A hosted women’s pickleball getaway in the heart of Paso Robles wine country — designed for intermediate players who want to improve their game, connect with great people, and enjoy a truly elevated experience.

Stay four nights at the beautiful Allegretto Vineyard Resort Paso Robles, a Tuscan-inspired luxury resort known for its peaceful grounds, spa atmosphere, and perfect wine country setting.

This is not a massive tournament-style event. It’s a curated small-group retreat where coaching, connection, fun, and relaxation all matter.

You’ll enjoy daily coached pickleball sessions with Coaches Kelly Mada and Rachel Kelterer, focused on helping you sharpen strategy, gain confidence, and elevate your play in a supportive environment.

Off the court, unwind with private wine tasting, memorable group dinners, and the charm of Paso Robles.

Hosted by Picklebilly Travel, known for intimate, high-touch pickleball experiences where guests leave with stronger games and new friendships.

Only 16 spots available. Once full, registration closes.
Reserve your place with a $500 deposit.

Coach Kelly Mada is a certified PPR coach with over six years of experience helping players elevate their game with clarity and confidence. As a competitive tournament player and medalist, she brings real-match insight into every session—bridging the gap between practice and performance.

Kelly is known for her ability to quickly assess each player’s unique strengths and challenges, allowing her to tailor instruction that meets players exactly where they are—and moves them forward efficiently. Her coaching style is both strategic and supportive, focused on building solid fundamentals, smarter decision-making, and consistent execution under pressure.

A strong believer that mental fitness is just as important as physical skill, Kelly integrates mindset training into her coaching, helping players develop focus, resilience, and confidence on the court.

From nationally ranked junior tennis player to passionate pickleball coach, Rachel Kelterer has spent a lifetime mastering racket sports. After competing at the Division I level in college, Rachel stepped away from tennis to raise her children.  Once grown, Rachel discovered pickleball and immediately fell in love with the game! Rachel is known for her ability to break down technique, sharpen strategy, and help players understand why certain skills matter. Rachel creates a fun, supportive environment where players feel encouraged, challenged, and excited to improve.  Beginners love her patience; advanced players appreciate her eye for detail. When she’s not coaching, Rachel serves as a high school counselor in Thousand Oaks, where her supportive nature continues to make an impact. 

Arrive in beautiful Paso Robles—one of California’s most sought-after wine regions, just 30 minutes from the coast.

Settle into our upgraded hotel, the incredible Allegretto Wine Resort with delightful surprises around every corner.

In the evening, join us for a relaxed welcome reception.
Meet the group, get a feel for the weekend ahead, and ease into the experience.

The owner of the Allegretto has collected a diverse collection of art from around the world. Enjoy this video showing parts of his collection you'll see as you walk around the resort. https://youtu.be/vsB4vXNHYdk?si=41GDn-kGt9eOeQaM

Start the day with a morning pickleball session at 8:30 AM at the Paso Robles Sports Club. Transportation will meet you at 8 AM in the Allegrettos lobby.

Train with Kelly Mada and Rachel Kelterer; their approach goes beyond drills—they'll helps you understand why shots work, then adapt their coaching to your personal style so you can actually apply it in real play.

After the session, enjoy a relaxed afternoon.

Unwind by the pool and allow time in the hotel to walk around outside and enjoy all the artwork and landscape. You can walk around the vineyards, the firepits, gardens, the courtyard, a small Church and stroll a musical labyrinth. The grounds are beautiful. Friday evenings enjoy local acoustic music in the courtyard.

Start the day back at the Paso Robles Sports Club for another focused session with Kelly. Transportation will meet you in the lobby at 8 AM.

Kelly's coaching goes beyond repetition—she builds in real-game scenarios so you’re not just learning shots, you’re practicing strategy under pressure. You’ll feel the difference between drilling and actually playing, and start to trust your decisions on the court.

In the afternoon, we shift gears.

We’ll head to Parrish Family Vineyard for a private wine tasting and late afternoon feast. Enjoy a curated selection of local white and red varietals alongside a beautifully prepared meal featuring fresh, seasonal ingredients.

As the sun sets, settle into a relaxed, social evening—great conversation, great wine, and the kind of connection that makes these trips special.

Our final training session brings it all together.

Starting at 8:30 AM, you’ll focus on resets, driving the ball, and intentional placement—skills you can take straight into your everyday play. Kelly and Rachel will guide you through applying these in real-time so you leave feeling confident and sharp.

The afternoon is yours to rest, recharge, and get packed up.

Then we finish strong.

At 2:30 PM, we return to the courts for a lively King/Queen of the Court round robin. Local players will join in, giving you the chance to test your new skills in a fun, slightly competitive setting.

It’s the perfect way to wrap up the weekend—playing, connecting, and seeing just how much your game has grown.

We'll finish the day at a favorite local spot for a relaxed lunch featuring gluten-free pizzas, fresh salads, and house-made desserts. At this final meal, we'll close out the weekend—celebrating the connections made, the progress on the court, and the shared experience.

You’ll leave with a small parting gift from us as a thank you for being part of this special group.

Departure – Until Next Time

Enjoy a relaxed morning, final goodbyes, and departures.

Before you head out, we’ll gather briefly to close out the weekend—celebrating the connections made, the progress on the court, and the shared experience.

You’ll leave with a small parting gift from us as a thank you for being part of this special group.