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Partnering with Resorts Worldwide — Build Your Pickleball & Padel Program

Now booking for upcoming dates across Barbados and Jamaica.

Pro Coaches. Premium Gear. Caribbean Courts. One Trip.

pro pickleball player wearing a blue athletic jacket and black cap on a white background

THE EXPERIENCE

Not Just a Vacation. A Pickleball Experience.

A Fortyfour Getaway is a multi-day trip built around the sport you love. You show up with your paddle and your luggage. We handle everything else.

Every trip is led by Lauren Hidalgo-Smith, a top 50 PPA Tour professional and the #1 ranked pickleball player from the Dominican Republic. Lauren runs morning clinics split by skill level so you are always learning. Afternoons are for open play, match play, or the beach. Evenings are for group dinners, pro exhibitions, and the kind of friendships that only happen when you spend a week on the court together.

Every session is coached by a real pro who does this for a living. Every paddle, ball, and net on the court is Fortyfour equipment. Every trip is capped at a small group so Lauren knows your name, your game, and what you need to improve.

You go home a better player. That is the point.

What Sets Our Getaways Apart

Pickleball and Padel

We are the only getaway program in the Caribbean offering both pickleball and padel instruction. Two sports. One trip. No one else does this.
Real Coaches, Small Groups

Every trip is capped at 8 to 20 players with a coach-to-player ratio as low as 6:1. Your coaches are professionals who teach for a living, not influencers running a branded vacation.
Fully Inclusive

Accommodation, meals, coaching, equipment, airport transfers, excursions. You book one trip and everything is taken care of from the moment you land.
Premium Equipment Provided

Every session we offer Fortyfour gear. Pro-level paddles, fresh balls, portable nets. You do not need to pack anything but your shoes and your game.
pro pickleball player lauren-hidalgo Smith in blue athletic jacket and cap standing on a tennis court with greenery in the background

Lauren Hidalgo-Smith

Ranking: #1 in the Dominican Republic | Top 50 Women's PPA Tour

Sports: Pickleball

Django Chassang

DUPR: 5.5

Certified PPR coach and athletic trainer.

Sports: Pickleball

Kalen Harbaugh

Certified PPR coach and athletic trainer.

Sports: Pickleball

Jason Huang

Coaching Home: The Fort

Sports: Pickleball

A TYPICAL DAY

Mornings on the Court. Afternoons on the Beach.

Every day follows the same rhythm, designed around how players actually want to spend their time in the Caribbean.

Mornings start with structured clinics. You are grouped by skill level and coached through drills, strategy, and match play for 3 to 4 hours. Your coaches adjust the programming to what the group needs, not a one-size-fits-all script.

Afternoons are yours. Open play if you want more court time. The beach, the pool, or a local excursion if you want to explore. We build in real downtime so you come back to the court fresh every morning.

Evenings bring the group together. Welcome dinners, casual group meals, pro showcases, and the kind of conversation that only happens after a long day of great pickleball. By the end of the trip, your group is not just a travel party. It is a community.

One Price. Everything Covered.

Resort Accommodation

3 or 7 nights at an all-inclusive or upscale Caribbean resort. Double or single occupancy available.
All Meals

Breakfast, lunch, and dinner daily at all-inclusive properties. Welcome dinner and farewell event included.
Daily Professional Coaching

3 to 4 hours of structured clinics every morning, split by skill level. Pickleball, padel, or both depending on the trip.
All Equipment Provided

Fortyfour paddles, padel rackets, balls, and nets on every court. Play with the same gear our pros use.
Airport Transfers

Round-trip transfers between the airport and the resort. No taxis, no navigation, no stress.
Curated Excursion

At least one guided cultural or adventure experience included in every trip. Explore the island beyond the resort.

GETAWAY PACKAGES

Weekend or Full Week. You Choose.

Pickleball & Padel Getaways

Different ways to enjoy

Choose How You Vacation

Decide between staying a weekend or a week, Essential or our Premium packages.

Fortyfour Getaway: Weekend Premium
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By Fortyfour Sports

Fortyfour Getaway: Weekend Premium

From $2,200.00
Fortyfour Getaway: Weekend Essential
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By Fortyfour Sports

Fortyfour Getaway: Weekend Essential

From $1,400.00
Resort guests participating in Fortyfour Sports pickleball tournament weekend event
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By Fortyfour Sports

Fortyfour Getaway: Week Premium

From $3,400.00
Certified pickleball coach leading group lesson at resort through Fortyfour Sports coaching network
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By Fortyfour Sports

Fortyfour Getaway: Week Essential

From $2,200.00

WHERE WE PLAY

The Caribbean Is the New Home Court

The Caribbean has become one of the fastest-growing regions for pickleball in the world. Resorts are building courts at record pace. Players are booking trips specifically to play. And the conditions are unmatched: warm trade winds, year-round sunshine, ocean views from the baseline, and a pace of life that makes every session feel like a reward.

This is pickleball the way it should be played. Great courts, great weather, and coaching that actually makes you better. No crowded recreation schedules. No rental paddles from the front desk. Just real programming run by real professionals at properties we have personally vetted.

We run getaways across the Caribbean and add new destinations throughout the year. Join the waitlist to be first in line when new dates open up.

Pro Coaches on Every Trip

Premium Equipment Provided

Small Groups, Real Coaching

All-Inclusive Packages

Weekend and Full Week Options

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GET ON THE LIST

Be First When New Dates Drop

Our current getaway dates are full. New trips and destinations are added throughout the year.

Join the waitlist and you will be the first to know when new spots open up. No payment required. No commitment. Just priority access to book before the public.

In your message, include: the sports you play (pickleball, padel, or both), your skill level, how many people are in your travel group, and which package tier interests you (Essential or Premium, Weekend or Full Week).

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