Come enjoy your favorite sport on 10 DEDICATED COURTS with your friends from Midwest Pickleball Club while enjoying paradise!
Pickleball in Paradise Vacations is creating a tropical adventure exclusively for you in Castries, Saint Lucia. This secluded 220 acre resort is set on a gorgeous, half mile crescent shaped beach. While your friends in the states are still enduring the end of a long winter season, you will be enjoying the Saint Lucian sunshine! Designed especially for your group, this experience includes white sandy beaches, cocktails/mocktails, 5-star global gourmet dining and 10 dedicated courts reserved especially for your group!
You will be spending 7 nights at the beautiful Sandals St Lucia Regency La Toc, playing pickleball on gorgeous courts reserved exclusively for our group for 3 hours each morning.
Join the group for an unforgettable pickleball vacation experience led by Matthew Barlow, Director of Pickleball at Midwest Pickleball Club. Whether you’re looking to sharpen your skills or simply enjoy great pickleball in a beautiful resort setting, this daily experience combines expert instruction with relaxed, social play. Each morning features an optional 1.5-hour clinic followed by 1.5 hours of open play, giving you the perfect balance of learning, competition, and fun—on and off the court.
Pickleball in Paradise Vacations will be here to help you all along the way, and provide you with step-by-step instructions on getting through the airport, the resort transfers, what to pack, and all of the other fun activities you can enjoy in addition to pickleball.
Meet Your Coach
Matthew Barlow
Matthew Barlow is the Director of Pickleball at Midwest Pickleball Club and a 6.0+ DUPR-rated professional with wins over top-10 players in the world. He has been teaching pickleball since 2019 and brings a fun, energetic, and player-focused approach to the court. Matthew specializes in helping players improve their skills in a relaxed, enjoyable environment—combining high-level instruction and strategies to be implemented directly into your game.
Included in Your Stay
- Pickleball Mixers, Round Robins Shootouts, Open Play and More!
- 5 Star All-inclusive luxury resort accommodations
- Gourmet Dining: all food and beverages
- Unlimited premium drinks and cocktails
- Water and Land sports
- Fitness center
- Multiple restaurants
- Daily activities and nightly entertainment
- Transfers to and from the airport
- Private Cocktail Party
- Private Beach Farewell Dinner
- Most Gratuities
NOT Included in Your Stay
- Airfare
- Travel Insurance
- Gratuities for Butlers and shuttle drivers
Location and Accommodations
Set on a sprawling 220-acre estate of rolling hillside, Sandals Regency La Toc is a stunner. This is a resort that inspires from every angle — whether you’re peering down at the shore from the private pool of your oceanview villa or enjoying a glass of wine on your beachfront patio. Swim up to the bar or dine by the water — and savor all the dining at two nearby Sandals Resorts in Saint Lucia. If you’re into putting around, our nearby Cap Estate Golf & Country Club offers an 18-hole course with breathtaking ocean vistas.
Emerald Honeymoon Hideaway Grande Luxe $3998 ($1999ppdo)
This is the room which comes with your package! If you would like to upgrade, please contact us after you make your deposit.
Beautifully styled and impeccably furnished, these delightful second-floor rooms are hidden among the resort’s tranquil gardens. Beautiful white-washed vaulted ceilings crown the romantic interiors boasting classically contemporary mahogany furnishings in a warm palette of off-white with splashes of vibrant color and cool stone floors. Caribbean sunlight streams in through two large picture windows. For your refreshment, your room includes Robert Mondavi varietal wines and a refrigerator stocked with bottled water, juice, soda and local beer.
Emerald Honeymoon Oceanview $4298 ($2149ppdo)
Upgrades available. Contact for details!
Located in the heart of the resort, these classically elegant island-style rooms offer a range of beautiful views overlooking the resort’s iconic main pool, the crystalline sea or the lavishly landscaped grounds. Romantic and serene, with all the touches of modernity, each is appointed with dark crown moldings, mahogany furnishings and cool stone floors set against a palette of soft cream and ivory. Enjoy the scents and sounds of the Caribbean from a decorative French balcony of floor-to-ceiling sliding glass doors protected by a white wrought-iron rail in all other rooms. For your refreshment, your room includes Robert Mondavi varietal wines and a refrigerator stocked with bottled water, juice, soda and local beer.
Emerald Oceanfront $4398 ($2199ppdo)
Upgrades available. Contact for details!
The epitome of island glamour, these oceanfront rooms boast idyllic views of the resort’s manicured lawn, gorgeous trees, firepits and charming wedding gazebo. A French balcony of floor-to-ceiling sliding glass doors protected by a decorative wrought-iron gate allows the warmth and wonder of the Caribbean air to fill the elegantly appointed room trimmed in dark wood moldings and classic mahogany furnishings. For your refreshment, your room includes Robert Mondavi varietal wines and a refrigerator stocked with bottled water, juice, soda and local beer.
Optional Upgrades
- Room upgrades (based on availability)
- Butler service
- Private airport transfer
- Expedited airport services
- Extra nights at the resort at a discounted rate
- Island excursions
Trip FAQ’s
Yes! Many of our guests arrive early or stay late to enjoy all the amenities our gorgeous resorts offer. We are pleased to help you save some money, too, by offering you the group rate we have negotiated with the resort.
No! Vaccination requirements have been lifted for all of our current destinations.
Sandals Resorts offer only one king bed in all of their rooms. However, we can request a rollaway for your room.
We highly encourage you to purchase travel insurance. After you have made your deposit and completed your client tasks on our portal, we send you travel insurance quotes from Allianz, a highly respected agency.
Yes! The resorts we use are luxury resorts that cater to anyone who is looking for fun in the sun. There is so much to do at the resort that you can easily fill your day and night without stepping foot on the pickleball court. Those looking for some relaxing down time will find that here too! The lounge chairs throughout the properties, both on the beach and at the pools, offer plenty of places for some R&R.
Discounts are not offered to non-players for the simple reason that we do not charge anything extra for our pickleball clinics or tournaments. All of our guests get a fantastic rate with lots of extra special touches, such as a private dinner on the beach for our group, a private cocktail reception for our group, a Meet & Greet, and a Welcome Bag. Pickleball is included for FREE!
A deposit of $400 is required to secure your room for your Pickleball in Paradise vacation.
- In the event that you need to cancel your trip, $200 of the deposit is refundable 95 days before your departure. Or, if you are unable to keep the reservation for your originally booked dates but would like to change to a different trip, the full deposit amount may be transferred to another Pickleball in Paradise trip through Straight Away Travel in the same calendar year.
- 95 days before the trip – the full balance for the trip is due.
- 95 days before the trip – all payments are nonrefundable.
VIP Extras Included with Every Pickleball in Paradise Trip
- Discounted group rate for a luxury all-inclusive vacation
- Stress-free planning at no cost to you (when you book through Pickleball in Paradise we take care of every detail and you get discounted group rates that are cheaper than if you would have booked the trip online.)
- Private cocktail reception with a selection of appetizers
- Private beach dinner for the group
- 5 X 7 group photo
- and so much more!
