Italy Travel Guide

We’re back from Italy and settling into our new place! Ambrose and I have always wanted to visit Italy. When the opportunity came to travel after residency and moving, we knew where it had to be: Italia! Visiting this beautiful country was a first for both my husband and me. We wanted to cover as much as possible.

This post will be an overview of the trip. I’ll cover our general itinerary, stand out activities, restaurants, and hotels. If you’re interested in more specific city guides let me know on our Instagram! It’s easy to say that it was easy to fall in love with the country, people, and cuisine.

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Italy Itinerary

  1. Milan

  2. Lake Como

  3. Venice

  4. Florence

  5. Tuscany

  6. Cinque Terre

  7. Rome

  8. Sorrento

  9. Capri

  10. Positano

  11. Ravello

  12. Milan

Top 3: My most loved cities were Como, Florence and Ravello. Como is a laid back town on Lake Como and visually stunning. The temps are also cooler since you can see the Swiss Alps from the water. Florence is a romantic, old stone covered city. Around every corner is a quaint shoppe, baroque fountain, or vine covered nook. Priceless works of renaissance art can be found in any city square, and the public museums hold the most breathtaking pieces. Ravello is on the Amalfi Coast but it’s tucked away in the mountains as opposed to the beach towns like Positano or Amalfi. It’s a quiet mountain town with lush greenery and delicious local restaurants. The views are absolutely insane, and it feels like you’re in the heavens. We arrived during the feast day of Ravello’s Patron Saint, so it was extra exciting with fireworks and live band performances.

Travel Planning Tips: As novice trip planners we relied heavily on Rick Steve’s Italy Travel Guide. Additionally, I have been following this blogger for many years and her tips on the Amalfi Coast are spot on. We moved around often so hauling our large suitcases around was not ideal, and at one point, Ambrose’s suitcase handle literally fell off! Next time, I would just take a carry-on and book an Air BNB with laundry. The trains in Italy are crucial for getting around. However, the trains are also a cluster and very stressful. Ambrose has offered to guest appear to share some helpful advice on the next post!


Mini Review of Each Stop on the Italy Itinerary 1-6

Milan: The highlight of our time in Milan was visiting the world famous La Scala Opera House. I had literally never seen an Opera before, but La Scala did not disappoint with it’s ornate decor, private boxes, and gorgeous architecture. Tickets are available for purchase ahead of time, however buyer beware. The seats in the boxes that are not the first row are literally stools and if you had a tall person sitting in front you would be out of luck. Once we found this bit of information out, we went for the first row. If you had several nights in Milan and could be flexible. there are day-of tickets which are deeply discounted. In regards to the dress code, men mainly wear slacks and button down shirts while women can wear dresses, skirts, or nice pants (no ballgown required).

A short walk from La Scala, Milan’s massive gothic-style Duomo its piazza make a wonderful spot to stroll around with gelato in hand. Shopping in Milan is on point. If you’re looking for a deal, know that a VAT tax refund will roughly save you 14% on items (make sure to ask a sales person how to get this refund). The Galleria Vittorio Emanuele II is the most impressive “mall” I have ever seen. It’s a stunning gold covered place to window shop. Don’t forget to spin on the bull mosaic for good luck! Two days in Milan felt like plenty of time.

White Eyelet Dress//Red Dress Boutique


Lake Como: This cool climate, lake getaway is only a 20 minute train ride from Milan (talk about convenient)! Lake Como had been on my dream list for several years and I would say it lived up to the hype. There are several towns on the lake, with the most popular being Varenna or Bellagio. We stayed in Como as it had easy train access and a newer Hilton property that was walking distance to the town center. The hotel had the most incredible view from the rooftop pool and bar, as shown above. We enjoyed a handcrafted cocktail every evening watching the sunset over the lake, usually with live music (so good!)

The vibe is very casual and laid back all over Lake Como. Note that transportation around the lake is hectic and hard to navigate between towns during peak season (July and August). There is a ferry that makes its way around the lake but know that it will take several hours to get anywhere so plan accordingly (or order a glass of prosecco while on board). We did a private tour on a wooden boat with AC Boat Rental which was something I will never forget!

Red Dress//Reformation Espadrilles//Cole Haan (the MOST comfortable and lightweight travel shoes EVER!) Lion Necklace//Reagan Charleston Jewelry


Venice: We almost did not make it here but I am so glad we did! It was a quick trip to this old floating city but it’s worth the trek. Caffe Florian was my favorite stop in Venice. It is a nearly 300 year old cafe that is luxurious and ornate, yet very comfortable. The waiters wear tails and serve drinks on silver trays while live music plays on the veranda. I would recommend the ice cream with hot chocolate syrup to share! We also went to the top of the tower on the square on recommendation from my sister-in-law which served up stunning 360 degree views, as shown above. It is worth the small entrance fee, don’t skip it!


Florence: Where to start on the city that stole my heart? Florence is incredibly lush and romantic with delicious cuisine, Renaissance art, and charming architecture. Art history is of major interest of mine, so tours of the Uffizi and Academie (housing the statue of David) were a must. The guides really bring the art to life by sharing details of the artist’s lives and hidden meanings in the paintings.

One of the best things we did the entire trip was to take a cooking class. The Tuscan cooking class with Walkabout Tours was everything I hoped it would be and more. The location is a short bus ride away from the city. It is set in the Tuscan hills in a gorgeous farmhouse with insane views and an entire kitchen built for this class with open air patio and fresh herb garden. The chef, Issac, was so funny and explained every step of the process. We made bruschetta with fresh herbs, homemade pasta with ragu sauce, roast pork with sage, topped off with Tiramisu. Needless to say, it was the most wonderful meal and the view looking out over the countryside was the cherry on top. Also, be sure to stop at Hotel Continental’s roof top for bellinis, pricey but worth it for the view!


Tuscany: After doing a little research it became clear that instead of taking a bus tour out to a winery, we wanted to stay at a winery. We rented a car in Florence and drove out to Il Borro, which was very do-able. The Tuscan countryside makes for a lovely drive. However, note that this was the was only time we drove on the trip.

After talking to my brother-in-law, the wine guru, we wanted to stop at the famous Antinori winery on the drive through Tuscany. It is a modern take on a winery (looks like an evil super villain’s lair) but beautiful none-the-less. After researching this, we decided on Il Borro. It is a medieval village that has been restored completely and turned into a working winery and resort. Each house in the village is a hotel room and there are local craftsmen in the shops selling their homemade wares. The resort also has two delicious restaurants (those olives!) and serene pools. We did a wine tasting at Il Borro which was in their picturesque ancient cellar. We recently dined at a steakhouse in Iowa, and I took a peak at the wine menu, both Antinori and Il Borro had wines listed!

Striped Maxi Dress//JCrew (on SALE!)


Cinque Terre: Known as the “Five Towns” along the sea, Cinque Terre has beautiful views in each town and on the hiking trails in between. We stayed in Riomaggiore and Vernazza which both have quaint little bays surrounded by bars and restaurants. We hiked between Vernazza and Corniglia one day. It was a moderate hike (some children were doing it) but we were definitely ready for a break after.

Ambrose fell in love with anchovies while in Cinque Terre as it is there specialty! Dau Cila was his favorite spot for seafood, it’s found right on the bay of Riomaggiore. The daytime crowds in Cinque Terre were immense and, if possible, avoid peak season or stay the night in town to experience it when the crowds thin out. The beaches were rocky but worth renting a chair for a day on the umbrella-lined coast of Monterosso. It’s like being in a Gray Malin photo.


The last 5 stops will be continued on the next post! Let me know if you have any specific questions you want answered. Thanks for stopping by our Italy Travel Guide!