by Elizabeth Higginbottom
You know how it starts. You’re sitting on the bench between games, the adrenaline is pumping after a particularly spicy rally, and someone says those five dangerous words: “We should all go away together!”
Suddenly, the whole group is buzzing. “Let’s go to the Caribbean!” “Let’s find somewhere with great food!” “We need at least eight courts!” And then, inevitably, everyone turns their head and looks at you. Congratulations, you’ve just been unofficially elected as the Trip Coordinator. Usually, this is the moment where the excitement dies and the stress begins. You’re thinking about spreadsheets, chasing people for deposits, arguing over room types, and trying to coordinate court times with a resort halfway across the world.
Stop right there. Take a deep breath. At Pickleball in Paradise, we believe the person who suggests the trip should actually get to enjoy the trip.
If you are looking to organize a pickleball club trip that will be talked about for years (for all the right reasons), you’ve come to the right place. We specialize in turning your group’s “what if” into a seamless, high-end reality. This isn’t just a vacation; it’s a luxury private pickleball trip designed specifically for intermediate and advanced players who want the best of both worlds: serious play and serious pampering.
We Do the Heavy Lifting (So You Can Perfect Your Third Shot Drop)
The biggest barrier to a private pickleball trip is the logistics. How do you find a resort that actually has quality courts? How do you ensure the group stays together? How do you handle the money?
When you partner with us, we become your personal concierge. We don’t just book a block of rooms; we curate the entire experience.
- The Perfect Match: We help you select the ideal destination based on your group size and budget. Whether it’s the brand-new Sandals St. Vincent, the stunning shores of Turks and Caicos, or the sophisticated vibes at Joia, we know these properties inside and out.
- Custom Landing Pages: Forget about the “Who paid what?” headache. We build a dedicated landing page specifically for your club. Your members can go online, see the details, pick their room category, and pay their deposits directly to us.
- The Travel App: We provide a personalized itinerary via our travel app. Everything from your daily schedule to clinic times is right in your pocket.
- No Service Fees: That’s right. We handle all of this, the planning, the coordination, the court bookings, with no hidden service fees. Plus, as a thank you for bringing your group of 10 rooms or more, trip leaders often receive a complimentary room or resort credits. This perk can be used for your own room, given to your club’s Pro (if applicable), or the total value can be spread across all rooms in your group to lower the cost for everyone. Please note: this leader perk is only available when you bring your own Pros; it does not apply when we supply the teaching Pros for your trip.
Luxury All-Inclusive: The Paradise Part of the Name
We don’t do “budget” when it comes to your downtime. We focus on luxury all-inclusive resorts like Sandals, Beaches, and Joia because we want your only worry to be whether you should have the lobster or the steak for dinner.
Imagine waking up in a suite with a view of the turquoise Caribbean Sea. You head down for a gourmet breakfast before hitting the courts. Throughout the day, you have access to unlimited premium drinks and cocktails (though we recommend waiting until after the afternoon clinic for that second margarita!).
While most gratuities are included in our all-inclusive packages, meaning you can leave your wallet in the room safe, please keep in mind that some external services, like shuttle drivers or certain off-site excursions, may still appreciate a small tip.
Want to level up the luxury? We can help you secure optional upgrades like oceanfront views or even butler service, depending on availability. There is nothing quite like having a butler bring a tray of cold towels and drinks to the courtside during a heated match.
Top Notch Coaching for Serious Players
Our pickleball vacations are exclusively for intermediate and advanced players. We know you’re not here to learn the rules; you’re here to sharpen your edge.
We can bring in top notch Pros to lead our clinics if your group wants them. These aren’t just people who play well; they are elite instructors who know how to analyze your game. However, we’re all about flexibility—you can also choose to bring your own Pros, or if you just want to spend every minute on the court without formal instruction, we can organize a trip solely focused on open play. We focus on the high-level strategy that wins matches:
- Mastering the Transition Zone: We spend time working on those tricky mid-court shots, ensuring you can move from the baseline to the kitchen with confidence.
- Shot Selection: We’ll dive deep into the “why” behind the “what,” helping you choose the highest-percentage shots to keep your opponents off-balance.
- The Soft Game: You’ll refine your dinking and resets, turning defensive positions into offensive opportunities.
VIP Touches: Making It a Private Event
What sets a luxury private pickleball trip apart from a standard vacation are the “extra” moments. When you book a private group with us, the resort treats you like royalty.
We organize private cocktail receptions where your group can bond over the day’s best (and worst) shots. We also arrange private group dinners where the table is set just for you, allowing your club to truly unite and forge those “forever friendships” we’re known for. You’ll also receive a welcome bag with a custom Pickleball in Paradise T-shirt and other goodies to remember the trip by.
Beyond the Caribbean: European River Cruises
Looking for something a little more adventurous for your next pickleball club trip? We are thrilled to offer two very special European River Cruises that combine country exploration with a pickleball twist.
- AmaMagna Charter (July 12, 2026): This is a rare opportunity! The AmaMagna is one of the only river ships that offers an onboard court with reserved time blocks.
- AmaCello Charter (August 5, 2027): This itinerary includes an optional pre-cruise clinic in Paris to get your arm warmed up before we set sail.
Please note: While these cruises are a dream for any traveler, European River Cruises do not include scheduled pickleball play on the ship itself (with the exception of the AmaMagna’s reserved blocks). Instead, we focus on the breathtaking scenery and cultural immersion, with pickleball as the common thread that brings our community together.
Ready to Lead the Pack?
Stop stressing about the “how” and start dreaming about the “where.” Whether it’s the white sands of Turks and Caicos or a luxury resort in St. Lucia, your club deserves a getaway that is as high-level as your game.
Hone your skills, connect with your friends, and let us handle every single detail. From court reservations to that private sunset dinner, we’ve got you covered.
Pack your bags: paradise is waiting.
Contact Us!
Elizabeth Higginbottom
Director, Pickleball in Paradise
Email: [email protected]
Phone: 843-331-6955
Website: www.pickleballinparadise.com
