MONTEGO BAY, JAMAICA

Play-Based

Date:

April 8-13, 2027

Duration:

6 days / 5 Nights

Price:

$1899 USD

Book Now

< Back

PICKLEBALL, PARADISE & CARIBBEAN LUXURY

Join TPA's Cameron Taylor in Jamaica for a week of organized, play-based pickleball where rhythmic island vibes meet great competition, new friendships, and effortless Caribbean luxury. From April 8–13, escape to the vibrant shores of Montego Bay for a getaway designed for players who love to get on the court, enjoy organized match play, and experience the very best of the Caribbean.

At Iberostar Selection Rose Hall Suites, you'll be immersed in a lively, all-inclusive beachfront resort featuring turquoise waters, exceptional dining, and a fun, social atmosphere. It's the perfect setting for active mornings and afternoons of organized pickleball, followed by relaxing evenings with fellow players.

For those seeking a more elevated, adults-only experience, JOIA Rose Hall by Iberostar offers refined luxury with personalized service, beachfront tranquillity, gourmet dining, spa experiences, and beautifully appointed suites—the ideal place to unwind after a day on the courts.

Together, these two exceptional resorts offer the best of both worlds: vibrant social energy and sophisticated relaxation.

THE EXPERIENCE

Play
Organized daily play, rotating partners and opponents, and mentored gameplay
Compete
Fun competitions, themed days and an MLP-style Team Tournament
Relax
All-inclusive beachfront resort with time to enjoy the amenities
Connect
Meet new friends and play with and against same-skilled players

TPA is excited to partner with Liz & Jen from Trevello Travel for this trip, and they will be your 'Everything Travel' related experts to ensure you have an excellent experience with TPA Trips!

Liz Liabotis & Jen Pearce with Trevello Travel

200 - 2010 Winston Park Drive, Oakville, ON L6H 5R7

TICO # 5003057

Liz - 905-599-9657 | eliabotis@trevello.com

Jen - 416-301-3511 | jpearce@trevello.com

Your TPA Experience Includes:

5 nights all-inclusive accommodation at either Selection Rose Hall Suites or Joia Rose Hall (Adults only)
Room type: option of 1 king bed or 2 double beds
All meals, snacks & drinks (including alcoholic and non-alcoholic beverages)
All nightly entertainment, sports & activities provided by the resort
20+ hours of pickleball court time, including 15+ hours of organized gameplay
Theme days, Play with the Pros & mentored gameplay led by TPA Founder Cameron Taylor
Exciting MLP-style Team Tournament on the final day with prizes and bragging rights
Welcome TPA Dinner Event, TPA Farewell Cocktails Event & Awards
Leisure time to enjoy resort amenities - Spa, Pool, Gym, etc. - or go on an excursion
Shared airport transfers (based on a minimum of 8 people per transfer)
TPA Welcome Swag Bag

Not Included:

Flights - contact Liz/Jen for guidance on which airport to travel to based on your preferred departure airport
We recommend flying into Montego Bay Airport no later than the evening of April 8th to enjoy our special welcome dinner that night before the pickleball kicks off on the morning of April 9th
Private Transfers (shared transfers are included based on a minimum of 8 people per transfer)
Resort Tipping
Travel Insurance (highly recommended - our travel partners can provide options and pricing to each guest to ensure proper coverage to protect the investment of their trip)
Personal Expenses

Pricing:

In USD and includes all taxes and fees.

Double Occupancy:

Selection Rose Hall: $1,899 USD per person
Joia Rose Hall (adults only): $2,200 USD per person

Single Occupancy:

Selection Rose Hall: $2,885 USD per person
Joia Rose Hall (adults only): $3,410 USD per person

Deposits: (Due at time of booking)

Selection Rose Hall

Double Occupancy: $750 USD per person
Single Occupancy: $850 USD per person

Joia Rose Hall (adults only)

Double Occupancy: $800 USD per person
Single Occupancy: $900 USD per person

Final Payment: Due January 25th, 2027

Terms & Conditions:

Please note that all payments are final and non-refundable.
Should you need to cancel, we are unable to offer refunds or future travel credits.
To protect yourself in the event of an unexpected cancellation, we strongly suggest securing travel insurance with trip cancellation benefits to protect your trip investment.
Must have a valid Passport for 6 months post-travel required for this adventure

Availability:

32 Pickleball players
Non-pickleball players welcome - contact Liz & Jen for specific pricing

Want to Join Us?

Book Your Jamaica Experience Today

A PICKLEBALL TRIP BUILT AROUND PLAY

Each day, we've carved out 5+ hours of pickleball on courts reserved exclusively for TPA guests, giving you plenty of time to play, connect, compete, and enjoy the game in one of the Caribbean's most beautiful settings.

This trip welcomes players of all skill levels. Using TPA's extensive experience organizing pickleball events and trips, we'll create playing groups and pods based on skill level to ensure balanced, enjoyable games while also providing opportunities throughout the week to challenge yourself by moving up and playing against stronger competition.

Led by TPA Founder Cameron Taylor and the experienced TPA team, every session is thoughtfully organized to maximize your time on the court. From managing matchups and rotating partners to offering helpful tips, strategy, and mentorship during gameplay, we'll ensure every player enjoys competitive, engaging, and fun pickleball throughout the week.

No two days are the same. Look forward to Play with the Pros sessions, themed afternoons, fun social formats, king and queen of the court, team challenges, and competitive organized gameplay—all designed to keep the experience fresh while creating opportunities to meet new people and play with a wide variety of partners and opponents.

The week concludes with an exciting MLP-style Team Tournament, where you'll compete alongside your teammates in a fun, high-energy format featuring team spirit, exciting matches, prizes, and plenty of unforgettable moments.

From Beginner to Advanced, see where you belong before you book - view our TPA Skill Level/DUPR Guide

Itinerary is subject to change based on weather, resort operations and TPA programming.

Meet Your Coaches:

Cameron Taylor

Your Jamaica Playcation is led by TPA Founder Cameron Taylor.

Cameron Taylor is one of Canada's most respected pickleball leaders. As an NCCP Level 3 Coach, Co-Founder of the Canadian National Pickleball League (CNPL), and Master Facilitator for the Canadian Pickleball Coaching Program, Cameron has helped shape the growth of pickleball across Canada while creating exceptional on-court experiences for thousands of players.

Joining Cameron is the experienced Taylored Pickleball Academy team, whose passion for the game and expertise in organizing players ensures every day runs seamlessly. From creating balanced playing groups and rotating partners to organizing themed play sessions, fun competitions, and engaging social formats, the TPA team is focused on delivering an outstanding pickleball experience for every guest.

Throughout the week, you'll have opportunities to play with the Pros, enjoy mentored gameplay, receive helpful tips and strategic insights during matches, and experience a variety of organized formats designed to keep every day fresh, fun, and competitive.

Your Home in Jamaica

Iberostar Beachfront Resorts

Set along the breathtaking shores of Montego Bay, Jamaica offers the perfect backdrop for an unforgettable pickleball escape. With its white-sand beaches, turquoise waters, vibrant culture, and legendary Jamaican hospitality, this island destination delivers the ideal balance of adventure, relaxation, and connection.

Iberostar Selection Rose Hall Suites

Experience the vibrant, all-inclusive atmosphere of Iberostar Selection Rose Hall Suites, a beachfront resort designed for guests who want the perfect blend of activity, relaxation, and social connection. Located on a beautiful stretch of Montego Bay coastline, this resort features spacious suites, stunning ocean views, multiple swimming pools, a private beach, a variety of restaurants and bars, and daily entertainment that brings the spirit of Jamaica to life.

JOIA Rose Hall by Iberostar (Adults Only)

For guests seeking a more elevated and tranquil experience, JOIA Rose Hall by Iberostar offers an adults-only luxury escape with exceptional service, sophisticated surroundings, and premium amenities. This refined beachfront resort features elegant suites, personalized butler-style service, gourmet dining experiences, luxurious pools, a serene beach setting, and access to the world-class SPA Sensations wellness experience.

This is more than a pickleball trip. It's a week of great games, unforgettable connections, and a Caribbean paradise.

Explore Selection Rose Hall Suites

Explore Joia Rose Hall (Adults Only Resort)