When your girlfriends call you at 11pm on a weeknight. You answer the phone.

View from Rooftop of Westin Excelsior Florence

When they ask if you want to go to Italy, because they are bidding on a trip at an auction. You say Yes.

This is how the trip started! Eight girls in a Tuscan Villa outside of Cortona, with a swimming pool and private chef. Yes, I love Italy...and you must know that by now. But a private villa in the countryside.. EVEN more so!

My mom had never been to Italy and I thought, if I am flying to Tuscany with my girlfriends...maybe the trip should extend and have her fly out and meet me in Rome. My sister, Dr. Dre would also be joining the trip and extending for a weekend in Rome.

The planning began:

Itinerary

Florence-1 Night,2 Days
Tuscan Countryside-7 Days
Rome-4 Days
Positano-3 Nights
Capri-2 Nights

Day Trips

Siena
Wine Country
Cortona
Pompeii
Sunday Market in Arezzo

I had the luxury of flying from NYC, the flight to Florence was direct. Florence is a city that I absolutely love. It's intimate and filled with history and beauty. I had been here once before, for Thanksgiving, but never experienced the city in the summer. My first trip was spent at Hotel Lungarno, which I highly recommend. It's a Ferragamo Hotel, located right on the river. It's a boutique hotel that was recently renovated. *Also, gives you free access to the Ferragamo Museum. We stayed in this gorgeous "castle" room with exposed stone in a tower. I felt like a modern day princess--no joke :) (SIDE TIP) If you love to run--> the Florence Marathon is during American Thanksgiving and it is supposed to be a great PR course. It's also a great time to visit Florence.

This trip I stayed at the Westin Excelsior Florence. I mainly chose this option, because it is an SPG hotel to earn points. The hotel is centrally located in the city, along the river, with walking distance to the train and every tourist destination. Florence is an exceptionally easy city to see by foot.

My girlfriends were arriving to Florence a few hours after me via train from Rome, and the other 5 girls would meet us at our Villa in Tuscany a day later. I rented a car at the Florence Airport. Driving was surprisingly easy, I rented a Fiat and have been learning Italian on Rosetta Stone and Duolingo for months prior (Road Signs weren't an issue! Speaking was a bit more difficult.)

The hotel allowed me to park right on the street outside the hotel, which couldn't have been more convenient. My friends had never been to Florence, so we were planning on packing in a full day and a half of tourism in.

After checking in...and having an Aperol Spritzer, we walked down the river towards the Boboli Gardens. SIDE NOTE: IF you haven't read "Inferno" by Dan Brown, you should. It helps so much with the landscape of Florence.

The Gardens are nice, more of a walking excursion. Then you can stroll across Ponte Vecchio, the very famous bridge that is the only one still standing from WWII. The bridge used to be covered with fresh fish, but the wealthy families (MEDICI FAMILY) said it smelled too badly, which I don't disagree would, and is now filled with jewelry shops. *Surprisingly enough, jewelry is not an interest of mine; however, it is definitely worth stopping at. You can barter on everything: so do so. Do not forget about the VAT tax for when you leave Italy. It adds up, but you must show the purchases prior to boarding flight, so don't pack the merchandise in your check-in.

After crossing the bridge, do stop for some gelato. I love the sorbet flavors, but that is just me, I'm not one for the sweets. On this side of the bridge, which is also the same side as the hotel, is the leather quarter and Uffizi Gallery and maybe the most notable: the Duomo. I recommend seeing the Duomo in the day time and at night. There are many fascinating places in Florence and all walking distance, but the Duomo is outstanding. At night, there is a merry-go-round in one of the squares close to the Duomo and shopping streets. I recommend getting a glass of vino or some gelato and taking a ride. It's very romantic.

There is a leather store called David 2 Leather in the center of the square, right around the corner from the leather market. Tell Franco, "your friend Ali from Chicago sent you," he will take care of you: show you beautifully tailored jackets to your liking and offer you some of Italy's best wine. I met Franco in Chicago, then went to visit him in Florence. I love him and you will too!

Our dinner on the first night was spent at Il Parione. This is a restaurant i've had the pleasure to dine at several times now and it's always intimate and exquisite. The owner is generally always there and he is adorable. *My recommendation is to dine in the basement if possible. It is their wine cellar with exposed stone. If you are noticing a trend: yes I love exposed stone! After dinner, just as I had priorly suggested. We grabbed gelato and headed back towards the Duomo to see at night. The three of us were very jet lagged, so the night crept up on us and we stayed out much later than anticipated. Luckily, we had the morning to sleep off our journey.

My little sister was meeting us the next day and then I would drive us to the Tuscan Countryside. Only first stopping at the Piazzale Michelangelo. It is a square with a panoramic view of Florence, there are options for wine, souvenirs, and gelato: located in the Oltrarno district. I recommend going here before sunset to catch the sky line, offers exquisite views of the entire city especially the Duomo.

This was our last stop in Florence, off to our Villa, located 10 minutes from Cortona! Ciao!

NOTABLE RESTAURANTS IN FLORENCE:

I'Parione
Trattoria Camillo
Trattoria Dante
Zaza pizzeria
Regina Bistecca
Osteria de' Cicalini

Villa: La Colombaia

As mentioned prior, the villa we were staying at holds up to 10 people. Several bedrooms, pool, private chef for breakfast and dinner, as well as a complimentary wine tasting...oh and a little black cat from one of the neighboring houses. I named him Felix and forever will love this little house guest.

The Route from Florence to the house was mainly direct and simple, except for our GPS. Google maps had slightly different plans; however, it was trying to shave off minutes. To the extent, we were taken on a route through a surrounding neighbor's backyard on a path barely wide enough for our car, with ditches on either side. Fortunately, I have learned the hard way (Bottom of a hill and trying to get into gear) and also being stuck in sand, to learn my gears and how to get us to the house. The drive was definitely a fun and interesting way to start our girls week in the romantic countryside of Tuscany.

Before arriving to Italy, we had a spreadsheet inquiring everyone's excursion requests for the week. 1. Wine Tasting 2. Siena 3. Sunday Market Shopping in Arezzo 4. Pool Day 5. Cortona and a few unplanned days to live on a whim.

After our first night, we realized quickly...we needed much more wine than purchased for the house. After an excursion to Siena, my car took a detour and ended up at a family owned vineyard. We grabbed a jug of red table wine for the dinners as well as a case of miscellaneous wine.

We were driving on a back country road, when we saw the sign for a winery: Fattoria Cantagallo. As we pull up to the driveway, an Italian man was mowing the lawn and saw us entering his property. He stopped and inquired about our visit. We expressed that we had interest in his winery. He smiled, hopped off the lawn mower and guided us to his basement. His son answered the door as well as his wife. They offered us homemade breads and cheese. They walked us through their wine collection set in the heart of the Tuscan countryside. Eduardo Capecchi, the son and winemaker helped by his mother and father, welcomes us into their cellar and gave us the most intimate experience. This was not what we intended to find, but this was exactly what we wanted. The four of us sat at the table, with their family enjoying wine and giggling about the fact that every other sentence was lost in translation.

La Dolce Far Niente, xoxo Ali, Jayme, Bryce, and Dre

One of my favorite parts of travel is the "no-agenda" plan. Hop in the car, grab a map and if something seems interesting, go and check it out. We do this a lot in Ireland and have come across the nicest people in the world. Italy is a country similar to that: kind people, amazing food and wine, endless adventures with winding back country roads, with stories to last the ages. The memories of a trip generally always come from the people you meet not the things you see.

Dinners at the house were mapped out by our chef: Gabrielle

On one of our last nights in the house the group made dinner from scratch as well as our dessert: tiramisu. We rolled out pasta and made a classic Tuscan pasta sauce with bacon blended in a food processor. We enjoyed wine and our meal with Gabrielle, our chef who lives in Cortona and speaks several languages (unlike most of our group.)

Breakfasts were prepared for us and set at the table every morning by the time we woke. I enjoyed waking early and running through the local village before everyone was awake and coming home to breakfast with fresh fruits, strong coffee, and always an Italian flatbread. One morning, I went for my usual run through town and a large group of men were gathered outside laughing and telling stories. I wasn't...and am still unsure if they arrived incredibly early to breakfast or still had not made it home.

The next agenda on the to do list was wine tasting!

Winery:

La Braccesca : the vineyard lies on both Montepulciano and Cortona creating the unique capability of creating traditional noble wines of the north and Syrah of Cortona. The property was previously owned by the Count of Bracci and Marchesi Antiori now owns the Estate. * The vineyard produces a wine called "Bramisole" which if you recall from the movie Under the Tuscan Sun is the name of the villa Diane Lane purchases in Cortona.

We had a traditional wine tour, followed by a tasting paired with an overwhelming amount of food. After indulging our taste senses, we headed back to enjoy our pool with plans to see Cortona in the evening.

Cortona is a great town we were fortunate to be 10 minutes from. We went there a few times for lunch and dinner, one night we did a wine tasting in the center square. The town is great for souvenirs with wine shops and places to buy cheese and olive oil. There are plenty of options for dining and grabbing snacks.

One afternoon we hiked to the top of Cortona to see the church, this was a much steeper walk than anticipated, but worth it for the view of the countryside.

Restaurant on the top of Cortona overlooking Tuscan Countryside

Every night there was a beautiful sunset. We would gather in the backyard or the field across the street with our wine and enjoy the moment..... Sometimes making album covers....as shown below!

Overall we had a fun packed trip exploring local towns, wineries, and excursions. In my next post, I will expand on our trip to Siena as it deserves it's own post! The sunsets never disappointed, the wine never left us thirsty, and our appetite was never starved! The Tuscan region is romantic and relaxing, beautiful and savory, and a must on your Travel Lists.

This will be my first post in a series of posts about my travels to Italy this summer, still to come:

Siena
Rome
Positano
Capri
Cinque Terre
Lake Como
Venice

Until Next Time, Safe Travels xoxo

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