Sep 3 to 5 · 2 nights
Florence
Aperitivo in the Oltrarno, the Mercato Centrale, a pasta class, and the Michelin night.
tre fermate
The route
Fly into Florence, drive out to the vineyards, then hop down to the Adriatic and fly home from Bari. No backtracking.
Sep 5 to 7 · 2 nights
Chianti
A wine estate with a pool. Harvest-season tastings with a driver on Labor Day.
Sep 7 to 12 · 5 nights
Puglia
Boat day to the sea caves, a beach club, Ostuni's white old town, and a lot of nothing by the pool.
a tavola
Where we eat (and drink)
Restaurants, wine, the pasta class, boats and beach clubs, sorted under the day they fit. Checked open as of November 2026. Prices and Michelin stars will move by 2027, so confirm before booking.
prenotiamo
Book these
Every place that takes a reservation, in the order to book them. Tap to book, call or message. Tick the box once it's booked. Ticks sync between your phone and Alec's.
dove dormiamo
The stays shortlist
35 Airbnbs picked from 196 for a modern, designed look. Prices are the listed totals for our dates when we searched. Tap one to open it on Airbnb.
biglietti
Flights
Searched Oct 18, 2026 for September 2027. Prices are per person and will move. Flying into Florence and home from Bari means no backtracking.
quanto costa
Budget
Estimates for two. The stays target is what we're aiming for after asking hosts for a better price.
Il conto
per due persone
Flights, Pittsburgh to Florence, home from Bari$2,850 to $3,000
Pisa to Bari, plus checked bagsabout $170
Stays, target$4,200
Food, wine, Michelin night, boat day, drivers$2,300 to $2,800
Totaleabout $9,000
grazie!
Florence$8002 nights · Sep 3 to 5stay budget
Chianti$9002 nights · Sep 5 to 7stay budget
Puglia$2,5005 nights · Sep 7 to 12stay budget
da ricordare
Good to know
Hotel backups
Florence: Velona's Jungle, from about €320. Chianti: Castello di Ama, from about $300. Puglia: Paragon 700 in Ostuni, from about €320. Prices are past snapshots.
Before booking
The September 2027 Pisa to Bari schedule isn't published yet. Drive and walk times on each stay are estimates from the map pin.
Booking a stay
Hosts answer in Airbnb. A yes or a counter arrives as a Special Offer, booked through normal checkout. Never pay a host outside Airbnb.