Pickleball Getaway With Gina Cilento in Montego Bay 2027

Max Attendees: 12 Rooms

Experience a luxurious 5 Star All-Inclusive Pickleball Retreat at Sandals Montego Bay.

Secure your room with a $500 refundable deposit.

Pricing on this page is based on staying in the Crystal Lagoon Honeymoon Oceanview Luxury Room with Balcony Tranquility Soaking Tub –
OLX. Other room options available upon request.

Please submit form below to hold your room and be a part of this amazing group filled with people that love the game but love vacation even more!

Unbeatable Value, No Extra Fees

  • Enjoy this pickleball retreat at the same cost you would pay if you booked directly with Sandals Resort.
  • Gain all the exclusive pickleball inclusions at no extra charge, along with our VibeGetaways professional travel services.
  • Let us handle the details while you focus on the fun, competition, and camaraderie in one of the most picturesque destinations on earth.

Alongside structured training sessions, participants will enjoy playtime with personalized coaching and constructive feedback in a comprehensive and enjoyable learning environment. Even those who have never played before will receive a crash course, quickly leveling up and gaining confidence on the court. Whether you’re a seasoned player or new to the game, this getaway promises an unparalleled opportunity to refine your skills in paradise.

Elevate Your Game

  • Start each day with two hours of private court time for our group where you’ll sharpen your skills under Gina’s expert guidance.
  • Wrap up the day with two additional hours of private court time in the evening with fun open play, featuring exclusive group sessions and plenty of opportunities to play alongside our pro.
  • Don’t worry! The courts are open all day long and under the lights in the evening for you to play as much pickleball as you can handle!
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What

Pickleball Getaway With Gina Cilento in Montego Bay 2027

When

03/01/2027 - 03/06/2027

Where

Sandals Montego Bay - Montego Bay, Jamaica

Accommodations

  • 5 nights at Sandals Montego Bay for as low as $5535* per 2 adults
  • 6 nights at Sandals Montego Bay for as low as $6642* per 2 adults
  • 7 nights at Sandals Montego Bay for as low as $7707* per 2 adults

Room availability and pricing subject to change until deposit is paid.

Military personnel past and present, firefighters, and police officers get a 10% discount. Thank you for your service!

You must book your room through VibeGetaways to ensure you are in the group.
For personal assistance booking your room contact Trish and Adam by phone at (262) 207-4364 or email trishandadam@vibegetaways.com.

Check Availability
More Pickleball group getaways

Details

Meet Your Host

Gina Cilento is a top-ranked Senior Pro and a dominant force in competitive pickleball. Sponsored by CRBN Paddles, she is an APP multi-medalist, collecting gold, silver, and bronze across mixed doubles, women’s doubles, and singles on the APP Senior Pro Tour. Gina has also been a top female pick, competing in the National Pickleball League for the 2024 and 2025 seasons, representing both the Indy Drivers and the Denver Iconics. Gina was named female MVP in June for 2025 NPL.

Off the court, Gina brings the same energy and expertise to coaching and community building. She is a highly sought-after instructor with consistently sold-out clinics and co-founder of The Pickleball Lab in Cedarburg, WI, a private indoor training facility.  She is also the creator of The Pick, an athleisure apparel line offering stylish, comfortable, pickleball-inspired fashion.

Gina serves as the Director of On-Court Wisdom and Off-Court Content at Empower Pickleball, where she helps produce engaging, educational content for players of all levels. She also co-hosts Keeping It Real with Gina & Neil, an unfiltered podcast that dives into the sport’s most challenging topics while championing the fun and community spirit of pickleball.

In the corporate world, Gina leads dynamic team-building events and curates exclusive pickleball travel experiences through partnerships with Sandals Resorts and Vibe Getaways.

From elite competition to coaching, content creation, and travel experiences, Gina is dedicated to elevating the sport, growing the game, and making pickleball more exciting and inclusive for everyone.

What to expect from lessons 

Volleys: punches, rolls, resets, and when to use each
Transition zone: mid-court volleys, resets, and court awareness
Third ball drops & drives: technique, strategy, and placement
Offensive shots: overheads, lobs, and aggressive serves
Defensive shots: volley resets, lob recovery, and strategic serve returns

After working hard on the court we will enjoy the resort and all of its incredible offerings from scuba diving to beach parties to fire dancers and plenty more!

What is included

  • 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

Check Availability

Fill out this quick form and Trish and Adam, a VibeGetaways vacation specialist, will get back to you.

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Or call Trish and Adam at (262) 207-4364

* 10% deposit required.
Prices do not include airfare.
Prices will vary depending on your room category and travel dates.
Please contact Trish and Adam to receive an exact quote.

5-Star Vacation Planning

Richard H.
3 weeks ago
Adam was great to work with and very accommodating. He knows the properties so well and makes wonderful recommendations. We had such a great time on our vacation we booked another one before we left. Would highly recommend.
Jada C.
3 weeks ago
Michelle and VibeGetaways were the best with our first trip and wedding at Sandals. Any problems or questions I had, Michelle was a phone call away. I have got here already on our next trip!
Polly F.
4 weeks ago
We just got home from our first trip with VibeGetaways at Sandals in Curaçao and WOW… what an incredible week! We’re already planning our next trip with them. It was that amazing! From the very beginning, everything was thoughtfully planned and beautifully executed. Adam’s care, communication, and attention to detail made the entire experience feel easy, personal, and special from start to finish. Once we arrived, the entire team made it such a fun, welcoming, and memorable experience. Adam, as owner, led everything seamlessly, while Will and Marko brought incredible energy and expertise as our pickleball pros. Anne and Daniel were fantastic supporting the coaching and keeping things running smoothly, and Drew, representing Pickleball Union, added to the overall experience. Even though Trish wasn’t on this trip, you could feel her presence behind the scenes. Everything was so well organized and intentional. Thank you for making my birthday feel incredibly special! The coaching was superb! Will and Marko have a gift for meeting you where you are and giving you simple, visual takeaways that stick. Each coach brought something unique that made the week even more meaningful. What we’ll treasure just as much are the people. We met an amazing group of pickleball players from all over the country and now have friends in so many places to visit, play, and hopefully meet up with again on another Vibe Getaways trip. This was more than a vacation, it was an experience, an adventure, and truly a gift! We are so grateful to everyone who made it possible and so special. If this has even crossed your mind, call Adam and Trish at VibeGetaways and just go. You won’t regret it. We absolutely will be doing this again. Polly & Mike Figueroa
Jolene L.
2 months ago
Michelle was incredible to work with to plan our first Sandals vacation. She was very knowledgeable and helped me through the entire process. Michelle was very quick to reply and helped when our flight was canceled. Im so thankful for her, she was such a vital contact throughout the entire process.
Luke S.
2 months ago
We had an amazing experience working with Whitney and the team at vibe getaways!! From start to finish, everything was handled professionally and stress-free! They took the time to understand exactly what we were looking for and put together a trip that exceeded our expectations. Every detail was covered — from flights and accommodations to recommendations for things to do — which made the entire process smooth and enjoyable. Communication was always quick and helpful, and it was clear they truly care about their clients’ experience! If you’re looking for someone who goes above and beyond to make your trip unforgettable, I highly recommend using them. We’ll definitely be booking again for our next getaway!!
Barbieb S.
3 months ago
My husband and I just returned from a two week stay in Jamaica, one week at Sandals Royal Plantation and second week at Sandals Dunn’s River which was all set up by Beth Wisowaty. She took care of every detail and we would highly recommend you contact her for your next vacation.
Kirby M.
3 months ago
Amazing people to work with.
samantha B.
3 months ago
We had an absolutely excellent experience working with WeddingVibe for our wedding travel! Our travel agent (Michelle) was knowledgeable, responsive, and truly went above and beyond to make everything seamless and stress-free. From organizing details to answering all our questions, we felt supported every step of the way. Highly recommend WeddingVibe to any couple planning destination travel for their wedding!
Elisa F.
4 months ago
Working with Michelle Plemmons was super helpful! She helped us book our honeymoon and it ended up incredibly memorable! Thankful to have had an expert to consult on all of the details and to help ease the stress of planning.
Mary G.
4 months ago
Adam, Trish, and their entire staff did an amazing job planning our trip. They kept us informed throughout the planning process and made everything run very smoothly so all we had to worry about was having a great time!
Kristin F.
4 months ago
Lisa was the best agent! She provided me and my husband the best information and was so personable and kind. We appreciate her so much!
Nicole A.
5 months ago
We had an amazing experience working with our travel agent, Michelle. She was incredibly attentive, super friendly, and always available to answer any questions we had. From start to finish, she made the entire planning process easy and stress-free. Her knowledge and responsiveness truly made a difference, and we’re so grateful for her help in creating such a wonderful trip.
Brittany R.
6 months ago
We just returned from Sandals Grenada for our honeymoon that was planned by Lisa. She was wonderful through the whole process, helping us to narrow down options for destinations to helping us book the resort. I had never heard of this location prior to meeting with her and I could not imagine finding a better place to spend our honeymoon. Lisa even helped us do a split stay so we could stay in two different room types during our 10 day trip. She was also very responsive every time we had a question and was such a source of knowledge for navigating this type of trip. I would highly recommend Lisa and we have already re-booked our next trip!
Grace V.
6 months ago
We had the best honeymoon and Michelle was a huge reason for that! Our room was better than expected, and she helped us decide the right resort for what we wanted to get out of our vacation. We are so happy that we worked with Michelle and would definitely recommend her!
Krystal B.
7 months ago
We just recently returned from our honeymoon in St. Lucia at Regency La Toc. Lisa was amazing throughout the whole process and answered any questions I had and helped so much along the way.

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