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Pickleball Getaway
Serve. Rally. Relax.
A Sandals Resort Pickleball Destination Experience
Escape to Jamaica for an exceptional pickleball experience at Sandals Montego Bay. Enjoy luxury accommodations, expert instruction, tournament play, and island elegance—all in one unforgettable package.
Bruce Billings
Bruce Billings is a PPR-certified instructor/coach and Director of Pickleball at Prestonwood Baptist Church in Prosper, Texas. He has coached at Pickleball Kingdom and is currently the Pickleball Pro at Chicken-N-Pickle. A USAP Ambassador and Selkirk Sports Affiliate, Bruce has over five years of tournament experience, earning numerous Gold, Silver, and Bronze medals across PPA, APP, and local events—qualifying and playing for the highly competitive Nationals and World Pickleball Championships.
His high energy and passion for pickleball are contagious. He loves helping others with strategy and improving their skills. Private lessons will be available upon request.
Event Details
February 22-26, 2027. Montego Bay, Jamaica; Sandals Resort. Prices starting at $3,500 for double occupancy room.
Package Includes:
- All-inclusive resort stay
- Round-trip airport transfers
- Oceanview / Oceanfront accommodations
- Meals, beverages, snacks, and resort activities
- 12+ hours of designated play
- Private lessons available upon request
- Tournament and programming with certified pickleball host & coach
- Tournament merch and prizes, and more
Accommodations & Pricing
4 Nights – All-Inclusive | Total Cost per Couple
Starting at $3,509 – Crystal Lagoon Honeymoon Oceanview Luxury Room
- 4-Night All-Inclusive Stay at Sandals Montego Bay
- All Meals, Drinks, Snacks & Resort Activities
- Round-Trip Airport Transfers
- Pickleball Community where all skill levels are welcome
- Dedicated Pickleball Courts reserved for free play, drills & lessons
- Welcome Party to kick off the fun
- Group Photo Session to capture the memories
- Tournament Play with fellow guests
- Awards Dinner to celebrate the champions
- Flexible schedule for non-playing guests
- Deposit: $250 per couple (non-refundable)
- First Payment Due: October 15, 2026
- Final Payment Due: December 15, 2026
* Your reservation must be booked through Crazy Imagination Travel to ensure inclusion in the group.
Paddles, Paradise & Poolside Perfection
Beyond the courts, immerse yourself in the luxury of one of the world’s most breathtaking beaches. Savor unlimited gourmet dining and premium beverages, unwind by the pool, and enjoy an array of watersports and resort activities at your leisure.
Whether you choose to join group events or relax on your own schedule, this retreat offers the perfect blend of recreational play and indulgent downtime in paradise.
Overwater bars, swim-up bars, and elegant retreats offer the perfect way to unwind at the end of the day. Relax and enjoy, knowing every cocktail is crafted with premium spirits, the wine selection is top-tier, and best of all — it’s all included.
Let us take care of the logistics while you focus on play, relaxation, and connection in one of the Caribbean’s most idyllic settings.
Sandals Montego Bay features twelve specialty restaurants, each offering a unique and exceptional dining experience. With skilled chefs at the helm of every kitchen, every meal is crafted to world-class standards.
Spots are limited—reserve yours today and experience a pickleball vacation like no other, where certified coaching meets tropical luxury.
