Livewire Pickleball
The Cayman Islands
February 23rd – March 1st, 2025
Dylan and Jamison are again bringing Livewire Pickleball to the stunning Cayman Islands. This trip is the ultimate way to get away from it all and improve your pickleball game at the same time! 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 5 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 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 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. Stunning Seven Mile Beach is a 3 minute walk away and the hotel provides complimentary backpack beach chairs and towels. 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 at The Locale Hotel 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 fantastic onsite restaurant, The Roost (up to $25 KYD per person, per day). 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 (up to $40 KYD per person, per day). No matter your mood or tastes, there’s something for everyone! Your first evening will include a Welcome Reception so you can get to know your fellow pickle guests before you hit the courts.
Coaching Clinics, Round Robin Play & Court Time
Quality coaching is the best way to up your game, so why not train in paradise with fun and friendly coaches? Dylan and Jamison have developed a curriculum for improving both the tactical and technical sides of pickleball in a super fun and positive way. With a combined nine years of coaching under their belts, this program has been perfected through experience. They strive to offer world class instruction in a format that allows clients to learn and practice techniques, then immediately reinforce new skills through simulated game play drills. You will also have a great time on the court while doing it! We are proud to hear from our many students that their style of teaching has allowed them to reach new heights in their pickleball game and have a fantastic time while learning. We would be honored to offer you the same experience during your stay in the incredible Cayman islands!
The instruction will be divided into two separate skill levels, 3.0 and 3.5+. The sessions for each skill level will be two hours a day and will be offered at alternating time slots with the 3.0 group beginning at 8am the first day while the 3.5 group will begin at 10am. The following day the 3.5 group will begin at 8am and 3.0 will be at 10am. There will be opportunities for round robins and open play after. Please join us for the pickleball vacation of a lifetime and opportunity to up your game in paradise!
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 and 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!
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!
Package Price: $2,849
Price per person, based on double occupancy. Taxes, fees and gratuities are $248. Single occupancy supplement $224 per night
Choose from 2 room categories below:
Sleeps 4 guests max. 
2 Queen beds 
1 Bathroom 
425 Sq. ft. 
Not playing pickleball?
Enjoy the accommodations, all meals, excursions and airport transfers for $1,995
Price per person, based on double occupancy. Taxes, fees and gratuities are $219.
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.
Drop-in clinics and private lessons are available for an extra fee.
A 25% deposit is required at time of booking.
Deposits are 100% refundable up until 30 days of arrival.
Remaining balance is due 30 days prior to arrival.
Reservations are non-refundable within 30 days of arrival.
Your Host
Dylan Lammers
Dylan grew up playing club tennis in Cincinnati, Ohio. He found pickleball in 2011 in Boise, Idaho where he currently resides. He has been playing 5.0 level pickleball for more than 8 years, winning multiple medals at the 5.0 and pro level. Dylan currently competes in senior pro PPA series as well as multiple open tournaments each year.
Dylan has more than 6 years coaching experience and is a PPR Certified Coach. He is passionate about helping clients improve their game and achieve their personal pickleball goals. Dylan’s teaching style focuses on helping clients improve their form and strategy while having fun on the pickleball court! Experienced in coaching clients from beginner through advanced level, Dylan can offer skill and mental development necessary to move your game to the next level. He is often recognized for his ability to help people develop the strategies used by high level players as they work on the form and skills necessary to compete at the highest levels.
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!