Three Days in Tuscany

March 23-26, 2023

I had been trying to get my father to come visit me and Andy from the moment we knew we were moving and I started planning out what we wanted to do with him as soon as he booked a trip. It was Dad’s first time in Europe and, naturally, I wanted to take him to a place I knew he would absolutely love: Tuscany. Andy and I hadn’t visited Tuscany together since our two-week trip to Italy in 2019, so we were equally as excited to simply be back in one of our favorite places.

We arrived in Florence on Friday afternoon and headed straight to Oltrarno Splendid, a fantastic boutique B&B in an 18th-century palazzo in my favorite neighborhood in the city. Our rooms were beautiful and the location couldn’t have been better, but we immediately headed across the River Arno to do some sightseeing before things shut down for the evening. Most importantly, I wanted to take Dad to Scuola del Cuoio, a leather workshop located in the former dormitory of the Franciscan Monastery of Santa Croce that was initially donated to the friars by none other than the Medici family. Aside from being an absolutely stunning property, Scuola del Cuoio also sells some of the most beautiful (and reasonably priced) handmade leather goods in the city. After our successful shopping excursion, we headed back to Oltrarno and happily changed our focus to introducing my father to Florentine food and wine, starting with incredible charcuterie and a few glasses of wine at Il Santino before dinner at Ristorante Trattoria Angiolino.

The wine tour portion of our trip kicked off the next morning in Chianti, which covers a surprisingly vast and mountainous stretch of Tuscany that includes several overlapping Denominazione di Origine Controllata (DOC) and Denominazione di Origine Controllata e Garantita (DOCG) production zones. We spent most of our time safely within Chianti Classico DOCG territory, but our first stop was at Castello di Nipozzano, an 11th-century estate in the Chianti Rufina sub-zone owned and operated by one of the most prominent Florentine noble families. The Frescobaldi family is in their 30th generation of producing wine at Frescobaldi Toscana, and the high-quality experience (and incredible wine) offered at the oldest of their eight estates in Tuscany was a perfect introduction to the region. After lunch and a three-wine tasting at Castello di Nipozzano, we stopped for a quick tour and tasting at the lovely Castellare di Castellina before making our way to our stunning accommodations at Castello di Fonterutoli in the heart of Chianti Classico. We relaxed a bit and enjoyed an excellent bottle of the estate’s wine before heading to dinner at the 12th-century Castello di Albola, one of the highlights of the entire trip.

Dad specifically requested incorporating the beach into our trip, so we set out on Sunday morning for the Costa degli Etruschi (Etruscan Coast) in search of fresh seafood and Bolgheri wines. The absolutely crazy ~two-hour drive from the hills of Chianti to the coast of the Tyrrhenian Sea (part of the Mediterranean) was not for the faint of heart, but the hairpin turns and dramatic elevation changes were immediately forgotten as soon as we arrived at Restaurant La Pineta in Marina di Bibbona. It looked like a beach shack in the middle of nowhere at the end of an unpaved road through a stone pine forest, but this family-owned restaurant has a Michelin star and the meal we had here was nothing short of perfection. Our table sat above the waves crashing onto the beach, and the service and the wine were just as wonderful as the freshly caught seafood.

After lunch, we checked into our final bed and breakfast, the absolutely lovely Locanda dell’Aioncino in Bibbona. Dad decided to take a nap, but Andy and I powered through and made it to our final wine tasting at Podere Il Castellaccio. The estate is run by a husband and wife, and we had a phenomenal private tour and tasting with the latter. The wines were incredible on their own, but our conversation with Enrica was really what made the experience so special. She gave us an excellent crash course on Bolgheri wines, a relatively young DOC that has quickly become one of the most popular and prestigious Italian appellations. This introduction to the area’s wines and history set us up perfectly for dinner that evening at Osteria Enoteca San Guido, the fantastic restaurant operated by the producer of Sassicaia, the legendary wine that started the ‘Super Tuscan’ revolution and put Bolgheri wines on the map.

From the wines to the food to the absolutely perfect weather, our trip was everything I had hoped it would be and it’s hard to say which of the three of us enjoyed it more. All I know is that our three days in Tuscany with my Dad (and the time he spent with us back in London) will forever be one of my favorite memories from our European adventures.

If you’re planning a trip to Tuscany, click here to access and download my Google Maps list of saved locations in Italy. You can also check out my earlier post about our two-week trip in 2019 for additional recommendations for Florence and Val D’Orcia, among other places.

Food & Drink

• Florence
  • Ristorante Trattoria Angiolino – Ai 13 Arrosti: Ristorante Trattoria Angiolino is the perfect introduction to Tuscan meats and wines, which made it ideal for our first meal in Tuscany…especially since it was just down the street from our hotel in Oltrarno. Andy and I ate at this traditional and family-run restaurant during our first trip to Florence in 2019, and the bistecca alla fiorentina has been just as amazing each time we’ve visited.
  • Il Santino: The little sister and neighbor of the popular Santo Bevitore restaurant in the trendy Santo Spirito district of Oltrarno is a tiny, cozy wine bar and deli with just a handful of tables and barstools. Despite its size, Il Santino serves top-notch snacks and an excellent menu of local wines from smaller producers. We all agreed that the charcuterie and starters we had were some of the best dishes we had on the entire trip.
• Chianti
  • Castello di Nipozzano: Just a half-hour drive from Florence, the incredible Castello di Nipozzano is the oldest of the estates belonging to the legendary Frescobaldi family, which has been producing wine in Tuscany since 1308 and is one of the largest and most influential winemakers in the region. The property is characterized by an 11th-century castle overlooking the Arno that was originally one of the family’s summer homes and now houses the family’s truly impressive private cellars containing wines dating back to the 19th century, a small portion of what remained after Nazi looting and destruction during World War II. We had a lovely tour of the property and production facilities, followed by an incredible lunch and three-wine tasting in a private room containing a beautiful and gigantic 18th-century fireplace.
  • Castellare di Castellina: Our first stop in Chianti Classico proper was at the utterly charming Castellare di Castellina, a 70-acre estate in the commune of Castellina that is known for its commitment to only growing and producing local grape varietals, as well as its unique watercolor labels featuring local birds and flowers. Our private tour and five-wine tasting lasted an hour (and was just €25 per person), which made for a perfect pit stop on the way to our hotel.
  • Castello di Albola: The medieval village of Castello di Albola sits just north of Radda in Chianti among some of the highest hills of Chianti Classico (up to 2,100 feet above sea level) and the tour, tasting, and dinner we had here comprised one of the highlights of our entire trip. We booked the Premium Dinner Experience, which included a guided tour of the 12th-century castle and its historic cellars, followed by a wonderful dinner paired with some of the estate’s most notable wines. Everything about the experience was absolutely phenomenal (especially our tour guide, Danny) and we enjoyed the wine so much that we ended up shipping two cases of the Chianti Classico back to the U.S.
  • Castello di Fonterutoli: We stayed at a magnificent 275-acre estate in the heart of Chianti Classico that has been owned by one of the oldest and most influential winemaking families in the area since 1435. The Mazzei family’s history is absolutely fascinating (for example, in 1398, Ser Lapo Mazzei wrote the oldest-surviving reference to the Chianti wine denomination), and everything about our experience at Castello di Fonterutoli was equally impressive. Even though it describes itself as a ‘wine resort’, the accommodations were genuinely charming and felt much more like a tiny bed and breakfast. We didn’t take a formal tour, but we had an excellent breakfast at the osteria, which exclusively featured fresh local produce, and also enjoyed a bottle of wine in the informal tasting room (which doubled as the hotel reception area).
• Bolgheri
  • Restaurant La Pineta: Despite being directly on the beach at the end of an unpaved road through a pine forest and looking like a fisherman’s shack from the outside, the Michelin-starred Restaurant La Pineta serves what is almost unanimously considered to be the best seafood in Tuscany. The Zazzeri family of fishermen opened the beachfront restaurant and lido (swimming area) in 1964 and to this day, the family still operates three fishing vessels—an uncle delivers fresh-caught fish and crustaceans directly to the kitchen every day. We sat behind one of the picture windows offering an almost surreal view of the waves crashing into the beach just below us and the food (especially the grilled fish), wine, and service couldn’t have been more exquisite.
  • Podere Il Castellaccio: A smaller and relatively new wine producer, Podere Il Castellaccio primarily grows local Sangiovese, Pugnitello, and Foglia Tonda grapes, which is unusual for the area but resulted in some of the best wine we had on our entire trip. The gorgeous property had breathtaking views of the medieval hilltop village of Castagneto Carducci and the ocean in the distance, and we had an absolutely wonderful tour, tasting, and conversation with Enrica, who co-runs the estate her husband’s family has owned since the 1960s. There were also several recently renovated apartments available for guests that looked just as fantastic as the rest of the property.
  • Osteria Enoteca San Guido: Tenuta San Guido, producer of the legendary Sassicaia, isn’t open to the public for tours and tastings. However, they do operate a wonderful all-day restaurant and bottle shop with an impressive selection of top wines located in a lovely garden space just off Bolgheri’s famous cypress-lined avenue. We had a fantastic dinner here on Sunday and thoroughly enjoyed the range of options featuring local Chianina beef—and some incredible Bolgheri DOC wine, of course.
  • Locanda dell’Aioncino: We stayed at a fantastic B&B in Bibbona, just at the edge of Bolgheri. The accommodations were great, but the highlight of the property was definitely its restaurant. The outdoor seating areas were perfect for enjoying the gorgeous weather, and the restaurant was absolutely packed for lunch and dinner. We didn’t have a chance to eat a larger meal here during our stay, but we did have breakfast on our last morning and it was honestly one of the most delicious and extensive breakfasts I’ve ever had in Italy.