Pickleball Trips

04/23/2026

Cancun, but make it pickleball. 🌴☀️🎾

Days on the court, sunsets on the beach, and a crew that makes every moment even better… this is what our trips are all about.

If you’ve been waiting for the right time to join us—this is it. 😉

See what trips are coming up:
👉 pickleballtrips.net/upcoming

Let’s get you there. ✈️

04/10/2026

Antigua looks good on you. 🌊☀️

This isn’t just a trip—it’s a full week of playing, relaxing, and living your best island life with an incredible group.

If you’ve been thinking about joining us… this is your sign.�

👉 pickleballtrips.net/upcoming
Come for the destination. Stay for the experience. ✈️

04/04/2026

Patty and I had the privilege this morning to meet up-and-coming PPA stars Valerie and Victoria Simon (originally from New York, but now residing in Wesley Chapel, Florida). Valerie has an amazing story, and has founded a nonprofit called Serve For Strength (https://serveforstrength.org/), dedicated to helping children with long recoveries ahead of them find hope and healing through supporting world-class medical teams and affiliated organizations. We will be dedicating one of our upcoming Pickleball Group Trips to this cause, and these two extraordinary young women and a few of their PPA friends and coaches will be leading the pickleball events for the week. Stay tuned for more info . . .

The girls were kind enough to team up with me and another young man for a quick game at their home courts in Tampa. Real quick, actually, although, for the record, my team somehow managed to score 4 points. I may or may not have heard one of them whisper "don't quit your day job."

04/04/2026

POV: You said "YES" to a pickleball trip in Turks & Caicos… and now you’re not sure how regular vacations will ever compare 😏🌴

This is your sign to stop scrolling and start planning.
We’ve got more trips in the works 👇

👉 pickleballtrips.net/upcoming

Let’s get you on the court (and the beach). 🎾🌊

03/24/2026

One last, extended gaze at this beautiful beach....and we're headed back home. What an incredible group, and a wonderful Pickleball adventure! See you soon, Turks and Caicos!

03/24/2026

✈️ Travel day ✈️ Today is the day we say goodbye to this beautiful beach.🌴☀️ Tournament play was yesterday & our winners were happy with their medals! We'd love to make this happen for your friend group too, or if you're solo join one of our upcoming group pickleball trips at www.pickleballtrips.net

03/22/2026

Turks & Caicos March 2026

03/14/2026

Tournament Weekend in Quincy, IL
PickleballTrips.net is giving away a Caribbean Vacation to one lucky tournament winner!!
RPAS Travel

03/09/2026

Thank you to all our participants in the Paddle Up Pickleball & Pickleball Trips Getaway Tournament!

03/07/2026

03/07/2026

Snoop ❤️ PickleballTrips.Net