Pickleball Cayman Islands

This amazing vacation week in the Cayman Islands is the ultimate way to get away from it all and immerse yourself in a paradise of pickleball.

Perfect your game on beautiful shaded outdoor courts, enjoy private excursions, and explore the white sand beaches and vibrant culture of this island paradise. With a week full of daily round robins, open play, and a special tournament on your last day, this trip has something for everyone. Enjoy modern accommodations with inspired spaces. Guided group tours provide unforgettable experiences like swimming with stingrays and some of the world’s top dive sites. Explore amazing snorkeling amongst the reefs teeming with colorful marine life or relax on stunning Seven Mile Beach as you soak up all that the islands have to offer. This perfect blend of pickleball playtime and vacation promises an experience sure to be remembered for years to come!

Don't miss out on this one-of-a-kind Pickleball experience. Book a call with our Travel & Pickleball Experts and let us help you book your stay.

Trip Dates

What's Included In Your Pickleball Vacation

Round Robin Play & Court Time

Your vacation week in Cayman offers plenty of opportunities for you to play pickleball. You’ll get daily court time, as well as round robins with local players and even an optional tournament on the last day. So, get ready to show off your skills and have some fun on the courts!

All Transfers

Your package includes transportation to and from the airport, the pickleball facility, and all excursions. So, the only thing you have to worry about is having a great time!

Luxurious Accommodations

Accommodations at the Locale Hotel

Package includes 6 nights in your choice of accommodations. Enjoy modern, spacious rooms and an incredible location that’s less than 500 feet from Seven Mile Beach! The boutique hotel is set in the heart of the business and entertainment district and is only an 8-minute shuttle ride to Pickleball Cayman. Guests have access to numerous hotel amenities including a saltwater pool, crossfit station, onsite dining, free WiFi, smart TVs, and more. As one of the best rated hotels in the Cayman Islands and TripAdvisor’s #1 best value on Grand Cayman, guests are sure to have a relaxing and comfortable stay.

Daily Breakfast, Lunch, & Dinner

Package includes breakfast, lunch and dinner daily. A hot made-to-order breakfast is a great way to start the day! For lunch, choose from light and healthy meals like wraps and salads or more substantial street food favorites at Pickleball Cayman’s onsite restaurant, The Roost. Dinners will be arranged each evening with some of Cayman’s leading restaurants, with a new and unique option to enjoy every night. Options include everything from delicious regional specialties to modern fusion dishes. No matter your mood or tastes, there’s something for everyone

Popular Local Tours

This trip doesn’t just offer pickleball – it also includes some amazing excursions that’ll make your trip even more memorable! You can hang out with friendly stingrays in the shallow waters at Stingray City, snorkel along the pristine protected reefs, experience a magical golden-hour sunset sail catamaran cruise with snacks and drinks, and visit the Cayman Spirits Distillery to learn about the rum-making process and try their award-winning spirits. These excursions are the perfect mix of fun, relaxation, and culture, making your trip unforgettable!

Book a call for package pricing.

Travel Insurance, Trip Cancellation and Protection Plan will be recommended and quoted at time of booking.

Connection to Pickleball requires a signed waiver if Travel Insurance is declined.

This trip was the best adventure I have ever experienced. Playing pickle on shore with the locals was fantastic! Language was no barrier, all you need are smiles and fingers for score. It was the love of pickleball that brought congeniality to the group. No arrogance just camaraderie. Our friendship will last forever. It was perfectly organized. I would go again.

This past month I had the honor to be on the Amadeus Star inaugural Pickleball & Classical Danube Riverboat Cruise, from May 18 - 27, 2023. What an amazing time we had, having the opportunity to combine our passions for pickleball and travel. We had a fabulous time with other players, who quickly became friends, as well as talented Hungarian players, including a national champion. This was a first class trip, well organized and executed. Thank you Connection to Cruise and Amadeus Cruises. The Amadeus Star is a beautiful ship, with world class accommodations and service. A voyage of a lifetime!