The Best of Tuscany – May 2025

  • Florence Italy

Limited availability! – May 17-24, 2025

Join us for a week of exploration under the Tuscan sun. This is the perfect itinerary for a first time or repeat visit to this fascinating region. Inspiring views, fantastic cuisine and immersion in the spectacular Italian culture, art and history will provide you with memories of a lifetime.

Our May 2025 week in Tuscany takes place at a beautiful villa just outside of Lucca, Italy!!  Our days start with delicious buffet breakfast provided by our own personal chef before we head out for our daily excursion to explore the region.

Day 1 (Saturday, May 17): Ben venuti in Italia!!  Plan your flights so that you arrive in Florence sometime this day.  You’re picked up at the airport or the central train station and brought to this fabulous villa where you will check in, freshen up a bit and relax!  Maybe a little stroll around the villa property…. And/or relax next to the pool with an aperitivo to kick off our week in Tuscany!

Day 2 (Sunday, May 18): Today’s excursions start with Pisa, where we’ll check out the famous Leaning Tower.   Then, we head to Lucca for a private tour of this charming little town.  Later, dinner is prepared for us at the villa by our own personal chef for the week!

Day 3 (Monday, May 19): You’re in for a treat today, with a private guided walking tour of beautiful Siena, the center of which is a designated UNESCO World Heritage site!  We’ll see it all, including the iconic shell-shaped piazza which is the site of the annual Palio horse race.

Day 4 (Tuesday, May 20): Today is hiking day! Well, for those up for the challenge, that is…. We’ll take on the iconic “blue path” Cinque Terre hike from Monterosso to Vernazza (don’t worry, there are options for non-hikers who still want to explore these fabulous towns!). From Vernazza, we can continue the hike (if the path is open) or we can hop from town to town on the very convenient train that runs along the coast.  Regardless, our ultimate destination will be Manarola, where we will savor our “aperitivo” and take in the gorgeous coastal scenery.

Day 5 (Wednesday, May 21):  Today, we will continue that Tuscan vibe with our own private cooking class and a visit to San Gimignano!  Lunch today will be the result of our own work – an authentic Italian meal, made by YOU (wine sampling will also be on the menu)! Afterwards, we’ll head to San Gimignano, where we’ll have some free time to explore this charming walled-in town, famous for its many towers, saffron, and a wonderful white wine.

Day 6 (Thursday, May 22): Our destination today is the beautiful heart of Tuscany, Florence!!  We’ll have a full day to spend in this beautiful city. Our private tour guide will meet us for a guided walking tour that will include all of the key landmarks in Florence. We’ll also have skip-the-line access to the Accademia Gallery where you can see the original Statue of David with your very own eyes. The rest of the day is open for you to spend how you choose – shop, eat, explore!! 

Day 7 (Friday, May 23): The grand finale for our week in Tuscany is today – a tour through the Chianti region!  First stop is a private visit at a family-run olive estate in Chianti. It’s perched on a hill, covered with olive trees, overlooking Florence in the distance.  We’ll have a tour of the estate and learn about its history from the owner.  We’ll also learn a bit about how top-quality extra virgin olive oil is produced, along with sampling!!   Afterwards, we’ll head to an organic farm to learn how balsamic vinegar is made and do some sampling of the local specialties paired with some of their delicious wines. We’ll finish the day at a beautiful family-owned boutique castle winery where they’ve been making wine since 1596!  The castle, where the owners reside, dates back to 1577 and we get a private tour!!!  After visiting the estate and the cellar we’ll enjoy a tasting of their award-winning Chianti wines accompanied by some local Tuscan specialties.

Day 8 (Saturday, May 24): Sadly, all good things must come to an end. We check out by 10am – transportation back to the Florence airport or central train station will be provided.


  • 7 nights/8 days accommodation at a fabulous villa just outside of Lucca (about 45 min from Florence), includes city taxes
  • Each bedroom has private bathroom, AC, Wi-Fi (TV in common area)
  • Amenities at the villa include a pool, spa, electric bikes, washer, etc
  • Airport transfers to/from Florence airport or central train station
  • Meals at the villa – all breakfasts, and dinners when not on excursions, includes table wine with dinner
  • Cooking class
  • Optional day trip excursions outlined above are included in the price – Cinque Terre hike, Siena, Florence, Chianti region, Pisa, Lucca, San Gimignano

Does not include: air fare, travel insurance, tips, meals during excursions, incidental purchases

Pricing:  $5300 pp double occupancy; $5900 pp for a single

Limited availability — don’t wait! $500 deposit to reserve your spot