Milos, Athens, the Umbrian countryside and Rome. Flights, ferry, boat, the Umbria farmhouse, the Milos, Athens and Rome stays, travel insurance and the Rome/Umbria hire car are booked - the Milos hire car is the last live decision.
🗣️ Say it! · Greek + Italian phrase trainer (kids mode too) →
PNR 9NCTGK · operated for AEGEAN · nonstop 40 min · ComfortFlex Economy · ATR 42 · €564.48 paid
Bags for each of Richard, Nadine, Piper and Jude: 1 × 23kg checked + 1 × 8kg cabin + 1 personal item
Milos airport car pickup: 13:00-13:15, after baggage collection.
TR50 · SIN T1 01:15 → ATH 07:45 · seats 17A-D · one shared 35kg checked bag · BoardMeFirst
OA024 · ATH 11:50 → MLO 12:30
PNR 9NCTGK · ComfortFlex · each has 23kg checked + 8kg cabin + personal item
Scoot return for all four: S$2,768.64 paid
Airbnb in Plakes Village (host Filio) · S$979.45 paid for the six nights · check-in from 16:00, checkout by 11:00. Ricki, Nadine, Piper (5) and Jude (3). OA024 lands 12:30. Automatic family car still to book, with child seat + booster; airport pickup 13:00-13:15.
Firiplaka Boat Rental - own self-drive boat, same water and 10:00 start as the Savages. Full 8h day, 10:00-18:00, €275 paid, ref SLT-103470474. €450 security deposit instructions arrive the day before; fuel settled after use. Meet 09:50 at the first white house on Firiplaka Beach.
SeaJets Champion Jet 2, Adamas 12:45 → Piraeus 16:05. Ref 1112UQUCC, €290.20 paid, all four in Platinum seats. Online check-in opens 48h before (4 Oct). One night in Athens: Airbnb booked for 6-7 Oct (host Christos, S$192.61 paid, check-in from 14:00, checkout by 11:00).
Ryanair FR 1199, ATH 16:25 → FCO 17:35. Ref OUE67Y, Family Plus, €400.10 / S$590 paid. Seats: Jude 24A, Piper 24B, Nadine 24C, Richard 24D. Bags: Nadine 20kg + 10kg checked; Richard, Piper and Jude 10kg each. Checkout at the Athens Airbnb is 11:00 but bags stay inside the apartment until 13:30 (host confirmed), so no luggage problem before the flight. Boarding passes are Ryanair-app only - no printed passes, so the app goes on a phone before the day. Land 17:35, evening in the city, then two nights in Trastevere at Ad Maiora Domus (Airbnb booked, 7-9 Oct).
Full day in Rome - second night at Ad Maiora Domus, so nothing to pack up or move. On the morning of the 9th: check out, pick up the hire car - Enterprise Roma Prati, Viale Carso 50, at 11:00, with the two child seats - and drive about 2h to Umbria for farmhouse check-in.
Il Leccio at Forte Sorgnano, Gualdo Cattaneo - booked direct with host Marco Frattari via fortesorgnano.com on 14 Sep, beating the Airbnb rate. €890 total (~S$1,312) including final cleaning for six nights, 9-15 Oct. Setup: 2 bedrooms + 1 sofa bed + 1 baby cot - fits the two families (4 adults, Piper (5), Jude (3) + baby). Agriturismo with restaurant, pool, playground and farm animals; Orvieto stays a day trip from here. Arrive on 9 Oct and leave on the morning of 15 Oct for the 13:00 flight.
Address: Via Cerquiglino 62, 06035 Gualdo Cattaneo (PG), Umbria, Italy · Google Maps pin
Arrival notes: the last 3.5 km is an unpaved road in good condition - go slowly and follow the wooden Forte Sorgnano finger signs. Phone signal is weak on that stretch, so download offline maps before the drive. Check-in is listed as 16:00 and checkout as 10:00 by booking sites, but the property does not state them - confirm with Marco.
Check out of the farmhouse in the morning, drive ~1.5-2h direct to FCO and return the car by 11:00. Sky Express GQ821, FCO 13:00 → ATH 16:00 - ref HLCWNZ, SKY joy+, €341.36 / S$500 paid. Each passenger has 15kg checked + 8kg cabin + personal item. Web check-in opens 48h before (13 Oct). Night by the airport: Boutique Athens Airport Apartments booked for 15-16 Oct (€107 / S$158, free cancellation through 30 Sep, check-in 16:00-17:00 approved), then a short hop to the terminal on the 16th.
Scoot TR51 · ATH 09:00 → SIN T1 01:10 on 17 Oct. Booking V9DGYC. Seats 17A-D, one shared 35kg checked bag, BoardMeFirst. Airport check-in target 07:00.
Booked 30 Sep ATH → MLO, AEGEAN, PNR 9NCTGK. Olympic Air OA024, operated for AEGEAN: Athens 11:50 → Milos 12:30, nonstop, 40 min, ATR 42. ComfortFlex Economy (booking class Y). Passengers: Richard, Nadine, Piper and Jude Taiaroa. Each passenger has 1 checked bag up to 23 kg, plus 1 cabin bag up to 8 kg and 1 personal item. Total €564.48.
Booked 7 Oct ATH → FCO, Ryanair FR 1199, ref OUE67Y. 16:25 → 17:35, Family Plus, €400.10 / S$590 paid. Seats 24A-D; Nadine has 20kg + 10kg checked, the others 10kg each. Digital boarding passes via the Ryanair app only. Two nights in Trastevere at Ad Maiora Domus (Airbnb booked, 7-9 Oct), then drive to Umbria on 9 Oct.
Booked 15 Oct FCO → ATH, Sky Express GQ821, ref HLCWNZ. 13:00 → 16:00, SKY joy+, €341.36 / S$500 paid, 15kg checked + 8kg cabin + personal item each. Web check-in opens 48h before. Direct morning drive Umbria → FCO the same day.
Booked Champion Jet 2, Adamas 12:45 → Piraeus 16:05. Ref 1112UQUCC, €290.20 / S$425 paid, all four in Platinum seats. Online check-in opens 48h before departure (4 Oct), booking ref + surname.
Milos 30 Sep-6 Oct: five-seat automatic, child seat and booster. Still to book; local benchmark from €65/day (~€390 / S$575 for six days). Milos airport pickup around 13:00-13:15, after OA024 lands at 12:30 and bags are collected.
Rome/Umbria 9-15 Oct: Booked Enterprise Standard Wagon automatic (Skoda Octavia or similar), confirmation 1696317596. Pickup Enterprise Roma Prati, Viale Carso 50, Fri 9 Oct 11:00; return Rome FCO airport Thu 15 Oct 11:00, before the 13:00 flight. Unlimited mileage, two child seats, Damage Waiver and Theft Protection included. €568.71 / S$838 due at pickup, free cancellation. Nadine is lead driver; Ricki added as second driver at the counter (both bring NZ licences + IDPs). Note: the base Enterprise rate carries a €1,700 excess - Allianz Section J covers up to S$1,000 per insured adult (see insurance card below).
Booked Firiplaka Boat Rental, Sat 3 Oct 10:00, full 8h self-drive - same water and start time as the Savages. €275 / S$405 paid, ref SLT-103470474 (manage booking). €450 security deposit instructions arrive the day before; fuel (€40-60) settled after use. Arrive 10 min early at the first white house on Firiplaka Beach. Explore Milos, Skipper Milos and Aphrodite are off the table.
In place Allianz for all four, covering the full trip 30 Sep - 17 Oct (policy on Nadine's side). Cover confirmed in writing for Greece and Italy - corrected documents reissued, no extra cost.
Rental-car excess (Rome/Umbria car, 9-15 Oct): Section J of policy B2CSGA400018079 covers rental-car excess up to S$1,000 per insured adult; the Enterprise base booking carries a €1,700 excess. Unconfirmed whether the two adults' S$1,000 limits stack on one claim. The driver at the time of any damage must be a named driver on the rental agreement; damage must be reported within 24h or at return, and theft to the police promptly.
Best character pick. Inside the walls, 2 bedrooms, sleeps 4, roof garden, kitchen and washer. Drive in to unload, then free nearby parking. Overnight rate was not verified; retain as a possible day-trip landmark/base idea only. Listing.
Historic boutique hotel in two medieval palaces, with one family room and guarded paid parking. Strongest hotel option for service and atmosphere; less space than an apartment. Overnight rate not pursued - Orvieto stays a day trip from the farmhouse. Official site.
Three-bedroom apartment in a 12th/14th-century palazzo, panoramic terrace and a 2-minute walk to Piazza del Popolo. Public parking nearby. Best space, but second-floor access may be awkward with bags. Overnight rate not pursued - Orvieto stays a day trip from the farmhouse. Official site.
Freshly renovated apartment in the medieval centre with kitchenette and air conditioning. Private/paid parking available. More practical than romantic, but an easy family base. Overnight rate not pursued - Orvieto stays a day trip from the farmhouse. Official site.
Booked ATH → MLO on 30 Sep 2026 · PNR 9NCTGK · invoice 8278632 dated 2 Sep · total paid €564.48.
Booked passengers: Richard (ticket 390-2485823779), Nadine (390-2485823778), Piper (390-2485823777), Jude (390-2485823776).
Flight details: OA024, operated by Olympic Air for AEGEAN, Athens 11:50 → Milos 12:30, nonstop, 40 min, ATR 42. ComfortFlex Economy, booking class Y. Each passenger has 1 checked bag up to 23 kg plus 1 cabin bag up to 8 kg and 1 personal item. Plan Milos airport car pickup for about 13:00-13:15 after baggage collection. This booking covers only Athens → Milos; the 7 Oct Athens → Rome leg (Ryanair FR 1199, ref OUE67Y) and the 15 Oct Rome → Athens leg (Sky Express GQ821, ref HLCWNZ) are both booked - see the cards above.
Booked Airbnb for the night of the 6th (host Christos) · S$192.61 paid · check-in from 14:00, checkout by 11:00. The ferry lands at Piraeus 16:05, so straight there on arrival. Host Christos has confirmed bags can be left inside the apartment after the 11:00 checkout until 13:30 on 7 Oct - covers the gap before the 16:25 Ryanair FR 1199.
Booked Ad Maiora Domus, Trastevere (host Alessio) - two nights, 7-9 Oct · S$650.30 via Nadine's side · free cancellation before 2 Oct 3pm. Drive to Umbria on the morning of the 9th.
Booked Boutique Athens Airport Apartments · €107 / S$158 · free cancellation through 30 Sep (auto-charge still pending) · check-in 16:00-17:00 approved. GQ821 lands 16:00; TR51 leaves 09:00 the next morning.
★ Assisi · ★ Montefalco · ★ Orvieto · Perugina chocolate factory (book ahead) · Lake Trasimeno if the day is sunny · ★ Bagni San Filippo for a reliable thermal-water day.
Perugia in early October is roughly 22°C by day and 11°C at night. Lake Trasimeno averages about 16°C, so natural-water swimming will be cold. Mole di Narni is not a swim stop because of dangerous hydro releases. Bagni San Filippo's thermal water emerges around 48°C.
Milos sea in early October is around 23°C and should still suit a boat/swim day.
La Fonte's restriction is apartment/central heating until 15 Oct, not pool heating. Pools confirmed open are unheated. Babysitters are best handled after accommodation is locked.