Where we're staying
La Terrazza Sul Duomo
Arrive & Picnic at Sunset
- Land in Florence, train to hotel, drop bags
- Light wandering depending on arrival time
- Evening: grab a pizza and head to Piazzale Michelangelo for a sunset picnic
The Big Sights
- Early AM: "Alone in the Duomo" small tour booked
- Uffizi Gallery — Renaissance art booked
- Ponte Vecchio — old bridge with shops
- Lunch in Piazza della Signoria
- Accademia Gallery — Michelangelo's David booked
- If time: hunt for wine windows, leather shopping
Chianti Wine Day
Private driver · ~$650 · arranged through hotel
- ~9:00am pickup, drive to Chianti (~1 hr)
- Greve in Chianti — main square, first stop
- Castello di Verrazzano — guided tasting, views
- Lunch in Panzano — food & wine heaven
- Castello di Ama — boutique & artistic
- Back to hotel by 6–7pm, dinner in Florence
🚄
Jul 2 · High-speed train to Rome · 1h 30m · $336
Where we're staying
Hotel Giolli Nazionale
Easy Arrival in Rome
- Train from Florence to Rome Termini Station (1h 30m)
- Check into hotel, drop bags
- Borghese Gardens — free entry, rent a small boat ($7 / 20 min)
- Walk to Pincian Terrace for views
- Castel Sant'Angelo museum
- Sunset walk & dinner near Campo de' Fiori
Ancient Rome
- Early AM: Colosseum, Roman Forum & Palatine Hill booked · non-refundable
- Lunch in Monti neighborhood (8 min walk)
- Evening: Trevi Fountain — best after sunset
- Spanish Steps — 11 min walk from Trevi
- Dinner in Trastevere
The Vatican
- At opening: Vatican Museums, Sistine Chapel, St. Peter's Basilica booked
- Lunch near the Vatican
- Piazza Navona — historic square
- Pantheon
- Dinner in Testaccio — best authentic Roman food
🚄
Jul 5 · Train to Ostuni · $432.80 · pick up rental car on arrival
Where we're staying
San Michele Suite
Arrive in Puglia
- Train to Ostuni, pick up rental car
- Check in, settle into the masseria
- Wander town, easy first dinner
Beach Day
- Dorino Gite in Barca — private boat tour, ~$350 / 1.5 hr
- Torre Guaceto Nature Reserve — swim, snorkel, bike
- Specchiolla Beach — beach clubs & restaurants in Carovigno
Ostuni & Alberobello
- Day trip to Ostuni (the white city) and/or Alberobello (trulli houses)
- Wine & olive oil tastings around town
- Cooking class
- Dinner in Ostuni or back near hotel
Lecce — "Florence of the South"
- Start at Piazza del Duomo (quiet in the morning)
- Lecce Cathedral
- Basilica di Santa Croce — free entry, paid guided tours available
- Roman Amphitheatre of Lecce — visible from Piazza Sant'Oronzo at any hour
- Walk the shops, lunch, sweet treats
- Back to hotel by 3–4pm
- Dinner: Grotta Palazzese — cliffside restaurant, north of hotel
Fly Home 😢
- Drive to Bari (BRI) airport
- American Airlines BRI → MCO
The Journey
The whole trip on one map.
- Florence · 6/29–7/2
- Rome · 7/2–7/5
- Puglia · 7/5–7/9
Tap any pin · 91 places, all linked back to the source
Ideas & Recommendations
Picks from TikTok, Instagram & the wider internet.
Inspiration, not commitments.
City:
Type:
Nothing matches that combo yet. Send me a TikTok or IG link and I'll add it.
Packing List
Tap to check off. Your progress saves on this device.
Documents & Essentials
Clothes (Hot June/July)
Toiletries
Electronics
For the Plane
Nice to Have
Practical Info
Flights
Jun 28 · MCO → FLR · Delta · $3,322
Jul 9 · BRI → MCO · American · $5,214
Trains
Jul 2 · Florence → Rome · 1h 30m · $336
Jul 5 · Rome → Ostuni · $432.80
Pre-Booked & Paid
- Alone in the Duomo Tour — $420.24 (charges 6/26)
- Uffizi & Accademia — $234.54 (charges 6/27)
- Vatican / Sistine / St. Peter's — $198 (charges 7/1)
- Colosseum / Forum / Palatine — $377.16 (non-refundable)
- San Michele Suite — $1,636.48 paid 4/22; balance due 10 days before arrival
Driver & Car
Jul 1 · Private driver for Chianti — ~$650 (book through La Terrazza Sul Duomo)
Jul 5 · Pick up rental car in Ostuni for Puglia
Good to Know
- Italy emergency number: 112
- US Embassy Rome: it.usembassy.gov
- Tipping: 10% nice restaurants, round up at cafes
- Most museums close Mondays — verify before going
- Carry small euros for restrooms & espresso
- Validate train tickets before boarding (regional only)
Trip Total (so far)
~$18,177
Hotels $7,642 · Flights $8,536 · Tours/transit ~$2,000