Curator’s statement
Lucca and Siena are the perfect pair of destinations to experience Tuscany's iconic charm: rolling hills, Renaissance architecture, comfort food and romantic hilltop villages. The towns are separated by a one to two-hour drive, with Florence situated at the perfect midpoint. In Lucca, incredible Renaissance walls enclose a historic city center that still feels lived-in and local today. Siena offers a breathtaking aesthetic, made for enjoying leisurely walks down its beautiful winding streets and taking in the incredible cultural and architectural sites.
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Things to do
Lucca
Walk or bike Lucca's city walls: The historical city center of Lucca is surrounded by walls that make up an elevated 5k loop of tree-lined paths perfect for seeing the city sights. Walk or bike the path yourself, or book one of the guided tours who can explain all of the fascinating historical, cultural and foodie landmarks.
Climb Torre Guinigi: Recognizable as the tallest structure in Lucca with distinctive trees on top, Toree Guinigi was built in the 1300s by wealthy families looking to project status and security. Climbing the 232 steps to the top provides a breathtaking view of Lucca and the surrounding area.
Piazza del Anfiteatro: Formerly a second century Roman amphitheater, this elliptical plaza is now a central local gathering place in Lucca with a multitude of restaurants and shops. Don't write these off as tourist traps! The restaurants are quite good for an al fresco aperitivo and relaxed people watching.
Siena
Contrade of Siena: Each neighborhood in Siena is called a "contrada" and has its own distinct animal and emblem. As you make your way down Siena's winding streets, see if you can spot them all.
Piazza del Campo: One of the greatest medieval squares in Europe, the Piazza del Campo feels like a central and lively city gathering place. Each summer is marked by the Palio di Siena – a horse race where riders representing each contrada compete in a crowded lap around the Piazza.
Cathedrals: The Duomo di Siena and the Basilica Cateriniana San Domenico provide incredible examples of the architecture and history in Siena. Stop by these sites (indoor or outdoor) for an example of Italian Gothic architecture, and to see where St. Catherine of Siena spent her days.
Markets: Every Wednesday morning in Siena near La Lizza, an outdoor market is set up with endless rows of stalls selling clothing, home goods, and all kinds of wares. Locals and tourists alike gather to comb through racks of items at incredibly affordable prices.
Eat & drink
Lucca
Ristorante Cantine Bernardini Lucca: A charming eatery in the basement of the Palace Bernardini with seasonal Tuscan dishes and a well-curated wine selection. The "Nonna Maria" special here made us shed small tears of joy. You'll need to call to make reservations.
Da Ciacco: An impressively affordable wine bar with paninis and charcuterie plates, perfect for a relaxed lunch or dinner al fresco.
StraVinSky: A cozy, casual spot for lunch, featuring regional wines and a selection of light meals.
L'Imbuto: For those wanting to splurge a bit, L'Imbuto is a Michelin-star restaurant where guests select the number of courses they want and are treated to a unique and creative dining experience.
Siena
Osteria la Sosta di Violante: A more casual eatery with generously portioned, classic Tuscan fare. Don't sleep on the lasagna here.
Nannini: Great for a quick stop to grab a cappuccino and ricciarelli, the chewy almond cookies that are a Siena specialty.
Ristorante Tar-Tufo: An upscale restaurant where you can get your much anticipated Tuscan truffle fix with five- and seven-course truffle tasting menus.
La Taverna di San Giuseppe: An ancient Etruscan cellar serving upscale Tuscan classics and an altogether delightful selection of wines.
Day trips
From Lucca, it's not much further to travel out to the Cinque Terre (park in nearby La Spezia and take the train into Cinque Terre towns). You can also explore the Apuan Alps Park for day trips with hiking and incredible views. If using this itinerary, I recommend renting a car for maximum flexibility.
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Misha Sharp
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For more European travel, check out my guide for the 'Best Things to Do in Berlin, Germany'!