Past Pickleball Trips

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!

Planning Your Pickleball in Paradise Vacation is Super Easy!

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.

credit-card-front 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!

 Book Upcoming Trips  Plan a Private Trip

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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