Question 1

What are the steps to booking a TPA trip?

Accepted Answer

Booking Your TPA Vacation is Easy & Stress-Free!
Ready to join us? We’ve made the booking process simple so you can spend less time worrying about the details and more time looking forward to your vacation!Click BOOK NOW
When you’re ready to reserve your spot, simply click the Book Now button on your chosen vacation. You’ll be directed to our secure Travel Partner booking form.
Verify Your Email
The booking form requires an electronic signature, so we first need to verify your email address. Simply enter your name and email address, and you’ll receive a verification code to confirm that the email belongs to you.

Don’t worry — this is simply a security step required to complete the electronic booking process.
Complete Your Booking Details
Once your email has been verified, you’ll be guided through a series of questions about your trip. This information is required by our Travel Partners to arrange your vacation and ensure everything is set up correctly.
You’ll have the opportunity to provide details such as:Your personal and contact informationYour pickleball skill levelWho you’re travelling withRoom or accommodation preferencesSpecial requests or requirementsOther information needed to complete your travel arrangementsConfirm & Get Ready to Go!
Once your information has been submitted, our Travel Partner will process your booking and deposit payment according to the terms of your selected vacation.

And that’s it! You’re officially on your way to your next TPA adventure.Questions? We are Here to HelpWe want booking your TPA vacation to be just as enjoyable as the vacation itself. If you have any questions about the booking form, payment process, travel arrangements or anything else, please don’t hesitate to contact us.Our goal is to make the process as easy, comfortable and stress-free as possible — so you can focus on what really matters: packing your bags, grabbing your paddle and getting ready to play!

Question 2

What makes a TPA trip different from others?

Accepted Answer

What sets a TPA Trip apart? It’s simple: we’re teaching professionals first. Every detail—from programming to player grouping—is intentionally designed with one goal in mind: helping you improve your game while delivering an unforgettable experience.

Unlike many pickleball trips that offer little to no instruction, we strike the perfect balance. Each day includes 2–2.5 hours of focused instruction, 2 hours of open play, and wraps up with a fun round-robin tournament. You’ll enjoy some of the most on-court time available—while still having plenty of space to relax and enjoy your trip.

We also don’t rely on local instructors. Every TPA Trip is led by our own TPA- and NCCP-trained coaching team, ensuring a consistent, high-quality learning experience no matter where you travel.

And most importantly—we know how to have fun. This is your trip, after all. Expect the perfect blend of skill development, great play, and well-earned rest and relaxation.

Question 3

What level of player do I need to be to join a TPA trip?

Accepted Answer

All skill levels are welcome. Whether you’re building your foundation or refining advanced strategy, we group players thoughtfully so you’re always challenged—but never overwhelmed.

When you book, you’ll be asked to self-assess your skill level (we provide a simple guide to help). From there, instruction is organized into two or three groups depending on the size of the trip:
Advanced Beginner / Early Intermediate (2.75–3.25)
Intermediate to Intermediate Plus (3.5–3.99)
Advanced (4.0+)

This approach ensures you’re learning, competing, and improving alongside players at a similar level—making the experience both effective and enjoyable.

Question 4

Can I book as a single traveller?

Accepted Answer

Absolutely—and many do. Our trips are intentionally social, welcoming, and community-driven. You’ll arrive solo and leave with a whole new crew.

Question 5

Can I bring a non-pickleball friend/spouse?

Accepted Answer

Absolutely! Our trusted travel partners can quote you and your plus one pricing for non-pickleball travellers for all our trips!

Question 6

Do you offer travel insurance?

Accepted Answer

TPA Trips does not directly offer travel insurance; however, we strongly recommend purchasing coverage for any international trip. Travel insurance can provide valuable peace of mind and protection against unexpected situations.

Our trusted travel partners are happy to assist you in arranging travel insurance should you require that service, or you may choose to explore options on your own.

Taking a few extra steps to secure the right coverage ensures you can fully relax and enjoy your TPA Trip experience.

Question 7

Can I extend my Trip?

Accepted Answer

Absolutely—why limit a great trip to just one week? One of the perks of booking your own flights is the flexibility to arrive early or stay a little longer. And if you’d like a hand planning it, our trusted travel partners are happy to help you customize the perfect extension.

Question 8

Why do you quote and charge for some trips in US dollars?

Accepted Answer

We work directly with our international partner resorts to bring you the best possible pricing and packages. These resorts (although not owned by US entities) quote and invoice us in U.S. dollars, so we list and charge in USD to keep pricing consistent and transparent from the source. This ensures there are no hidden conversion markups from the resort side and allows us to pass along the most accurate and competitive rates for your trip experience.

When we work with Canadian-based resorts, we naturally quote and charge in Canadian dollars. This ensures you are always paying in the same currency that the resort itself uses, keeping pricing consistent and straightforward no matter the destination.

Question 9

TPA's Event Policy

Accepted Answer

At Taylored Pickleball Academy, our trips are thoughtfully designed, professionally hosted experiences — far beyond a typical resort stay. Each trip is curated over many months (often more than a year), with trusted partners, detailed planning, and pre-paid commitments to deliver the high-level experience our guests have come to expect.

Because of this, all TPA trips operate under group event policies that differ from standard individual travel bookings.

We strongly recommend that all participants purchase comprehensive travel insurance. Throughout the booking process, we provide multiple reminders and access to preferred coverage options to help protect your investment and give you peace of mind leading up to your trip.

Please note that all payments are non-refundable after the final payment date, regardless of the reason for cancellation. This includes circumstances such as weather events, travel disruptions, health concerns, or changes in travel requirements. Due to the nature of our advance planning and contractual commitments, we are unable to make exceptions.

In today’s evolving travel landscape, securing travel insurance is not just recommended — it’s an essential step in ensuring you can fully enjoy your experience with confidence.

Thank you for your understanding and for choosing to travel with TPA Trips. We’re committed to delivering an unforgettable week both on and off the court.

MONTEGO BAY, JAMAICA

Play-Based

PICKLEBALL, PARADISE & CARIBBEAN LUXURY

THE EXPERIENCE

What are the steps to booking a TPA trip?

What makes a TPA trip different from others?

What level of player do I need to be to join a TPA trip?

Can I book as a single traveller?

Can I bring a non-pickleball friend/spouse?

Do you offer travel insurance?

Can I extend my Trip?

Why do you quote and charge for some trips in US dollars?

TPA's Event Policy

A PICKLEBALL TRIP BUILT AROUND PLAY

Meet Your Coaches:

Your Home in Jamaica

Iberostar Beachfront Resorts

Stay in the TPA Loop

New destinations. Upcoming experiences. Pickleball stories.
And the occasional excuse to pack a paddle.

MONTEGO BAY, JAMAICA

Play-Based

PICKLEBALL, PARADISE & CARIBBEAN LUXURY

THE EXPERIENCE

What are the steps to booking a TPA trip?

What makes a TPA trip different from others?

What level of player do I need to be to join a TPA trip?

Can I book as a single traveller?

Can I bring a non-pickleball friend/spouse?

Do you offer travel insurance?

Can I extend my Trip?

Why do you quote and charge for some trips in US dollars?

TPA's Event Policy

Stay in the TPA Loop

New destinations. Upcoming experiences. Pickleball stories. And the occasional excuse to pack a paddle.

New destinations. Upcoming experiences. Pickleball stories.
And the occasional excuse to pack a paddle.