10 DAY ITALY ITINERARY: CINQUE TERRE, PORTOFINO, MILAN, TRENTINO, AND VENICE

Italy is by far one of my favorite places to visit! Ryan and I got married in Positano and we always try to visit every year in hopes that we get to explore all of Italy one day! My last trip of the summer in 2021 was to Italy with a few girlfriends where we spent 10 days exploring Cinque Terre, Portofino, Milan Dolomites, and Venice. So here is my 10 day Italy itinerary!

WHEN TO VISIT ITALY

Italy is a great destination to visit almost year-round but I highly suggest visiting from late May to mid to late September. Summer is always busy in Italy so ideally, the shoulder months such as May and September are best. For this trip, my friends and I visited the first week of September and it was still pretty hot, we did however get a few days of rain at the end of our trip to Venice.

10 DAY ITALY ITINERARY

CINQUE TERRE: 2 DAYS

I first started in Cinque Terre. I flew into Milan and took a train which is just a little over four hours. I usually use trainline for convenience, you can download the app to purchase tickets and it also gives you live train schedules. I spent 2 full days in Cinque Terre, but I suggest spending at least 3 days here to truly experience all five villages along the Italian Riviera.

Read my Cinque Terre Travel Guide here with everything you need to know!

PORTOFINO: 2 DAYS

From Cinque Terre, my friends and I purchased our train tickets to Portofino for two nights. If you don’t have time this is a great day trip from Cinque Terre too. It’s a little over an hour by train from La Spezia to Santa Margherita Linqure, the town is quite small but I absolutely loved it. It’s a great town to enjoy and relax for a day or two.

WHERE TO STAY

We stayed in a 2 bedroom Airbnb with a balcony. It was super convenient right at the center of town and had a great view!

I also suggest Splendido, A Belmond Hotel for if you’re looking for a luxury hotel. It’s located on the hilltop with amazing views of the harbor and a stunning pool. They also have a property at the center of town Splendido Mare.

If you’re looking for a more budget-friendly hotel, Hotel Piccolo is right below A Belmond Hotel with similar views and has its own private balcony for the beach.

THINGS TO DO AND EAT

Baia Cannone Portofino is an iconic bay where you’ve seen images of the golden villa. We loved it here and spent both days at the beach but it’s a rocky beach so I suggest bringing water shoes.

Portofino Church on the top of the hill has a great viewpoint of the Portofino Marina for photos!

Climb up to Brown’s Castle from the marina. It’s a 15th-century castle that was built to defend against pirates.

Trattoria Concordia: Is rated one of the best restaurants in town. We loved it and I suggest making reservations for dinner.

Ristorante Puny: Is also a very popular restaurant for which we were unable to get reservations and is located at the marina.

Ristorante Delfino: Is located right at the marina which we thought would be a bit touristy but surprisingly we really enjoyed the food here.

MILAN: 1 DAY

From Portofino to Milan is about three hours by train. Milan is a beautiful city and need to still explore more of it! I usually spend most of my time around the Duomo di Milano.

WHERE TO STAY

Last year I was in Milan twice and stayed at two locations. Amabilia is an apartment located right across from the Duomo with an amazing window view directly of the cathedral! I highly recommend this apartment, it just opened last year but they only have 4 rooms and you will need to make sure to request a room with a view of the Duomo. When I arrived they will meet you out front to take you to the apartment.

Rosa Grand Milano is a hotel if you prefer having a hotel for the services they offer. This hotel is a great option and is located just behind the Duomo so it’s super convenient!

THINGS TO DO BUT MOSTLY JUST EAT

Duomo di Milano is a must when visiting Milan. I’ve been inside and to the top my first time visiting in 2014 but have not had a chance to go back since. It’s definitely worth a visit and will have great photo opportunities. Check tickets online here and get rooftop access.

The Galleria Vittorio Emanuele II is Italy’s oldest active shopping gallery and where a lot of the rooftop bars are also located. Take photos inside or stop by the Camparino cafe for a fancy cappuccino and people watch.

Milan has a lot of great rooftop bars with views of the Duomo and I suggest visiting at least 1-2 of them! Here’s a list below:

Terrazza Duomo21: I loved this one for the best side view but they don’t allow professional cameras here.
Terraza Aperol: Located just a few steps closer to the Duomo on the same side as Terrazza Duomo21. I personally did not think the food was great but if you love Aperol and the view it’s worth visiting.
The Dome Milan: This is located on top of a hotel which I thought was super cute but hard to get good photos of the Duomo if that’s what you’re looking for.
IL Bar: This is located right on top of the La Rinascente department store. Located right. next to the Duomo and a great spot for happy hour.
Terrazza 12: A restaurant and lounge. I haven’t been to this one but it looks gorgeous.

D & G Martini Bar by Dolce & Gabbana is stunning with lush greenery everywhere! I absolutely plan to go here next time I’m back in Milan.

Marchesi 1824 is located inside the Galleria. It’s a super cute cafe by Prada and I definitely recommend visiting for photos, coffee, and dessert.

TRENTINO: 2 DAYS

From Milan, my friend and I rented a car and drove three hours to Vermiglio in Trentino to stay at Chalet Al Foss. It’s near The Dolomites which is a place I would love to still explore.

Chalet Al Foss has been on my bucket list for years, and it truly lived up to my expectations. The property is stunning, it has an infinity pool with views of the mountains, alpacas and they offer the most amazing experiences. The property is made for Instagram with hot tub experiences, romantic dinners in chalets, breakfast with alpacas and so much more! They also offer long flying dresses for rent for photoshoots. It’s an adult-only property and it’s a great honeymoon destination too. Summer or winter are both amazing times to visit this property.

VENICE: 3 DAYS

From Chalet Al Foss my friend and I drove a little over three hours to Venice to drop off our rental. While in Venice, there are no cars, everything is walkable and transportation is by boat.

WHERE TO STAY

Hotel Palazzo Barocci is where we stayed. It’s one boat ride from the Rialto Bridge but also walkable to most places. It was pretty convenient, but I did notice we spent a lot more time near Rialto Bridge and would love to stay closer to there in the future.

A few other great hotel options I would love to stay at next with amazing interior, views, and balconies are Bauer Palazzo, The Gritti Palace, Baglioni Hotel, Palazzetto Pisani Grand Canal, and Appartamento Duodo o Barbarigo.

THINGS TO DO AND EAT

Rialto Bridge is the famous bridge that goes over the Grand Canal. It connects the San Marco and San Polo districts of Venice with lots of shops and restaurants along the canal.

St. Mark’s Square is a great place to hang out, sit outside with coffee, and walk around.

St. Mark’s Basilica is the most famous building in Venice since 1092 and continues to remain one of the most important religious buildings in Northern Italy.

The Campanile of St Mark or Bell Tower has a great view from the top. Visitors can visit the top, vest to do this at sunset! Tickets are 10€; free for children up to 6 years of age.

Day trip to the colorful towns of Murano, Burano, and Torcello. I visited these islands during my first trip to Italy and wished I had time to go back! It was raining the day we wanted to go but it’s totally worth it.

Ice cream at Gelatoteca Suso. Everyone knows gelato in Italy is the best and this location is actually one of the best! Definitely recommend and get a photo of it on the bridge.

Antico Forno for the best pizza in Venice in my opinion! We loved it so much we went twice.

From Venice to Milan I suggest taking the speed train which is about 2.5 hours. I hope this 10 day Italy itinerary was helpful, and make sure to read my other Italy blog posts below.