Coastal Tuscany & Pisa Vacation

Itinerary at a glance

Lucca (2 nights) may be Europe’s most beautiful medieval city, and you can judge for yourself on our get-acquainted walk that includes the park atop the city walls. The new day begins with a stroll in the classic countryside and a visit to a friend’s farm for a cheese-tasting. Later, we dine by candlelight at the castle of Montecarlo.

A picturesque path to Bolgheri begins at our hotel’s doors, so of course we take it, leaving time to stop by the workshop of a terra cotta craftsman. We’ve also arranged a tasting at one of the region’s renowned vineyards.

On the promontory of Cala Piccola (2 nights), our villa hotel overlooks the coast. It’s a brief ferry ride to the island of Giglio, where we balance a walk from the castle with a relaxing trattoria lunch. The Etruscans civilized this region and we’ll explore a fascinating archeological site near Populonia. Then a brief drive takes us to our 150-acre estate hotel near Sassetta (2 nights). We cap the week with a walk to the winery run by the family of Andrea Bocelli, followed by a cooking instruction and a farewell farmhouse dinner. On our final day, we part company in Pisa where you can easily make transfers to Florence or Rome.