Where pickleball

takes you places.


Exceptional coaching. Beautiful destinations.

Small-group adventures with people who love the game.

Sharpen Your Skills. Elevate Your Game.

For intermediate and advanced players ready to build consistency, refine technique, and strengthen strategy through expert coaching, focused drills, and competitive guided play. Whether you’re learning the fundamentals, building consistency, or refining advanced strategy, our exceptional coaches help you take the next step. 

YOUR NEXT CHAPTER STARTS HERE

Good games. Extraordinary places.

Wine · Food

California

California’s Central Coast pairs exceptional pickleball coaching with the pleasures of Paso Robles wine country. Spend time sharpening your game, then explore welcoming wineries, a lively downtown, and nearby coastal towns. It’s a relaxed setting for good food, new friendships, and rewarding days on the court.

Nature · Adventure

Costa Rica

Lush tropical scenery and Costa Rica’s welcoming pura vida spirit set the stage for a memorable pickleball retreat. From Tamarindo’s Pacific beaches to the green landscapes near La Fortuna, each location offers its own blend of focused coaching, outdoor adventure, and time to unwind.

Culture · Cuisine

Vietnam

Discover a different side of pickleball in Vietnam, where time on the court opens the door to cultural experiences and connections with local players. Hanoi offers historic streets and a vibrant food scene, while Da Nang pairs coastal beauty with access to the lantern-lit charm of Hoi An. Expert instruction anchors a journey filled with discovery.

Desert · Sunshine

Arizona

Wide desert skies, mountain views, and striking Southwestern scenery create an inviting backdrop for improving your game. Our Arizona retreats pair expert pickleball coaching with comfortable accommodations and time to enjoy the region’s distinctive food, landscapes, and relaxed desert atmosphere.

Welcome to Picklebilly Travel

A love of the game. A world of possibilities.

Picklebilly brings together expert pickleball coaching, thoughtfully chosen destinations, and the pleasure of traveling with a small group. Our retreats typically welcome 16–20 travelers, with personal attention throughout the journey.


We organize the details—from court time and accommodations to shared meals and excursions—giving you time to learn, explore, and enjoy the people beside you.

More than a game. Better together.

The Picklebilly way

The Picklebilly experience

Everything you love. All in one journey.

Quality Pickleball

Find your rhythm. Elevate your game.

Beautiful destinations

Places that stay with you.

Meaningful connection

New faces. Lifelong friendships.

Curated experiences

A little discovery, every day.

Time to simply be

Unwind. Recharge. Take it all in.

The best part? The people.

Come for the pickleball.
Stay for the people.


The shared meals. The laughter after a long rally. The new friends who feel like old ones. The unexpected moments that become your favorite memories.


You're not booking a tournament. You're joining a curated experience—and a community that travels with you long after the final game.

Great people to learn from

Your game. In good hands.

Passionate coaches who love the game—and love helping you grow.

Senior pro · Coach

Scott Fliegelman

A former Division I tennis player and top-10 senior pickleball player. Scott pairs thoughtful strategy with a genuine belief in teamwork, trust, and camaraderie.

Certified pickleball coach

Ali Vassigh

A certified coach and enthusiastic tournament player. Ali brings energy, experience, and a love of the game to help players improve while keeping every session social and fun.

PPR-certified coach

Kelly Mada

With over six years of coaching experience, Kelly combines solid fundamentals, smarter decision-making, and mental fitness to build confidence on and off the court.

Strategy · Teamwork · Experience

Dave and Tracy Wilcox

Dave and Tracy Wilcox bring over 30 years of coaching experience and have taught more than 5,000 pickleball players. Combining expertise in strategy, technique, and mental performance, they help players of all levels make smarter decisions, improve their skills, and build confidence on the court.

Competitive Play · Expert Coaching

Sarah Bowman

Sarah Bowman is a former nationally ranked junior tennis player and Division I athlete with professional pickleball experience. She combines competitive expertise and a passion for teaching to help players of all levels improve their skills and elevate their game.

Technical Skills · Confidence

Rachel Kelterer

Rachel Kelterer is a former Division I tennis player who brings expert instruction and an encouraging approach to pickleball, helping players of all levels build confidence and improve their game.

Beyond the baseline

The destination is

part of the experience.

Local flavors. Unexpected discoveries. A different perspective.

Because the best journeys have more than one kind of magic.

Meet your host

A personal touch.

From the very beginning.

Janice Mundee founded Picklebilly to bring together her love of pickleball, travel, and connecting people. Based in Paso Robles, California, she personally scouts destinations and shapes each retreat with attention to coaching, accommodations, and the experiences that make a trip memorable.


From your first question to your time on the trip, Janice brings a welcoming, hands-on approach.

The memories speak for themselves.

From our traveling community

Janice did a wonderful job organizing this pickleball camp in Pasa Robles. I liked the small group format- only 16 participants. This allowed for lots of contact with the coaches and the ability to spend a lot of time on the courts practicing. The coaches provided excellent instruction and really focused on strengths. I highly recommend Picklebilly camps! 

Janet L

What a blast! Great hotel and grounds made me feel like I was in a villa in Italy. Lots of places to sit and savor the vibe. Pickleball instruction was excellent, lots of great lessons to go home with. The group of women who attended, both locals and out-of-towners, were so fun to play with on and off the courts. The excursions to the coast, rooftop restaurant, dancing, and winery lunch were lovely additions to a perfect weekend! Can’t wait to come back next year! 

Cristi M

What a fabulous experience! The trip was extremely well organized, and Janice did a great job keeping us informed before and during the trip. She added special touches and created a space where all felt welcomed and included. The coaching was absolutely fantastic! I learned so much and know the new knowledge/skills will improve my game. Thank you for a wonderful time.

Amy M

Hear It From the Pickleball Crew

A LITTLE ADVENTURE. A LOT OF CONNECTION.

Your next great game might be somewhere beautiful.

California Pickleball Retreat with Sarah Bowman

California Pickleball Retreat with Sarah Bowman

<p>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.</p><p></p><p>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.</p><p>This is not a massive tournament-style event. It’s a curated small-group retreat where coaching, connection, fun, and relaxation all matter.</p><p></p><p>You’ll enjoy daily coached pickleball sessions with Kelly Mada, focused on helping you sharpen strategy, gain confidence, and elevate your play in a supportive environment.</p><p></p><p>Off the court, unwind with private wine tasting, memorable group dinners, and the charm of Paso Robles.</p><p></p><p>Hosted by Picklebilly Travel, known for intimate, high-touch pickleball experiences where guests leave with stronger games and new friendships.</p><p></p><p><strong>Only 16 spots available. Once full, registration closes.</strong><br>Reserve your place with a <strong>$500 deposit</strong>.</p>

Rating:
Location: Paso Robles, CA 93446, USA
Duration:
Pax:
From:
TRACY WILCOX: Women's Pickleball Retreat /Costa Rica

TRACY WILCOX: Women's Pickleball Retreat /Costa Rica

Rating:
Location: Arenal Volcano, Alajuela Province, San Carlos, Costa Rica
Duration:
Pax:
From:
Vietnam with Dave and Tracy Wilcox

Vietnam with Dave and Tracy Wilcox

<p>Vietnam is one of those destinations that stays with you long after you leave — the energy of Hanoi's ancient streets, the silence of limestone islands rising from emerald water, the warmth of a culture that welcomes strangers like old friends. This 13-night journey takes you through three of the country's most extraordinary places: four nights in Hanoi's storied Old Quarter, two nights aboard a luxury cruise through the UNESCO-recognized waters of Ha Long Bay, and seven nights at New World Hoiana Beach Resort — a Forbes four-star property on the Central Vietnam coast, named the World's Leading Fully Integrated Resort two years running.</p><p>And then there's the pickleball. Four dedicated morning sessions with Scott Fliegelman, one of the most sought-after coaches in the country, on eight courts steps from the South China Sea. Between sessions: a water puppet show performed on a lake stage, ancient Cham ruins hidden in jungle, the most spectacular outdoor performance production in Southeast Asia, a basket boat ride through a water coconut forest, and a hands-on cooking class in the streets of Hoi An. This trip is built for players who want to get better, see something real, and share it with people who love the game as much as they do.</p>

Rating:
Location: Hanoi, Vietnam
Duration:
Pax:
From:
Vietnam with Sarah Bowman

Vietnam with Sarah Bowman

<p>Vietnam is one of those destinations that stays with you long after you leave — the energy of Hanoi's ancient streets, the silence of limestone islands rising from emerald water, the warmth of a culture that welcomes strangers like old friends. This 13-night journey takes you through three of the country's most extraordinary places: four nights in Hanoi's storied Old Quarter, two nights aboard a luxury cruise through the UNESCO-recognized waters of Ha Long Bay, and seven nights at New World Hoiana Beach Resort — a Forbes four-star property on the Central Vietnam coast, named the World's Leading Fully Integrated Resort two years running.</p><p>And then there's the pickleball. Four dedicated morning sessions with Scott Fliegelman, one of the most sought-after coaches in the country, on eight courts steps from the South China Sea. Between sessions: a water puppet show performed on a lake stage, ancient Cham ruins hidden in jungle, the most spectacular outdoor performance production in Southeast Asia, a basket boat ride through a water coconut forest, and a hands-on cooking class in the streets of Hoi An. This trip is built for players who want to get better, see something real, and share it with people who love the game as much as they do.</p>

Rating:
Location: Hanoi, Vietnam
Duration:
Pax:
From:
Sarah's Pickleball Retreat

Sarah's Pickleball Retreat

<p>Join us for an unforgettable pickleball retreat in Tamarindo, Costa Rica, combining high-level coaching, match play, and a fun, social travel experience. You’ll train, compete, and connect with a great group while enjoying beautiful surroundings and curated activities. This trip is designed for players who want to improve their game and have an incredible time doing it.</p><p></p><p>The Villa is located in a private subdivision in Tamarindo "Hacienda Pinilla." Hacienda Pinilla&nbsp;is located within its own 4,500-acre master-planned gated community, often referred to as the&nbsp;Hacienda Pinilla&nbsp;Resort and Residential Community located on the Gold Coast of the Guanacaste province in Costa Rica. It is situated near Santa Cruz and adjacent to beaches such as Playa Avellanas and Playa Langosta.&nbsp;<br><br>• Location: Guanacaste, Costa Rica (Pacific Coast).<br>• Composition: It is a large-scale development divided into8 specific residential communities.<br>• Communities: Individual gated communities within the larger property include Las Golondrinas, Palma Real, La Dulce Vida, and El Jaguar.<br>• Key Amenities: Includes the JW Marriott Guanacaste, an 18-hole golf course, and a Beach Club.&nbsp;<br></p>

Rating:
Location: Guanacaste Province, Tamarindo, Costa Rica
Duration:
Pax:
From:
Costa Rica with Ali Vassigh

Costa Rica with Ali Vassigh

<p>Join us for an unforgettable pickleball retreat in Tamarindo, Costa Rica, combining high-level coaching, match play, and a fun, social travel experience. You’ll train, compete, and connect with a great group while enjoying beautiful surroundings and curated activities. This trip is designed for players who want to improve their game and have an incredible time doing it.</p>

Rating:
Location: Guanacaste Province, Tamarindo, Costa Rica
Duration:
Pax:
From:
Scott Fliegelman Pickleball Retreat

Scott Fliegelman Pickleball Retreat

<p>Join us for an unforgettable pickleball retreat in Tamarindo, Costa Rica, combining high-level coaching, match play, and a fun, social travel experience. You’ll train, compete, and connect with a great group while enjoying beautiful surroundings and curated activities. This trip is designed for players who want to improve their game and have an incredible time doing it.</p>

Rating:
Location: Guanacaste Province, Tamarindo, Costa Rica
Duration:
Pax:
From:
California Pickleball Retreat with Sarah Bowman

California Pickleball Retreat with Sarah Bowman

<p>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.</p><p></p><p>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.</p><p>This is not a massive tournament-style event. It’s a curated small-group retreat where coaching, connection, fun, and relaxation all matter.</p><p></p><p>You’ll enjoy daily coached pickleball sessions with Kelly Mada, focused on helping you sharpen strategy, gain confidence, and elevate your play in a supportive environment.</p><p></p><p>Off the court, unwind with private wine tasting, memorable group dinners, and the charm of Paso Robles.</p><p></p><p>Hosted by Picklebilly Travel, known for intimate, high-touch pickleball experiences where guests leave with stronger games and new friendships.</p><p></p><p><strong>Only 16 spots available. Once full, registration closes.</strong><br>Reserve your place with a <strong>$500 deposit</strong>.</p>

Rating:
Location: Paso Robles, CA 93446, USA
Duration:
Pax:
From: 279,900
TRACY WILCOX: Women's Pickleball Retreat /Costa Rica

TRACY WILCOX: Women's Pickleball Retreat /Costa Rica

Rating:
Location: Arenal Volcano, Alajuela Province, San Carlos, Costa Rica
Duration:
Pax:
From: 289,900
Vietnam with Dave and Tracy Wilcox

Vietnam with Dave and Tracy Wilcox

<p>Vietnam is one of those destinations that stays with you long after you leave — the energy of Hanoi's ancient streets, the silence of limestone islands rising from emerald water, the warmth of a culture that welcomes strangers like old friends. This 13-night journey takes you through three of the country's most extraordinary places: four nights in Hanoi's storied Old Quarter, two nights aboard a luxury cruise through the UNESCO-recognized waters of Ha Long Bay, and seven nights at New World Hoiana Beach Resort — a Forbes four-star property on the Central Vietnam coast, named the World's Leading Fully Integrated Resort two years running.</p><p>And then there's the pickleball. Four dedicated morning sessions with Scott Fliegelman, one of the most sought-after coaches in the country, on eight courts steps from the South China Sea. Between sessions: a water puppet show performed on a lake stage, ancient Cham ruins hidden in jungle, the most spectacular outdoor performance production in Southeast Asia, a basket boat ride through a water coconut forest, and a hands-on cooking class in the streets of Hoi An. This trip is built for players who want to get better, see something real, and share it with people who love the game as much as they do.</p>

Rating:
Location: Hanoi, Vietnam
Duration:
Pax:
From: 399,900
Vietnam with Sarah Bowman

Vietnam with Sarah Bowman

<p>Vietnam is one of those destinations that stays with you long after you leave — the energy of Hanoi's ancient streets, the silence of limestone islands rising from emerald water, the warmth of a culture that welcomes strangers like old friends. This 13-night journey takes you through three of the country's most extraordinary places: four nights in Hanoi's storied Old Quarter, two nights aboard a luxury cruise through the UNESCO-recognized waters of Ha Long Bay, and seven nights at New World Hoiana Beach Resort — a Forbes four-star property on the Central Vietnam coast, named the World's Leading Fully Integrated Resort two years running.</p><p>And then there's the pickleball. Four dedicated morning sessions with Scott Fliegelman, one of the most sought-after coaches in the country, on eight courts steps from the South China Sea. Between sessions: a water puppet show performed on a lake stage, ancient Cham ruins hidden in jungle, the most spectacular outdoor performance production in Southeast Asia, a basket boat ride through a water coconut forest, and a hands-on cooking class in the streets of Hoi An. This trip is built for players who want to get better, see something real, and share it with people who love the game as much as they do.</p>

Rating:
Location: Hanoi, Vietnam
Duration:
Pax:
From: 399,900
Sarah's Pickleball Retreat

Sarah's Pickleball Retreat

<p>Join us for an unforgettable pickleball retreat in Tamarindo, Costa Rica, combining high-level coaching, match play, and a fun, social travel experience. You’ll train, compete, and connect with a great group while enjoying beautiful surroundings and curated activities. This trip is designed for players who want to improve their game and have an incredible time doing it.</p><p></p><p>The Villa is located in a private subdivision in Tamarindo "Hacienda Pinilla." Hacienda Pinilla&nbsp;is located within its own 4,500-acre master-planned gated community, often referred to as the&nbsp;Hacienda Pinilla&nbsp;Resort and Residential Community located on the Gold Coast of the Guanacaste province in Costa Rica. It is situated near Santa Cruz and adjacent to beaches such as Playa Avellanas and Playa Langosta.&nbsp;<br><br>• Location: Guanacaste, Costa Rica (Pacific Coast).<br>• Composition: It is a large-scale development divided into8 specific residential communities.<br>• Communities: Individual gated communities within the larger property include Las Golondrinas, Palma Real, La Dulce Vida, and El Jaguar.<br>• Key Amenities: Includes the JW Marriott Guanacaste, an 18-hole golf course, and a Beach Club.&nbsp;<br></p>

Rating:
Location: Guanacaste Province, Tamarindo, Costa Rica
Duration:
Pax:
From: 379,900
Costa Rica with Ali Vassigh

Costa Rica with Ali Vassigh

<p>Join us for an unforgettable pickleball retreat in Tamarindo, Costa Rica, combining high-level coaching, match play, and a fun, social travel experience. You’ll train, compete, and connect with a great group while enjoying beautiful surroundings and curated activities. This trip is designed for players who want to improve their game and have an incredible time doing it.</p>

Rating:
Location: Guanacaste Province, Tamarindo, Costa Rica
Duration:
Pax:
From: 299,900
Scott Fliegelman Pickleball Retreat

Scott Fliegelman Pickleball Retreat

<p>Join us for an unforgettable pickleball retreat in Tamarindo, Costa Rica, combining high-level coaching, match play, and a fun, social travel experience. You’ll train, compete, and connect with a great group while enjoying beautiful surroundings and curated activities. This trip is designed for players who want to improve their game and have an incredible time doing it.</p>

Rating:
Location: Guanacaste Province, Tamarindo, Costa Rica
Duration:
Pax:
From: 379,900
Your next chapter starts here

Good games. Extraordinary places.

Join our upcoming trips for exceptional pickleball experiences in thoughtfully chosen destinations with expert coaching and small groups

New places. New friends. Stories you’ll tell for years.

The best trips leave you with more friends than you started with.

Go somewhere beautiful. Play a little. Laugh a lot.

Come for the adventure. Go home with the stories.

Travel is the only thing you buy that makes you richer.

We travel not to escape life, but for life not to escape us.

"To travel is to live.”

— Hans Christian Andersen

**“Once a year, go someplace you’ve never been before.” **

— Dalai Lama

“Life is short and the world is wide.”

— Anonymous

“Wherever you go becomes a part of you somehow.”

— Anita Desai

What you'll learn

Line drawing of a lightbulb with a small face and curved lines beside it.

Better Technique

Professional coaches fix your grip, stance, and swing mechanics for serves, dinks, and volleys.

Light bulb icon with a checkmark inside and rays around it

Smart Strategy

You learn and practice high-level tactics like the third-shot drop, transition zone footwork, and how to outsmart opponents at the kitchen line.

Black-and-white line drawing of a tennis racket and two tennis balls

Targeted Drills

Camps replace casual play with repetitive, high-volume practice so your body learns to hit shots consistently.

Outlined circle with small hollow circles arranged inside like a pattern or perforated disk

Personalized Feedback

Instructors use one-on-one observation to spot hidden mistakes in your gameplay. 

Women's Trip to Paso Robles

Wine Country

California, USA

September 17-21, 2026

Pickleball in Tamarindo



Costa Rica

February 14-21, 2027

Pickleball in Aruba



Aruba

September 17-21, 2026

Woman in flowing white dress dancing in a sunlit canyon, fabric billowing in the wind
Collaborate

Partner With Picklebilly

We love collaborating with passionate coaches and exceptional destinations to create meaningful pickleball travel experiences.

Trophy cup icon with a star in the center

Are You a Coach?

Do you love the game, spend time on the court, and feel called to bring your community together through travel? Picklebilly partners with coaches who want to lead unforgettable retreats without having to manage all the logistics alone.



We help with planning, coordination, guest experience, and operational support so you can focus on what you do best — coaching, connecting, and creating a great week for your players. Whether you’re exploring your first retreat or looking to grow your travel offerings, we’d love to collaborate.


Simple black line drawing of a hut and palm tree on a small island by water

Are You a Resort or Club?

Do you have a beautiful property, pickleball facility, or destination that would be a great fit for hosting small groups of enthusiastic players? Picklebilly works with resorts and clubs to bring curated groups of 16–30 guests who value quality experiences, great play, and a welcoming environment.


We partner with destinations that want to showcase their location while creating memorable stays for guests and long-term relationships built on trust and collaboration.

Our Story

About Picklebilly
Travel

2020

Branding

25+

Destinations worldwide

500+

BrandHappy travelersing

4.8★

Branding

Picklebilly Travel creates small-group pickleball retreats in beautiful destinations around the world, blending great play, connection, and unforgettable travel experiences.


It evolved from Picklebilly Hosted Housing — a global network that connected players with places to stay and play — which revealed the power of bringing people together through pickleball.


Today, Picklebilly builds on that foundation by offering thoughtfully curated trips designed to feel seamless, social, and genuinely fun.

2020

Branding

25+

Destinations worldwide

500+

BrandHappy travelersing

4.8★

Branding

Testimonials

What Our Community Says

“None of this retreat would have been possible without Janice Mundee, who curated every detail — housing, food, registration, and excursions. Absolute magic.”

Tracy Wilcox

“Being part of the instructional staff in Costa Rica was incredibly meaningful to me. The camaraderie among the group was special, and I truly enjoyed working alongside such supportive, passionate people. I also gained valuable personal insights from the experience, which made the trip even more rewarding. ”

Kelly Mada

“I was terrified—flying halfway around the world to join a group of strangers in Costa Rica? No clue what to expect. But I took the leap of faith, and it was AMAZING! Wild game nights that left us crying with laughter, gourmet feasts from our private chef fueling every adventure, top-notch coaching that pushed me to expand, and challenging open play to practice our newfound tips and tricks. Beautiful friendships, stronger pickleball skills, mental tenacity that’s changed me, and memories I’ll cherish forever. Worth every penny. Can’t wait for the next one!”

Giselas Plazas