Ann’s Tuscany Adventure

I’ve been to Tuscany before, but always with Florence as my home base. Doing day trips to Siena or Lucca, or heading out into the countryside for a day of winetasting before retreating back to the city. When the opportunity arose to spend a whole week in Tuscany, I jumped at it! 

The focus for this trip was romance travel (destination weddings and honeymoons). We had the opportunity to tour some gorgeous properties and meet some fantastic local business owners (florists, caterers, event planners, and photographers). And, of course, eat and drink some amazing local food and wine.

If you’ve ever dreamed of getting married in Tuscany, we can absolutely hook you up!

[Photo: The dining hall of Corte dei Papi villa in Cortona]

But I am really excited about Tuscany in general, and what a different experience it offers vacationers when compared to the big cities.  


We stayed at the Buccelletti Casali and Cantina, in Castiglion Fiorentina. It’s a charming property that has been in the Buccelletti family since 1625. They’ve been growing olives and making olive oil for generations, and they now make wine as well.

They have converted the old farm workers’ houses into clusters of villas and apartments. Plus, they’ve turned the olive oil mill into a stunning event space. It was the perfect home base for a week spent exploring the surrounding countryside.

[Photo: Buccelletti Casale and Cantina]

The accommodations themselves were the first big difference from previous trips to Italy. I was in a cute little house with two bedrooms and bathrooms, a living/dining area and small kitchen, and a private yard/garden.

We could prepare our own breakfasts of farm-fresh eggs, homemade bread, and locally produced yogurt, jams, honey, and fruit. We had bottles of wine and olive oil produced right there on site. And the cuisine could not have been more “farm to table”. So different from staying in a hotel! 

When you’re out in the country at an agriturismo like this, it does help to have a car, so that you can get out to the local shops and markets. But at the Buccelletti Casali, we had a basket of provisions (replenished mid-week) and it was more than enough for breakfasts and snacks.  

The Countryside

We were a group, with a very organized itinerary (and drivers/guides), but I would highly encourage clients to rent a car and enjoy a more independent stay in Tuscany. The roads are great, the traffic is light, and they drive on the right side of the road. It’s very manageable for American drivers.

[Photo Credit: MIP Studios via Shared Adventures – a road in Cortona]

While we were there, we had a busy itinerary filled with site inspections at hotels/inns/B&Bs, guided tours of Tuscan hill towns, tastings at local vineyards, and many lengthy multi-course meals with wine pairings. Brutal, I know.

We learned how cheese is made. We met mayors, hoteliers, restauranteurs, and the fascinating couple who purchased and renovated the villa featured in “Under the Tuscan Sun”.

[Photo: Ann & Kristy at Villa Laura]


Some of the highlights, for me, included: 

  • Cortona – a town of steep streets, gorgeous views, Etruscan history, and tempting shops.
  •  Pici – traditional hand-rolled Tuscan pasta, made from just the “poorest” of ingredients (flour and water).  
  • Podere il Casale – a pecorino cheese producer, organic farm, and farm-to-table restaurant outside of Pienza, where we enjoyed a fabulous meal completely sourced from right there onsite. (So delicious that I purchased and carried home their very heavy hardbound cookbook in the hopes of recreating that magic
  • Brunello di Montalcino wines – made with 100% Sangiovese, bold and fruity, one of the best Italian reds!

The Tuscany Takeaway

Tuscany is all about the slow food movement, slowing down to take it all in, and enjoying the views.

There’s no long list of “must-sees”. You can while away an afternoon (guilt-free) sitting by the pool sipping wine and snacking on prosciutto. Or riding an e-bike through the countryside. Or rolling up your sleeves for a cooking class.  

I realize now that I was doing it all wrong when I visited Tuscany as a quick side trip from Florence. Tuscany invites you to stop, linger, indulge, experience, and enjoy. And I can’t wait to come back and do it all again! 

[Photo: Villa Le Prata in Montalcino]

Easy, Breezy Italy

Loved, loved, loved receiving this feedback from Jaime and Matt!  Not just because they had such a fabulous time in Italy, but because it was the little touches (great guides, fabulous and reliable drivers, pre-arranged train tickets, and helpful concierges) that made such an impression on them. Anyone can plan a trip to Italy, but a true travel professional knows how to make it all seamless so that you can just relax and enjoy the ride 🙂

Hi Ann!

We can’t thank you enough for your amazing planning expertise. Our trip was wonderful and your itinerary made it so easy.  I could have seen us making some mistakes with language barriers and perhaps booking trains and maybe making an error so we both agreed it felt so nice to have a professional take care of all the arrangements so we could just relax and enjoy!! Not to mention the hotels were amazing and in great locations.

I’ll start with Aer Lingus… really nice flight, the red eye on the way there was a bit difficult. I was a zombie pretty much the first day but we did push through as you recommended and I was fine the next day. On the way back, Aer Lingus was a bit hard to find in the airport in Venice but we also arrived 3 hours early so we had to wait for them to set up their check in. That could be a bit confusing for people if they arrive early like we did… also Aer Lingus seemed to share check in space with Jet Blue. The flight back was much better as we got back around 8 pm from Boston and it was really 2 am for us so we were able to go right to sleep and then wake up this morning being fully rested and ready to go to work. It was helpful that we cleared security in Dublin and when we made it back to Boston we were already done. It was nice you gave us a heads-up because that could potentially be a bit confusing it seemed like we had to go through twice.

Our driver who met us at the airport in Rome was wonderful and awaited us with a sign with our names. Made it super easy and nice to have someone waiting. He even bought us a cappuccino since our driver was running a few minutes behind schedule but our driver was amazing! So helpful, informative and spoke great English… I would definitely use Rome Cabs again!

River Palace was awesome! The people at the desk were so helpful and informative. They gave us a complimentary bottle of wine. The hotel was in a great location. We felt very safe and were able to walk to sites. The concierge provided a map and circled places of interest, called cabs, and were just generally friendly and helpful. It really felt like a little home for the few days we were there. I loved all the detail you provided on the itinerary about local city tax and credit card for incidentals… etc… just helped us know what to expect. The concierge also confirmed our tours for us!

We loved our tour guide for our Colosseum tour. His name was Gigi he was so passionate about the information and very funny! The only thing I would say about this tour is again we arrived very early to the meeting place and were a little worried because it wasn’t an office it was just a park, but as soon as it got closer to the time of the tour we saw plenty of people also waiting, i think initially we just weren’t sure we were in the right place.

Our Vatican tour was also really great, we liked that the meeting place was in an office and we actually showed up right on time for this one so we were very lucky it was easy to find!

Next we set off for the Naples train station. We were happy you shared to be vigilant. We didn’t run into any problems but we did witness a man take advantage of some ladies traveling alone. He grabbed their luggage despite their protest and took the bags on the train, then he stood there until they gave him some money and when they gave him one euro he was not happy and let them know it!! Just another heads-up story for people about the train station. He wasn’t in uniform but wore clothes very similar to one and was sort of an imposter, asking to see people’s tickets to try to confuse them into thinking that he was an employee and then grabbed their bags and demanded tips.

Next we met our absolute favorite driver!! His name was Carmine and he was just the sweetest! He was practically giving us a tour on our drive and was super friendly! The only thing was we thought we could pay by credit card and he said it was cash only so we were just happy we had enough…

Posa Posa was a great hotel in Positano. It was more basic and more beachy feeling with a tile floor and just basic furniture, did not have a luxury feel like the Rome hotel but we were happy with the mix. Plus, the balcony was amazing! We literally woke up to a view of the sea, it had a table and chairs out there so we were able to sit and drink wine and relax!! That was our same view for the breakfast each morning as well! The people working at this hotel were also very nice and helpful with anything we needed. It was a great location. A few restaurants in Positano that we greatly recommend are di Vincenzo’s, Constantinos, and a very cool experience where you get taken to a place without a menu and they serve you a 6 course meal for 40 euros made by “mama” called La Tagliata. We hiked the Path of the Gods while we were there and took a boat to Capri which we recommend. Our driver back to Naples was also very nice, (he knows you) Fabrizio.

honeymoon couple in front of Italian grotto

The trains that you booked were fast and easy. We loved not having to purchase tickets and just having to hand them to the staff!!!

Our Florence hotel was amazing!!! So swanky haha… the breakfast was quite impressive!! They hooked us up with some champs, and aperitivo, when we arrived.  I think if we had to do it all over again, we would have done one more night to explore more in Florence and one less night in Venice, just our personal preference.

The only time we “messed up” was we didn’t realize you booked our rental car pick up at 10 am and we didn’t show up until 12-1. It didn’t end up being an issue. We picked up the car and put it in a lot so we could spend a few more hours exploring Florence before driving out into the countryside.

The next part of the trip was probably our favorite!!! We absolutely loved Radda in Chianti! The view from our room in our hotel looked like a back drop or a painting!!! We absolutely loved this hotel and Linda our favorite receptionist. She sent us to 3 wineries, one a small family run and two others, one was a castle, and one an old monastery.  We did not expect so much history on our wine tasting tour but it was so interesting!! The mom and pop winery gave us a free tour and tasting and of course we bought some amazing wine! But it was pretty cool to have a private tour and see how the wine is made, and a private tasting as well!!!! We also drove to check out San Gimignano and Siena  — very cool to explore. Returning the car was very easy and the car came with a gps which made navigation a breeze.

a view like a painting! Honeymoon at Radda in Chianti, Italy

Our least favorite part of our trip was Venice. It’s very cool to see because it’s unique, but we just loved the other places so much more. The hotel there was just ok compared to the others as well as the concierge and location. We had been so spoiled though to be honest… we got off the train and found the water bus without a problem… it was only 7 euro each for a one way, and only took about 45 minutes, plus the boat ride was pretty cool. We did the same on the way back to the airport, all the people at the waterbus ticket stations spoke English and were able to explain exactly what to do to catch the waterbus back to the airport. It was only 15 euro each and took about 1 hour and 30 minutes as opposed to 30 minutes with a private taxi. We were happy to save a few bucks here and it worked out with our flight times so we didn’t mind that it took a bit longer. We didn’t really feel like we even needed too much time in Venice as we were kind of spent on seeing churches and sites and just wanted to chill at this point.

a honeymoon in Italy wouldn't be complete without Venice

The only other thing we wished was that we gave ourselves a bit more spending money in our overall budget because we did end up spending twice as much as we thought we would. We never skipped wine at dinner and always had more than one course haha… plus we shopped a bit to bring back wine and leather 😬

a happy man across a huge pizza in Italy

Overall we felt like our itinerary was a great mix of adventure, relaxation, sight seeing, and learning/ touring. Italy is our new favorite place and we absolutely want to return!!! The people were great, food amazing, views incredible, wine delicious, and just overall history and culture so interesting and impressive.

a smiling honeymooner on a wall with beautiful rolling Italian hills

Thank you so much for your time and attention to detail with planning this trip. We kept mentioning how incredible it was that after only meeting once, we felt like you completely got our vision and nailed it!! We loved that you yourself have used some of the vendors on your own trips! We will definitely be calling you as soon as we save up for our next trip and send our friends your way!!

With gratitude,

Jaime and Matt

Eating and drinking our way through Italy

Taste of Tuscany — October 2012

I just returned from a food-and-wine-focused group “escape” to Italy, and I can’t wait to share my feedback and photos from this amazing experience. We were a small group (fourteen people in total), escorted by my favorite chef (Kait Roberts, owner of Easy Entertaining, Inc.), and we had a wonderful time eating and drinking our way through Tuscany!

My husband and I flew over a couple of days early to spend some time in Rome before meeting up with the rest of the group in Florence. We arrived at the Rome airport at about 9 am on a Friday morning, and were met by a driver from Rome Cabs, who successfully navigated the rush hour traffic and delivered us safely to our hotel – the BorromeoDespite the early hour, the room was ready and we were able to check in right away (a great surprise!)  The room was quite small, but the hotel is a clean, safe, three-star property in a great location on via Cavour, within easy walking distance of the train station and the Colosseum, and it served us well as a place to sleep for two nights, which is all that we wanted.

standing in front of a domed church in Italy

After a shower and a brief nap, we took a cab over to the Vatican to grab some lunch before our afternoon tour. We enjoyed our first taste of Roman thin-crust pizza (pizza Margarita for me, and a pizza rustica — white pizza with prosciutto — for him) and their house red wine. Ahh, Italy 🙂

Our four-hour guided tour that afternoon (by Dark Rome) included skip-the-line access to the Vatican Museum, Sistine Chapel, and Raphael’s Rooms. It was great to have the guide providing history and context for everything we were seeing, but the sheer volume of art surrounding us was a bit overwhelming (especially when working on two hours of sleep!) In retrospect, while I’m really glad we got the chance to see it, I don’t think it was the best idea to tackle the Vatican on our arrival day!

inside the Vatican in Italya marble statue of Mary and Jesus in Italy

After the tour, we cabbed back to the hotel (TIP: be sure to ask the price before you get into the taxi; we found that quotes varied greatly, and we haggled to get the best one) and asked the front desk to recommend a nearby restaurant for an early dinner. At their suggestion, we walked a few blocks up the street to Trattoria Nuova Stella for a dish of pasta, a bottle of wine, and some tiramisu.  It was fine, and exactly what we needed at that moment (quick, close by, and plenty of available tables), but nothing to rave about.

Saturday morning, after a nice restorative sleep, we were up and out bright and early for our morning walking tour of Ancient Rome (with Dark Rome, once again). We grabbed a cappuccino and cornetto along the way, and met our guide just outside the Colosseum. This fascinating four-hour tour included the Colosseum, the Forum, and Palatine Hill, and I would recommend it to everyone. They provided so much background and history that it really made these ancient sites come alive in our imagination!

the inside of the Colosseum in Rome

After the tour, we grabbed our map of Rome and set out to see the rest of the city on foot. Of course, we first had to find a trattoria with a little outdoor terrace (In Roma restaurant, on the Piazza de Consolazione) so we could sit down and enjoy some bruschetta, gnocchi, red wine, and my new favorite pasta dish – “cacio e pepe” (pecorino and pepper). So simple, but so delicious!

Suitably fortified, we wandered all over the city, to the Piazza Navona, the Pantheon, the Trevi Fountain, the Spanish Steps, the Quirinale, the Medici Villa and its beautiful gardens overlooking the city, the Piazza Barberini and the Triton Fountain, and more. It was a lot of walking in one afternoon, but Rome was worth it.

a busy street in Italythe trevi fountain in Rome

That evening we met up with friends for dinner (they had arrived that day) at Da Giovanni, which had been recommended by Chef Kait (from her student days in Rome).  What a find! It was an out-of-the-way little place filled with locals, and it felt like we were eating in my husband’s grandmother’s kitchen. We feasted on homemade pasta, grilled meats, local cheeses, and house wine, and the whole tab (for six people) came to about 140 Euros. On the leisurely stroll back to the hotel, we somehow found room to stop for gelato 🙂

Sunday morning we enjoyed breakfast on the hotel’s rooftop terrace and then checked out and walked to the Termini train station (about 4-5 blocks away). We already had our tickets, so it was a fairly simple matter of figuring out which track we needed and, before we knew it, we were on our way to Florence. After a 90-minute (scenic) ride, we arrived at Florence’s Santa Maria Novella station. From there it was an easy walk to our hotel – the Hotel de la Ville.

the famous Duomo in Florence

The entire group stayed at this hotel, a lovely four-star property on a quiet pedestrian-only street (the Piazza degli Antinori) just three blocks from the Duomo. We loved the large lobby bar (presided over by the friendliest bartender I’ve ever met), the daily breakfast (my morning cappuccino sported a different decoration every day!), and the gorgeous two-floor suite that they upgraded us to. Less wonderful was the ongoing problem with air conditioning (some rooms had none; some had too much), and the sometimes “chilly” front desk staff. All in all, though, it was a great home base for exploring the city.

standing by the window in the Italian Hotelthe front of the Hotel De La Ville in Italy

Sunday evening the whole group met up for the first time for happy hour in the lobby bar and a welcome dinner right there at the hotel. It was the perfect way to break the ice, and it set the right tone for the rest of the week.

Monday morning we met in the lobby for a half-day guided walking tour of Florence. Our guide, “Yadri”, was an art historian with a real passion for the social and cultural history of the city, and she gave us a fantastic overview as we explored the Medici Chapels, the Duomo and its Baptistry, the Piazza della Repubblica, the Piazza d. Signoria, and the Ponte Vecchio. After the tour our afternoon was free, so several of us enjoyed some paninis and a little bit of shopping.

We met up again at the hotel that evening for a highlight of the trip – our authentic Tuscan dinner at Ristorante del Fagioli, another one of Chef Kait’s local favorites. They welcomed us with open arms into this cute little local “find”, and Kait ordered for the whole table. The rest of that evening is a blur… the dishes just kept coming! Antipasto, bruschetta, bottles of homemade wine, several kinds of fresh pasta, porcini mushrooms, potatoes, and the star of the night – the Bistecca Fiorentina (the beef is hanging in the open kitchen and they hack off the desired amount to bring out for your approval before putting it on the grill!)  The whole thing was unbelievably inexpensive, and we left stuffed and happy.

a crowd looking at the David in Florence

Tuesday morning was drizzly, but we grabbed our umbrellas and met up with our guide for a half-day tour of Florence’s most famous museums – the Accademia and the Uffizi Gallery. This was my first visit to the Accademia, and I was not prepared for the impact of Michelangelo’s “David”. No matter how many times you’ve seen it in pictures, experiencing the real thing in person is just breathtaking!

two cups of coffee with cute decorations in Tuscany

After our morning in the museums, we had some more free time to explore Florence on our own. Several of us stopped into Trattoria Anita (yet another Chef Kait recommendation) for a “workman’s lunch” with the locals. We were clearly the only English-speakers there, and they did seat us in a separate room, but it was more than worth it for the decadent “pasta quattro formaggio”.

Later that afternoon we all boarded a mini-bus for our first excursion — a winetasting in Greve in Chianti. We drove through the beautiful countryside to Castello Vicchiomaggio, where we enjoyed  breathtaking views over the Tuscan hills and a tour of their winemaking facilities. We also tasted their Chianti Classico and some delicious super-Tuscans.  Needless to say, after such a busy day, we had a quiet ride back to Florence and an early dinner and bedtime.

walking through the narrow Italian streetsa wine cellar in Italy

Wednesday morning we re-grouped in the lobby for an informal walk around the city with Chef Kait. She introduced us to her favorite coffee shop, her favorite vendors in the San Lorenzo market, her favorite shoe store, jewelry store, etc. It was great to have these personal connections, and I know that many in the group took advantage of them (I saw lots of new leather jackets and silk scarves by the end of the week!) Then we picked up paninis to go and hopped back on the mini-bus for a daytrip to Lucca.

a fruit market stall in the Italian streetsa view of Ponte Vecchio in Florence

Along the way, we visited a beautiful little agriturismo called Fattoria di Fubbiano. It was up a treacherous winding road in the hills outside Lucca, but it was more than worth the scary drive! The scenery was gorgeous, and we were treated to a crash course in both wine-making and olive oil pressing, and then enjoyed an over-the-top tasting experience in an ancient wine cellar, with locally made cheese and honey, their own olive oil, red and white wines, Tuscan salami, bread, and more.  The white wine was so good that we purchased several bottles to enjoy during our cooking class the following night.

a view of the lush green Tuscany hills dining at a long table under stone arches in Florence

After the wine tasting we stopped in Lucca for a short visit. Some of the group headed into the center of town with Kait for coffee, shopping and sightseeing, while the rest of us took a relaxing stroll along the top of the ancient city walls.  Back in Florence that evening, some of us had dinner at an outdoor trattoria on one of the main piazzas, and another visit to what was quickly becoming “our” gelato shop – Grom, on the via del Campanile.

Thursday was our last day in Florence, and we made the most of it! We met Chef Kait bright and early for a visit to the Mercato Centrale to shop for ingredients for our cooking class. Everyone marveled over the huge market filled with specialized vendors selling only the freshest local produce, meat, cheese, and other products. It took hours for us to see, taste, and decide on everything, and we loved it! We spent the rest of the day shopping and exploring on our own, and then met up at the hotel for a short bus ride to Syracuse University’s villa on the outskirts of Florence, where we had rented the kitchen and courtyard for the evening for our cooking class.

shopping for fresh foods at the market in Italydeciding which salami to get in a market in Florence

Chef Kait assigned the “boys” to assemble the antipasto while she toasted some bruschetta and demonstrated her talent at making homemade pasta (it looked so EASY when she did it!) She taught us two quick pan sauces (one with dried and fresh porcinis and cream, and one with tomatoes and garlic) and fielded a wide range of questions from novice and experienced cooks, and then we dug in. The wine flowed freely, and it was as if the fourteen of us had known each other forever.

learning how to make pasta at an Italian cooking class

Friday morning came all too soon, and we packed up and checked out of the hotel. The lucky ones were continuing on to Venice, Rome, or another Italian city, but Everett and I were headed home to the kids.   One quick connection in Frankfurt, and then we found ourselves back at Logan Airport with nothing left to do but daydream about our next trip to Italy.

If you want to see more. The photos from Rome and Florence are available on my Facebook page. And a short video of our market visit and cooking class can be found here. We’re already working on another trip for 2013, so let me know if you’re interested!

Taste of Tuscany 2012

I’m thrilled to announce the third annual “group escape” for Annie’s Escapes’ clients, friends and family. This year, we’re teaming up with Chef Kait Roberts from Easy Entertaining, Inc. to jointly host a delicious five-day exploration of the sights, sounds and tastes of Tuscany!

The trip is scheduled for October 7 – 12, 2012 (which conveniently includes the Columbus Day holiday) and the detailed itinerary (and pricing) can be found here. We’ll be basing ourselves in Florence, with day trips to Chianti and Lucca, and will be enjoying some unique tastings and tours, as well as a hands-on cooking class with Chef Kait.  For those who are interested in extending their vacation, we can also help with pre- or post-tour visits to Rome, Venice and more.

The group size is limited to 16 people total, and we expect it to sell out quickly. The land-only price is $1,750 per person (based on double occupancy) and airfare and insurance are additional. If you are interested, please let me know as soon as possible. Call 401-270-4834 or email me at

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)