Upcoming
Pickleball Escapes
Jamaica Escape
Grab your paddle and your flip flops! it’s time for sunshine, rallies, and good vibes in beautiful Jamaica!
October 31 - November 4, 2026
This is your chance to play, connect, and let loose! Whether you’re chasing the perfect dink shot, cheering on new friends, or sipping something tropical poolside
- Daily organized pickleball play
- All-inclusive island fun
- Starts at $1961.50 Per Person - Based on Double Occupancy
Croatia Escapes
Pickleball Escape at Sea: Croatia & the Mediterranean
August 28 - September 4, 2027
Set sail on a private charter yacht along Croatia’s breathtaking coastline, playing pickleball in Croatia with island-hopping through the Mediterranean’s most stunning ports. Discover historic towns, crystal-clear waters, and unforgettable cuisine—all while enjoying the camaraderie of the game at sea.
- Island-Hop Along Dalmatian Coast
- Luxury Yacht, Curated Experiences
- Pickleball Play in Split
Alaska Escape
Pickleball Escape on Discovery Princess
August 7 - August 14, 2027
Set sail through breathtaking Alaskan glaciers abour the Discovery Princess, where pickleball meets world-class cruising. Experience stunning scenery, unforgettable ports, and elevated dining - blending adventure, camaraderie, and comfort at sea.
- Glacier Views
- Play Pickleball at Sea
- Sail with Princess Cruises Luxury
Los Cabos Escape
Ace the Experience: Pickleball Escape to Hard Rock Los Cabos
Play, connect, and unwind at the all-inclusive Hard Rock Los Cabos. Enjoy organized pickleball sessions, stunning ocean views, world-class dining, and high-energy luxury—where great matches meet rock-star relaxation.
- Daily organized pickleball play
- All-inclusive island fun
- Dates & Pricing Coming Soon!
City Smashes
Pickleball Escape to CityPickle NYC
Experience high-energy pickleball in the heart of Manhattan at CityPickle in Times Square. Play above the city lights, then explore iconic sights, dining, and nightlife—where competition meets the electric buzz of New York City.
- Play in Times Square
- Skyline Views & Nightlife
- Urban Energy, Great Competition
- Dates & Pricing Coming Soon!
Magic & Matches
Pickleball Escape to Walt Disney World
Serve up the fun with a one-of-a-kind getaway that combines exciting pickleball play with the magic of Walt Disney World. Enjoy organized games, great company, and unforgettable moments—then dive into the parks, dining, and entertainment that make this destination legendary.
- Play, Then Park-Hop
- Fun For All Skill Levels
- Dates & Pricing Coming Soon!
Your Next
Pickleball Escape
Starts Here
Let us handle the planning while you focus on playing, relaxing, and enjoying the destination.