Pickleball Getaway With Gina Cilento in Montego Bay 2027

Details:

Elevate Your Game

• Start each day with private court time for this group!
• There will be drills and coached open play where you will receive helpful advice to enhance your pickleball game!
• Wrap up the evening with more private court time for our group under the lights!
• View Sample Itinerary

Embrace the Island Life

• When you’re not on the courts, soak up one of the world’s best beaches, indulge in unlimited gourmet cuisine and premium drinks, and explore a range of water sports, pools, and activities.
• Daily Snorkel and Scuba diving trips are included with equipment! You are allowed up to 2 tanks per day!
• Feel free to spend as much—or as little—time with the group as you’d like, creating the perfect balance between improving your pickleball game and savoring your downtime in paradise.

Unbeatable Value, No Extra Fees

• Unlimited Fine Dining at all Restaurants
• Unlimited Premium Brand Drinks at all Resort Bars
• Unlimited Land and Water Sports (Scuba Diving, Glass Bottom Boat, Water Skiing, Paddle Boarding, Kayaking, Snorkeling, and More!)
• Nightly Entertainment
• Airport Transfers
• In-Room Stocked Fridge with Beer, Wine, Soda, and Juices
• Pickleball court times set and scheduled for you
• Let us handle the details while you focus on the fun, competition, and camaraderie in one of the most picturesque destinations on earth.

Spouse or roommate doesn’t play pickleball?

• No problem! There is so much to do and so much included at Sandals Montego Bay that they do not have to play to come join in the fun!!!! They will still have an incredible experience at this amazing resort!

Are singles allowed?

• Absolutely! Sandals room pricing is based on the room itself, not the number of guests, so many solo travelers choose to bring a friend or family member—even if they don’t play pickleball.We can also request a rollaway bed if needed. Since there is no additional charge for the pickleball programming, non-playing guests can fully enjoy all the incredible amenities and experiences the resort has to offer.

Daily Court Time

• Mornings include 2 hours of private court time for this group. Where the first half includes specific drills followed by the second half of regular gameplay reinforcing the skills taught in the first hour.
• Evenings will include 2 hours of open play.
• If that’s not enough, no worries—courts will be available for you to keep playing all day and even under the lights at night!

About Your Coach

Gina Cilento is a top-ranked Senior Pro and CRBN-sponsored athlete, earning multiple APP Senior Pro Tour medals in singles, women’s doubles, and mixed doubles. She has competed in the National Pickleball League for the Indy Drivers and Denver Iconics and was named the 2025 NPL Female MVP.

Beyond competition, Gina is a sought-after coach, co-founder of The Pickleball Lab in Cedarburg, Wisconsin, and creator of The Pick athleisure apparel line. She also serves as Director of On-Court Wisdom and Off-Court Content at Empower Pickleball and co-hosts the Keeping It Real with Gina & Neil podcast.

Gina also leads corporate team-building events and hosts pickleball travel experiences through partnerships with Sandals Resorts and Vibe Getaways. Whether competing, coaching, or creating content, she is passionate about growing the game and making pickleball more fun and accessible for all.

Frequently Asked Questions: 

What is the age range of the group?

These pickleball getaways are open to adults of all ages and skill levels. Most guests are typically between 55–75 years old, but everyone is welcome!!!

Does the price include airfare?

Airfare is not included in our prices. EVERYTHING else is! That includes accommodations, food, drinks, activities, transportation, and pickleball programming. We are more than happy to help assist you with flights! 🙂 

How do I get from the airport to the resort?

Airport transportation to and from the resort is included in your package. Once you arrive, simply visit the Sandals kiosk at the airport, and they will coordinate your transportation to the resort.

Still have questions?

Text or call us anytime at (262) 207-4364 — we’re happy to help!