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Italy Itinerary Lake Como Boat Tour - Brenna Anastasia

8-Day Italy Itinerary

If you are looking for your next travel destination, I absolutely recommend adding Italy to your list! In this post, I'm taking you from city to city, and sharing the experiences that made it one of the most memorable summer trips.. ever!
FLORENCE
Italy Itinerary - Brenna Anastasia
Florence - Osteria Pastella Tagliatelle - Brenna Anastasia

I recently got back from an 8-day trip to Italy, where we wined, dined and shopped our way through 4 different cities. Florence was our first stop and was definitely one of my favorite cities that we visited! It was the first and last stop of our trip and I’m so glad we were able to visit this city twice. It’s no surprise that the city is visited by over 10 million tourists each year! We stayed at ‘The Place: Firenze‘ and it was absolutely beautiful. This hotel was more of a boutique style and felt very welcoming! Waking up in Florence felt like a dream! Florence is such an incredible city full of history, beauty and amazing food!

FOOD & DINING EXPERIENCES

A few restaurants we dined at included La Giostra, Trattoria ZaZa, and Osteria Pastella. In my opinion, Osteria Pastella has the best pasta in Florence! I recommend the Truffle Tagliatelle – (they make it in a cheese wheel in front of you which adds amazing flavor – check it out here!) We ate here twice during our stay. You’ll definitely want to make a reservation, the first night we had a reservation and the second time we waited in line for almost two hours, but it was worth it! 

FAVORITE THINGS WE DID

Florence is a super walkable city. You can walk from one end to another in about 30 minutes! One of our favorite sites to see was The Duomo Santa Maria del Fiore Cathedral. We enjoyed shopping in the City Center and watching the sunset from the Ponte Vecchio Bridge where we veered off to grab some evening gelato, which of course, originated in Italy!

MILAN
Italy Itinerary - Milan Terrazza Aperol - Brenna Anastasia
Italy Itinerary - Milan La Gioia - Brenna Anastasia

We took the train from city to city during our stay in Italy and it was fairly easy! You can buy tickets at the train station, however, I definitely suggest booking tickets in advance. Our second stop of our Italy trip was Milan! We stayed at the NH Collection Milano President! Just a 5-minute walk from the fashion district!

FOOD & DINING EXPERIENCES

I definitely recommend checking out Terrazza Aperol for cocktails! It only felt right to order an aperol spritz. This bar has beautiful views of the Duomo di Milano! Another great spot to check out is La Gioia – it’s the perfect date night spot and has a more elegant dress code. You have to get the Cacio e Pepe–it was amazing!

FAVORITE THINGS WE DID

Milan is known as a global capital of fashion. Needless to say, we got some ‘necessary’ shopping done at Galleria Vittorio Emanuele II (Italy’s oldest active shopping gallery)!

LAKE COMO
Lake Como Italy - Brenna Anastasia
Lake Como Italy - Brenna Anastasia
Italy Itinerary Lake Como Boat Tour - Brenna Anastasia
Italy Itinerary Lake Como Villa - Brenna Anastasia

I highly recommend a day trip from Milan to Lake Como! It’s about a 45 minute train ride. Lake Como is like no other. I have dreamt of visiting for years and it was one of the highlights of our trip!

FOOD & DINING EXPERIENCES

We stopped for lunch at Villa d’Este, a luxe 5-star hotel with stunning views of the lake. The Villa was even more beautiful in person. It truly felt like a day dream.

BOAT TOUR

If you ever visit Lake Como, you have a book a boat tour! Our captain picked us up in a classic wooden water taxi boat right on the dock. We spent two hours exploring the lake and seeing all of the stunning Villas. Villa Balbiano and Villa del Balbianello are a must-see!

VENICE
Italy Itinerary - Brenna Anastasia
Venice Italy - Brenna Anastasia
Venice Oro - Brenna Anastasia
Venice, Italy - Brenna Anastasia

After Florence, Lake Como and Milan, we headed to Venice! The entire city is on water so it doesn’t have any roads – just canals! The easiest way to get around is by boat. We stayed at H10 Palazzo Canova Venice. I loved this hotel!! It was comfortable, modern, and clean.

FOOD & DINING EXPERIENCES

For dinner, Oro is a must! It is a Michelin Star restaurant where we had an incredible dining experience. To get there, you take a boat to the iconic Belmond Hotel – check it out here!

WHAT WE DID IN VENICE

We took a gondola ride along the canal and it was an unforgettable experience. I feel like you cannot go to Italy without taking a gondola ride. Other places we visited and loved were St. Mark’s Square and the Rialto Bridge. This is the oldest of the four bridges across the Grand Canal in Venice. There’s truly so much to enjoy in Venice, even if you just walk around to explore the city, shop, and eat! 

FLORENCE
Florence - Westin Excelsior - Brenna Anastasia
Florence - Westin Excelsior - Brenna Anastasia

We came back to Florence for the last part of our trip and I’m so glad we did! This time, we stayed at The Westin Excelsior. This hotel is full of history and definitely feels like the true essence of Florence.

FAVORITE THINGS WE DID

We booked a driver for a day to do a private wine tour in Tuscany! Definitely suggest visiting the Tenuta Torciano Winery Estate for an incredible experience. I also recommend visiting the city of San Gimignano if you can! It is a medieval hill town in Sienna about an hour from Florence.

PACKING TIPS

My best tip to help you pack as efficiently as possible is to pack light. You will have to carry your own luggage on and off the train, roll over cobblestones, etc. I only brought two carry-on suitcases for the entire trip! The lightest I’ve ever packed! If you want a suitcase recommendation, check out the Away Bigger Carry-On. It’s perfect and fits in overhead storage or under the seat on airlines and trains. The Convertible Mini Weekender was my personal item! I love that it fits a ton, has pockets inside, and also has a removable bottom compartment which is perfect for shoes!

I packed a lot of dresses and comfortable pieces that I could build multiple outfits. Check out my Italy Outfit Guide here! Also, shoes are important!! We walked a TON. I’m so glad I packed a pair of comfortable white sneakers that were easy to style with both dresses and my workout gear!

Italy was truly a dream! Hopefully this guide helps you plan your next trip!

WITH LOVE, B