Wine country, handmade pasta, medieval villages, Renaissance art, and the greatest hits of Rome — paced for a multigenerational group of eight.
Every reservation for the trip is now confirmed, flight home included. Pasta Urbana on Thursday remains a casual takeout plan rather than a booking.
IADIMPRUNETABOLOGNAFIRENZEROMA
8 DaysSept 6 overnight departure to Sept 13 return
2 Home BasesCasa di Miei, Impruneta (3 nights) & central Rome (3 nights)
Group of EightSix adults, kids ages 3 and 5
Trip dashboard
Eight days, two bases, one comfortable pace
Every reservation for the week is confirmed, flight home included. Pasta Urbana on Thursday is a casual takeout plan rather than a booking.
Sun–Mon, Sept 6–7 — IAD → Impruneta
Arrive Italy
Depart IAD on UA 884 at 5:35 PM. Land FCO 8:15 AM; rail to Florence; rental car; explore Impruneta; Casa di Miei; Bellavista.
Tue, Sept 8 — Chianti Countryside
Palagina & Chianti Hills
Palagina at 10:00 AM; lunch; Montefioralle; Greve; Airbnb reset; Piazzale Michelangelo; Hostaria del Bricco.
Wed, Sept 9 — Bologna Food Day
Bologna Food & History
Drive, park at Ex-Staveco, full walking route, recharge stops, Osteria Al 15.
Thu, Sept 10 — Florence to Rome
Accademia & Transfer
Checkout; return car at FLR; Accademia and central Florence; train to Rome around 6:00 PM.
Fri, Sept 11 — Ancient Rome
Colosseum, Forum & Palatine
7:00 AM Spanish Steps walking route; Campo de' Fiori, Torre Argentina and Jewish Ghetto; quick lunch; Walks tour 2:15–5:15 PM; Trastevere; 8:00 PM Ditta Trinchetti.
Sat, Sept 12 — Vatican + Villa Borghese
Vatican, Borghese & Early Dinner
Walks Complete Vatican Tour 10:15 AM–1:15 PM; Scialla takeaway lunch; optional Castel Sant'Angelo exterior; Villa Borghese, lake and Pincio; 6:00 PM Sgarro Bistrot — confirmed.
Sun, Sept 13 — Departure
Early Checkout
UA 885 departs FCO 10:20 AM, arriving IAD 2:15 PM; confirmed 6:00 AM transfer from the Airbnb to FCO.
Family profile & lodging
Two home bases
Family Profile
Six adults and two children ages 3 and 5. Transportation can split into two groups when convenient, but sit-down meals and major reservations should keep all eight together. The itinerary favors authentic experiences, room to move, regular meals, and true recharge periods rather than constant sightseeing.
Impruneta town center; confirmed for 8 and request a highchair if needed.
Delay Rule
If the rental car is delayed past about 3:00 PM, shorten or skip the Impruneta stroll. Prioritize groceries, Casa di Miei check-in, and the 7:30 PM Bellavista reservation.
Impruneta Arrival Ideas & Parking
Piazza Buondelmonti: the main square, an easy first stop and introduction to the town.
Basilica di Santa Maria all'Impruneta: step inside if open, or simply enjoy the piazza and facade.
Terracotta browsing: look for a local shop; Fornace Agresti is an optional bonus only if timing and opening hours cooperate.
Use signed public parking near Piazza Buondelmonti and follow local restrictions — there's no need to drive into Florence on Monday.
Keep the stop compact and low-pressure so a flight or rail delay doesn't derail the evening. If everyone is tired, skip sightseeing and go directly to groceries and Casa di Miei.
Coop Impruneta is most convenient for the Airbnb and a complete first-night shop. Coop Tavarnuzze is a larger backup if it falls naturally on the route. Forno Zini is an optional bakery add-on for bread and breakfast pastries.
Confirmed for 8 at 7:30 PM. Located beside Piazza Buondelmonti, so dinner keeps the first evening centered on Impruneta.
Family-friendly with straightforward pasta, chicken, potatoes and other child-friendly choices.
If the family is fading, ask whether takeaway is available or simplify dinner at the Airbnb.
Raffa Tip
Monday is about arriving well, not sightseeing hard. A short walk through Impruneta, groceries, time at Casa di Miei, and Bellavista dinner is a successful first day.
02
Palagina & the Chianti Hills
Tuesday, September 8 Base: Casa di Miei
Chianti villages by day, a Florence sunset, and a San Niccolò dinner by night.
Via di San Niccolò 8R. Confirmed for 8 at 7:30 PM. After dinner, walk back uphill to the car and return to Impruneta.
Harvest Question
September may overlap with vendemmia. Ask Palagina whether the family can observe grape picking, sorting or early winemaking activity during the visit.
Montefioralle & Greve Parking Guide
Montefioralle: navigate to signed visitor parking outside the historic village — do not drive through the medieval center. Primary: Piazza Santo Stefano when available. Backup: the signed gravel visitor lot below or outside the village approach. Expect uneven stone paving and slopes; a carrier may be easier than a large stroller.
Greve in Chianti: navigate to a lot outside the historic-center ZTL, not directly into Piazza Matteotti. Options: Piazza Resistenza, Piazzale Ferrante Mori, or Piazzale Finetti. Pay at the meter or approved app and keep the receipt visible. ZTL hours can change seasonally — follow current signs.
In Greve: walk the arcades around Piazza Matteotti, browse Antica Macelleria Falorni for salumi and cheese, and finish with gelato or coffee rather than another formal tour.
Enjoy the view before dinner, then walk downhill to Via di San Niccolò. The return walk to Piazzale Michelangelo is uphill.
Raffa Tip
Tuesday now has two acts: Chianti countryside by day, then a Florence sunset and San Niccolò dinner. Keep Greve departure close to 5:00 PM so the evening never feels rushed.
03
Bologna Food & History Day
Wednesday, September 9 Base: Casa di Miei
A full city day with two real recharge periods and a traditional dinner.
Traditional Bolognese dinner; confirmed for 6 at 7:00 PM.
8:45–9:00 PM
Return to car
Walk back to Ex-Staveco and begin the drive to Impruneta.
10:15–10:45 PM
Arrive Casa di Miei
Quiet return and immediate bedtime.
ZTL Rule
Set navigation directly to Parcheggio Ex-Staveco. Do not accept last-minute shortcuts through the historic center, where camera-enforced restrictions operate.
If Timing Slips — Priority Order
Protect the Quadrilatero, handmade pasta, Piazza Maggiore, Santo Stefano, and the two recharge stops (Salaborsa and Giardini Margherita).
Via Piella canal window and the Archiginnasio Anatomical Theatre are the easiest optional cuts.
Bologna Must-Eat Shortlist
Tagliatelle al ragù · Tortellini in brodo · Tortelloni
Mortadella · Parmigiano-Reggiano
Crescentine or tigelle, when available
Traditional balsamic vinegar tasting · a local dessert such as zuppa inglese · artisan gelato
Rain Plan & Dinner Backups
Bologna's porticoes make bad weather manageable — extend Salaborsa, browse the Quadrilatero slowly, and shorten Giardini Margherita rather than abandoning the day.
Dinner backups if Osteria Al 15 isn't available: Trattoria Amedeo, Trattoria Anna Maria (reserve well ahead), or Trattoria da Me.
04
Florence & Transfer to Rome
Thursday, September 10 Base: Rome (from tonight)
Renaissance highlights without risking the evening train.
Via Belsiana 94. Order takeout and bring it back to the Airbnb rather than sitting down — an easy, low-key arrival-night meal after everyone settles in.
Priority Order
Duomo and Signoria first, quick lunch, then the 12:15 Accademia. Enjoy Ponte Vecchio and Oltrarno afterward, but begin the walk back toward the station around 4:15 PM, aiming to be at Firenze SMN by about 5:20 PM for the 6:00 PM train.
05
Ancient Rome
Friday, September 11 Base: Rome
A historic-center sunrise walk, the confirmed Ancient Rome tour, and a Trastevere dinner.
Walk over and see the Republican-era ruins and look for the famous cats. The cat sanctuary itself may not be open yet.
11:10–11:50 AM
Jewish Ghetto
Walk Piazza Mattei and the Turtle Fountain, Via della Reginella, Portico d'Ottavia and the Theatre of Marcellus. View the route to lunch →
~11:50 AM
Walk toward Ancient Rome
Continue via the Capitoline/Piazza Venezia area and the Imperial Forums — sightseeing and transportation at the same time.
~12:20 PM
Quick lunch
La Prezzemolina near the Colosseum — pizza al taglio, supplì/fritti, lasagna, salads. Keep lunch quick so the group has plenty of buffer before the 2:15 PM tour.
1:00–1:40 PM
Tour prep
Bathrooms, water, coffee if wanted, then walk to the confirmed Walks meeting point. Aim to be there around 1:40 PM.
Reserved dinner for all 8 at Via della Lungaretta 76. After dinner, enjoy Trastevere after dark, then split into two taxis back to Via Bocca di Leone.
Confirmed Anchors
Walks Ancient Rome tour, 2:15–5:15 PM, ending at Palatine Hill; Ditta Trinchetti dinner, 8:00 PM, reserved for all 8. The rest of Friday should protect those two times.
Friday Route Notes
Keep the café stop at Trecaffè brief — Forno Campo de' Fiori is the real late breakfast, bakery-style grab-and-go, so the group can eat in or around the piazza rather than expecting one table for eight.
Lunch stays intentionally quick: La Prezzemolina is the sole planned Friday lunch stop before the Ancient Rome tour.
The Ancient Rome tour ends at Palatine Hill. Regroup after the tour and use two taxis to Trastevere if convenient.
Trastevere route: Piazza Trilussa / Ponte Sisto → neighborhood lanes → Santa Maria in Trastevere → dinner.
06
Vatican City, Villa Borghese & Early Farewell Dinner
Saturday, September 12 Base: Rome
Confirmed Vatican tour, Villa Borghese in the afternoon, and Sgarro Bistrot for dinner — lunch is takeaway from Scialla, so seating isn't a concern.
Scialla the Original Streetfood, Vicolo del Farinone 27 in Borgo. Roman pizza/pinsa, pasta and tiramisù to go — no need to worry about seating for all 8.
If timing and energy are good, spend about 20 minutes at Castel Sant'Angelo and Ponte Sant'Angelo for photos only. Skip this without hesitation if lunch runs long.
~2:45 PM
Taxi to Villa Borghese
Split into two taxis and head to the central/eastern side of the park so the afternoon can flow toward Pincio.
Early dinner at Sgarro Bistrot, Via Belsiana 14, reserved for all 8.
After dinner
Back to the Airbnb + pack
Walk back to Via Bocca di Leone 32. Pack luggage, set out Sunday travel clothes, charge devices and confirm the airport-transfer plan.
Saturday Checkpoints
Scialla lunch: takeaway from Vicolo del Farinone 27 around 1:30 PM — no need to worry about seating for all 8.
Castel Sant'Angelo is exterior-only and optional; cap it at about 20 minutes so Villa Borghese stays the priority.
Villa Borghese priorities: Piazza di Siena, lake/rowboats, free exploration and the Pincio Terrace. Skip Bioparco and Galleria Borghese this afternoon — both deserve more time than this schedule allows.
Sgarro Bistrot is confirmed for 6:00 PM at Via Belsiana 14, reserved for all 8.
Tour Note
The Sistine Chapel is included. Access from the museums to St. Peter's Basilica can change because of Vatican operations, ceremonies, or security.
07
Early Departure
Sunday, September 13 Base: Rome
Fully locked: UA 885, FCO to IAD, and a confirmed 6:00 AM transfer from the Airbnb to the airport.
~5:30 AM
Wake & final pack
Finish packing, gather passports, medications and chargers.
~5:45 AM
Early checkout
Check out of Via Bocca di Leone 32 and return keys.
6:00 AM
Transfer to FCO — Confirmed
Confirmed departure from the Airbnb at Via Bocca di Leone for all 8 plus luggage and any child-seat arrangements.
~7:00 AM
Arrive FCO
Check in and drop bags for UA 885. Aim to be at the airport about 3 hours before departure.
~7:30 AM
Security & passport control
Move as one group where possible, then find the gate.
10:20 AM
Depart FCO — UA 885
Boeing 777-200, United Economy (W). Nonstop to Washington Dulles.
2:15 PM
Arrive IAD
Washington, DC. Flight time approximately 9h 55m.
Confirmed Flight — UA 885
FCO → IAD, Sunday 9/13, departing 10:20 AM and arriving 2:15 PM; duration 9h 55m on a Boeing 777-200, United Economy (W).
Seats: 50L, 50K, 50J, 51L, 51K, 51G, 50G, 50F — all 8 travelers together across two adjacent rows.
Departure Checklist
Airport transfer confirmed for 6:00 AM departure from Via Bocca di Leone.
Ask the accommodation about early checkout and key return.
Pack the night before and keep passports, medications and chargers together.
Allow additional time for child-seat arrangements if using a private transfer.
Reservation tracker
Where everything stands
A running list of what's locked in, what still needs booking, and what's still open.
Confirmed
UA 884
IAD to FCO; Sunday 9/6 at 5:35 PM, arriving Monday 9/7 at 8:15 AM.
Confirmed
Leonardo Express + Frecciarossa 9532
Monday 9/7: Leonardo Express FCO → Roma Termini, 11:08 AM–11:40 AM; Frecciarossa 9532 Roma Termini → Firenze S.M.N., 12:05 PM–1:46 PM.
Saturday 6:00 PM, Via Belsiana 14; early farewell dinner reserved for all 8.
Confirmed
UA 885
FCO to IAD; Sunday 9/13 at 10:20 AM, arriving 2:15 PM. Seats 50L, 50K, 50J, 51L, 51K, 51G, 50G, 50F.
Confirmed
Sunday airport transfer
Confirmed 6:00 AM departure from Via Bocca di Leone to FCO.
Version 2.5 note
The entire trip is now confirmed — every restaurant reservation, the Vatican and Ancient Rome tours, Villa Borghese pacing, and the flight home (UA 885) with its 6:00 AM airport transfer. The only casual item left is Pasta Urbana on Thursday night, which is a takeout plan rather than a sit-down booking.
The Raffa rules of the road
Five things to remember mid-trip
One excellent experience is better than three rushed ones.
Gelato is a legitimate scheduling tool.
Use taxis before everyone is exhausted, not after.
Keep one optional stop every day that can be dropped without regret.
The best family memories may happen between the landmarks.