Planning

Started planning the trip a bit late about 2 months before travel. I would suggest 6 months.

Day 1 Land in Milan, checkin and explore. Night in Milan
Day 2 Explore Milan. Night in Milan
Day 3 Leave for Lake Garda. Explore. Night in Riva DEL Garda.
Day 4. Explore Lake Garda. Leave for Venice. Night in Venice.
Day 5 Explore Venice. Night in Venice.
Day 6 Leave Venice for Cinque Terra. Stop at Lambo Museum. Night in La Spezia.
Day 7 Explore Cinque Terra. Night in La Spezia.
Day 8 Leave for Florence. Explore Pisa and Lucca. Night in Florence.
Day 9 Explore Florence. Night in Florence.
Day 10 Explore Tuscany. Sienna and Chianti. Night in Florence.
Day 11 Explore Tuscany. Night in Montepulciano.
Day 12 Leave for Rome. Night in Rome.
Day 13 Explore Rome. Night in Rome.
Day 14 Explore Rome. Night in Rome.
Day 15 Leave for US.

I booked a rental car from last day in Milan to first day in Rome. Park the car in Venice and Florence and use as needed. Lot of people suggest to use trains and use rental cars as needed. I did not want to deal with picking up and dropping cars, and also train stations. Rent a compact car. Travel light so stuff fits in a compact car. It is suggested that you prepay ur rental car. I was not able to even though I had called.

Day 1
Land in Milan at 1:40pm.
Taxi to Apartment. Approx. €105
Apartment: link to Airbnb reservation. https://abnb.me/dwRzsye2SN
Check-in and freshen up.
Explore Local Shops, Brera Neighborhood
Food - Ristronte Nabucco

Day 2: Explore Milan
AM
Duomo (Cathedral) / Piazza (Main Square) / Galleria
Food- Panzerotti Luini - Pizza - Lunch
PM
Sforzesco Castle & Sempione Park
For Dinner to the Navigli area.
Eating options Rita/Mag-cafe in the vibrant Navigli area

Video-
https://www.ricksteves.com/watch-read-listen/vi…

Day 3: Leave for Lake Garda
Pick up Rental Car from Central Station. Rental car office was not exactly at the train station, took a bit to find it.
When driving from Milan, go up the west side stop at Limone sul Garda for lunch.
Restaurant in Limone for lunch?

From there we will go to the hotel.
Hotel Savoy Palace - TonelliHotels - Rvia Del Garda
After check-in Explore and Dinner .

Day 4- Lake Garda
In the morning go to the Local Market. Then take a boat to Malcesine.
In Malcesine we will visit the old town and the castle and take a cable car to the top of Monte Baldo.
Lunch?

Come back to the hotel. Drive to Venice.

At Venice, there are two parking options...
1) Piazzale Roma (autorimessa Comunale. Garage San Marco). Has the option to pre-book.
2) Tronchetto and then people mover to Venice. No pre-booking required.

Day 5
VENICE
Visit the Piazza San Marcos, its basilica and the Doge's Palace, lots of museums (the Guggenheim is really great). Walk through San Polo district, crossing the Rialto bridge and visiting its fish market. Walk through Dorsoduro district and try the typical cicchetti (Venetian tapas). Night in Venice.

The articles below were helpful in planning Venice.

http://www.way-away.com/italy/venice-itinerarie…
https://www.tripadvisor.com/ShowTopic-g187870-i…
https://www.quora.com/What-is-a-good-location-t…

Day 6: Leave for Cinque Terra
Drive to Bologna to Lambo Museum. Have lunch close to the Museum.
After the Museum drive to La Spezia.
Directions: https://goo.gl/maps/Kokqhs2zsZF2

Day 7: Explpore Cinque Terra
Monterosso: http://www.cinqueterre.eu.com/en/monterosso
Vernazza: http://www.cinqueterre.eu.com/en/vernazza
Corniglia: http://www.cinqueterre.eu.com/en/corniglia
Manarola: http://www.cinqueterre.eu.com/en/manarola
Riomaggiore: http://www.cinqueterre.eu.com/en/riomaggiore

La Spezia to Monterosso: By Train
Monterosso to Vernazza by boat
Vernazza to Corniglia hike
Corniglia to Riomaggiore by train
Riomaggiore to Manarola by train or boat

Manarola is the best place to be at sunset. That is why you want to end your day there.
Dinner: Nessun Dorma in Manarola
Bar: A Pie’ di Ma’ in Riomaggiore
Swimwear and quick-drying towels for the beach
CT TRAIN SCHEDULE: http://www.cinqueterre.eu.com/en/cinque-terre-t…

https://fullsuitcase.com/cinque-terre-practical…
https://fullsuitcase.com/cinque-terre-one-day/

Day 8
Leave for Florence
Stop at Pisa for photo op
Stop at Lucca; Explore a bit
Check in Florence; explore and dinner

Day 9
6 hr Walking tour booked with Viator

Day 10
Chianti, wine tour and lunch

Day 11
Drive to Montepulciano
Stop at San Gimignano

Day 12
Drive to Rome. Return car.
Vatican tour booked.

Day 13
Explore Rome; Piazza Navona, Spanish Steps, Pantheon, Trevi Fountain
and Shopping

Day 14
Colosseum tour booked. Palatine Hill and Roman Forums

Day 15
Pack and depart. Flight at 1.30pmRead more