Pickleball Vacations

All-inclusive Pickleball Vacations to the Caribbean at 5 Star Resorts

Pickleball in Paradise

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Do You Love Pickleball and Vacationing? 

Then you found the right place.


Barb Strait, founder of Straight Away Travel has been a professional in travel for 11 years and has paired up with some of the best pickleball instructors around. This ultimate pickleball vacation includes instruction from some of the nation’s top pickleball players at the Caribbean’s best all-inclusive resorts. Pickleball in Paradise is a vacation adventure of a lifetime! Whether you are a beginner or a 4.5 player, your vacation will not only be relaxing and fun but also improve your game while playing lots of pickleball with current and new friends!

Our groups are open to any level as we split the groups up for part of the session by skill level. We also work with pickleball clubs to build custom pickleball in paradise adventures exclusively for your group or club.

View the Highlights of a Pickleball and Paradise Trip

What’s Included in Your Pickleball Vacation Trip

Pickleball instruction and plenty of court time with a national pro

5 star global gourmet dining and top shelf drinks (ALL food and drinks are included)

Snorkeling adventures (scuba training optional)

5-star resort accommodations (upgraded concierge and butler suites are available) 

Private beach dinner with all participants

Welcome cocktail reception for all participants

Watersports (hobie cat sailing, waterskiing, paddleboarding, kayaking and more)

Optional yoga and fitness classes available

Best pickleball courts in the Caribbean. Play as much or as little as you want

Interested in a private pickleball trip instead? We can customize a trip for your family, friends, and pickleball group!

Always a Five-Star Experience

My wife Lynn and I had so much fun at Pickleball in Paradise last year that we are headed to Jamaica again this year! The pickleball and players were fun and we never went thirsty or hungry. Our private snorkel boat trip to Peter Tosh Reef was a highlight as was our group dinner on the beach. Lynn and I usually don’t do all inclusive because we enjoy cooking and look for deals. It was nice to travel light and to have all our food prepared and drinks made for us. We also could use the paddle boards and kayaks when we wanted.

Thanks for putting this together Barb,

~Pat and Lynn Patterson

Straight Away Travel made going to Sandals even more VIP than it already is. Our agent arranged to have our favorite wine and appetizer brought to our room as soon as we got there. She informed us off all the must visit restaurants and even made sure that we had lobster on the beach one day for lunch. As a free service, there is no question, we will always use her for our trips and have recommenced many others to her. Thank you!

Barb did an absolutely amazing job coordinating our Pickleball in Paradise vacation last year. It was everything we had hoped. She had tons of activities for us but no pressure to do anything. It was fantastic. The pickleball was great and we had lots of fun playing with the pro for sure.

~Carla Chavez

My husband & I are going back to Jamaica for our 2nd Pickleball in Paradise trip in September. Barb Strait takes care of everything! She makes vacationing so easy. We were able to relax knowing everything was taken care of. There are plenty of Pickleball drills & games. Plus, there was still time for all the other resort fun; swimming, snorkeling & eating fantastic chef inspired food. I highly recommend this experience to beginner players to the 5.0 player; there’s room for everyone

~Christina Scott

This was a fantastic experience. We enjoyed learning how to improve our pickleball game from Kyle Yates who was so fun and engaging. We made new friends and the resort was absolutely beautiful. Highly recommend.

~Natalie Macdonald

Upcoming Pickleball Trips

Trips are currently planned at the gorgeous Sandals’ resort in South Coast, Jamaica, Sandals Royal Bahamian Spa Resort and Offshore Island, and Beaches’ Turk and Caicos .  Dates and pros for each group are listed in the event calendar below.

There are no upcoming events at this time

Frequently Asked Questions

Pickleball is the fastest growing sport in the USA.  It is the fastest growing sport not only because it is so much fun to play and keeps you active, but people of all athletic abilities and ages can play.  Pickleball is a racket/paddle sport that was created by combining elements of several other racket sports. Most people describe pickleball as a combination of ping pong and tennis.  

Everything is included except airfare.  

  • Transportation from the airport to the resort,
  • A “welcome” to the resort from a staff member who will take care of your luggage, hand you a cooling spa towel for your neck, and check you in, 
  • 5 star resort accommodations,
  • A private cocktail reception with the pickleball pros and players,
  • Pickleball clinics every morning and the option to play in the evenings as you have access to 12 courts for the duration of your stay,
  • All food and beverages (you will not have to pay for any additional food or drinks the entire stay!),
  • All water-sports (snorkeling, kayaks, waterskiing, windsurfing, sailboats, tubing, paddle boards, glass bottom boats, wakeboarding, kneeboarding),
  • A private beach dinner with the pickeball pros and players,
  • Transportation back to the airport. 

You will never need your wallet.

Yes, in addition to the water-sports, there are also lots of land sports included – ping pong, shuffleboard, lawn chess, croquet, basketball, beach volleyball, tennis, board games, bocce ball.

Our 2022 groups will all be going to the gorgeous Sandals South Coast in Jamaica.  

No, that is the only additional cost to the trip.  

No, we include that with your Pickleball in Paradise package

Not this one, sorry, we must be 18 to be at the resort. Enjoy your adult time away from the kids.

Each trip has either a national pickleball pro or a certified pickleball instructor. You are sure to leave with new skills and be a better player.  

Yes, we welcome all levels of players and you will be paired and instructed based on your level of play.  

You can travel alone but you will have to pay for a double occupancy room so it is better to bring a friend even if they don’t play.  We have many players that bring a spouse or a friend that doesn’t play as they can relax on the beach, use the water-sports, or sleep in while you are on the courts.  

Yes, bring them for sure! We have many players that bring a spouse or a friend that doesn’t play as they can relax on the beach, use the water-sports, or sleep in while you are on the courts.  

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