Tuscany

For my long-delayed 50th birthday (2+ years due to Covid), I finally realized my dream vacation of bringing 12 friends together for a week in a villa in Tuscany.

A lot of prep work and planning went into this, as friends flew in from as far away as Australia, so I was relieved and excited when we arrived at the magnificent 9-bedroom Villa Benedetta in the terrific little town of Greve in Chianti. This was our home base as we explored the towns, wineries and sights of the heart of Italy. Along with my BFF Trevor, who handled all the finances and logistics, we mapped out a ridiculously good itinerary that I'll share with you all. First things first for a trip of this size, we organized a pre-villa meet-up in Florence to see some highlights of Renaissance art and to have our first Aperol spritz. 

Florence, Italy

The Westin Excelsior was a great home base in Florence as my friends started to gather from all across the world. The hotel location was amazing, right on the banks of the Arno, proximate to all the sights without feeling crowded and - best of all - a terrific rooftop bar/restaurant called Sesto. Sesto has excellent views over the rooftops of Florence and a great drinks menu, the Hugo Spritz was my favorite with elderflower and mint. Having a host hotel was key - everyone could gather for a few days to reset time zones and check out some of the world-class art museums in town - the Uffizi Gallery and the Accademia for Botticelli's Birth of Venus and Michaelangelo's David. I highly recommend getting a guided tour of these two museums to skip the lines and maximize your time, as you'll need the better part of a day to see all of the art, including the Duomo and Ghiberti's Baptistry doors. 

Highlights of Renaissance Florence

We wrapped up our Florence pre-trip with dinner at 4 Leoni, a great trattoria on the Oltrarno - the quieter side of the river opposite all the monuments. The service was super friendly, we had some great Chianti wine and the Florentine Bistecca was the best of the whole trip. Check out the size of these steaks!

Once we were all together, we packed up our bags into three rental cars and headed 40 minutes south to our villa in Greve in Chianti!

Villa Benedetta 

FRIENDS!

Villa Benedetta was the perfect mix of privacy, large enough for everyone to have their own bedroom, and sociability, with many inside and outside areas to sit, eat and relax. We cooked steak on the outside grill one night, had a few catered dinners, including the last night with a 4-course meal that was out of this world. The pool area was stunning and we had a spritz party every afternoon from 4pm - 6pm. We ventured into the town of Greve, which was about 15 mins away by foot (you did have to climb a pretty steep hill coming back home) but there was a few really nice restaurants, a town square that had some sort of daily activity - an antique car show, a flea market, etc - and a VERY fun wine bar Enoteca Falorni - which had dozens and dozens of wines from all across Italy that you could sample by using a pre-loaded credit card and pick the size pour you want to try. Villa life is a really relaxing way to go and everyone pitched in along the way to make things work - cleaning dishes, clipping roses for the dinner table, doing a few loads of laundry and troubleshooting the spotty internet service. 

Villa Life

If it looks like all we did was eat and drink wine....you're right. As much as we loved villa life, there were a few destinations that were on our list...so we went out to eat and drink! Here are some of our excursions...

Anitnori Winey Cellars and Restaurant

The Antinori winery is like a James Bond villain lair. It's $120M euros worth of cor-10 steel, glass and handmade terra cotta tiles. The property is just mindblowing - it's built into a hillside in the heart of the Chianti region and was probably the most impressive winery I've ever seen. We spent the first two hours touring the vineyards and the tasting room (cantilevered above the barrel storage) before heading off to their restaurant, shaded in the canopy of trees and flowers. Although they are Italy's largest producer, Antinori's hospitality, excellent tasting room and dynamite restaurant made this a top destination for everyone on the trip. 

Castello di Ama

Another outstanding winery was Castello di Ama - which is part contemporary art installations and part winery. Scattered around the ground and in the small cluster of buildings and old churches were artworks by such luminaries as Anish Kapur, Louise Bourgeois and Michaelangelo Pistoletto. The mashup of art and wine is not new - but I've never seen it done so seamlessly and to such great effect. The Anish Kapur installation is a red light on the floor of a 12th-century church - it glows like some portal to the netherworld and looks, alternatingly, convex and concave as it radiates light. The juxtaposition of contemporary art with ancient architecture was just really cool and the context brought up a dialogue about heaven, hell, salvation and sin. Another work I loved was a 25-foot-long mirror wall with cutouts like picture frames that reflected and literally 'framed' the horizon.  The red Revolution spelled backward (but LOVE spelled out) in the barriq storage room was amazing - a super successful work from South African Kendel Geers. This is a totally unique place and would definitely recommend! 

Villa Bordoni - Cooking Class

One of the highlights of the trip for everyone was our cooking class at the impossibly quaint Villa Bordoni. Located less than a mile from our villa, we set out together around 3pm for cooking class. We divided up into 2 groups - one made pasta, while the other made a beef stew. The wine was flowing from the start - as we pulled together a focaccia dough with local red onion so it could rise while we got on with our tomato sauce and tiramisu. This was just the right mix of hands on - the pasta making was just fun - and instruction that everyone had a blast. David - the proprietor, originally from Scotland - was one of the most naturally hospitable people I have ever met. He guided us from station to wine to another task and then set us off in the garden as they put the finishing touches on dinner. A long lingering sunset made the night just amazing. We stumbled home well past dark with lots of memories and laughs from a great group of people. 

Enoteca la Fortezza - Brunello di Montalcino

Built in 1361, the Fortress of Montalcino overlooks the Val D'Orca and houses one of the best selection of Brunellos in the world. Enoteca la Fortezza is located inside these ancient walls and is a jewel box of a wine store. We arranged for a tasting of 5 Brunellos (that got extended 4 more bonus rounds - it was just that good!) that represented the best of Brunello and were of such limited quantity production that we were lucky to snag a bottle (one wine only had 500 bottles produced in one vintage). Enoteca la Fortezza is just a great example of terroir - that idea that taste, flavor and style are all a result of the specific location you're in - and their ability to show the range of Brunello - all 100% Sangiovese grape - yet distinctly different made this a world class wine experience. This is just not to be missed. A+

Special Thanks to BFF!

Quick Quack with Spritz!

None of this would have been possible without my best friend in the whole world. Trevor brings planning skills matched with a zest for life that makes life an incredible adventure. Cheers to you Trevs!!! Mille Grazie QQQ!!!

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