Italy, Croatia, Greece 2026
Jonathan & Bronwyn · Thu Sep 3 to Mon Oct 5, 2026
Italy, 15 daysCroatia, 8 daysGreece, 9 days33 days
✈️Auckland → Singapore
SQ286 · AKL 14:10 → SIN 21:00 (Thu Sep 3). 4h30 layover.
Conf DK7W3F · seats 53D/53E
✈️Singapore → Rome
SQ366 · SIN 01:30 → Rome FCO 08:05 (Fri Sep 4).
Conf DK7W3F
🚗Budget car pickup
Fiat Grande Panda handed over at pickup, in place of the booked "Peugeot 3008 or similar". Smaller car — watch boot space on the Sep 18 airport run.
Conf 48187760NZ5 · RA 349961710 · €827.50 · pick FCO Sep 4 09:00, drop Sep 18 15:00 · unlimited km, CDW + theft + glass incl.
🏠Airbnb "Luxury VISTA LAGO Trasimeno"
Host Stefano. Easy landing after the long haul.
Via II Giugno 1, Passignano sul Trasimeno PG · check-in 16:00, check-out Sep 8 11:00
What to do
- Fri 4, arrival via Orvieto: Duomo and lunch at Trattoria del Moro Aronne (park Campo della Fiera, not the clifftop ZTL). Evening: Rocca di Passignano, sunset aperitivo, dinner Del Pescatore (regina in porchetta).
- Sat 5, olive-oil tasting (booked): 11:00 at Agriturismo Baldeschi, La Fattoria del Rio di Sopra, Tuoro. Easy afternoon.
- Sun 6, slow lake day: Castiglione del Lago (Rocca del Leone, Palazzo della Corgna), ferry to Isola Maggiore.
- Mon 7, Assisi + Perugia: Basilica of St Francis (strict dress code, shoulders and knees covered), then Perugia (Corso Vannucci, Rocca Paolina).
- Tue 8, on to Montepulciano via Cortona: MAEC and Santa Margherita view. Check out by 11:00.
- Parking: the apartment has none of its own, use the public Piazzale Acton car park right outside (blue lines paid by day, usually free overnight).
🏠Agriturismo Nobile, Montepulciano
Your Val d'Orcia base in Vino Nobile country.
SS 146 Km 24.100, Montepulciano · check-in 15:00, check-out Sep 13 10:30 · conf 6375967765 (confirmed, 2 adults)
What to do
- Tue 8, arrival dinner (booked): eating at the agriturismo, 19:30. No ZTL, no parking, no drive home after Cortona. Osteria del Conte has moved to Wed 9.
- Wed 9, Crete Senesi loop: breakfast at Lalma Cafe in town (closed Thu), then a back-roads circuit via Montisi, the Palazzo Massaini winery and the cypress-lined Cypress Rd (SP38, SP71, SP15). Lunch at Il Barrino, Montisi. Dinner booked: Osteria del Conte, 19:30 for two (Via di San Donato 19). Montisi is ~30 min back, so leave the loop by 18:30; phone ahead if you are running late. Park P1 Porta al Prato or P8 Collazzi.
- Thu 10, cooking class (booked): Le Caggiole pasta menu for two, wine included. Town: Piazza Grande and cellars Contucci or De' Ricci.
- Fri 11, Pienza day (Val d'Orcia loop): San Quirico d'Orcia, Bagno Vignoni and Monticchiello around Pienza. Lunch at Trattoria Latte di Luna, Pienza (lunch only, 11:30–16:00, no dinner; ring +39 0578 748606, closing day is disputed). Dinner left loose: Osteria La Porta, Monticchiello (+39 0578 755163, terrace, sunset ~7:40pm, call that morning), or Sperone Nudo, Pienza (+39 0578 748641, 19:00–21:30, closed Mon), or Acquacheta in Montepulciano for the bistecca. Park outside the walls.
- Sat 12, slow day + dinner (booked): pool, casual lunch, optional tasting at Fattoria del Cerro. Dinner at Dopolavoro La Foce, Strada della Vittoria 90, Pienza (+39 0578 754025), ~20 min via SP146/SP40, booked 19:00, free parking, no ZTL.
- Sun 13, drive to Chianti.
- Parking: free on site plus town shuttle. Do not drive the ZTL, park at P1 Porta al Prato.
🏠Airbnb "Samantha GECO Vacation Rentals"
In the heart of Chianti Classico.
Via Martiri di Pratale 12, Barberino Tavarnelle FI · check-in 16:00, check-out Sep 18 10:00
What to do
- How picks are made: TripAdvisor rating and review count checked 12 Sep 2026, hours cross-checked on each venue’s own site. Target 4.5+ and about €120 for two with wine. Anything below the bar shows its real number.
- Sun 13, arrival via Monteriggioni: walk the ramparts, then golden hour at the Abbazia di San Michele Arcangelo. Dinner: La Cantinetta di Rignana, Loc. Rignana 13 (+39 347 453 4884, daily 12:00–23:00) — 4.5/5, 1,287 reviews, €€–€€€, a converted mill 15 min away with a terrace over the vines. Last bit is unpaved; the coach parties are a lunch thing, so go early evening. Book it. Fallback: Divino Terrace, Badia a Passignano (+39 370 376 0761), walk-in but only 4.4/5 on 200.
- Mon 14, San Gimignano: towers, Collegiata frescoes, gelato Dondoli. Dinner L’Antica Scuderia 19:30, confirmed ✓ (Via di Passignano 17, +39 055 807 1957). Heads up: 4.3/5 on 837 and €€€€, so under the rating bar and over budget. Booked and 5 min from base, so keep it, but order with the bill in mind.
- Tue 15, Siena, full day. Leave 08:45, park Santa Caterina (fills by 10:00). Buy the OPA Si Pass and the Porta del Cielo slot online the night before.
10:00 Duomo first — floor fully uncovered 18 Aug to 15 Nov. Cathedral, Piccolomini Library, Crypt, Baptistery, ~90 min.
11:30 Museo dell’Opera then the Facciatone, 130 steps, better view than the Mangia and in the pass. Skip the Mangia.
12:15 Porta del Cielo, the walkways above the cathedral vaults. Pre-booked timed slot, not in the pass, ~30 min. Added with the hour the sandwich lunch frees up.
13:00 lunch, hole in the wall: Du’ Cose Da Berna, Via Diacceto 11 — 4.7/5 on 256 reviews, €, #1 of 25 bars in Siena, daily from 11:30. Schiacciate stuffed to order, minutes from the car park, a local room not a tourist one. Famous alternative: Gino Cacino, Piazza del Mercato 31 (4.5/5 but on 2,326 reviews, Mon–Fri 10:00–17:00) — Angelo works alone, so a 20–40 min queue and no substitutions.
13:30 eat it in the Orto de’ Pecci. A path off Piazza del Mercato drops into a green valley inside the walls: vines, olives, donkeys, benches under the trees. Free, 5 min from the Campo, almost nobody finds it. Added.
14:15 Santa Maria della Scala, the pilgrim hospital, daily 10:00–19:00, always quiet.
15:30 Museo Civico for Lorenzetti’s Good and Bad Government. The one interior not to skip.
16:30 Basilica di San Domenico, free — Santa Caterina’s relics and the best view back at the Duomo. Added.
17:15 walk a contrada: the Oca round Fontebranda, or the Torre along Via Salicotto.
18:15 a drink on the Fortezza Medicea ramparts, 5 min from the restaurant. Sunset ~7:30pm.
19:30 dinner, booked ✓ Ristorante Pier Pettinaio, Vicolo Beato Pier Pettinaio 7, table for 2, TheFork ref 1695818984. Late? +39 348 778 2408 (or +39 0577 280042). 4.8/5 on 95 TripAdvisor, #34 of 418; 9.2/10 on 472 TheFork; ~€34 a head, so well inside budget. Sienese cooking, handmade pasta, down a lane off Piazza dell’Indipendenza. Already forwarded to TripIt. Five minutes from San Domenico and the car park.
21:15 walk down to the Campo for the lit piazza and a digestivo. Home ~22:30. (Taverna di San Giuseppe and La Sosta di Violante no longer needed.) - Wed 16, Greve and Castellina: Piazza Matteotti, Falorni, Le Cantine di Greve self-pour. Lunch Il Guardingo 1:30pm ✓ — 4.7/5 on 230, and it is Villa Bordoni’s restaurant, Via San Cresci 31, one venue not two. Afternoon Castellina (Via delle Volte). Long lunch, so no dinner: tagliere and a glass at Falorni, plate at home.
- Thu 17, Poggio al Sole + a table you have not picked. Tasting and lunch nibbles at Poggio al Sole, Strada Rignana 2 (+39 055 807 1850), organic, 5 min from base. Light day. Dinner is open and needs booking — three that clear 4.5 inside budget:
• La Sosta di Pio VII, Barberino Val d’Elsa, 4.6/5 on 2,049, #3 of 19, daily 19:30–22:00, free parking, 10 min. +39 055 807 5923. The easiest yes.
• Ristoro di Lamole, 4.7/5 on 2,291, terrace over the valley, ~35 min. Go early for the light.
• Ristorante La Castellana, Montefioralle, 4.7/5 on 1,189, ~30 min.
Osteria di Passignano removed at your call. - Fri 18, departure (tightest day): leave by 12:00 to 12:30 for Rome FCO (2.5 to 3 hrs), car back 15:00, refuel, then the 18:00 flight. No detours.
- Cut: Antinori nel Chianti Classico and Florence (your call, so Castellina returns to Wed); Castello di Brolio (35 min the wrong way out of Siena); the Panzano day.
- Parking: free on site. Hill towns are ZTLs, park outside the walls.
✈️Rome → Split
Croatia Airlines OU381 · FCO 18:00 → Split 19:05 (Fri Sep 18). Drop the car at FCO by 15:00.
Conf E5QP7K
Tightest day of the trip: leave Chianti by 12:00 to 12:30, target FCO ~14:00 to refuel and return the car by 15:00, then clear the 18:00 international check-in.
⛵Catamaran charter
cat-stretch.com. Boarding in Zadar Sep 19 at 15:00, sailing the Dalmatian coast with the Steeles and Shepherds. Nothing to plan, you have it covered.
⚓Sep 26 (Sat) · off the boat, Marina Kaštela
Take the bags with you and store them in Trogir, do not leave them at the charter base — that forces a 19 km backtrack at the end of the day. You cannot check in early: Split counters open ~15:55 for OU304 and close 16:55. Online check-in Fri evening when the 36-hour window opens at 17:55. Book both taxis the day before; Bolt and Uber run here.
Marina: 8 km to Trogir, 11 km to SPU, 12 km to Split
🚕08:45 · taxi to Trogir with bags
15 min, ~€20–25. Optional first: Kaštilac, the fortified islet village at Kaštel Gomilica, 10 min walk from the marina.
🧳09:05 · bags into storage
Booked — Bounce, Eos Travel Agency, near Trogir bus station. Ref V2Y5969P, 2 bags, €13.40 paid. Open 08:30–20:00, Ul. Kardinala Alojzija Stepinca 12a. Show the code from the Bounce app, so load it into your phone wallet before you sail. Walk-in fallback at the same address, €5 a suitcase.
The old town is closed to cars — taxis stop at the mainland lot by the bus station, ~100 m from the stone bridge. Say “Trogir bus station” both ways
🏛️09:20–12:30 · Trogir old town
St Lawrence Cathedral (Radovan’s west portal; climb the bell tower), ~€4–5, open from 08:00. Kamerlengo fortress at the western tip, ~€5, open late in Sept. Plus Cipiko Palace, the north gate, the walls and the Riva.
🍽️12:30–14:15 · lunch
Konoba Trs or Tri Volta in the old town; Queen Teuta or Piccolo Ponte on the water. Ring ahead in the morning — Saturday lunch fills.
🏊14:15–15:20 · soft hour
Riva coffee, the market by the north gate, or over the bridge to Čiovo for a last swim.
✈️15:20 · bags, then airport
Collect at 15:20, taxi 15:30. Trogir to SPU is 6 km, 10 min, ~€15–20. At the airport 15:45; counters open 15:55, close 16:55. OU304 departs 17:55.
Fallback: if Trogir storage falls over, the charter base holding the bags still works — accept the backtrack and leave the old town at 15:00
✈️Split → Athens
Croatia Airlines OU304 · Split 17:55 → Athens 20:35 (Sat Sep 26).
Conf E5Z22A · transfer Welcome Pickups, pickup 20:50 (meets OU304), code 691578
🏠Airbnb "Lucas"
Central, steps from Monastiraki and Plaka.
Agiou Markou 11, Athina 105 60 · check-in 15:00, check-out Sep 29 11:00
What to do
- Sat 26, arrival night: late dinner O Thanasis (Mitropoleos 69, Monastiraki), then nightcap at 360 Cocktail Bar for the lit-up Acropolis.
- Sun 27, Agora + Lycabettus: Ancient Agora 09:30 (tickets on site, Rick Steves audio app). Lunch Cafe Avissinia. Plaka and Anafiotika. Sunset is 7:16pm, be at the top by ~6:40 (funicular from Aristippou St), drinks at Sky Bar. Dinner in Psyrri (Avli).
- Mon 28, Acropolis (booked): First Access guided tour 07:45 (2 adults, GetYourGuide ref GYG9962Y4ALL, $307.80, meet the main entrance 15 min early). Then Dionysiou Areopagitou, coffee in Thisio, lunch Karamanlidika tou Fani (Ermou 119).
- Mon 28, farewell night (booked): 6:30pm sunset drinks A for Athens (backup Bar 360 or Couleur Locale), 8:30pm dinner Lithos Tavern, Psyrri.
✈️Athens → Paros
SKY express GQ472 · ATH 11:40 → Paros 12:20 (Tue Sep 29). Transfer Welcome Pickups, pickup 08:50, code 691578.
Conf U2SM8V
🏠Parian Village Beach Hotel, Parikia (adults-only)
On the beach at Livadia.
Livadia, Parikia 84400 · check-out Oct 3 11:00 · conf 6875114633
What to do
- Wheels: hire a car or quad (carry your IDP). Quads ~€50/day, scooters ~€20–35/day. Hotel partner Auto Dermatas, +30 22840 24408 / WhatsApp +30 698 320 1767.
- Tue 29, arrival: settle near base. A beach club is a short walk down Livadia beach from the hotel for an easy dine and swim; or cheap sun beds at Paralia Agia Irini (south of Parikia), or a water taxi to Crios Beach bar. Evening in Parikia: drinks at Paralia Beach bar, casual dinner.
- Wed 30, Naoussa and the north: the old fishing port and Kolymbithres. Aperitif at Christos Gastro Bar, then dinner at Siparos (seaside sunset, book early). Yemeni (traditional taverna in town) is a casual option another night.
- Thu 1, villages and east coast: hilltop Lefkes (marble path) and Prodromos; seaside lunch at Piso Livadi; swim at Golden Beach (Paralia Golden), with the Blue beach club to dine and swim; Piso Aliki and Palm Beach as alternatives.
- Fri 2, Antiparos boat day: half-day catamaran to Antiparos and Despotiko (the Blue Lagoon).
- Sat 3, departure: checkout 11:00 but flight is 17:50; leave bags, lunch near Livadia (Ephesus on the beach, or Levantis in old-town Parikia), transfer ~16:45.
- Book ahead: Siparos fills up; confirm late-season opening.
✈️Paros → Athens
SKY express GQ477 · Paros 17:50 → Athens 18:30 (Sat Oct 3).
Conf U2SM8V
🏠Spata airport apartment
Double room with mountain view beside Athens airport (free shuttle).
19 Avgylou, Spata 19004 · check-out Oct 4 11:00 · conf 6325553363
✈️Athens → Istanbul → Singapore
Aegean A3990 · ATH 08:00 → IST 09:35 (Sun Oct 4). Then SQ391 · IST 13:10 → Singapore (arr Oct 5 04:55).
Conf DK7W3F · Aegean rescheduled this leg (notice 14 Jul): now 08:00/09:35, still an ample connection to SQ391 at 13:10
✈️Singapore → Auckland
NZ281 · SIN 08:35 → Auckland 23:15 (Mon Oct 5).
Conf DK7W3F
✈️ Airport transfers
Athens, both ways (booked): Welcome Pickups, code 691578. Arrival Sep 26 pickup 20:50 (meets OU304). Departure Sep 29 pickup 08:50 for the Paros flight.
Paros arrival (booked): confirmed by Parian Village 25 Aug. Driver meets you at the airport exit with a name sign, for GQ472 arriving 12:20 Sep 29, 2 people. €45, cash to the driver, not at the hotel.
Paros return (still to do): the Oct 3 run back to the airport for the 17:50 flight (leave ~16:45) is not booked. Email info@parianvillage.gr to add it, €45 one way, cash.
Spata: nothing to book, the apartment runs a free shuttle for the Oct 4 departure.
🚗 Driving, tolls and ZTL (Italy)
Pay tolls at the booth: use the white or blue card lanes or green attended cash lanes, contactless works. Avoid the yellow Telepass-only lanes. Hill towns (Montepulciano, Pienza, Siena, San Gimignano, Cortona, Orvieto) are camera-enforced ZTLs, park in the signed lots outside the walls. Return the car with a full tank.
🛡 Travel insurance (sorted)
Kiwibank Credit Card Travel Insurance (Allianz, 1 Jul 2025, ref KBNACPV0000170), activated by paying the flights on the card. Max 40-day trip, yours is 33. Windscreen and glass cover taken at the Budget counter. Rental excess covered to $6,000 (less a $200 excess). Policy PDF (also saved in this 01 Itinerary folder).
Settled at pickup — the car is a Fiat Grande Panda. It's a B-segment 5-door hatchback, not an SUV, so it sits inside the Amex Rental Vehicle definition ("sedan, campervan, hatchback or station wagon"). The whole hire went on the Amex, so Airpoints Platinum's $3,000 excess cover now responds — where the booked 3008 would not have qualified. Knock-on: Kiwibank 5.1(e) excludes an excess recoverable from another source, so its larger $6,000 (less $200) cover likely stands down. Only matters if Budget's excess tops $3,000 — that figure is on rental agreement RA 349961710 in the car, and on a small car with CDW, theft and glass cover already taken it is normally well under. You can only claim once, from one source. Reading of the wordings, not advice.
🛵 Scooters and quads on Paros
Hire at Parikia port or via hotel delivery. A New Zealand licence is non-EU, so carry your International Driving Permit (sorted) or you cannot legally hire and insurance is void. Hotel partner Auto Dermatas, +30 22840 24408, WhatsApp +30 698 320 1767, parosrentcars.com.
🍽 Restaurants worth booking
Chianti, two calls left. Picks checked on TripAdvisor 12 Sep 2026, target 4.5+ and ~€120 for two. (1) Thu 17 dinner is still open — La Sosta di Pio VII +39 055 807 5923 (4.6/5, daily, 10 min), or Ristoro di Lamole / La Castellana (both 4.7/5) for the view. (2) La Cantinetta di Rignana, Sun 13, +39 347 453 4884. Tue 15 Siena is done: Pier Pettinaio 19:30, TheFork ref 1695818984. Plus the OPA Si Pass and Porta del Cielo slot online the night before Siena. Mon 14 L’Antica Scuderia 19:30 is confirmed. Reserve any Athens rooftop-with-Acropolis table.
Paros, from the hotel (25 Aug): Ioanna says no need to book far ahead at that time of year, a day out or a walk-in is fine. For the sunset dinner she'd take the Parikia waterfront over Siparos, the sun sets straight out over the sea. Seaside in Parikia: Mortari, Mouragio, Alexandros, Moira, Nice to Meat You. More traditional and local, off the water: Koutouki, Mirmitzeli, Boundaraki, plus the fish tavern Porfyra at Pounda port. Still worth checking Siparos and the beach clubs are trading Sep 29 to Oct 3.
Tap a leg to expand. Today opens automatically while you travel. Times local. Reformatted from your full itinerary. Updated 7 Sep: Trogir bag storage booked and paid (Bounce ref V2Y5969P, €13.40); Osteria del Conte rebooked for Wed Sep 9 at 19:30, and Tue Sep 8 dinner set at the agriturismo, 19:30; Budget rental agreement RA 349961710 e-signed at pickup Sep 4. Updated 11 Sep: the car handed over is a Fiat Grande Panda, not the booked 3008 — as a hatchback it qualifies under the Amex wording, so the Amex $3,000 excess cover responds and Kiwibank's $6,000 likely stands down; car and insurance notes rewritten. Earlier, 30 Aug: Dopolavoro La Foce booked Sat Sep 12 19:00; Fri Sep 11 reworked (Latte di Luna is lunch only). Earlier: Paros arrival transfer confirmed, Oct 4 Aegean time corrected, rental on the Amex (Kiwibank excess cover unaffected; Amex wording excludes SUVs). Updated 11 Sep (Chianti): Sun 13 dinner at Divino Terrace; L’Antica Scuderia to move from Tue to Mon 14 19:30 (its site lists closed Tuesdays); Tue 15 built as a full Siena day, lunch All’Orto de’ Pecci, dinner in town; Antinori slotted Wed 16 10:00 before the Il Guardingo lunch (= Villa Bordoni), Castellina dropped; Thu 17 kept light, Poggio al Sole then Osteria di Passignano; Brolio and Panzano cut. Updated 12 Sep: L’Antica Scuderia confirmed Mon 14 19:30; Siena lunch switched to a hole-in-the-wall schiacciata eaten in the Orto de’ Pecci, freeing an hour for the Porta del Cielo walk and San Domenico; Antinori, Florence and Osteria di Passignano removed at Jonathan’s call, so Castellina returns to Wed and Thu 17 dinner is open; all picks now carry a TripAdvisor rating against a 4.5+ target and a €120-for-two budget. Later on 12 Sep: Siena dinner booked — Ristorante Pier Pettinaio, Tue 15 at 19:30 for two, TheFork ref 1695818984, forwarded to TripIt. 4.8/5 and ~€34 a head, so it beats both previously listed options. Tuesday evening resequenced around it. Thu 17 is now the only unbooked dinner.