Florence - Florence is the capital city of Tuscany, and the most visited. The best-known and most easily viewed sights to tackle early are the Cathedral, the Baptistery, Giotto's bell tower, and Santa Maria Novella. These are open until early evening except on Sundays, making them suitable opening-day attractions. Not to be missed are the monastery of San Marco; Michelangelo's remains in Santa Croce; the Boboli Gardens; the Accademia, to view David; and at least a brief tour of the Uffizi.

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Pisa and Lucca - A trip to Tuscany is not complete without a picture at the leaning tower of Pisa. Lucca is one of the most loved cities in Tuscany. Located near the Apuan Alps and close to the coast, the surroundings of the city will enchant you before you arrive within it's walls or have a bike ride on top of those very walls. Stroll through the Piazza of San Michele, the Basilica of San Frediano as well as the Clock Tower and Guinigi Tower. Oh, and great shopping as well!

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Uncharted Tuscany - Castagnetto Carducci and Bolgheri. These “off the beaten track” areas are known for their “super-Tuscan” wines and fresh pasta. The region straddles the sea to the west and mountains with natural thermal baths to the east.  Have fresh pasta workshop in a classic Tuscan restaurant, run by three generations of women, in Bolgheri.  Finish off the day exploring the medieval town of Volterra 

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Volterra, San Gimignano, and Pisa

Visit the Alabaster City of Volterra, an excellent example of Etruscan culture and one of the lesser-known gems in Tuscany. San Gimignano is often referred to as the "Manhattan" of Tuscany due to its impressive towers. Spend a few hours wandering its medieval streets and enjoy the specialty shops. Next, you can head to Pisa to see the Leaning Tower, snap the de rigueur photo, then visit the rest of the Campo dei Miracoli.

Cinque Terre
Strung along 18km of serrated cliffs between Levanto and La Spezia, the Cinque Terre is one of Italy’s treasures. Five villages – Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore – are interwoven by mountains heavy with olive groves and dry-stone-walled vineyards.

The Cinque Terre became a Unesco World Heritage site in 1997. Wine growers still use monorail mechanisms to ferry themselves up and the grapes down these unique lands, and in some cases have to harvest their grapes boat. If the terraced hillsides are not worked, they will quite literally slide into the sea.

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Siena

The cathedral is one of Italy's most interesting, especially with its recently discovered new room, the so-called "crypt" underneath, containing a cycle of 13th-century frescoes. The Piazza del Campo is perhaps one of the most charming places in all of Tuscany to sit and enjoy the bustling town, and the synagogue is just down the street of of the piazza. 

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Chianti Wine Country

Sienna, Chianti, and wine - Italy's famous medieval city with the famous Il Campo central piazza where a medieval Synagogue is still active! The areas around Sienna - the Chianti wine region host two fully kosher wineries and a few more that produce special editions of kosher wine. A bike or electric bike ride through the rolling hills of Chianti, or a morning Truffle Hunt followed by a cooking workshop and wine tasting is highly recommended!