Upcoming Trips in 2026
COMING SOON - PINEAPPLE BEACH CLUB, ANTIGUA
DATES: 2026 - To be advised
ADULTS ONLY
Pineapple Beach Club Antigua, where crystal-blue Caribbean waters and sultry white-sand beaches meet to create an all-inclusive, exclusively adults, tropical hideaway unlike any. Experience beachfront paradise along the quarter-mile of brilliant, powdery white-sand beach, swim in our three sparkling pools, or seek adventure as you explore crystal-clear Caribbean waters on your kayak, stand-up paddle board, or Hobie Cat catamaran.
Whether you’re a passionate pickleball enthusiast or a novice looking to start a new adventure, Pineapple Beach Club Antigua is for you. Imagine rallying on the court with stunning ocean vistas and lush tropical surroundings as your backdrop.
This event will only host 20 players (couples only).
Sandals St Vincent - WAITLISTED
DATES: Nov 14-21, 2026
ADULTS ONLY
In a private cove bordered by a lush forest and gently flowing river, you’ll find Sandals Saint Vincent. We are excited to be able to offer St Vincent and the Grenadines in 2026! Sandals Resorts has 4 dedicated pickleball courts at this stunning Luxury All Included Adults Only resort.
This event will only host 20 players (couples only).
Pricing starts at $5399 CAD per person (double occupancy). Flights extra.
Sandals Royal Bahamian- SOLD OUT
DATES: May 25 - 31, 2026 (6 Nights)
ADULTS ONLY
Sandals Royal Bahamian, the most elegant all-inclusive resort with an exotic offshore island adventure. This beach resort offers two sky-sized pools, the all-new Coconut Grove lounge area, 5-Star Global Gourmet™ dining with 12 dining options, including 2 all-new food trucks, and an award-winning Red Lane® Spa. Experience the royal treatment at this glamorous adults-only resort!
This group will host a maximum of 20 players (couples only).
Pricing starts at $4099 CAD per person (double occupancy) and INCLUDES direct flights from Toronto, airport transfers, 6 nights luxury all inclusive & 1 checked and 1 carryon bag per person.
TRS Yucatan, Riviera Maya - SOLD OUT
DATES: Jan 24-31, 2026
ADULTS ONLY
Come improve your pickleball game on 4 DEDICATED COURTS and 16 lined courts at the Adults Only TRS Yucatan section of the Grand Palladium complex on a gorgeous beach in beautiful Mexico. Beachfront suites with whirlpool bathtubs, 24-hour butler and room service, and a pool and beach waiter service with a VIP Zone .
This event will only host 20 players.
Prices start at $2999 CAD per person (double occupancy) This price INCLUDES direct flights from Toronto, airport transfers, 7 nights adults only all inclusive & 1 checked and 1 carryon bag per person.
Beaches Turks & Caicos -WAITLISTED
DATES: June 17 - 22, 2026
Beaches Turks & Caicos is the number 1 All Inclusive resort for families in the Caribbean - and we are pleased to offer this for the 1st time in 2026! With 8 brand new, dedicated pickleball courts, your group will have so much fun in the sun!
This group will host a maximum of 40 players.
Pricing starts at $5299 CAD per person (double occupancy). Flights extra.