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10 Days In Italy: A Hilton Grand Vacations Owner’s Guide To Milan, Verona, Pisa And Tuscany

Plus four things to love about Borgo alle Vigne, a Hilton Grand Vacations Club

The Vacationeer
Aerial view of Lake Como, Italy

*Editor's note: Marla S. has been a Hilton Grand Vacations Owner since 2015. This is her story.

One year, I had unused Hilton Grand Vacations ClubPoints that I couldn’t roll over to the following year. The challenge was to use them or lose them.

The decision was easy when I found that Borgo alle Vigne, a Hilton Grand Vacations Club in Tuscany, Italy, was available for New Year’s Eve. My husband and I decided to extend the trip — this was Italy, after all. We planned to visit Milan, Verona and Pisa, ending with our stay at Borgo alle Vigne. Here’s our itinerary of how we spent 10 days in Italy.

Exterior of the cathedral Duomo di Milan in Italy 

Day One: Milan

How to get there: We took a red-eye flight from Boston to Milan, arriving at the Linate Airport — the smaller of Milan’s airports. The Starfly bus stop was just outside the terminal for a short, inexpensive trip to the Milan Centrale Train Station.

Where to stay: We booked a stay at Hilton Milan, a beautiful hotel just a short walk from the train station.

Where to eat: The concierge suggested we try dinner at the Il Tavolino, two blocks away. Our meal was reasonably priced and very good. I enjoyed an appetizer of rolled eggplant, and my husband had spinach gnocchi.

What to do: Walking around Milan around Christmas, I was surprised to see how crowded it was, with vendors, decorations and a light show. Incredible.

Day Two: Lake Como

What to do: I pre-booked a fantastic Lake Como tour, with transportation, a one-hour boat ride and scenic stops. There was time at each stop to wander, shop, have a gelato and visit the Christmas vendors for great gifts to take home. It was a long day, but absolutely worth it.

Where to eat: We ended the night at one of the best places we had dinner during our entire stay in Italy: Cantina Meridionale. The food, the ambiance and the wait staff were all delightful.

Juliet's balcony in Casa di Giulietta in Verona, Italy 

Day Three: Verona

How to get there: We arrived in Verona after an hour-and-15-minute train ride.

Where to stay: I booked two nights at the Relais Empire, a bed and breakfast within walking distance of the train station.

What to do: We bought the 48-hour Verona Card from a ticket office by the Roman arena, just off the main square, and enjoyed the local sights and shops. This pass was a combined entry ticket to many of Verona’s historical sites and museums, including the Casa di Giulietta, the Romeo and Juliet house and balcony.

Where to eat: We ate dinner at a local-recommended restaurant, Ristorante Greppia, which served excellent Veronese food and wine.

Day Four: Verona and Lake Garda

What to do: Our original plan was to take the short train ride to Lake Garda. However, we missed the local train, and the next one didn’t leave for three hours. We traipsed back through town and headed over the Ponte Pietra, across the street and up the funicular to see Castel San Pietro. The views from the top were breathtaking.

Afterward, we headed to the Museo Archeologico al Teatro Romano and returned to the station to catch the Lake Garda train.

Where to eat: Casamatta Bistrot, on the main street of Verona, was a great find. We enjoyed drinks with neat hors d’oeuvres like thinly sliced meats, bread and olives.

The Leaning Tower of Pisa in Italy 

Day Five: Pisa

How to get there: Pisa was a compact, walking city. Parking may be difficult if you rent a car. Besides an underground parking area near the train station, there were satellite parking lots around the city. Trenitalia trains are easy to book, efficient, and very clean. Our trip from Verona to Pisa took three hours by train.

What to do: The Leaning Tower was easy to find — just follow the crowd.

At night, Pisa was magical, the canals full of twinkling lights. It was lovely to wander down the main street and visit the many shops.

Where to eat: We used TheFork to make a reservation at Osteria San Paolo. My husband and I experimented with unfamiliar dishes and were satisfied with this cozy restaurant.

The living room of a Suite at Borgo alle Vigne, a Hilton Grand Vacations Club in Italy 

Day Six: Borgo Alle Vigne

How to get there: We finally headed to Borgo Alle Vigne on day six. The Pisamover shuttle took about five minutes to reach the airport, where we picked up our rental car.

How quickly and easily we navigated from the Pisa Airport to the resort surprised me. It’s about a 35-minute drive. Even though my husband and I can both drive stick shifts, we found navigating the Tuscan hills easier with an automatic car.

We stopped by a supermarket and picked up necessities like fruit, milk, coffee, pastries and wine.

Where to stay: Our stay at Borgo alle Vigne was the heart of our trip. Check-in was seamless. I was pleasantly surprised by how well-appointed our Suite was.

Here are a few of the things we loved about this resort:

  • Location, location, location. Borgo alle Vigne was close to the airport, train station, markets and points of interest like Volterra.
  • The views. I sigh when remembering the glorious sunrises and sunsets. We saw fireworks from at least seven locations on New Year’s Eve.
  • The Suites had fully equipped kitchens, including a stove, oven, microwave, dishwasher, fridge, freezer and combined washer/dryer. There were also pans, utensils, plates, silverware and glassware. Cleaning products and detergent were on hand, too.
  • There were useful printed materials about nearby points of interest at the registration desk, including Volterra, Cinque Terre and San Gimignano. The staff was also helpful and congenial.

Day Seven: Tuscany

What to do: We started the day by wandering outside the Fortress of Castruccio in Peccioli. Peccioli was an interesting town, with colorful, elevated walkways juxtaposing ancient walls and buildings. Next, we saw the Temple of Minerva. Lajatico was next on our list, the birthplace of Andrea Bocelli. We then headed to Lari, home of the famous Martelli Pasta factory and shop. It was closed on January 1, so we returned the next day and bought gifts and souvenirs.

A lake at one of the villages of Cinque Terre, Italy 

Day Eight: Cinque Terre

Tip: Read the fine print of every tour you book. We booked a tour ahead of time, thinking it would be the best way to see the five villages of Cinque Terre. We got lost, missed the group and drove an hour and a half to La Spezia instead. In hindsight, the train from Pisa to La Spezia was the best option to avoid toll booths.

How to get there: A dedicated train from Pisa takes you to all five villages.

What to do: We only visited the three middle villages: Manarola, Corniglia and Vernazza. Each town was unique. In Corniglia, we climbed 300 steps for breathtaking views. We took a much-needed break for lunch in Vernazza, where we enjoyed pizza and wine. Prepare yourself for stunning views and lots of walking.

A wine tasting at a winery in Tuscany, Italy, near Borgo alle Vigne, a Hilton Grand Vacations Club 

Day Nine: Tuscany

What to do: Most Tuscany vineyards near Borgo alle Vigne were closed for wine tours in December and January. I booked a tour and lunch with Poggio Amorelli in Castellina In Chianti, run by the Mazzarrini family. The individualized and instructional tour was a highlight of the trip. We tasted five or six glasses of wine that complemented lunch. It was a two-hour foodie experience that was just amazing. I bought bottles of their wine and olive oil to be mailed home to us.

The winery was set high in the hills, where we could see the church towers of Florence. There are Etruscan tombs down the road from the winery, and San Gimignano is on the way back to the resort for more sightseeing.

How to get there: It was a long drive on winding Tuscan roads to get to Poggio Amorelli from Borgo alle Vigne. We learned to be careful where we parked after getting a ticket.

Roman ruins in Volterra, Italy 

Day Ten: Volterra

What to do: Volterra was quite large, but many historical sites, stores and eateries were closed for the season. We ambled through the city’s many alleyways, visited the Rossi Alabastri Volterra for its famous alabaster and bought a pass at the Guarnacci Etruscan Museum. We couldn’t walk through the Roman amphitheater but saw the ruins from some nearby hills.

We left on the 11th day with wonderful memories. If you get the chance to come to Italy, don’t hesitate. Any season would be glorious at Borgo alle Vigne.

Travel Tips

  • A complicated trip requires considerable research and planning. I used several search engines to find the best airfare costs to travel into Milan and from Pisa.
  • The Trenitalia’s schedules weren’t available until late November. I booked and prepaid a train trip from Milan to Verona and then Verona to Pisa for our December trip to ensure we had a seat. First-class tickets weren’t much more expensive than coach prices.
  • We booked our tours ahead of time, especially for destinations we wanted to visit, like Lake Como. It’s also wise to make reservations for the restaurants. TheFork was an easy-to-use app similar to OpenTable.
  • Google Maps has an icon on the bottom left-hand side, which utilizes your phone’s camera to show the correct direction clearly. This was especially useful for navigating around Italy.
  • Be prepared for lots of walking on cobbled streets.

Read “Top Reasons Why I’m Ready To Go Back To Italy After My Tuscany Vacation With Hilton Grand Vacations” for another Owner’s review of Borgo alle Vigne.

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The Vacationeer

The Vacationeer is a collective of Hilton Grand Vacations storytellers whose goal is to inspire travelers to go further. We're always on the lookout for new destinations to explore, useful travel tips, and unique ideas to help you plan the most memorable vacations possible.

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