Only 2 player spots left!

Join Us for 7 days and 7 nights at a private historic villa in the heart of Tuscany. Players will be coached by Lee Whitwell the #1 Ranked Female Senior Pro and Will Tams, Road to 4.0 Co-Founder and Head Coach. Come experience what happens when you combine the best of Italy with the best of Pickleball to create a unique and magical experience.

APRIL 19–26, 2025

For more information, see the links above for pricing, itinerary, and an overview of the trip, or contact us.

Geared Towards Upper-Intermediate to More Advanced Players (3.5 – 4.0 Level Players)

~ Limited to 16 players ~
RESERVE YOUR SPOT
Image of the villa and surrounding area as well as sample bedroom in a collage format

Trip Highlights 

  • 7 days and 7 nights accommodations in a luxurious private, historic Tuscan villa with private swimming pool and 4 pickleball courts. Under 45 minutes from Florence and Siena
  • 5 day pickleball intensive clinic with #1 ranked Senior Pro Lee Whitwell and Road to 4.0 Co-founder and Head Coach Will Tams. 24 hours of on-court time with the coaches, plus unlimited personal use of the courts
  • The clinic series culminates in a festive round robin tournament and final ceremony
  • Ability to bring along a spouse, partner, significant other, or friend (who does not play pickleball) at a discounted price
  • Guided excursions with private drivers to breathtaking local sites organized and led by our European partner, diVino Tours of Italy
  • All meals*, including wonderful dining experiences, catered directly at your villa by a private chef (*Except one free night on your own in Siena.)
  • Day 6 special full-day group outing on a diVino exclusive tour of Montepulciano and Pienza
  • Local expert Tuscan guide (who also loves pickleball) available throughout your stay to provide assistance, insight, and well-timed humor to your journey
  • Organic Italian wines (including alcohol-free options) perfectly paired with each meal by your personal sommeliers
  • Multiple days with a private massage therapist on-site at the villa for optional booking after a long day of pickleball and excursions in Tuscany
  • Free custom travel planning with diVino Tours to arrange your stay in Italy before or after the Road to Tuscany Tour.
 
Still have questions? Send us an email
~ Limited to 16 players ~
RESERVE YOUR SPOT

Get In Touch

If you have any questions, please send an email or use the contact form.

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Road to Tuscany Tour 2025

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ANDREA ANICHINI

Lead Chef and Owner
A Man from Chianti

Born in the Chianti Classico region and growing up with the values of cooking food with ingredients all from within 1 kilometer of our home shaped who I am today. And if you accompany this meal with a great glass of wine, now you have been introduced to my world.

I am a Man from Chianti, a man with a rustic but sincere personality. I wish to share with you those wonderful emotions I still feel today when I prepare a “pinzimonio” or simply look outside my window.

Andrea Anichini is an artist who crafts his plates with simple, organic, local ingredients creating unique and exquisite meals with just a handful, “one or two ingredients” as he likes to say.

FEDERICO “FRED” MARCONI

Executive Trip Manager Expert Guide and Sommelier
diVino Tours of Italy

Federico Marconi was born in Siena in the fuzzy Seventies, and since then, he has always been in motion. Having long lived abroad and traveled to countless countries, Fred is truly a World citizen with a broad and multi-faceted understanding of different cultures, languages, and countries.

By day, Fred is the Executive Trip Manager and expert guide for the Tuscany Region, as well as being a trained Sommelier with a true love for wines.

By night*, he is a true *Rockstar* to the bone. He is the lead singer of a band where his other side is able to come out. Lastly—and like the rest of us—he is a pickleball fanatic. Fred fell in love with the sport in the early 2020s when there was little to no sign of Pickleball in Tuscany and he began building “guerrilla courts” to be able to play. One of his greatest claims to fame is having built the first ever pickleball court in Tuscany in 2021 in an abandoned parking lot.

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AMY WADMAN

Founder and Director
diVino Tours of Italy

Amy is the Founder, Owner, and Director of diVino Tours of Italy and has been running the business since 2003. Originally born in Boulder, Colorado, she has lived in Italy for more than 35 years now and as a result, has a one of a kind perspective on travel—and life—in Italy. Being both bilingual and bi-cultural, she is uniquely qualified to share her experience with people who are seeking a deeper understanding of the Italian lifestyle.

Amy personally hand crafts diVino’s Custom Tours, where she works with each individual traveler, creating one of a kind itineraries catering to each client’s unique interests and needs. Though her trips are gourmet in nature she also weaves unique art and history experiences into her tours and arranges exclusive events throughout Italy at www.divinotours.com

Besides running diVino Amy also owns an organic farm and olive grove in Le Marche where she produces a rare varietal of olive oil, wines, honey, and blackberry jam. Her site is at: www.costadigiano.com

WILL TAMS

WILL TAMS

Co-Founder and Head Coach
Road to 4.0

I’ve been completely obsessed with Pickleball for the last six years. I love both the social aspect of open play as well as the intensity of competing in high-level tournaments. I’ve participated in tournaments nationwide, including the 2022, 2023, and 2024 Pickleball Nationals.

In 2023, I secured gold in mixed doubles and singles at the APP Qualifier in Mesa, Arizona, earning Golden Tickets to Nationals. In November of 2023 at Nationals, I finished 6th out of 40 teams in Men’s doubles and 7th in singles in a field of 25. But beyond medals and finishes, my true passion lies in coaching and helping others improve. Pickleball, to me, is an exploration of learning and potential, where the court becomes a laboratory for experimentation and self-expression within the sport’s boundaries.

Most of all, I absolutely love this game and my student’s say that my enthusiasm is contagious and helps energize and motivate them to continue to improve their games.

LEE WHITWELL

LEE WHITWELL

#1 Ranked Senior Pro
Womens and Mixed Doubles

Lee Whitwell has a distinguished career and has made significant achievements in the sport, including being voted MVP for the Major League Pickleball in both the 2021 and 2022 season.

Often referred to as “Lady Gibraltar”, Lee has had a trailblazing career in pickleball. She is celebrated not only for her outstanding performances but also for her vibrant personality and dynamic presence both on and off the courts. Consistently voted as fan favorite, Whitwell’s background and experience in pickleball have made her a prominent figure in the community, inspiring many up-and-coming players with her coaching, her story, and her accomplishments both on, and off, the court.

An avid coach, Lee has run clinics all over the world, from the US to China, Mexico to Europe. The same passion she brings to the courts shines through in her dynamic, and accessible, teaching style.