These posts are placeholders for an upcoming European adventure that’s currently in the works. Beginning June 3rd, we will be backpacking across 33 cities in Europe over the course of three months, an experience we’re incredibly excited to share.
Along the way, we will be reviewing AI-generated itineraries in real time—putting them to the test and sharing what works, what doesn’t, and how they stack up against the reality on the ground. You can expect regular updates as the journey unfolds, with insights, tips, and firsthand experiences from each stop.
Once we’re back home, we’ll expand the blog with a wider range of content, including in-depth guides, recommendations, and reflections from the full trip. Be sure to check back often because we will be updating along the way and bringing you along for every step of the adventure!
explore it yourself:
The journey and accommodations:
We arrived by train from Rome on the afternoon of July 21st and stayed until the morning of July 23rd. We arrived into and departed from Firenze Santa Maria Novella Station.
My parents and siblings joined us for this leg of our trip so to accommodate the size of our group short term rentals were the most affordable option. We ended up selecting an Airbnb located in the center of Florence.
Note: * our additions to ai itinerary
Day 1: florence arrival afternoon
Piazzas and Leather
- Panetteria e Stuzzicheria De Neri*, sandwich
All’Antico Vinaio- Loggia dei Lanzi
- Palazzo Vecchio
- Walk to Piazza della Signoria, see the Neptune Fountain and outdoor sculptures
- Fotoautomatica*, photo booth
- Divina Terrazza Rooftop Bar* (get reservation)
- Massimo Leather*
- Adam Leather Factory*
- Ponte Vecchio, sunset
Day 2: Florence's Renaissance Heart
Piazza del duomo Complex
- Piazza del Duomo*
- Shake Cafe*, iced coffee
- Start early at Cathedral of Santa Maria del Fiore (Duomo), main floor is free
- Marlu Jewelry*
- View on Art Rooftop Cocktail Bar*
- Caffee Gilli*, oldest cafe in Florence
- Piazza della Repubblica*
Wine Bars and shops
- Cafe Odeon*
BREAK AT AIRBNB, OLTRARNO, and piazzale michelangelo
- Ponte Santa Trinita, photo op
- BABAE*
- Momo Vintage*
- Sbrino – Gelatificio Contadino*
- Giuliano Ricchi Jewelry*
- Filippini & Paoletti*, purse charms
- Gusta Pizza*
- Palazzo Pitti*
- Taxi to Piazzale Michelangelo, sunset
- Taxi back to Palazzo Vecchio to AirBnb
Departure Day
Coffee & Breakfast
- Melaleuca Florence Bakery*, cinnamon roll and iced coffee
- Walk to Train Station
final thoughts:
Overall Rating:
Would I go again?
Favorite moment:
Bailey’s favorite:
Parker’s favorite:
Any surprises?
Anything we missed?
How did ai do?
Nailed it: We’ll add our thoughts here after our trip!
Needs work: