A South Tuscany Itinerary: 7 Day Journey Through the Maremma

Rome's two airports, Fiumicino (FCO) and Ciampino (CIA), sit closest to this stretch of coast, roughly 1.5 to 2 hours drive from villas around Orbetello and Monte Argentario. Pisa (PSA) and Florence (FLR) are options too, though the drive south runs closer to 2.5 hours from either.

All of these airports have direct flights from the UK and Europe's main airports, however, Rome Fiumicino Airport also offers direct flights from North America.

Our extensive guide on how to get to Tuscany provides more in-depth information on your travel options, should you need it.

Distances here run longer than in the more compact hill towns further north, so hiring a car is a sensible choice for this itinerary.

• Car hire: necessary for Val d'Orcia, the wine country and the drive to Elba's ferry port.
• Chauffeur-driven wine tours: book ahead for Day 4, since neither Montalcino nor Montepulciano are places you'd want to rush the tasting to get back on the road.
• Boat charters: several of Monte Argentario's best coves have no road access at all, so a boat is the only way in.

• Day 1: Grosseto and the Maremma's Hill Towns
• Day 2: A Choice of Two Beaches
• Day 3: A Day in the Val d'Orcia
• Day 4: A Taste of Tuscan Wine
• Day 5: A Day at Sea around Monte Argentario
• Day 6: North to Castiglione della Pescaia and Populonia
• Day 7: A Day's Island-Hopping to Elba

The Maremma’s capital, Grosseto, boasts a fine, unspoilt old centre with a 13th-century cathedral, an impressive archaeological museum, and a web of attractive streets. 

If time allows, soldier-on toward the Lazio border for Manciano and Pitigliano, two hill towns that see a fraction of the visitors their appearance would suggest they deserve. Between Grosseto and these two, you’ll have more than enough to fill a day; conquer all three in one, or slow the pace and save some exploration for a return trip, the choice is ultimately yours.

The Regional Park of the Maremma, comprises untouched stretches of sand, forested hills, a varied array of flora and fauna, a salt lagoon, walking trails, ruined towers and much much more. So if you'd rather trade a town for time outdoors, you’ve got options too.

Rather than one fixed stop, this day is really a decision between two very splendid beaches. Arguably the most scenic and paradisiacal of Tuscany’s beaches, Cala Violina is part of the verdant Bandite di Scarlino nature reserve and combines golden sand and rocks, transparent, shallow waters, views out towards Elba, and fragrant, emerald woods of pine and oak trees. It’s a bit of a walk to get there, but really worth the effort. 

A curvaceous, 6km-long crescent of green and gold framed by deep blues, Feniglia beach is one of two isthmuses that connect the semi-island of Monte Argentario to the mainland. It’s a heavenly, south-facing spot that’s hard to resist. There are a few lidos dotted around, mainly at the eastern and western ends, but little in the central section.

Either way, proximity is likely to make the decision for you, Cala Violina sits toward the north of the region, while Feniglia is a short drive from a southern base, so let your villa's location be the deciding factor.

Nowhere says ‘Tuscany’ quite like the Val d’Orcia, a UNESCO World Heritage Site where undulating hills are topped with farmhouses, country lanes of cypress trees disappear over the horizon, and beautifully preserved towns and villages vie for your attention.

The Val d’Orcia is a fabulous day out. You can stop to wander around Castiglione d’Orcia or San Quirico d’Orcia, take in the ancient thermal baths at Bagno Vignoni, or make a little detour to the serene and spiritual Abbey of Sant’Antimo, built, it is said, by Charlemagne.

Your final destination should be Pienza, a tiny Renaissance jewel built at the behest of Pope 

Pius II in the 15th century. After marvelling at the Duomo, Palazzo Piccolomini, the Town Hall, and the views out over the Val d’Orcia, make sure to stock up on some pecorino di Pienza, the town’s delicious cheese.

If you think of Italian wine, some of the first labels you’ll see in your mind’s eye will be from 

southern Tuscany. Chianti, Brunello di Montalcino, Vino Nobile di Montepulciano, Sassicaia, Tignanello and Vin Santo are all produced in the area, making it a paradise for wine lovers.

There can be few better ways of getting to know and appreciate these stellar wines than by embarking on one of our chauffeur-driven wine-tasting tours. You’ll be able to try some of the very best vintages of the top producers, while also sampling some delicious Tuscan culinary treats.

The magical promontory of Monte Argentario is connected to the mainland via a slender pair of beach-fringed isthmuses. It is a hilly, many-valleyed slice of paradise with numerous beaches (some of which are only accessible by boat), and two attractive, storied towns: Porto Santo Stefano and Porto Ercole.

For us, the best way of exploring Monte Argentario is by boat, and we’d be delighted to organise a day-long skippered charter for you. You’ll drop anchor to swim in deserted bays, explore hidden coves, and enjoy a delicious lunch, either on board or in a seafront restaurant.

Back at the villa that evening, arrange for a chef to cook rather than heading back out, a straightforward way to end a day spent mostly in swimwear without a restaurant booking to think about.

One of Tuscany’s loveliest and chicest coastal towns is Castiglione della Pescaia, whose long and beautiful sandy beaches are bisected by the mouth of the River Bruna. Its terracotta-roofed houses climb up the sides of a hill and wrap around a mediaeval castle and the impressive 16th-century Church of St John the Baptist. 

The views and sunsets from here are breathtaking. The town’s streets are lined with cafés, 

bars and restaurants, and there’s also a good selection of independent boutiques for those who like to shop.

Continue on to Populonia, an Etruscan settlement dating back to around 900 BCE, perched on a headland above Piombino. Its fortified walls and hilltop acropolis have earned it a place among Italy's officially recognised prettiest hamlets (Borghi Più Belli d’Italia), and the paths threading around the ruins make for a proper walk rather than a quick photo stop.

Close the week across the water. The ferry from Piombino to Portoferraio takes about an hour, landing you in Elba's historic capital with a full day ahead. Wander the old town, climb to Forte Falcone, the fortress Cosimo de' Medici built in the 15th century, and stop by the Palazzina Napoleonica dei Mulini, Napoleon's former residence and now a small museum. Spiaggia della Ghiaie is worth the swim before lunch at one of the harbourside restaurants and the ferry back.

On your last evening, swap the usual dinner out for something more hands-on: a chef can come to the villa and walk you through a Maremma dish or two, cacciucco included, so you take a recipe home along with everything else.

This route only covers half of what the Maremma holds, and that's rather the point, it's a starting sketch, not a fixed schedule. A Villa Specialist can reorder the week, swap a day trip for a slower one, or build around whichever of these villas suits your stay.

Browse the collection of luxury villas in Tuscany, or speak to a Villa Specialist to start building your own week.