I owe a lot to advice/trip reports from this forum and elsewhere on the internet, so here is my way of giving back! Beware, it will be LONG--but I have tried to break it into sections for easier navigation.
- Travel Preferences/Context
- Motivation for Trip
Things we wouldn’t do again
SUMMARY (Travel Preferences/Motivation/Itinerary)
My partner and I are in our early 30s and both prefer to take vacation travel slow, trying to stay at least two nights in any given location and building in flexible time for surprises. We take a “we’ll return” approach to travel, so don’t pack in activities: I usually schedule one major planned/prebooked activity per day and many optional activities in the neighborhood to add on as we like. We’re naturally frugal people, but based on our preferences and careers, days off are more precious than dollars spent while traveling, so we’ll pay for convenience and memorable stays/experiences if the value feels right to us.
My partner is a homebody and probably wouldn’t do a lot of international travel without me, however he LOVES food. Therefore, I plan our vacations around unique/memorable food experiences, and he’ll happily go along on any history/art/nature activities (my interests) make sense between eating. However, he has joint conditions that make extended walking difficult, so I plan in downtime to avoid being on our feet an entire day and try to balance heavy walking days with something like a travel day where we are more stationary.
This trip was originally to take place in June 2020, but was moved due to Covid. As a delayed honeymoon, we wanted to take it even more slow than usual, planning for lingering dinners and afternoons just wandering through pretty towns or neighborhoods. Goal achieved! This turned out to be one of our favorite trips ever.
This trip was 16 nights, flying out of Chicago O’Hare the evening of Tuesday, August 23 and returning Friday, September 9. When our schedule allows, I always look at how flight costs change when we +/- a few days on either end of our planned trip–it can make a huge difference. This particular schedule saved us something like $600 vs shifting the dates forward a day or two, and had the added benefit of a weekend to readjust after the trip, which meant we were in great shape for work the following Monday.
Our itinerary was:
Arrive 2:30pm in Florence. Stay 3 nights.
Pick up rental car at 11am; drive to Agriturismo near Pienza. Stay 7 nights.
Drive back to Florence, drop off rental car; take train to Modena. Stay 1 night.
Train to Bologna. Stay 3 nights.
Train to Florence. Stay 2 nights.
Late morning flight from Florence.
This itinerary worked very well for us in practice. If push came to shove, I would have taken a night off of the Tuscany countryside and given it to Bologna, but our agriturismo had a 7 night minimum during this peak travel time.
Italy in August was not my original plan, but with the COVID delays and other work considerations, it’s the time we were able to take, and we’re glad we did!
Let’s not mince words: it was HOT (peak of 85F most days, up to 95F). We worked around this by making sure all accommodations had air conditioning and by planning any site visits without aircon for first thing in the morning (looking at you, Florence Duomo). We also built in time to return to our hotel/airbnb during the hottest part of the day (2-5pm), stayed hydrated, and used the excuse to justify extra gelato. ;)
On the positive side, it was very dry, with only 2 or 3 days of rain during our entire trip. We found the Tuscany countryside to be bafflingly pretty, regardless of sun or cloud cover. It really did look like a painting the entire time.