Pickleball in Paradise, owned by Straight Away Travel, started in 2021 with their inaugural trip with Kyle Yates to Sandals South Coast, Jamaica. Since then, Pickleball in Paradise has continued to grow with 25 certified coaching pros and has sent over 1,000 players on pickleball vacations. Pickleball in Paradise predominantly sends players to the Caribbean but is growing into Bermuda and even to Europe in 2026. They are the trusted professionals which is proven with the trips listed below. They grow every year, are the leaders in the industry and are ready for you to be pictured in a future trip. Their private trips that they build for clubs are not listed here, but they have built many and would love to help you too!
Sandals Royal Bahamian, Bahamas
November, 2023
Pickleball Pro:
Lessa and John Walker
Attendees:
26
Sandals South Coast, Jamaica
October, 2023
Pickleball Pro:
Scott Golden, Erica Love
Attendees:
30
Beaches, Turks and Caicos
September, 2023
Pickleball Pro:
Chris Powers, Sally Novak, Jenn Markling
Attendees:
44
Beaches, Turks and Caicos
September, 2023
Pickleball Pro:
Leesa and John Walker
Attendees:
20
Sandals South Coast, Jamaica
September, 2022
Pickleball Pro:
Riley and Lindsey Newman
Attendees:
60
Sandals South Coast, Jamaica
November, 2022
Pickleball Pro:
Elizabeth and Bob Higgonbottom
Attendees:
52
Sandals South Coast, Jamaica
October, 2022
Pickleball Pro:
Kyle Yates
Attendees:
46
Sandals South Coast, Jamaica
September 2022
Pickleball Pro:
Leesa and John Walker
Attendees:
22
Sandals South Coast, Jamaica
October, 2021
Pickleball Pro:
Kyle Yates
Attendees:
26
In fall 2021, Kyle Yates hosted Straight Away Travel’s first-ever Pickleball in Paradise in Jamaica—launching a whole new way to combine travel, sport, and unforgettable vacation experiences.
There is no such thing as stress in paradise. That is why booking your vacation with Pickleball in Paradise is always easy and stress-free!
Choose a Trip
Check out our pickleball vacation trip calendar to find the perfect dates for your dream getaway. You can also contact us about booking a private trip for your group.
Secure Your Spot
Submit a deposit to secure your spot on the trip. Our trips fill up fast and we don’t want you to miss out on your dream vacation!
Pack Your Bags
Pack your bags and get ready for a pickleball getaway vacation experience like no other!
Pickleball in Paradise (PIP) is a subdivision of Straight Away Travel and we are delighted you found our site and the opportunity to join us on the courts in multiple locations in paradise. We combine our expertise in group travel with our passion for the sport to help you enjoy the ultimate vacation experience!
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