How to Drink and Eat Your Way Through Tuscany In Just Three Days

Come for Chianti, stay for the unforgettable gamberi rossi.

Wine Guide: Tuscan Coast

Dirk Renckhoff / Alamy Stock Photo

After a drive from Emilia-Romagna to Bolgheri that, thanks to utterly insane traffic, took several hours longer than it should have, I was greeted with a bag of anise-scented biscotti. We caught up with the rest of the small group midway through their walking tour of the historical center of Castagneto Carducci, and as the sun cast its golden-hour glow on the centuries-old building facades, Cinzia Merlini, a legend of the Tuscan wine firmament, casually handed me a bag with a bunch of local goodies, most notably the aforementioned biscotti.

This, it seemed to me, was the perfect way to be welcomed back to the Tuscan Coast after a three-year, pandemic-necessitated hiatus.

Tuscany is one of Italy’s most well-known wine and tourism regions, and deservedly so: Chianti and its surrounding appellations (Ruffino, Colli Senesi, Colli Aretini, and more), Brunello di Montalcino, and Vino Nobile di Montepulciano are all found here. The rolling hills of the region, the vines that blanket them, and the elementally transcendent, famously hearty food (bistecca alla Fiorentina! Ragù di cinghiale!) have become culinary calling cards around the world.

The Tuscan Coast is not only home to absolutely fantastic beaches, less-packed towns, and wonderful food, but also to some of the most iconic producers of so-called Super Tuscan wines in the entire region. A drive down Bolgheri’s iconic Viale dei Cipressi (the Road of the Cypresses), with the trees stretching up and standing sentinel along the straightaway, feels like a greatest-hits compilation for wine lovers: Here’s Ornellaia and Massetto! There’s Guado al Tasso and Tenuta San Guido! For collectors of the great reds of Tuscany — in many cases, the great reds of Italy — this is sacred ground.

I was in town to visit Le Macchiole, and to spend a few days with Cinzia Merli, who founded the estate in 1983 with Eugenio Campolmi. Today, Merli runs Le Macchiole alongside her sons Elia Campolmi and Massimo Merli. The winemaking is overseen by Production Manager Luca Rettondini, and as they’ve acquired more plots of land throughout the region, their wines seem to get better and better each year — an impressive feat considering the historically high quality of them to begin with.

Le Macchiole, like many other producers in Bolgheri, anchors its wines not with the more Tuscan-traditional Sangiovese but rather with Cabernet Sauvignon, Cabernet Franc, and Merlot. Syrah and Sangiovese are also permitted in the Bolgheri regulations, as are others in limited quantities, and Le Macchiole produces a 100% Syrah that is majestic. Indeed, the very definition of Super-Tuscan wine is one whose blend is reliant on, or inclusive of, non-Tuscan-native grape varieties. Sassicaia is based on Cabernet Sauvignon with a bit of Cabernet Franc. Ornellaia brings together those two, plus Merlot and Petit Verdot. 

Le Macchiole takes a different approach. Aside from their Bolgheri Rosso, which is a blend of Merlot, Syrah, Cabernet Franc, and Cabernet Sauvignon, their flagship reds are single-variety bottlings, and offer a unique lens through which to understand the region and all that it’s capable of. Over the years, they’ve grown their vineyard holdings from relatively modest beginnings (just four hectares, or a little less than 10 acres, along the Via Bolgherese in 1983), to 26.6 hectares (a little less than 66 acres), divided among six individual vineyards. All of the land is farmed organically and with an eye toward maximizing the clarity with which the grapes planted in each vineyard express that patch of the region.

This is the nature of wine at the highest echelon around the world: Striving to more clearly convey the character of a particular place. These wines do so with elegance, grace, and longevity.

Traveling Along the Tuscan Coast

The Tuscan Coast is an easy trip from tourist destinations like Florence and Siena. From the former, it’s about an hour-and-a-half drive to Livorno and under two hours to Bolgheri. (Assuming you don’t hit the kind of traffic we did this past May.) Siena is a bit closer to Bolgheri and further from Livorno, but not markedly so. In either case, you can be by the sea in less than two hours.

Where to Eat

Indeed, the entire Tuscan Coast is largely defined by its proximity to the sea, even when you can’t quite see it.  For seafood fans, this means one seriously delicious time; the beloved Michelin-starred restaurant La Pineta, for example, is a casual yet elegant spot on the Marina di Bibbona that’s been a favorite among locals and visitors for years. And while founder, passionate fisherman, and chef Luciano Zazzeri tragically passed away in 2019, his sons Andrea and Daniele are carrying on the tradition with verve and passion. I’ve been lucky to dine there several times, and a recent visit was every bit as excellent as I expected. Classic spaghetti alle vongole (spaghetti with clams) will set a new bar for all other versions moving forward; it was as if the sea were channeled, through some sort of tear in the space-time continuum, directly to my seat at the restaurant. Fried seafood and vegetables were impeccably prepared. Even steamed fish with teriyaki, sesame wafer, chicory, and string beans charmed me as the dish challenged preconceived notions about Tuscan coastal cuisine.

For something even more casual yet equally profound, make sure to check out Il Bucaniere, a quick walk from the Marina San Vincenzo, and where I savored lunch on the terrace overlooking the water below. The tartare of shrimp, ricotta, and artichokes was among my most decadent seafood dishes of the year, and the linguini cacio e pepe with impossibly tender gamberi rossi made me swoon. (I mean this literally: I was like an old-timey silent-film character at first bite.) I’ll be running back to both La Pineta and Il Bucaniere next time I’m in the area.

On my final night along the Tuscan Coast, I went to dinner at the beloved Osteria Magona, what can only be called a Meatopia-by-the-sea: The meats are from Dario Cecchini, and the cooking is from chef Omar Barsacchi. Over a blind-tasting lineup of Super Tuscans (yes, wine people actually do that at dinner!) and more bistecca alla Fiorentina than I probably should have eaten, we discussed just how far the Tuscan Coast has come. What started out as a place for producers who believed they could make better wines if they didn’t follow strict, existing DOC and DOCG rules has become a standard-bearer in the Italian wine firmament. The Tuscan Coast in general, and Bolgheri in particular, are now among the most justifiably prestigious places in Italy for the production of top-quality wine.

Before we left, Cinzia presented me with another gift: A bag of ground coffee that had been aged in barrels that had previously held red wine from Bolgheri. I brewed up a couple of berry-scented, layered shots on the stovetop Moka as soon as I returned home the next day, a fitting reminder of a place whose wines seem to constantly get better, even when their quality always appears to be at a high. That’s the beauty of this place.

What to Do

You can even catch your own fish on the Tuscan Coast. A local outfit called SparaPesca is helmed by Matteo Sparapani, a charming, knowledgeable, enthusiastic skipper who pointed us in the right direction time and again over the course of a thoroughly enjoyable four-hour tour that left from the Marina di San Vincenzo. And while I only caught one or two fish, a couple of colleagues managed to pull five times that from the Mediterranean. In fact, we brought our haul to Chef Pierangelini at Il Bucaniere afterward, and he prepared a crudo that still ranks as among my top dishes of the year. 

For more outdoor activity, book a tour of the incredible Padule di Bolgheri Wildlife Refuge, which is spread out on well over a thousand acres of land that was set aside by the Incisa della Rocchetta family in 1959. From birds to fish and everything in between, this is a side of Tuscany that doesn’t get nearly enough credit, but richly deserves to.

Where to Stay 

If you’re staying for a night or three, check out the airy, friendly, and beautifully appointed Relais dei Molini in Castagneto Carducci, which also features a delicious breakfast spread and a lovely afternoon space to enjoy an aperitivo. It’s available to be rented out in its entirety for corporate retreats and meetings, too, and its proximity to seemingly everything in Bolgheri make it an excellent center of gravity during a visit.

What to Drink

Le Macchiole

The 2018s are showing brilliantly right now, and all three of the producer’s flagships have the potential to continue aging for decades to come. The 100% Cabernet Franc Paleo Rosso is a gorgeous expression of the aromatic complexity of the variety, with richness to the chocolate and espresso, as well as notes of well-aged cigar tobacco, chamomile, brambly berries, singed spearmint, peppercorns, and minera.

Their 100% Syrah Scrio boasts a very subtle sizzle of peppercorns with fresh-picked cherries (red and black) and then a palate of remarkable savoriness, with a touch of meat anchoring plums and blackberries, blueberries, cured black olives, cocoa powder, and Earl Grey tea. The 100% Merlot Messorio, on the other hand, emerges from the bottle with a distinctly balsamic character, with subtle suggestions of sandalwood, cedar, and orange oils expressed on top of coffee. Flavors of kirsch, blackberry liqueur, and porcini powder are carried on a lively frame with decades of aging potential.


The 2019 Bolgheri Superiore from the iconic producer is a blend of 62% Merlot with 31% Merlot and a bit of Petit Verdot and Cabernet Franc. This is clearly a wine that’s built for the cellar, yet it remains so full of coiled energy on the palate that, with a stint in the decanter, it will also show brilliantly after a shorter rest of five years or so. 

Cherries and mixed mountain berries are framed by elegant yet assertive tannins, the hints of sarsaparilla and oolong tea complicated by singed sage, dried oregano, black raspberries, cured olives, and a deep core of mineral through the long, tobacco-flecked finish. If you have 25 or 30 years and a good wine fridge, your patience will be richly rewarded. I also recommend  their 2020 Poggio alle Gazze dell’Ornellaia, a white wine blended from 69% Sauvignon Blanc with 22% Vermentino and the rest Viognier and Verdicchio. It’s a rich, white wine with excellent concentration that finds a balanced counterpoint in mouthwatering acidity and plenty of minerality ringing through the notes of grapefruit pith and apricots, with excellent saline flourishes that linger through the herb-flecked and savory finish.


This top-quality producer has earned deep respect for its expressive, terroir-specific wines, and the 2017 Mongrana embodies exactly why. It’s a blend of Sangiovese, Cabernet Sauvignon, and Merlot, and it offers tremendous value for a Super Tuscan that can be found for under $30. It’s full of energy, with a mineral spine against which flavors of cherries, cedar, baseball-mitt leather, and dried oregano shine.

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