Aerial view of Florence, Italy, featuring the Florence Cathedral with its ornate white, green, and pink marble façade, the Cathedral's red-tiled dome, and a bell tower, with many historic buildings and hills in the background under a partly cloudy sky.
Close-up of a white marble statue of a man with curly hair, shown in profile, with detailed muscular features and hands clasped near his chest.
Two people on a tennis court, one woman and one man, exchanging a tennis racket while laughing, with tennis balls scattered on the red clay court.
Medieval hillside town with stone towers, houses, and lush green landscape under blue sky

October 10-17, 2026

DAYS

8 days/7 nights

TRIP DATES

Courts & Culture in Chianti

Join The Next Chapter Travel for an unforgettable 8-day journey through Tuscany, where world-class tennis meets la dolce vita. From the medieval splendor of Siena to the rolling hills of Chianti, this all-women small-group trip offers an unparalleled experience combining active mornings on the court with afternoons savoring the finest pleasures of Italian life. Known for its rich culinary traditions, historic villages, and stunning landscapes, Tuscany provides the perfect backdrop for an authentic Italian retreat.

When you travel with The Next Chapter Travel, every detail is carefully curated to ensure a truly indulgent blend of luxury, culture, and adventure. Whether it’s savoring the local cuisine, relaxing at exquisite accommodations, or enjoying spontaneous discoveries during free time, throughout the journey, you can expect delightful surprises and exclusive experiences that immerse you in Tuscany's rich heritage and timeless charm.

Assorted handmade cheeses stacked on a display table with green leaves for decoration.

Your curated trip…

Highlights:

  • Begin each morning honing your skills with professional tennis instruction and match play from top Italian tennis pros while surrounded by the breathtaking Tuscan countryside, and spend the afternoons immersed in the local culture

  • Discover the historic heart of Siena on a private walking tour, exploring winding medieval streets and local treasures

  • Indulge in a multi-course lunch and wine tasting overlooking the medieval hill town of San Gimignano

  • Experience the thrill of a traditional truffle hunt, then transform your findings into traditional delicacies in an intimate cooking class in a local home

  • Glide through the Chianti countryside on an E-bike tour, effortlessly traversing the rolling hills among  historic vineyards and olive groves

  • Participate in the time-honored tradition of olive harvesting, followed by a memorable al fresco lunch 

  • Join a local Italian mixologist in their home to master the art of authentic local cocktails, learning cherished recipes for classic aperitivi and contemporary creations

  • Shop the finest leather artisans of Florence with an optional private fitting for a custom leather jacket, a treasured souvenir of your Tuscan adventure

  • Savor multi-course dinners at authentic local restaurants, where regional specialties and carefully selected wines tell the story of the local cuisine

  • Enjoy time to relax at your historic Tuscan villa, whether getting a massage, strolling the estate grounds, or engaging in delightful conversations with fellow travelers

And while these highlights promise to be memorable, we've also reserved a few special moments that will unfold along the way, making your adventure truly unforgettable...

What is included:

  • Seven nights accommodation in a beautifully appointed Tuscan villa

  • Six mornings of tennis instruction and match play with professional coaches

  • All breakfasts, four lunches, and all dinners with wine

  • All transportation on chauffeured luxury coaches, including gratuities

  • Airport/Hotel group transfers for participants on suggested arriving flights

  • All excursions listed in the itinerary, including entrance and guide fees and gratuities

What is not included:

  • Massages and other fee-based activities not on our itinerary

  • Private tennis instruction (available for booking directly with pros)

  • Three lunches

  • Airfare

  • Travel Insurance (Highly recommended)

Accommodations:

A sprawling Italian villa with a beautiful kitchen and numerous relaxing spaces to gather and connect, a jacuzzi, sauna, and massage room, and several terraces with gorgeous Tuscan views.

Transportation:

Luxury Coach with a Driver/Guide

Bedroom with open window showing a scenicCountryside landscape, bed with white bedding, yellow and brown patterned pillow, and side tables with decorative items.
Living room with stone and brick walls, wooden ceiling beams, large windows, and beige furniture, including sofas and armchairs, decorated with colorful pillows, a wooden coffee table with a green plant and decorative objects, and a balcony with outdoor seating visible through the open door.

Pricing:

Double Occupancy: $7,490 (per person)

Single Occupancy: $7,990

Maximum 12 people

*A $1,000 deposit is due at booking, and the balance is due no later than 90 days prior to departure.

The deposit and final balance are non-refundable. Travel insurance is highly recommended.

We accept payments via PayPal

Cancellation Policy:

Cancellations made more than 90 days prior to the tour start date will receive a credit towards a future Next Chapter Travel tour commencing within a year of the canceled tour.

Cancellations made less than 90 days prior to the tour start date will receive no credits or refunds. Contact your travel insurance advisor to make a claim.