Play Pickleball in Paradise at Sandals Montego Bay-4/19/26 – 4/24/26

Clinic

April 18

-

April 24, 2026

Jamaica

prices starting from

$2749

per person based upon double occupancy

Come level up your pickleball game while enjoying paradise.

Pickleball in Paradise Vacations is headed to gorgeous Montego Bay, Jamaica for a pickleball getaway at Sandals Montego Bay. The resort boasts 4 Brand New Dedicated Pickleball courts with a shade structure!

Although the coaches for this trip have not yet been set, know that you will leave a much better player with two outstanding coaches from our team at the lead.  Join us in your gorgeous ocean view room on the ultimate all-inclusive pickleball vacation!

Meet Your Pros

TBA

The coaches for this trip have not yet been set.  However, take a look at the “Meet the Pros” section on our website to check out the talented, quality coaches we employ on our trips!

Included in Your Stay

  • Pickleball Instruction/Tournament
  • 5 Star All-inclusive luxury resort accommodations
  • Gourmet Dining: all food and beverages
  • Unlimited premium drinks and cocktails
  • Water and Land sports
  • Fitness center
  • Multiple restaurants
  • Daily activities and nightly entertainment
  • Transfers to and from the airport
  • Private Cocktail Party
  • Private Beach Farewell Dinner
  • Most Gratuities

NOT Included in Your Stay

  • Airfare
  • Travel Insurance
  • Gratuities for Butlers and shuttle drivers

Location and Accommodations

Crystal Lagoon Honeymoon Oceanview Luxury Room with Balcony Tranquility Soaking Tub

Located on the second and third floors of the Seagrapes building, and the first and second floor of Almonds building these rooms feature our signature Tranquility Soaking Tub for two on a private balcony. This romantic escape is adorned with refined interior touches such as custom-built furnishings, a plush king-sized bed, and a large HD Smart TV. In addition, you’ll find tasteful, contemporary accents like a spa-inspired bathroom with a custom back-lit mirror, a long-vessel double sink, and a spacious walk-in shower. For your refreshments, your room includes Robert Mondavi varietal wines and a refrigerator stocked with bottled water, juice, soda, and local beer.

ROOM VIEW: Oceanview, Pool, Tropical Garden

Prices $5498 ($2749 per person, based upon double occupancy) for a Crystal Lagoon Honeymoon Oceanview Luxury Room with Balcony Tranquility Soaking Tub

Optional Upgrades

  • Room upgrades (based on availability)
  • Butler service
  • Private airport transfer
  • Expedited airport services
  • Extra nights at the resort at a discounted rate
  • Island excursions

Trip FAQ’s

Do you want to improve your game from some of the best instructors around, watching as they demo a new skill or drill and then coach you while you attempt to model it?  A clinic trip sounds like a good fit.  

Our clinic trips feature three hours of scheduled pickleball activity each day except on arrival and departure days.  On arrival and departure day, you are welcome to use the courts but there are no scheduled clinics.  Clinic mornings feature a minimum of two hours of clinics taught by our fantastic Pros, followed by an hour of Open Play, with the Pros mixing in with clinic participants.  The clinics are separated in the best way possible, determined by our wise Pros, to accommodate a variety of skill levels.   Each Pro writes their own agenda for the clinic topics so we do not have that until approximately one month prior to departure .  However, rest assured you will learn lots from our talented group of instructors! Go home with new skills to show off along with your tan lines! 

The final full day of the clinic trip is a round robin.  The Pros will divide you into groups and set you up in matches.  Lots of fun rotating among the courts!

Yes!  Many of our guests arrive early or stay late to enjoy all the amenities our gorgeous resorts offer.  We are pleased to help you save some money, too, by offering you the group rate we have negotiated with the resort.

No!  Vaccination requirements have been lifted for all of our current destinations.

Sandals Resorts offer only one king bed in all of their rooms.  However, we can request a rollaway for your room.  If two beds are important to you, please consider one of our trips to Beaches Turks and Caicos. Beaches Turks and Caicos rooms offer both king beds and double queen bed rooms.

We highly encourage you to purchase travel insurance.  After you have made your deposit and completed your client tasks on our portal, we send you travel insurance quotes from Allianz, a highly respected agency.

Yes!  The resorts we use are luxury resorts that cater to anyone who is looking for fun in the sun.  There is so much to do at the resort that you can easily fill your day and night without stepping foot on the pickleball court. Those looking for some relaxing down time will find that here too!  The lounge chairs throughout the properties, both on the beach and at the pools, offer plenty of places for some R&R.

Discounts are not offered to non-players for the simple reason that we do not charge anything extra for our pickleball clinics or tournaments.  All of our guests get a fantastic rate with lots of extra special touches, such as a private dinner on the beach for our group, a private cocktail reception for our group, a Meet & Greet, and a Welcome Bag.  Pickleball is included for FREE!

A deposit of $400 is required to secure your room for your Pickleball in Paradise vacation. 

  • In the event that you need to cancel your trip, $200 of the deposit is refundable 95 days before your departure. Or, if you are unable to keep the reservation for your originally booked dates but would like to change to a different trip, the full deposit amount may be transferred to another Pickleball in Paradise trip through Straight Away Travel in the same calendar year.
  • 95 days before the trip – the full balance for the trip is due.
  • 95 days before the trip – all payments are nonrefundable.

VIP Extras Included with Every Pickleball in Paradise Trip

  • Discounted group rate for a luxury all-inclusive vacation
  • Stress-free planning at no cost to you (when you book through Pickleball in Paradise we take care of every detail and you get discounted group rates that are cheaper than if you would have booked the trip online.)
  • Meet & Greet with the Pros on the first evening of your trip
  • Private cocktail reception with a selection of appetizers
  • Private beach dinner for the group
  • Welcome Bag for each guest with a Pickleball in Paradise T-Shirt, Pickleball in Paradise Luggage Tags
  • 5 X 7 group photo
  • and so much more!

Book Your Pickleball Trip

Your pickleball vacation is just a step away! Submit your trip deposit to secure your spot on the trip (our trips sell out fast!) OR get a detailed quote for the trip upgrades.

Pickleball in Paradise Travel Inquiry
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A deposit of $400 is required to secure your room for your Pickleball in Paradise vacation. 

  • In the event that you need to cancel your trip, $200 of the deposit is refundable 95 days before your departure. Or, if you are unable to keep the reservation for your originally booked dates but would like to change to a different trip, the full deposit amount may be transferred to another Pickleball in Paradise trip through Straight Away Travel in the same calendar year.
  • 95 days before the trip - the full balance for the trip is due.
  • 95 days before the trip - all payments are nonrefundable.