




Confession: I didn’t happily jump into the pickleball world. As a tennis player, it just didn’t speak to me.
So I missed those early years, pre and during pandemic, when everyone was picking it up, when courts were open to all, no matter the level and when everyone was learning together.
I got behind the pickleball, so to speak. When I realized that most of my friends were playing, I knew for the sake of my social life and sanity, I was going to have give it a try.
But here’s the thing: Pickleball has evolved. And while it’s still super inclusive, my friends — and most regular players — have progressed and now beginners like me can throw a wrench in a round.
What’s a late adopter to do? Good news: Pickleball is so popular, you can weave it into just about any vacation — even if you don’t own a paddle. You can also weave it into fun day trips, either on your own, with other late-learner friends or with your already well-playing friends.
This past spring, I found time and places while on adventures to slowly build a game. If you’re like me and late to the pickleball party, consider these spots to not just bring you up to speed, but give you a day or more of fun on the side.
Day Trip: Bosse (bosse.net) in Natick, at 100,000 square feet, lays claim to being the nation’s largest pickleball facility with extensive amenities.
There you’ll find 21 state-of-the-art pickleball courts you can use to play with friends, work drills with a partner, take a lesson or clinic — or all of the above.
And there are plenty of other things you can do while there, making it a great spot to head to with other newbies or with your high-level playing pals, since it’s not just about pickleball.
You’ll find a state-of-the-art sports theater, golf simulators, darts lounge, fun zone, kids club, fitness center, and spa-like features such as a traditional hammam and cold plunge.
And then there’s the food and beverages. Bosse Enoteca, Bosse Café, and the Bosse Sports Lounge are all courtside and all offer their own unique chef-guided fare.
Overnight Game Focus Vacation: Pickleball is ubiquitous. It’s hard nowadays to find a resort or hotel that hasn’t added courts. But some do it extra well. Head to Brewster for a stay at Ocean Edge Resort (www.oceanedge.com) where you can discover your game on their 10 pristine pickleball courts.
They offer both group and private lessons, weekly clinics and round robins. They’ll even find you players should you be hankering for a game and not have brought along pals who play.
And the setting is sublime. Ocean Edge sits waterside (you can even walk out to working oyster farms at low tide), a fantastic golf course, great restaurants and tons of weekly activities and events. Head down for an escape and carve out time for a private lesson, a clinic and some play. Your vacation souvenir will be your now-steady game.
Vermont Made Pickleball: Oh, do they make great syrup. But head to Topnotch Resort (topnotchresort.com) in Stowe and you’ll find they make great pickleball players too.
First off, if you’re going to pick a spot to find your zen while learning something new, Topnotch is your spot. Their setting (nestled into the side of a Stowe peak) is spectacular. Their spa is world-renowned, as are their food and drinks.
And pickleball? Their top pros can start you out or elevate your game. Topnotch has been a top destination for building and improving a tennis game. Now you can sign up for private pickleball lessons on their indoor courts.
There with a loved one or more advanced player friend? Your pro can take you all out on the court and teach you drills to help you improve and doubles play to send you all home as future champs.
Plus, you’re in Stowe, the quintessential Vermont town, so there’s plenty to do pre and post game time.
Jamaican Seasoned Game: Okay, it’s not called jerk pickleball, but while at Half Moon Resort (halfmoon.com) in Jamaica, I took the time to take some private lessons with their top pickleball pro. I was honest with him from the start: While I am a confident tennis player, I had yet to feel the click with pickleball.
He took the time to help me understand where to be on the court and when; how to hit the ball and how to “dink” it; how the strategy works and how to serve well.
But most of all, he showed me fun. That didn’t just relax me, it built my confidence. I left that great trip relaxed, sunkissed, satisfied by the incredible food and happy.
But I also left thinking: I’m finally ready to play.
This week I joined my long-playing friends for some games. I’ve got a way to go, but I held my own. I’m no longer nervous and I now see how to have fun at it. I won’t be going pro, but I will be going to play with friends more.
That’s a vacation-worthy result.