Pickleball Gladiators: Travel and Play in Italy with Your Squad!
Embark on a one-of-a-kind Pickleball adventure that takes you deep into the heart of Italy’s most captivating regions: Piedmont and Puglia. Our journey begins in the shadow of the majestic Alps, where you’ll stay in authentic 17th-century estates and savor the true flavors of Italy, from polenta at the Oropa Sanctuary to a traditional Piedmont Merenda Sinoira. Explore the stunning Isola Bella and Borromean Islands, stretch pizza dough like a true Italian, and indulge in Piedmontese wine and gelato as you gaze over the serene Lake Maggiore.
As we head south to Puglia, the experience becomes even more intimate and exclusive. Your home in Puglia is a private 17th-century Masseria and Trulli, reserved solely for our group. With only 12 rooms, this beautifully restored estate offers the perfect blend of luxury and authenticity, ensuring a personalized experience for all. Our group is capped at just 22 players and their companions, plus our expert Pickleball instructor, creating a close-knit community where friendships are easily formed.
In Puglia, lose yourself in the region voted the most beautiful in the world. Walk through UNESCO World Heritage stone towns, live a day in the ancient city of Matera, and admire thousand-year-old olive trees. Indulge in the region’s iconic dishes like Burrata, Mozzarella, and “Bombette” BBQ, and learn to prepare Panzerotti - the typical Apulian fried pizza. Each day, you’ll play Pickleball with your group and at times against local players, capture stunning photos, and soak in the timeless beauty of the Mediterranean.
This exclusive 11-day Pickleball vacation is your chance to truly immerse yourself in the Italian lifestyle. With limited spaces, this is a rare opportunity to experience Italy like never before.
Take a closer look at your spectacular
Italy pickleball vacation itinerary
OPTIONAL PRE-TOUR
Are you interested in arriving a few days ahead of time before the start of the Pickleball group tour? Check out some of our recommendations in the Pre/Post Tour Section.
itinerary for 1 - 11 OCTOBER, 2025
October 1 » Piedmont
Welcome to Italy
• Arrive at Malpensa Airport (MXP), where our team will greet you and handle your transportation to the luxurious resort
• Unwind and settle into your stunning accommodations. Enjoy the resort’s top-notch amenities, including the pool, spa, and pickleball courts.
• In the evening, gather with fellow travelers for a sumptuous Welcome Dinner, setting the stage for an unforgettable journey.
October 2 » Piedmont
Pickleball & Alpine Adventure
• Morning: Start your day with an energizing pickleball session from 8:00 to 11:00 AM, where you can refine your skills and enjoy friendly competition.
• Afternoon: Venture to the breathtaking Mount Oropa Sanctuary, a UNESCO World Heritage Site. Enjoy a traditional Alpine lunch and explore the sanctuary, home to the revered Black Madonna.
• Evening: After some free time in the charming town of Biella, indulge in a hands-on Pizza Making Experience followed by a delightful dinner.
October 3 » Piedmont
Lake Maggiore Excursion
• Morning: Another spirited pickleball session from 8:00 to 11:00 AM.
• Afternoon: Spend the day exploring the beauty of Lake Maggiore, one of Italy’s largest and most famous lakes, surrounded by picturesque landscapes.
• Evening: Choose between a serene dinner at the resort or a lakeside dining experience based on group preference.
October 4 » Piedmont
Discover Lake Orta
• Morning: Sharpen your pickleball game with a morning session from 8:00 to 11:00 AM.
• Afternoon: Journey to Lake Orta, a hidden gem known for its stunning scenery and quaint villages. Explore some of Italy’s most picturesque spots.
• Evening: Enjoy a themed dinner at the resort, inspired by the flavors of the region.
October 5 » Piedmont
Medieval Wonders & Vineyard Elegance
• Morning: Engage in another round of pickleball from 9:00 AM to 12:00 PM, followed by a light Piedmontese lunch at the resort, featuring local delicacies.
• Afternoon: Explore the medieval fortified village of Ricetto in Candelo, a step back in time with its ancient granaries and wine cellars.
• Evening: Visit one of Piedmont’s most renowned wineries for a guided tour of the vineyards and cellars, culminating in an elegant dinner amidst the vines.
October 6 » Piedmont » Puglia
From Piedmont to Puglia
• Morning: After breakfast, we’ll transfer you to the airport (Milan Malpensa MPX or Turin Caselle TRN) for a direct domestic flight to Bari (BRI).
• Afternoon: Upon arrival, we’ll head to the enchanting town of Polignano a Mare for lunch and a guided tour of this coastal gem.
• Evening: Settle into our private 17th-century Masseria and Trulli in Puglia, reserved exclusively for our group. Enjoy an authentic Apulian BBQ dinner to kick off the southern leg of our journey.
October 7 » Puglia
Trulli & Panzerotti
• Morning: Pickleball training and play from 9:00 AM to 12:00 PM at our resort’s courts.
• Afternoon: Explore the iconic Trulli houses in Alberobello, a UNESCO World Heritage Site, and marvel at these unique, ancient structures.
• Evening: Participate in a Panzerotti-making lesson, learning to prepare this beloved Apulian fried pizza, followed by a delicious dinner.
October 8 » Puglia
Matera Magic
• Morning: Hit the pickleball courts from 9:00 AM to 11:30 AM for another fun session.
• Afternoon & Evening: Discover Matera, a UNESCO World Heritage Site and one of the world’s oldest continuously inhabited cities. Wander through its ancient cave dwellings and immerse yourself in its cinematic landscape. End the day with a special dinner and a magical night-time tour of Matera.
October 9 » Puglia
Ostuni & The White City
• Morning: Enjoy a final morning of pickleball from 9:00 AM to 12:00 PM.
• Afternoon: Visit Ostuni, known as the White City, with its dazzling whitewashed buildings and rich history. After a guided tour, enjoy some free time to explore.
• Evening: Savor dinner at the resort or in Ostuni, depending on the group’s preference.
October 10 » Puglia
Puglian Traditions & Culinary Delights
• Morning: Pickleball session from 9:00 AM to 12:00 PM.
• Afternoon: Experience the rustic charm of an ancient Apulian Masseria. Trek through its scenic landscapes and enjoy a tasting of fresh Mozzarella and Burrata, made on-site.
• Evening: Learn to make Orecchiette, Puglia’s signature handmade pasta, and enjoy a final dinner celebrating the rich flavors of the region.
October 11 » Departure from Puglia
Farewell to Italy
• Morning: After a leisurely breakfast, we’ll transport you to Bari Airport (BRI) for your journey home, carrying memories of Italy that will last a lifetime.
OPTIONAL POST-TOUR
Are you interested in extending your vacation with a few extra days in Europe? Check out some of our recommendations in the Pre/Post Tour Section.
OPTIONAL PRE-TOUR
Are you interested in arriving a few days ahead of time before the start of the Pickleball group tour? Check out some of our recommendations in the Pre/Post Tour section below.
OPTIONAL POST-TOUR
Are you interested in extending your vacation with a few extra days in Europe? Check out some of our recommendations in the Pre/Post Tour section below.
5-night accommodation » RELRELAIS SANTO STEFANO: A Tranquil Retreat in the Heart of Piedmont » Piedmont
RELAIS SANTO STEFANO: Elegance Redefined
Experience the essence of Piedmont at our exclusive Relais Santo Stefano, a beautifully restored 18th-century estate that once served as a noble residence. This unique property has been thoughtfully transformed into a sanctuary for both physical and spiritual well-being, all while preserving its historical charm and the rich cultural heritage of the Piedmont region. Surrounded by picturesque vineyards and rolling hills, this Relais is a true symbol of Italian elegance and tradition. The lush gardens and serene landscapes create a tranquil ambiance that invites guests to disconnect from the world and reconnect with nature. At Relais Santo Stefano, where history meets modern luxury, you will embark on a journey of rejuvenation, enveloped in the timeless beauty and sophisticated charm of Piedmont.
5-night accommodation » Masseria Quit Ut Deus: Serenity and Elegance » Puglia
Masseria Quit Ut Deus: Whispers of the Olive Groves
Experience the essence of Puglia at our exclusive 17th-century Masseria, a beautifully restored estate that once served as a farmhouse, stable, and chapel. This unique property has been meticulously transformed into a sanctuary for both physical and spiritual well-being, all while preserving its ancient charm and the rich cultural heritage of the Puglia region. Surrounded by iconic dry stone walls and monumental olive trees, this Masseria is a true symbol of the Mediterranean’s millenary tradition. The olive trees, revered for their nutritional, therapeutic, and symbolic significance, create a mystical ambiance that connects heaven and earth. Here, amidst the serene landscapes and timeless beauty of Puglia, guests are invited to embark on a journey of rejuvenation and inner peace, enveloped in the harmonious blend of history, nature, and luxury.
Inclusions
• 10 nights at distinctive 4+ star resorts: 5 nights in Piemonte and 5 nights in Puglia.
• All Pickleball group activities: Includes clinics, instruction, and a tournament.
• Airport group transportation: To and from the airports at a pre-arranged time. This is a group transfer, not individual transfers. If you arrival/departure time doesn’t match, we can arrange private transportation with an added cost
• Domestic flight included: Transportation on Day 5, plus a domestic flight from Milan Malpensa (MXP) or Turin Caselle (TRN) to Bari Airport, up to a maximum of $200. If the cost of the ticket exceeds $200, you will be charged the difference.
• Daily buffet breakfast.
• 4 Authentic Italian Dinners: Including a welcome dinner, pizza-making experience, panzerotti-making experience, and a farewell dinner featuring Orecchiette pasta.
• Private deluxe motor coach: For day trip excursions
• Guided tours with professional guides: Visits to Biella, Mount Oropa Sanctuary, Candelo fortified Castle, unique vineyards, Lake Maggiore, Lake Orta, Polignano a Mare, Alberobello, Matera, Ostuni, and a Masseria for Mozzarella & Burrata Experience, among others.
Exclusions
• International airfare
• Tips and gratuities
• Lunches
• Additional alcoholic beverages
• Optional extras and personal expenses
• Travel insurance
Airfare
We have consolidator and published airfare contracts available with all major airlines. If you’d like our assistance in securing your flight itinerary, please submit your request by clicking HERE.
Travel Insurance
Our preferred travel insurance partner is Travel Insured. We recommend the Worldwide Trip Protector policy.
Submit your Travel Insurance Request by Clicking HERE or access their website by clicking HERE to get a quote and purchase the policy.
Coverage and policy details HERE.
Optional pre-post stays & tours
If you’d like to extend your European vacation with an optional pre- or post stay, or visit another destination before or after your vacation, we can help. Not sure of what to pick? Schedule a consultation with us and we can come up with ideas tailored to your needs. Submit your extension request here.
Terms and Conditions
See Evyssa Vacations' Terms and Conditions by clicking here.
Have questions?
For all things Pickleball ask George by clicking HERE.
For all things Travel & Bookings ask Csilla by clicking HERE.
Pricing
To confirm your reservation, a non-refundable deposit of $2,000 per room is kindly requested at the time of sign-up. Please refer to the payment schedule below for a detailed summary of various charges and their due dates.
DOUBLE OCCUPANCY
• $7,995/person – Standard room (4)
• $8,345/person - Superior room (1)
• $8,445/person - Junior suite (1)
• $8,495/person - Trulli room (4)
• $8,695/person - Suite (1)
SINGLE OCCUPANCY
• $2,995 available in standard room only (1)
Options to upgrade your Piedmont accommodation, based on availability:
• Junior Suite $350/person in double occupancy
• Superior Suite $650/person in double occupancy
• Spa Suite $1,000/person in double occupancy
Contact us if you are interested in upgrading. The upgrade fee will be due upon confirmation of the upgrade.
Terms and Conditions:
• Deposit payments are non-refundable/non-transferable.
• Any Cancellation Requests must be submitted in writing by filling out the Trip Cancellation Request Form: Click HERE.
• The airfare cost included in this itinerary is just estimated at the time of deposit. • The airfare cost may vary depending on when you sign up for the tour and will be guaranteed only after 50% of the trip payment has been submitted.
• Those who pay their trip cost in full by 15 JAN will not be affected by any potential airfare cost increases included in this itinerary.
Payment schedule and due dates
Deposit: Due at the time of sign-up.
• 15 Jan 2025 - 1st installment of $3,000/person
• 15 May 2025 - Final Balance Due
*You may pay more than the minimum installment due anytime, or you may submit full payment anytime after the deposit has been paid and before the final due date. You can authorize any amount you wish to submit directly on your invoice link.
The following cancellation policy applies:
• All requests for cancellations must be submitted in written form by filling out the Trip Cancellation Request Form: Click HERE.
• Initial deposits are fully non-refundable, unless Evyssa Vacations cancels the tour due to lack of enough participants.
• Additionally, the following penalties will be imposed based on the timing of cancellations:
• Cancellations made by 15JAN will incur loss of deposit only.
• Cancellations made between 16JAN-15MAY will have a 30% penalty.
• Cancellations made between 16MAY- 10JUL will have a 50% penalty.
• Cancellations made from 11JUL will be at 100% penalty (non-refundable).
*If you cancel your reservation between 1 NOV-21 JUN, but can find someone else to go in your turn, we may be able to help transfer the funds over. Please note this is not guaranteed and will be dealt with on a first-come first served basis. No fund transfers will apply to bookings canceled on or after 21 JUN 2025. We strongly suggest insuring your trip cost.
**The cancellation penalty percentage is based on your total trip cost amount.
We highly recommend the purchase of optional travel insurance. We will be sending you a quote as soon as your deposit is submitted. A passenger becoming a single, as a result of a partner's cancellation, must pay the single supplement.
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Meet George Kas
Meet George Kas, a renowned certified Pickleball instructor, tournament champion and dedicated Du Page, IL Pickleball ambassador
"My mentor and coach was the number one women’s player Simone Jardim who I was so fortunate to have as my instructor. Instantly I was captivated by its fast-paced nature and social aspects, I immersed myself in learning everything about pickleball.
I honed my skills through countless hours of practice, participating in local and out of state tournaments, and seeking guidance and lessons from top pro players and coaches along the way. I decided to pursue being a pickleball instructor. I have completed coaching certifications, attended workshops and seminars, and continuously educated myself on the latest techniques, rules and strategies.
Because I am passionate and experienced pickleball instructor with a deep love for the sport of Pickleball with over 8 years of playing and coaching experience, I have become a respected figure in the pickleball community. I am a certified Professional Pickleball Registry (PPR) instructor/coach along with being a (USAPA) certified referee...."
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As certified travel agents, we work for you, our client. Customization is what we do best, and it looks different for each client. Our end to end services help you make travel decisions that best suit your needs, our creative consultants always come up with ideas and recommendations you might not otherwise consider, and we make sure your trip components are booked through trusted tour operators.
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We act as your advisor and your advocate, we help you understand where it makes sense to splurge or where to hold back, and assist in making sure that you make the best decisions for yourself and your family.
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