Italy

Day by Day

Day 1 Monday, August 31

Newark → In Transit

Departure Day

Evening departure from Newark Liberty (EWR) at 9:45 pmFlight
Flight: SWISS / Lufthansa via Zürich to Rome — Economy ClassFlight
Overnight transatlantic crossing

Sleep: In flight

Day 2 Tuesday, September 1

Rome

Benvenuti a Roma

Arrive Rome Fiumicino (FCO) ~12:35 pm local timeFlight
Transfer: Taxi or Leonardo Express train to city center (30 min)TrainTransfer
Check into hotel near Piazza Navona
Afternoon passeggiata through Centro Storico — Piazza Navona, Pantheon exterior, Piazza della Rotonda
First gelato at Giolitti or Frigidarium
Welcome dinner at a trattoria on Piazza Navona — cacio e pepe and supplì

Sleep: Rome

Day 3 Wednesday, September 2

Rome

Ancient Rome

Early morning skip-the-line entry to the Colosseum (arena floor upgrade recommended)
Roman Forum & Palatine Hill — allow 2–3 hours to explore the ruins
Lunch in the Monti neighborhood — Rome's boho quarter, try La CarbonaraTransfer
Afternoon at the Capitoline Museums — Dying Gaul, She-Wolf, Marcus Aurelius
Golden-hour aperitivo on the Hotel Forum rooftop terrace overlooking the Forum
Dinner in Monti — handmade pasta at Ai Tre Scalini

Sleep: Rome

Day 4 Thursday, September 3

Rome

Vatican City

Early-entry Vatican Museums & Sistine Chapel (book 7:30 am first-access ticket)
Raphael Rooms, Gallery of Maps, and the breathtaking Sistine Chapel ceiling
St. Peter's Basilica — Michelangelo's Pietà, climb the dome for panoramic views
Lunch in Prati — local neighborhood away from tourist prices
Afternoon visit to Castel Sant'Angelo & walk along the Tiber
Cross into Trastevere for dinner — Da Enzo al 29 or Tonnarello (arrive early or queue)Flight

Sleep: Rome

Day 5 Friday, September 4

Rome

Neighborhoods & Roman Food

Morning stroll through Campo de' Fiori market — fresh produce, flowers, people-watching
Walking tour of Trastevere's cobblestone lanes and ivy-draped piazzas
Lunch: classic Roman four-course at a Testaccio trattoria — artichokes, carbonara, amatriciana, tiramisuTransfer
Aventine Hill — Giardino degli Aranci (Orange Garden) for sunset views over Rome
Peek through the Knights of Malta keyhole for the iconic framed view of St. Peter's dome
Evening food tour through Testaccio — the original Roman foodie neighborhood

Sleep: Rome

Day 6 Saturday, September 5

Rome → Tivoli → Rome

Day Trip to Tivoli

Morning bus or train to Tivoli (~45 min from Rome)Train
Villa d'Este — Renaissance palace with 500 spectacular fountains cascading down the hillside
Lunch at a family trattoria in Tivoli's old town
Hadrian's Villa (Villa Adriana) — Emperor Hadrian's sprawling 2nd-century retreat
Return to Rome by late afternoon
Relaxed evening — aperitivo in Piazza del Popolo, dinner near your hotel

Sleep: Rome

Day 7 Sunday, September 6

Rome

Baroque Rome & Arrivederci

Borghese Gallery — pre-booked 9:00 am timed entry (Bernini's Apollo & Daphne, Caravaggio masterpieces)Transfer
Stroll through Villa Borghese gardens to the Pincian Hill overlook
Spanish Steps & Via Condotti — window shopping at Italian fashion houses
Trevi Fountain — toss a coin to guarantee your return to Rome
The Pantheon interior — the world's best-preserved Roman building, free entry
Farewell Roman dinner at a rooftop restaurant with views of the city's domes and rooftops

Sleep: Rome

Day 8 Monday, September 7

Rome → Milan

The Fast Train North

Check out of Rome hotel, taxi to Roma Termini stationTransfer
Train: Frecciarossa high-speed train to Milano Centrale (2 hr 59 min, depart ~9:00 am)FlightTrain
Arrive Milan ~noon, check into hotel near the DuomoFlight
Milan Cathedral (Duomo) — climb to the rooftop terraces among the Gothic spires
Galleria Vittorio Emanuele II — Italy's oldest shopping mall, espresso at Caffè Camparino
The Last Supper by Leonardo da Vinci at Santa Maria delle Grazie (pre-booked timed slot)
Farewell Italian dinner in the Navigli canal district — buzzing with aperitivo bars

Sleep: Milan

Day 9 Tuesday, September 8

Milan → New York

Business Class Home

Transfer: Malpensa Express train from Milano Cadorna to MXP airport (50 min)FlightTrainTransfer
Flight: SWISS Business Class MXP → ZRH → JFK, departs 10:15 amFlight
Enjoy the SWISS Business Class experience — lie-flat seat, Swiss chocolates, champagne
Arrive JFK ~3:35 pm same day — welcome home!Flight

Sleep: Home

Key Bookings

Transfer 218,800 Chase UR → Aeroplan Allow 1–2 business days for transfer to post

Book EWR → ZRH → FCO (Economy) via Aeroplan 39,400 pts × 2 pax = 78,800 pts · Aug 31

Book MXP → ZRH → JFK (Business) via Aeroplan 70,000 pts × 2 pax = 140,000 pts · Sep 8

Rome Hotel — 6 nights (Sep 1–7) Centro Storico or Piazza Navona area recommended

Milan Hotel — 1 night (Sep 7–8) Near Duomo or Milano Centrale for easy MXP access

Frecciarossa Train — Roma Termini → Milano Centrale Book on Trenitalia.com · ~€40–60/pax · Sep 7

Colosseum Skip-the-Line + Arena Floor Book at coopculture.it · Sep 2

Vatican Museums Early Entry (7:30 am) Book at museivaticani.va · Sep 3

Borghese Gallery Timed Entry Book at galleriaborghese.beniculturali.it · Sep 6, 9:00 am slot

The Last Supper Tickets — Milan Book at cenacolovinciano.org months in advance · Sep 7

Malpensa Express Train Ticket Milano Cadorna → MXP · Sep 8 morning

Our Route

Day by Day

Key Bookings