2018 Italy Planning: September Edition

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”?’

Read more: 2018 Fall & Winter TravelIMG_1635

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:

  1. I told Will I was dying to go back to Siena and Assisi to share those places with him
  2. He asked if I want him to put a flight watch on his many plane apps
  3. I said yes
  4. I randomly asked him over the next few months how prices were looking
  5. Finally one day 2 weeks ago he says tickets are good and asks if he should buy them
  6. I say “YES!!!”
  7. 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 (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 whats on the radar for this trip:

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


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, Rinollita, Focaccia & Schiacciata bread, Pappardelle alle Lepre, Vin Santo, Crostini di Povertà, Trippa alla Fiorentina
  • Top ten extreme restaurants: Fortezza Medica, 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

Read more: How to Plan a 2-Week Trip: Part 3

Next Steps

My goals for October include booking accommodations, sketching out my day-to-day plan, researching costs (& ways to save money), practicing my Italian again.


P.S. This post contains affiliate links, meaning if you click on items for purchase I can receive some compensation


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