TAMARINDO, COSTA RICA
ARRIVE — CONNECT — PLAY — REFLECT — CELEBRATE
JANUARY 12-19, 2027
An Elevated Pickleball Experience
Join us in Tamarindo for a curated week of pickleball, coastal adventure, and easy connection set in a private luxury villa. This experience brings together focused coaching, great play, shared meals, and the relaxed rhythm of Costa Rica.
Spend your days on court refining your game, enjoying the beauty of the coast, and connecting with a small group of like-minded players. With thoughtful hosting and seamless logistics, the week is designed to feel both energizing and effortless.
Whether you come for the pickleball, the people, or simply a memorable getaway, you’ll leave with new friendships and lasting memories.
Scott Fliegelman
Scott Fliegelman
About Coach Scott Fliegelman
Scott Fliegelman brings a lifetime of high-level competition, deep athletic experience, and a genuine love of the game to every court he steps on. A former Division I tennis player who competed professionally, Scott spent years immersed in endurance sports and high-performance training before discovering pickleball in 2019 — and quickly rising to become a top-10 senior player in both doubles and singles. Known for his strategic mind, competitive edge, and passion for continuous improvement, Scott has competed against the best players in the country, including in the National Pickleball League, where he served as a team captain and mentor. What truly sets Scott apart, though, is his ability to connect with players — he believes the heart of pickleball lies in teamwork, trust, and camaraderie, and he brings that philosophy into every coaching session. Travelers can expect thoughtful instruction, smart strategy insights, and a supportive environment that helps players elevate their game while enjoying the experience. Spending a week on court with Scott means learning from someone who not only understands high-level competition, but also loves helping others grow and have fun along the way.
What This January 12-19, 2027 Experience Includes:
Daily coached sessions + guided play led by Coach Scott Fliegelman
Seven nights in a private luxury villa in Tamarindo
Daily Breakfast and lunch or dinner daily prepared by our private chef
Double occupancy ensuite accommodations with air conditioning, a safe for valuables, and full WI-FI
Coached sessions + guided play led by Coach Scott Fliegelman
A lush pool and backyard oasis surrounded by palm trees — your own private retreat for relaxing, gathering, and unwinding
Opportunities to meet, play, and compete with local players
Live musicians during select dinners for relaxed, festive evenings
Morning yoga sessions on select days in the peaceful outdoor setting
Daily housekeeping so you can fully relax and enjoy your stay
Private transportation for group activities and scheduled outings
A snorkeling and sunset dinner cruise along the coast
Zipling, horseback riding, tubing, and a visit to Volcanic hot springs
Visit to the Tamarindo Night Market to explore local food, crafts, and culture
Access to a nearby beach club with full restaurant, pool, and cocktail service
Optional golf and bike rentals for additional exploration and recreation
Airport transfers and on-site support throughout the week
Time to unwind — beach walks, poolside lounging, and unstructured downtime
Shared meals and connection time with a small, welcoming group
Airfare NOT included
$3,799 pp/dbl occupancy
Sample Itinerary
Every retreat follows a thoughtfully curated rhythm of coaching, play, adventure, and time to relax. Activities may shift slightly based on weather, group preferences, and local opportunities — but the spirit of the experience remains the same.
Day 1 — Arrival in Costa Rica
Fly into Liberia International Airport (LIR)
Private transportation to the villa (approx. 1 hour 30 minutes)
Settle in and unwind
Afternoon pickleball coaching, training and open play
Welcome gathering and dinner at the villa
Day 2 — Settle Into the Rhythm
Breakfast at the villa
Early morning yoga
Pickleball coaching, training, and open play
Lunch
Relax by the pool (massages available)
Explore Tamarindo night market
Day 3 — Adventure + Play
Breakfast
Pickleball coaching, training, and play
Lunch
Massages by pool
local hike
Enjoy the villa’s resort-style pool
Dinner at a beach club
Day 4 — Nature + Local Culture
Breakfast
Tour: Zipline, horseback ride, tubing, hot spring soak and lunch
Dinner at the villa with live local musicians
Day 5 — Ocean Day
Breakfast
Pickleball coaching, training, and play
Lunch
Shopping in Tamarindo, Catamaran, snorkeling, and sunset dinner tour
Dessert back at the villa
Day 6 — Restore + Recharge
Breakfast
Guided nature hike
Lunch
Optional massages or spa time
Pickleball in Tamarindo with local players
Relax and enjoy the villa
Group dinner
Day 7 — Celebration Day
Breakfast
Pickleball coaching, training, and play
Lunch
Optional bike rentals or free time
Final farewell dinner with local musicians
Day 8 — Departure
Breakfast
Check-out
Private transportation to Liberia International Airport (LIR)
This itinerary is designed to balance structured coaching with plenty of space
to relax, connect, and enjoy Costa Rica at your own pace.
⭐ What Happens After You Reserve
1️⃣ Your deposit holds your place in the retreat and confirms your intent to join us in Tamarindo.
2️⃣ You’ll receive a confirmation with next steps and important trip details.
3️⃣ Trip updates + planning support. We’ll stay in touch with updates, reminders, and helpful planning information as the retreat approaches.
4️⃣ Final payment: Your remaining balance will be invoiced prior to the retreat.
5️⃣ After final payment, you’ll receive a detailed participant form to collect travel details, preferences, and final acknowledgements so we can prepare for your arrival.
6️⃣ Get ready for Costa Rica ☀️🏖️ Pack your paddle — we’ll take care of the rest.
Frequently Asked Questions
What level of player is this retreat for?
Players of varying levels are welcome. Coaching and play will be structured to support improvement in a relaxed and encouraging environment.
Are rooms shared or private?
Accommodations are double occupancy with ensuite bathrooms. Roommate matching may be available if needed.
What is a typical day like?
Expect a balance of structured pickleball sessions, free time, shared meals, and opportunities to enjoy and explore Tamarindo. A
What happens if it rains?
Weather in Costa Rica can include brief showers. We build flexibility into the schedule and adjust activities as needed to ensure a great experience.
Do I need travel insurance?
Travel insurance is strongly recommended to protect your investment in case of unforeseen changes.
Can I bring a non-playing partner?
Please reach out to discuss options — we will do our best to accommodate when possible.
What if I need to cancel?
Please refer to the cancellation policy section above for full details.
How many participants will there be?
The retreat is intentionally limited to maintain a personal, high-touch experience.
Will my valuables be safe?
Yes — each suite includes a personal safe for passports, electronics, and valuables. The villa is private and secure, allowing you to relax with peace of mind.
Is there air conditioning?
Yes — each suite has its own air conditioner so you can stay comfortable throughout your stay.
Do I need to exchange money?
No — U.S. credit cards and U.S. currency are widely accepted. It’s helpful to bring some cash for tipping, entry fees, paying for a brief taxi ride, or small purchases or incidentals.
As a general guideline, we suggest a gratuity of approximately $100 per person to be shared among the chef, housekeeping team, and property staff.
Is there housekeeping?
Yes — daily housekeeping is provided so you can relax and enjoy your time at the villa.
Is Wi-Fi available?
Yes — the villa has reliable Wi-Fi throughout the property.
What airport should I go to?
You will book your ticket to Liberia airport. We will collect everyone’s arrival flights and arrival times and coordinate transportation to the villa.