Exclusive HPPA

Grand Cayman Experience

December 10 – 15, 2023

Phillip Hayman, founder of HPPA, is bringing his academy to the stunning Cayman Islands. This trip 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 4 action packed days full of top quality instruction, your game will develop immensely. Enjoy luxurious accommodations with inspired spaces. 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. No trip to Cayman would be complete without a trip to the legendary Stingray City. The perfect blend of pickleball playtime and vacation promises an experience sure to be remembered for years to come!

Your Package Includes:

Accommodations at the Westin Grand Cayman Seven Mile Beach Resort & Spa

Package includes 5 nights in your choice of accommodations. Enjoy luxurious, spacious rooms and an incredible location right on the finest sand of Seven Mile Beach! The hotel is set in the heart of the entertainment district and is only an 10-minute shuttle ride to Pickleball Cayman. As one of the finest hotels in the Cayman Islands, guests are sure to have a relaxing and comfortable stay.

Daily Breakfast & Lunch

Your package includes a gourmet buffet breakfast at the hotel and lunch at Pickleball Cayman’s fun new restaurant, The Roost. Your first evening will feature a Welcome Reception where you can meet your fellow guests and enjoy canapes and cocktails. Dinners are at your leisure. The hotel’s own restaurants are excellent but if you feel like venturing out, we highly recommend exploring some of the wonderful nearby restaurants such as Bacaro, Calypso Grill, Ave, Agua and Steak Social that are a short walk or cab ride away. Come and discover why Grand Cayman is known as the Culinary Capital of the Caribbean.

All Transfers

The week in the Cayman Islands 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!

High Quality Coaching

Phillip Hayman is no ordinary Pickleball coach. He coaches Pickleball coaches! 4 days of expert coaching will take your game to a new level. There will be plenty of time to practice what you have learned with up to 3 hours of daily court time. If you want to play even more, why not sign up for open play round robins with local players? So, get ready to show off your skills and have some fun on the courts!

Click HERE to learn more about the Hayman Pickleball Performance Academy programming.

Popular Local Tours

This trip doesn’t just offer pickleball – it also includes two amazing excursions that’ll make your trip even more memorable! You can hang out with friendly stingrays in the shallow waters at Stingray City and snorkel along the pristine protected reefs. Then experience a magical golden-hour sunset sail catamaran cruise with snacks and drinks. These excursions are the perfect mix of fun, relaxation, and culture, making your trip unforgettable!

Package Price: $3,440

Price is per person, based on double occupancy, including all taxes and fees. Single occupancy supplement is $329 per night.

Choose from the 2 room categories below:

Sleeps 4 guests max.
2 Queen beds
1 Bathroom
392 Sq. ft.
Sleeps 2 guests max.
1 King bed
1 Bathroom
392 Sq. ft.

Have a partner that doesn’t play Pickleball?

Let them enjoy the accommodation, all meals, excursions and airport transfers for $2,445

How Do I Book?

It’s easy! Simply click on the “Book Now” button, fill in the booking request form and we will get in touch to confirm the details of your Pickleball adventure!

Terms & Conditions

Package rates are in US dollars and include government tax and all applicable fees.
Package rates are priced per person, and based on 2 people sharing 1 room.
Packages cannot be combined with any other discount or promotion.
Package rates are subject to change.
Flights to Grand Cayman are not included.
Alcoholic drinks are not included with meals.
A 25% deposit is required at time of booking.
Deposits are fully refundable up until 45 days of arrival.
Remaining balance is due 45 days prior to arrival.
Reservations are non-refundable within 45 days of arrival.

About Phillip Hayman

Phillip Hayman is professional pickleball coach, clinician and instructor based in Boston, MA, with extensive experience developing recreational and competitive players. The PTR and USPTA tennis professional played many different court sports and recognizes how pickleball can benefit from the many disciplines that are crossing over and how important that the proper teaching acumen be applied whether it be the casual player looking for socially engaging informal play, to the ambitious who want their competitive fires stoked and yearn to compete. The certified PPR, IPTPA and IFP professional, as well as PPR Coach Developer has spoken at pickleball conferences in Hilton, SC and Rancho Mirage, Ca. and traveled extensively certifying potential future pickleball instructors. The HPPA will be his opportunity to bring pickleball players together with instructors who truly know the game and are accessible. HPPA will give the pickleball playing community destination experiences both domestic and international with a keen eye towards team building, corporate outings, club and league functions, friendly Davis Cup style competitions and game building.


About Pickleball Cayman

Pickleball Cayman is the Caribbean’s premier destination for pickleball enthusiasts! Our mission is to provide top-notch facilities, programs, and services for players of all skill levels. Our state-of-the-art shaded and outdoor courts are designed to exceed international standards, featuring high-quality surfaces, lighting, and equipment. And when you’re not playing pickleball, you can explore the beautiful and vibrant island of Grand Cayman, with its stunning beaches, rich culture, and delicious cuisine. At Pickleball Cayman, we’re committed to providing a memorable and rewarding experience for all our guests.

Come join us for the ultimate pickleball adventure in paradise!