Eat, Dink & Stay Merry!

The Cayman Islands

January 20 – 24, 2024


World Class Pickleball meets World Class beaches on this incredible trip to the stunning Cayman Islands. Perfect your game on beautiful shaded outdoor courts at a brand new facility, enjoy private excursions, and explore the white sand beaches and vibrant culture of this island paradise. With 3 days full of coaching clinics, 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 a tour of a local distillery. 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!

Your Package Includes:

Accommodations at the Locale Hotel

Package includes 5 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 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! 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

Your vacation week in Cayman offers plenty of opportunities for you to play pickleball. You’ll start with an hour long daily clinic from Pickleball Cayman’s 5.0 level PPR certified Pros, then enjoy up to 3 hours of round robins with fellow guests and local players, and even an optional tournament on the last day. So, get ready to show off your new skills and have some fun on the courts! Private lessons can be booked upon request.

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: $1,995

Price per person, based on double occupancy. Taxes, fees and gratuities are $298. Single occupancy supplement $199 per night

Choose from 2 room categories below:

Sleeps 4 guests max.
2 Queen beds
1 Bathroom
425 Sq. ft.
Sleeps 4 guests max.
1 King bed + 1 queen sofa bed
1 Bathroom
575 Sq. ft.

Not playing pickleball?

Enjoy the accommodations, all meals, excursions and airport transfers for $1,495

Price per person, based on double occupancy. Taxes, fees and gratuities are $182.

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.
Drop-in clinics and private lessons are available for an extra fee.
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.

Your Hosts


Kristin Hudson

I am a full-service Travel Advisor, a competitive tennis player, and a recreational pickleball player. I also enjoy spending time with my husband, Kurt, exploring new destinations where we can remain active and do some of the things we love – diving, snorkeling, and sailing being at the top of the list. I am so excited to be working with Tammy Goldfisher and Pickleball Cayman to offer you this amazing vacation to Grand Cayman. I look forward to assisting you round out your trip, with optional flight bookings and travel insurance. And I can’t wait to experience this amazing, affordable trip together!


Tammy Goldfisher

I consider sports one of the major food groups. As an enthusiastic spectator and an avid participant, it’s an essential ingredient to my very being. Whether it’s watching soccer or baseball in the blistering sun, attending my daughter’s nerve-racking equestrian shows, or curling up rink-side, I’m the fan in the crowd exuberantly cheering. As a dedicated athlete, I go deep and relish the spirit, camaraderie, and sweaty commitment of a job well done.

After a lifetime of competitive gymnastics and representing the University of North Carolina – Chapel Hill, I turned to upping my tennis game and have had the good fortune to meet players from all over the world who share my love of the sport. I’ve been a coach my entire life and now enjoy mentoring college athletes. Diving into pickleball has proved to be just as thrilling. Originally borrowing from a mash-up of various racket games and the desire for make-shift entertainment, I completely understand why the sport has come into its own, attracting people of all ages and abilities who strive to master the short court while laughing. A lot.

I am thrilled to book time away from my day-to-day business of restructuring complex commercial real estate deals at The Henley Group, the company David and I founded 15 years ago. My children, Wyatt (20) and Elizaveta (18), make me immensely proud and are a constant source of inspiration.

So here’s the trifecta. A pickleball adventure, an exquisite seaside Caribbean holiday, and the chance to escape the winter blues. Come to Grand Cayman and enjoy the crystal-clear water of Seven Mile Beach in January 2024 and play the game you love.

I’m honored and privileged to be working with Pickleball Cayman, the Caribbean’s leading pickleball facility, which offers 12 shaded, floodlit courts, an amazing new bar and restaurant concept, and top-notch professionals. Along with my pickleball co-conspirator, Kristin, we’ve curated an affordable luxury vacation package for you that will rejuvenate, inspire, and surely help improve your game.


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!