Two Weeks In Italy + Four Cities Visited = 6 Happy Family Members

Walking the streets of Florence
Walking the streets of Florence

It had been ages since our entire family had been together for more than a night or two – with two kids in college and one on the west coast and the other playing sports at college, our schedules just never seem to blend.  But with a lot of planning and promises from my kids, we carved out two weeks at the beginning of July to take our first family vacation to Italy.  I hired Insider’s Italy, a bespoke travel agent based in Rome to help me plan our trip.  After filling out an in-depth questionnaire about our families’ likes and dislikes I was happy with our 16 day, four city visit.  The day before we were scheduled to leave, i received a voicemail message from Delta apologizing for canceling our flights but that there was nothing they could do.  You can imagine my reaction.  I quickly called them back and after an hour of negotiation (trying to find 6 seats from NY to anywhere in Europe on June 28th is almost impossible) I suggested we look at flights out of Newark.  This came as quite a surprise – I guess the Delta manager had no idea that Newark and JFK were sort of interchangeable.  Regardless, we had 6 seats leaving at almost the exact time as our old flights.

We arrived in Florence on a Saturday around 11am and went directly to the first “hotel” we would stay in on our trip.  I quote hotel because it was called a Residence and that’s exactly what it felt like.  Since there are six of us and we are all large people, we always need three rooms (the boys, the girls, the parents).  We stayed at Residence Hilda  and the rooms were actually like one bedroom apartments.  They were nicely furnished with big bathrooms and even a small kitchenette.  But what we gained in space, we lost in service.  They have one person on duty from late morning to mid-afternoon and so for the most part, you are on your own.  As this was the first stop on our trip, I would have appreciated a front desk and concierge to help with some of my questions.  Thankfully Florence is small and easy to navigate and we quickly settled in.  The best part about the Residence was it’s location.  Once outside the front door, you looked to your left and the Duomo loomed large overhead.

I’ll skip the obvious stops in Florence but we had a few off the grid experiences that are well worth writing about.

Food Related Recommendations:  Carapina for Gelato – yes there are thousands of places to go for Gelato, but not like this one.

Dinner: Il Quattro Leoni – very cool neighborhood on the other side of the river, waitstaff had tattoos, dreads and lots of piercings but don’t let that get in the way of a very good meal.  Clientele also super cool.

Cafe Italiano – sounds like a pretty obvious name but its known for it’s Florentine steak and it lives up to its reputation.  There was a literal butcher standing in the middle of the room with a cleaver and a meat counter and you could hear the butchering all through dinner.

Experience: Santa Croce Church.  There are literally thousands of churches to see in Italy but for the next few months if you are in Florence you should put this one on your list.  It’s very famous for the people who are buried there – Michaelangelo, Galileo and Machiavelli to name a few superstars but that’s not why you should go visit before October.  Santa Croce has the most amazing frescoes that are in the process of being restored.  The paintings were done by Agnolo Gaddi at the time of the renaissance.  You actually get to walk up the five stories of scaffolding and look at the brush strokes and stare directly into the eyes of the paintings.  Our experience was even more special because our fabulous tour guide Paolo Vojnovic (you can find her on linked in) works at the church and the day we were there it was closed to the public so we had our own private tour of the church.

Experience: The Palio Race in Siena.  Siena is a gorgeous place to visit at any time of year, but go for the Palio and you are in for a very unique experience.  I had some inside information about going the day before, to the dress rehearsal and so we planned our visit for July 1.  I had read a lot about the race beforehand and part of the dress rehearsal events included dinners that each neighborhood threw to celebrate the

Setting up for one of the contrada dinners the night before the Palio
Setting up for one of the contrada dinners the night before the Palio

next day’s race.  I wanted to go to one of those dinners.  When I asked my travel agent she said that she’d never had that request before and she thought it wasn’t possible for foreigners to attend.  But I didn’t give up.  I kept reading and found a few posts by tourists saying they were able to score some tickets.  Finally, after enough emails on my part, she was able to find someone who worked at the Inn we would be staying at in Tuscany who had a cousin who lived in Siena and could score some tickets for the dinner.  The entire night was an experience I will truly never forget.  So if you happen to be in Siena the night before the Palio race make sure you beg borrow or steal tickets to the dinner.

Tuscany:  We stayed at Il Borghetto, an agriturismo in Tuscany only about 40 minutes outside of Florence near Greve.  Our rooms were separate from the main farm house with a patio that overlooked the olive groves.  The inn was situated perfectly up a hill and the famous landscapes of the tuscan hills were everywhere.  There was a small pool to cool off in and there was even an etruscan tomb on the property.  In addition to making their own olive oil and wine there was a large organic farm where much of the food that was served to us originated from.  It was in this inn that we had our best meals in Italy.

One of the best meals we ate in Italy
One of the best meals we ate in Italy

Platters of fresh fruit and salumi, followed by homemade papparadelle pasta with fresh zucchini flowers and a creamy pesto sauce.  Then a salad of garden vegetables finished with homemade peach ice cream.  And a few icy bottles of white wine grown in the region.

Experience: We spent most of the three days in Tuscany visiting the small hill towns that dot the area, each one a little bit different.  Our favorites were San Gimignano, Greve, Castellina and Radda.

Experience: Do not miss the outlet shopping.  It’s simply called the Mall and its not far from Florence or most places in Tuscany.  It’s unlike any mall I’ve ever been to.  Bring your passport so you can get the tax back forms filled out.  We had a ton of success in the Prada store as well as Loro Piana.  Make sure you have a few hours to see it all.

After three long days and nights in Tuscany we took a train to Amalfi where the vacation part of the trip began.  We had rooms at La Luna Convento which was a former monastery but had been transformed over two hundred years ago into a hotel. Its perfectly situated a few minutes walk from town but it also has its own fabulous pool from which you can jump off the rocks right in to the ocean.

The hotel pool at La Luna Convento
The hotel pool at La Luna Convento

Dinners: Eat at La Luna’s restaurant in the saracen tower across the street from the hotel.  Eat at da gemma in Amalfi. Request a table outside on the terrace.

Experience: La Fontelina Beach Club in Capri.  Call ahead and make a reservation for beach chairs (or mattresses which are very comfortable) and umbrellas.  Also book a table for lunch.  Take the ferry from Amalfi, or wherever you are on the Amalfi coast to Capri.  Ten minutes before you arrive in Capri, phone La Fontelina and they will send a small wooden skiff to pick you up at the Capri dock.  The boat will take you ten minutes into the ocean, around a curve and there, tucked into the rocky cliffs of Capri is a magnificent private beach club where you get to spend your day.  Even though its quite small, they have set it up so that you have your own private spot where waiters will bring you drinks (try the white fruit sangria) and you can jump in and out of the ocean all day long.  The restaurant is under a thatched roof with a magnificent view.  Just make sure to take the boat back in time to get the ferry back home.

La Fontelina Beach Club
La Fontelina Beach Club

Experience:  The Ruins of Pompeii: we hired a car, driver and guide to take us to visit Pompeii.  Just be forewarned.  Take motion sickness meds before you get in the car.  Several of us had a big problem with the twisting winding roads that you must traverse in order to get to Pompeii.

Experience: Rent a private boat with a guide and tour the area from the water.  Ask to have a meal in a restaurant not frequented by tourists.  Our guide for this excursion was Giocondo, a jolly 60 something man who was born and raised in Amalfi.  He can be contacted via the staff at La Luna Convento.

Experience: Ravello is a great town to walk around and have lunch.  We ate at the Hotel Parsifal with a spectacular view and an unforgettable meal.

After five nights of sun and fun in the water, we said goodbye to Tom and Tom – work and school were waiting for them.  The three kids and I boarded a train for the last few days of our vacation in Rome.  Our hotel was Albergo Santa Chiara which was situated perfectly behind the Pantheon.  There is so much to see and do in Rome that it seems silly that I would have anything to add.  But i’ll try 🙂

Experience: All of our custom tours were booked with Context Tours which is a company founded by Americans that hires experts in their fields of art, architecture and food to serve as your bespoke travel guides.  We had several and they were all amazing in different ways.

Experience: We did the Vatican museum on Friday night.  It was not as hot as it would have been during the day and it was a lot less crowded.  I would highly recommend going at that time.

Lunch: Cul de Sac.  Al Piccolo Arancio.

Rooftop Cocktails: Hotel Minerva.  Hotel Raphael

Hotel Raphael for rooftop cocktails
Hotel Raphael for rooftop cocktails

Dinner: Pompierre in the Jewish Ghetto.  Order the artichokes and arancini rice balls.

da baffetto for pizza

Gelato: We were in Italy for 16 nights.  We ate gelato at least twice a day.  But there was nothing that could even come close to Gellateria Del Teatro in Rome.  We built our days around it.  Just go and go often.

The best gelato we had in Italy
The best gelato we had in Italy

On the night before we were to leave Italy and return home, I asked the kids when they thought they would return to Italy.

Hayden said when he was 20.

Sophie said 22.

Annie said 35.

I said 53.

Let’s hope its not that long… Arrivederci Italy!

3 thoughts on “Two Weeks In Italy + Four Cities Visited = 6 Happy Family Members

  1. This is so funny! We are headed to Rome in 5 weeks. We are staying at the Albergo Santa Chiara. We are doing Context tours -the owners of the company are old friends of mine. Such coincedence! And we never even talked!

  2. This is great, Lisa! I really enjoyed it. Gary and I were thinking about going to Italy for our 10th wedding anniversary in May (well, I was, anyway!) and you have given some great advice. I am going to check out the place you stayed in Tuscany. If you ever go back, a great friend of mine rents out a trullo (only 2-bed though!) in Puglia. I think her company is called Yours Trulli ( her name is Anna Maggio). If the kids are old enough, I think there might be other Trulli you can rent out close by. Anyway, I understand from her that it has olive groves etc… Is just really beautiful.

    Great to see you are still writing – let me know if you are ever doing some travel-writing in London. We are back there now, after a brief stint in Hong Kong. Interesting, but not a patch on Japan – for me, anyway.

    Take care,
    Gaby xx

    1. will definitely look you up on my next trip to london!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this:
search previous next tag category expand menu location phone mail time cart zoom edit close