A family trip to Tuscany is always a good idea. That is the conclusion we came to during our family Christmas dinner last December. As part of a very extended and scattered family, it is always a struggle to be able to see everybody throughout the year. So we all decided that 2019 was going to be the summer when we would all meet halfway, and where better than Italy, where the sun shines from April to late October and activities are as diverse as the landscapes. Besides the obvious -the beach, the country, the food, the people- Tuscany is in our opinion one of the best places to comfortably travel with a crowd, as large villas are plentiful; it involves some mandatory logistics and planning if you want everyone to remember this trip positively as an unforgettable experience. Here are some tips for arranging successful multigenerational Tuscany trips.

Should you want a countryside vacation, protected from the hustle and bustle of touristy cities, Pitigliano is your best option: our ancient, former convent Il Convento makes a perfect holiday seeing and will welcome you and 10 other family members. It is just a 15min drive away from this incredible town. Located in the south of Tuscany, Pitigliano is unquestionably one of the most beautiful, charming and interesting towns in the area. Its rich history goes from prehistory through Etruscan and Roman settlements and Italian Renaissance, all of which you can discover at The Orsini Palace, now the Civic Archaeological Museum of Pitigliano. Within its spectacular old city centre is an area known as a “Little Jerusalem” for its once large and active Jewish community that was active in the 15th century. Don’t miss the recently restored Synagogue! On top of its rich history, the town is also famous for its wine production. The vineyards in this area, aided by volcanic tufa and millennia-old soil, produce one of the most lauded Italian white wines: Bianco di Pitigliano, a DOC appellation and a must-have while on the Strada del Vino! From there you can also visit the nearby towns of Saturnia and Sorano, which have benefited from hot springs for centuries and are now a must-go spa destination.

For a seaside vacation, about an hour away from Pitigliano is the Monte Argentario and its fantastic archipelago! Perched on a cliff on the edge of the Mediterranean sea, the Villa degli Angeli gazes from Ansedonia at Italy’s most spectacular views, and can comfortably sleep up to 14 people. While there, though you may want to do nothing, there are plenty of possible excursions to keep you busy. In Ansedonia, don’t miss the remains of the ancient city of Cosa, an archaeological site of international interest dating back to 273 BC and included in UNESCO World Heritage Sites. You can also walk or bike in the nearby pine forest and beachcomb the long beach, that is if you tire of swimming in the sea from the private beach of your villa…

You can also explore Orbetello or discover traditional festivals such as the Balestro del Girifalco, stroll by boat in unspoilt places accessible only by the sea, dive into the Mediterranean waters and discover marine life, or try hang gliding at the many centres and schools in the region. We happily recommend Porto Santo Stefano and Porto Ercole, two fishing ports that have become seaside resorts, surrounded by high rocks and connected to the mainland by the wide sandy beaches of Gianella and Feniglia.

Closer to San Giminiano, Siena and Florence, perched on a hill and overlooking vineyards, is Castello Lorenzo. Located in San Casciano in Val di Pesa, where Niccolò Machiavelli wrote his most famous book, The Prince, Castello Lorenzo was originally a medieval fortress built in the eleventh century, converted in the fifteenth century into a magnificent villa of the Tuscan aristocracy with a unique charm and impeccable taste. With its 10 bedrooms and 9 bathrooms, it will easily welcome up to 20 guests! Don’t miss the Antinori Wine Estate, simply breath-taking: the winery overlooks the countryside from a terrace surrounded by vineyards, and while staying at Castello Lorenzo, you can visit the cellars and participate in tastings, but also have lunch in their restaurant Rinuccio 1180 located on the roof of the building. We will take care of your reservations, tastings and excursions!

Finally, further north in the Tuscan Maremma, we definitely recommend Castagnetto Carducci, home of La Civetta, a 14-people villa with pool and private access to the beach! There is shopping should you want to cook family meals yourself, or you can use our wonderful cook, but there are also plenty of restaurants to enjoy. Local foods are based on Maremma specialties, fresh fruits and vegetables, freshly made mozzarella and of course, the famous Super Tuscan Wines nearby. Not too far away, is the famous city of Pisa (and its leaning tower!) and Lucca is about 1-hour drive north.

At Commendable Rentals, we can help you plan your whole trip, from choosing properties to rent , to booking guides, boats, chef, cooking lessons, and museum tickets in advance; don’t hesitate to ask for our help!