🍋 Private Italy Itinerary

Welcome Back to Italy

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🍋 Melissa & Chris · 10 Year Anniversary

Sicily, Tuscany
& Lake Como

A romantic Italy return: Palermo arrival, a coastal Calabria stop, two nights at Borgo San Felice in Chianti, and a Lake Como finale in Bellagio before flying home from Milan.

10
Days
5
Stays
3
Regions
—
Days until Italy

🗺️ Route at a Glance

Columbus → Palermo
Sun Jun 28 · United via EWR · Arrive PMO Mon Jun 29 at 7:15am
Palermo / Sicily
Jun 29 to Jul 2 · Palazzo Balsamo · Superior View Room with Jacuzzi
Cetraro / Calabria Coast
Jul 2 to Jul 3 · Grand Hotel San Michele · Suite with terrace and sea view
Chianti / Tuscany
Jul 3 to Jul 5 · Borgo San Felice Resort · Premium Deluxe
Lake Como / Bellagio
Jul 5 to Jul 8 · Belvedere Bellagio · Elite room
Milan → Columbus
Wed Jul 8 · United via EWR · Depart MXP 9:45am, arrive CMH 4:10pm

☀️ Day by Day

Sun
28
Jun

Depart Columbus

CMH 1:15pm → EWR → PMO 7:15am next day
✈️ United1 stopUnited

Mission: sleep on the overnight leg. Pack Palermo day-one clothes, chargers, meds, and one change of clothes in carry-on.

Before departure

Eat a real lunch at CMH/EWR and buy a large water bottle before boarding the overnight segment.

Arrival setup

Have the Palazzo Balsamo transfer, hotel address, and online check-in code saved offline.

Mon
29
Jun

Arrive in Palermo

Land early, transfer to hotel, slow first day in Sicily
🍋 PalermoRecovery day
Hotel check-in
Palazzo Balsamo Boutique Hotel
Mon Jun 29 · 3 nights · Superior View Room with Jacuzzi · online check-in code saved separately

Arrive 7:15am at PMO. The hotel was asked to help arrange airport travel. Keep the day intentionally light: check in, wander, aperitivo, early dinner.

Palazzo Balsamo: 3 nights, Superior View Room with Jacuzzi, Bed & Breakfast, reservation saved separately, online check-in code saved separately, Via Divisi 93, Palermo.
Hotel check-in + contact details
Dates
Jun 29 to Jul 2 · 3 nights
Room
Superior View Room with Jacuzzi
Address
Via Divisi, 93 · 90133 Palermo
Phone / WhatsApp
+39 334 913 0661
Website
palazzobalsamo.com
Email
info@palazzobalsamo.com
Dinner
  • Osteria Ballarò for polished Sicilian classics
  • Buatta Cucina Popolana for a lively first-night meal
  • Seven Restaurant for a romantic rooftop option
Activities
  • Easy walk: Quattro Canti → Fontana Pretoria → Cathedral
  • Aperitivo near Piazza Bellini
  • Early night to recover from the flight
Tue
30
Jun

Palermo Full Day

Markets, architecture, seaside dinner
🍊 SicilyAnniversary pace

Prioritize one neighborhood walk, one major sight, and a long meal. Avoid turning the first full day into a checklist.

Dinner
  • Gagini for a special Palermo tasting menu
  • A'Cuncuma for intimate Sicilian fine dining
  • Ferro di Cavallo for casual local energy
Activities
  • Ballarò or Capo market in the morning
  • Palazzo dei Normanni + Cappella Palatina
  • Teatro Massimo tour or evening performance
Wed
1
Jul

Palermo + Optional Day Trip

Monreale, Cefalù, or stay local
FlexibleSea views

Best use: choose based on energy. Cefalù for beach town magic, Monreale for mosaics and easier logistics.

Dinner
  • Bye Bye Blues in Mondello for a splurge
  • Quattro Mani for refined seafood
  • Locale for cocktails + dinner near the center
Activities
  • Option A: Monreale Cathedral + cloisters
  • Option B: Cefalù beach town by train/car
  • Option C: Mondello beach afternoon
Thu
2
Jul

Pick Up Car + Drive to Cetraro

Enterprise Palermo → Grand Hotel San Michele
🚗 Audi A5 Avant or similarAutomatic
Hotel check-in
Grand Hotel San Michele
Thu Jul 2 · 1 night · Suite · breakfast included · check-in 3:00pm to midnight

Pick up the rental car in Palermo, then drive to Cetraro for a one-night coastal reset. Grand Hotel San Michele check-in is listed 3:00pm to midnight.

Hotel check-in + contact details
Dates
Jul 2 to Jul 3 · 1 night
Room
Suite · breakfast included
Address
Contrada Bosco, 30 · 87022 Cetraro
Phone
+39 0982 91012
Email
info@sanmichele.it
Car pickup
Via Umberto Giordano 8, Palermo
Hotel
Grand Hotel San Michele · Suite
Room notes
Breakfast included · terrace · sea view · high floor requested · free parking based on availability
Dinner
  • Use the hotel terrace restaurant if you arrive tired
  • Ask for a sea-view table at check-in
  • Keep it simple after the long drive
Activities
  • Sunset walk around the property
  • Pool or beach reset
  • Organize bags for the Tuscany drive
Fri
3
Jul

Drive to Borgo San Felice

Calabria coast → Chianti Classico
🌿 TuscanySan Felice
Hotel check-in
Borgo San Felice Resort
Fri Jul 3 · 2 nights · Premium Deluxe · check-in after 3:00pm

Long repositioning day. Arrive at Borgo San Felice after 3:00pm. This is one of the trip highlights, so keep dinner simple and enjoy the property.

Hotel check-in + contact details
Dates
Jul 3 to Jul 5 · 2 nights
Room
Premium Deluxe · 2 adults
Address
Località San Felice · 53019 Castelnuovo Berardenga, Siena
Phone
+39 0577 3964
Email
info@borgosanfelice.com
Reservation
Reservation code saved separately · check-in after 3:00pm · check-out by 11:00am
Dinner
  • Osteria Il Grigio for traditional Tuscan cuisine
  • Bar Archi for a low-key arrival drink
  • Save Poggio Rosso for the slower anniversary day
Activities
  • Check in, walk the borgo lanes
  • Pool or spa recovery after the drive
  • Sunset wine on property
Sat
4
Jul

Chianti Anniversary Day

Borgo San Felice, Siena, wine, spa, slow Tuscan dinner
🍷 Wine countryRomantic highlight

Make this the slowest luxury day: breakfast, pool/spa, short Siena visit or countryside drive, then a memorable dinner.

Dinner
  • Poggio Rosso for the signature special-occasion dinner
  • Osteria Il Grigio if you want more rustic/relaxed
  • Ask concierge about a wine pairing or estate tasting
Activities
  • Spa or pool morning
  • Siena for a short visit, not a marathon
  • Chianti wine tasting or countryside drive
Sun
5
Jul

Drive to Lake Como + Return Car

Borgo San Felice → Como / MXP rental return → Bellagio
🏔️ Lake ComoCar drop-off
Hotel check-in
Belvedere Bellagio
Sun Jul 5 · 3 nights · Elite room · Lake Como finale

Car drop-off is listed for Via Varesina 138, Como, ITA, MXP. After the return, transfer onward to Bellagio for three nights at Belvedere Bellagio.

Hotel check-in + contact details
Dates
Jul 5 to Jul 8 · 3 nights
Room
Elite room · 2 adults
Address
Via Valassina, 31 · 22021 Bellagio, Como
Phone
+39 031 950 410
Email
info@belvederebellagio.com
Dinner
  • La Terrazza at Grand Hotel Villa Serbelloni for a splurge
  • Dispensa 63 for modern Italian in Bellagio
  • Belvedere's restaurant if arrival timing is tight
Activities
  • Keep this primarily a transfer day
  • Sunset walk in Bellagio
  • Book ferry/boat ideas for the next morning
Mon
6
Jul

Bellagio

Lake day, ferries, villas, long lunch
🚤 Ferry dayBelvedere

Classic Como day: Bellagio lanes in the morning, ferry to Varenna or Menaggio, and come back for sunset.

Dinner
  • Salice Blu for a chef-driven dinner above Bellagio
  • Alle Darsene di Loppia for romantic lakeside dining
  • La Punta for classic lake views
Activities
  • Ferry to Varenna + Villa Monastero
  • Villa Melzi gardens in Bellagio
  • Private boat ride if the weather is strong
Tue
7
Jul

Final Full Day on Lake Como

Villa, boat, spa, or nothing at all
Slow travelLake views

Hold this day lightly. The best Lake Como day may be less itinerary and more views, wine, and wandering.

Dinner
  • Mistral for a final-night splurge
  • Ristorante Bilacus for charming Bellagio atmosphere
  • Belvedere for convenience and views
Activities
  • Villa Carlotta + Tremezzo
  • Hotel spa / pool time
  • Pack early for the MXP transfer
Wed
8
Jul

Fly Home from Milan

MXP 9:45am → EWR → CMH 4:10pm
✈️ United1 stopUnited

Early departure: plan a very early private transfer from Bellagio to MXP. This is the highest-risk logistics morning of the trip.

Morning

Prebook a private transfer, ask the hotel for a breakfast box, and leave a larger buffer than feels necessary.

Travel task

Confirm bags, passports, Global Entry cards if relevant, and United app check-in the night before.

🏨 Stays

Palazzo Balsamo · Palermo

Jun 29 to Jul 2 · 3 nights · Superior View Room with Jacuzzi · Bed & Breakfast · reservation saved separately · online check-in code saved separately · Via Divisi 93 · paid $1,583.87.

Grand Hotel San Michele · Cetraro

Jul 2 to Jul 3 · 1 night · Suite · breakfast included · terrace, sea view, high floor, parking requested.

Borgo San Felice Resort · Tuscany

Jul 3 to Jul 5 · 2 nights · Premium Deluxe · 2 adults · total EUR 1,344.00 paid in advance.

Belvedere Bellagio · Lake Como

Jul 5 to Jul 8 · 3 nights · Elite room · total EUR 3,279.00 · anniversary special request noted.

🚗 Transport

Rental company
Enterprise
Vehicle
Premium · Audi A5 Avant or similar · wagon · 5 passengers
Pickup
Thu Jul 2 · Palermo · Via Umberto Giordano 8
Drop-off
Sun Jul 5 · Como / MXP · Via Varesina 138
Price
$577.64 · pay at pickup
Confirmation
Saved separately

🔖 Confirmations & Watchouts

Flights

United reference saved separately. Outbound: UA 3596 / UA 735. Return: UA 18 / UA 3492.

Borgo San Felice

Reservation code saved separately. Full advanced payment. Check-in after 3:00pm, check-out by 11:00am.

Palermo hotel

Palazzo Balsamo reservation and online check-in code saved separately. Phone/WhatsApp +39 334 913 0661.

Private transfers

Book PMO airport transfer and Bellagio → MXP early-morning transfer. These are the two moments worth over-planning.

Driving

Confirm license and international driving permit requirements with Enterprise before departure.

Made for Melissa & Chris · Italy Anniversary Trip · Summer 2026

Last updated: May 30, 2026 at 10:06 PM ET

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