Pickleball in Paradise

Limited 2022 spots available

Improve your pickleball game while vacationing in a gorgeous all-inclusive Sandals resort is South Coast Jamaica.

Book your all-inclusive pickleball vacation trip to the Caribbean now!

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Pickleball in Paradise vacation travel

Improve your Pickleball skill, while enjoying paradise!

Have you just been introduced to the fastest growing sport in the US?

Have you been playing for a while and want to improve your game?

How is your 3rd shot drop, what about your 3rd shot drill?

Do you need to work on your serve? Your dinking game?

How about all of this while vacationing on the white sandy beach of Jamaica?

We have pickleball vacation trips planned that are sure to be one of your best travel experiences in a long time!! And you don’t just play pickleball… you relax, you snorkel, you meet new friends, you learn how to sail, you indulge in some guilt-free calories since you exercised that morning!

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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

Water-sports (hobie cat sailing, waterskiing, paddle-boarding, kayaking and more)

Optional yoga and fitness classes available

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

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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

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Hey there! It’s Barb Strait, the founder of Straight Away Travel. I have been a professional in travel for 11 years and have paired up with some of the best pickleball Pros around to bring you the absolutely BEST pickleball vacation experience. 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.

Upcoming Pickleball Trips

Trips are currently planned at the gorgeous Sandals’ resort in South Coast, Jamaica. 

Labor Day Pickleball in Paradise Getaway

Sep 2nd – Sep 6th 2022

Sandals South Coast, Jamaica

$1250 Per Person Based on (Double Occupancy)

An extended Labor Day weekend pickleball vacation that is sure to be one of your best travel experiences in a long time!! And you don’t just play pickleball… you relax, you snorkel, you meet new friends, you learn how to sail, you indulge in some guilt-free calories since you exercised that morning!

Your pros will be Leesa and John Walker, both IPTPA Level II Certified instructors and Ambassadors with USA Pickleball.

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Pickleball In Paradise with Kyle Yates!

Oct 6th – Oct 11th 2022

Sandals South Coast, Jamaica

$1700 Per Person Based on (Double Occupancy)

Play pickleball each morning with four-time #1 World Champion Kyle Yates, learning technique and proper form, and ultimately discovering what you truly need to work on! Individualized instruction at the Caribbean’s finest resort, Sandals’ South Coast, Jamaica!

Each day, you will have time on the courts while also enjoying the South Coast resort and the all-inclusive amenities Sandals has to offer.

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Which Pickleball vacation are you attending?
Do you plan on traveling alone or with a travel partner?

Pickleball travel room rates are based on double occupancy. Keep the cost down by bringing a partner on this trip.

Frequently Asked Questions

Friday September 2, 2022

Arrive to Montego Bay airport and be transported by Sandals to the resort check in, enjoy the pool, beach, restaurants, and and water activities

6:30- private cocktail reception on the beach to meet other pickleball players and the pros

Night entertainment- Ultimate Silent Headphones Party (this is SO much fun!)

Saturday September 3, 2022 (Itinerary subject to change)

8:00 am – 12:00pm  – 4 hours of playing and training (come and go as you’d like)

1:00 pm – 5:00 pm  Enjoy the resort, watersports, etc.

Dinner on own at any of the 9 restaurants (Straight Away Travel will get a list of your favorite cuisine and entrees and will help you with reservations)

Night Entertainment- Reggae Night, dance the night away to the most loved Reggae songs performed

Sunday September 4, 2022 (Itinerary subject to change)

8:00 am – 12:00pm-  4 hours of playing and training (come and go as you’d like)

1:00 pm – 5:00 pm –  Enjoy the resort, watersports, etc.

Dinner on own at any of the 9 restaurants (Straight Away Travel will get a list of your favorite cuisine and entrees and will help you with reservations)

Night Entertainment- Classic Piano Bar Fun!

Monday September 5, 2022

8:00am- 12:00pm- 4 hours of playing and training (come and go as you’d like)

1:00 pm- 5:00pm- Enjoy the resort, watersports, etc.

6:00 pm – Private Dinner on the beach and Player Awards , followed by a group photo

Tuesday September 6, 2022

Check out is 11am. If you are lucky enough to have a later flight, Sandals will hold your bags and there is even a locker room so you can play until your heart is content and then shower. Or you enjoy the white sand beach and any other resort amenities. Sandals will transport you back to the Montego Bay Airport in time for your flight home.

Thursday October 6, 2022

Arrive at Montego Bay airport and be transported by Sandals to the resort check in, enjoy the pool, beach, restaurants, and and water activities.

6:30- private cocktail reception to meet other pickleball players Kyle Yates.

Night entertainment- White Night, wear white and enjoy a tower of flowing chocolate (this is SO much fun!)

Friday October 7, 2022

8am – 11:30am  – 3.5 hours of clinics and playing with Kyle! (come and go as you’d like)

12pm-5pm- Enjoy the resort, water sports, swim up pool bars, etc.

5pm-8pm- Dinner at any of the 9 restaurants at Sandals South Coast

Night Entertainment- Reggae Night, dance the night away to the most loved Reggae songs performed

Saturday October 8, 2022

8am – 11:30 am- 3.5 hours of clinics and playing with Kyle!

12pm- private snorkeling adventure for the group

5pm-8pm- Dinner at any of the 9 restaurants at Sandals South Coast

Night Entertainment- Classic Piano Bar Fun!

Sunday October 9, 2022

8am – 11:30am  – 3.5 hours of clinics and playing with the Kyle! (come and go as you’d like)

12pm-5pm- Enjoy the resort, water sports, swim up pool bars, etc.

5pm-8pm- Dinner at any of the 9 restaurants at Sandals South Coast (Straight Away Travel will get a list of your favorite cuisine and entrees and will help you with reservations)

Night Entertainment- Reggae Night, dance the night away to the most loved Reggae songs performed

Monday October 10, 2022

8am – 11:30am  – 3.5 hours of clinics and playing with the Kyle! (come and go as you’d like)

12pm-5pm- Enjoy the resort, water sports, swim up pool bars, etc.

6:30pm- Private beach dinner with the group (string lights, music, with all of your new pickleball friends.

Tuesday October 11, 2022

Sadly, we head back to Montego Bay this morning and head home. Then we plan our next Pickleball in Paradise vacation!

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 pickleball 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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