and trails: Chianti Sculpture Park
Journeys of a Lifetime: 500 of the World’s Greatest Trips
- Walking in Umbria
Next Steps: My goals for October include booking accommodations, sketching out my day-to-day plan, researching costs (& ways to save money), and practicing my Italian again.
Read more: How to Plan a 2-Week Trip: Part 3
JMF
