Pickleball Getaway
Serve. Rally. Relax.

November 8-12, 2026 | Sandals Montego Bay, Jamaica

A Sandals Resort Pickleball Destination Experience

Featuring Certified Pickleball Coach and Host Bruce Billings

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.

Two women on an outdoor pickleball court smiling and giving each other a high five, holding paddles and a pickleball.
RESERVE YOUR SPOT

Meet Your Host

Smiling man in a Chicken N Pickle shirt and cap holding a red pickleball paddle and green ball in front of a wooden logo wall.

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.

sandals-pickleball
Close-up of a yellow pickleball and paddle lying on a court, with sunlight casting shadows.

Details

November 8-12, 2026. 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

* Room pricing and availability subject to change until deposit is paid.

What's Included

  • 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

Payment Details

Deposit:
$250 per couple (non-refundable)

Final Payment Due:
July 1, 2026

BOOK YOUR TRIP

* 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.

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.

Swim-up bar at Sandals Montego Bay featuring stone archways, submerged barstools, and a scenic ocean view with a sailboat in the distance.

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.

Swim-up bar at Sandals Montego Bay featuring stone archways, submerged barstools, and a scenic ocean view with a sailboat in the distance.
A tropical pool area at Sandals Montego Bay featuring a swim-up bar, a thatched-roof bridge, hot tub, lounge chairs, and a private beach overlooking the turquoise Caribbean Sea.

Spots are limited—reserve yours today and experience a pickleball vacation like no other, where certified coaching meets tropical luxury.

A tropical pool area at Sandals Montego Bay featuring a swim-up bar, a thatched-roof bridge, hot tub, lounge chairs, and a private beach overlooking the turquoise Caribbean Sea.
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