2 Weeks in Italy
- Jan 24
- 4 min read
I'm planning to visit Italy late summer 2026 with my partner. If you want to learn more about how we're budgeting the trip, take a look here. Let us know if there's anything on our list that we should/shouldn't see, or if you have a restaurant that slots in well with the neighborhoods we're visiting. Here's what's on the agenda.
1. Milan
Top Priorities:
AC Milan: We're planning much too far in advance to even know if AC Milan be playing at home on the weekend we're going, but seeing a game at San Siro Stadium would be at the top of our list.
The Last Supper: Knowing that the Serie A schedule comes out early summer, we won't count of trying to get tickets ourselves. Instead, we'll try to book a tour for whichever day ends up working around the game if there is one. Thus, the activities in Day 2 and 3 and interchangeable.
Day 1
The way the flights work out, we will be arriving in Milan in the evening. We'll check in to our hotel and then grab dinner somewhere.
Day 2
Morning: Duomo di Milano + Galleria Vittorio Emanuele II (shopping)
Afternoon: AC Milan + Leonardo da Vinci Museum
Evening: Dinner + Walk around the city
Day 3
Morning: The Last Supper + Castello Sforzesco
Afternoon: Pinacoteca di Brera + Bosco Verticale
Evening: Travel to Venice (3 hrs)
Looking for:
Restaurant recommendations.
Activities we should add or cut.
2. Venice
Top Priorities:
Piazza San Marco: Ever since seeing this painting at the Huntington Library, it has been a dream of mine to visit Venice.
Shopping: I would like a pair of Venetian slippers and possibly a book plate from Gianni Basso Stampatore!
Day 3
Evening: Check in to hotel + Dinner
Day 4
Morning: Doge’s Palace + Brunch
Afternoon: Grand Canal + Rialto Bridge + Gondola ride + Libreria Acqua Alta
Evening: Dinner + St. Mark’s Basilica @ night
Day 5
Morning: Explore the city + Lunch
Afternoon: Travel to Florence (2.5 hrs)
Looking for:
Restaurant recommendations.
Is it worth it to book the night tour of St. Mark's Basilica?
Where is the best place to buy Venetian slippers?
3. Florence
Top Priorities:
Cathedral of Santa Maria del Fiore: I just know that the photographs of the beautiful architecture cannot do it justice. I must see it for myself!
Pisa: Duh!
Cinque Terre: I have a strange reason for wanting to visiting the historic Cinque Terre. The treadmill I use has a screen that takes you through preloaded routes from around the world, and the Cinque Terre route is one of my favorites! I would love to actually walk through the towns in real life.
Day 5
Afternoon: Check in to hotel + Uffizi Gallery
Evening: Dinner + Palazzo Vecchio + Walk Around
Day 6
Day trip to Pisa through a tour group. On our way, we would stop at one or two of the towns in Tuscany. I don't fully trust myself to research how to to something like this myself, especially since I do not plan on renting a car.
Day 7
Day Trip to Cinque Terre through another tour group.
Day 8
Morning: Accademia (David) + Florence Duomo
Afternoon: Lunch @ Mercato Centrale + Leonardo Interactive Museum + Mercato San Lorenzo
Evening: Travel to Rome (1.75 hrs)
Looking for:
Restaurant recommendations.
Activities we should add or cut. Is this too ambitious to do in less than four days?
4. Rome
Top Priorities:
Vatican: I am not religious, but the Vatican is the Vatican.
Colosseum: As one of the seven wonders of the world, this is also at the top of our list to visit. I know tickets are super difficult to get, but I'm going to try anyways. I've read that the Attic tickets are great.
Aqueduct Park: Ancient Roman engineering has always interested me, and I would love to either bike or walk through the park.
Day 8
Evening: Check in to Hotel + dinner
Day 9
Morning: 7am Saint Peter’s Basilica/Piazza + Vatican Museums (Sistine Chapel)
Afternoon: Lunch in Prati + Castel Sant Angelo
Evening: Piazza Navona + Dinner @ Campo de’ Fiori
Day 10
Morning: Pantheon + Trevi Fountain + walk along Via Condotti + Spanish Steps
Afternoon: Lunch + Galleria Borghese
Evening: Dinner + Walk around
Day 11
Morning: Palatine Hill + Colosseum (get attic tix 30 days in advance) + Roman Forum tour
Afternoon: Lunch + Musei Capitolini + Trajan’s Market + Walk up the Gianicolo Hill → Tempietto
Evening: Santa Maria + Trastevere shopping + Apertivo / Dinner
Day 12
Morning: Aventine Keyhole + Aqueduct Park (Bicycle?)
Afternoon: Travel to Naples + check into Hotel
Evening: Dinner by Borgo Marinari
Looking for:
Restaurant recommendations.
Activities we should add or cut.
Shopping recommendations.
5. Naples
Top Priorities:
Herculaneum/Pompeii: I am not religious, but the Vatican is the Vatican.
Pizza: see Pisa
Day 12
Afternoon: Check into Hotel
Evening: Dinner
Day 13
Morning: Piazza del Plebiscito + Castel Nuovo + Lunch @ Brandi (Margherita Pizza)
Afternoon: Spaccanapoli + Sansevero Chapel + Duomo + Museo Archeologico Nazionale
Evening: Dinner in Tribunali
Day 14
Day trip to Pompeii and Herculaneum. This one is not well planned out yet. I don't think it will be too difficult to manage on my own.
Morning: travel to vesuvius to hike (need tix, 1 hr)
Afternoon: travel to herculaneum
Evening:
Day 15
Day trip to Amalfi Coast with a tour group. I have conflicting feelings about this one. One on hand I've been told that Positano/Amalfi Coast is amazing and I need to go. On the other hand, many travel blogs recommend at least 5-7 days there. I think going with a tour group will help us see the highlights; I just feel as though the essence of coastal relaxation will be missed.
Day 16
Morning: Breakfast + Head to FCO (2.5 hrs)
Looking for:
Activities we should add or cut. Is it worth doing a day trip to the Amalfi Coast?
Highlights in the city of Naples itself!
Comments