St. Augustine, Florida: Feb. 11 - 14, 2027
Start your year on the courts in the Sunshine State. Whether you're a casual or competitive player, our clinics are tailored to your current skill level and future goals. Off the court, join the group as we explore the charm of America’s oldest city with its historic streets, waterfront views, great restaurants, and laid-back coastal atmosphere.
About The Trip
Daily Premium Clinics
Spend 8+ hours improving your pickleball over four days at a private facility reserved just for us. We'll cover drills, play modified games, and coach you through live matches.
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Intimate Student-to- Coach Ratio
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Small groups ensure that instruction is tailored to your unique play style. You'll get to know all of the coaches as they help strengthen your game.
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Join the group in our reserved, private activities, tours, and dinners. You can pick and choose exactly when you want to join and when you want to escape on your own.
Planned Group Itinerary
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Trolley Tour, Chocolate Tour & Tasting, Winery Tour & Tasting, San Marcos National Monument Tour, Columbia Restaurant Since 1905, St. Augustine Fish Camp
Group Excursions & Dinners
Selkirk & Hydration Giveaway
Be one of the lucky winners in our blind draw where you have a chance to win Selkirk paddles, Selkirk gear, and hydration.
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Catered Welcome Dinner & Farwell Lunch
Get to know the group after the first clinic during the welcome dinner, and then celebrate a successful vacation after the last clinic over lunch.
St. Augustine Itinerary
Day 1: Trolley Charter, Pickleball, & Welcome Dinner
The Perfect Start
Get settled in at your hotel, and then join us on the Old Town Trolley Charter for your first experience of St. Augustine. Afterwards, we'll see you on the courts and will have the welcome dinner catered directly to us.
Day 2: Pickleball & Chocolate and Wine Tour
The Life Connoisseur
Enjoy a peaceful morning before heading over to the courts for an instructional clinic & play session. Then, in the afternoon, meet the group for the Whetstone Chocolate Factory & Tasting Tour followed by the San Sebastian Winery Tasting & Tour. After our apertif, tonight's group dinner is at the St. Augustine Fish Camp.
Day 3: Pickleball & Castillo de San Marcos Tour
A Blast from the Past
Wake up to another tranquil morning followed by an instructional clinic & play session. Then, in the afternoon, join the group on a private tour of the Castillo de San Marcos National Monument before walking down the renown St. George Street. This will take us directly to tonight's group dinner at the famous Columbia Restaurant since 1905.
Day 4: Pickleball, Selkirk Giveaway, & Farwell Lunch
One Last Rally
After a final peaceful morning, prepare for one last instructional clinic & play session before lunch is catered directly to us during the farwell Selkirk Giveaway.
View the full itinerary: CLICK HERE
Frequently Asked Questions
Can solo travelers join?
Absolutely. Every trip has solo travelers.
What skill levels is this trip suitable for?
Because of the way we structure clinics, we're able to personalize and separate the instruction to each skill level. Whether you're a beginner (2.5+) or an advanced player (4.5+), our expert coaches ensure everyone receives effective instruction in groups of similar skill.
What's included in the trip price?
You'll receive 8+ hours of premium, small-ratio clinics tailored to your skill, a like-minded community, a welcome dinner, a farewell lunch, and a planned group itineray where you can pick and choose your excursions for additional rates.
Are flights, hotel, and transportaion included in the package price?
Flights, hotel, and transportation are not included in the trip price. Your welcome email will include recommended hotels and car rentals. Travelers flying are responsible for booking their own airfare to Jacksonville International Airport (JAX). We can provide guidance on preferred flight times and car rentals.
What is the cancellation and refund policy?
121 days or more from the date of trip: 50% refund of the initial deposit
91 - 120 days from date of trip: Loss of initial deposit
61 - 90 days from date of trip: 50% refund of the total amount paid
60 days or fewer days from the date of the trip: No refund
Can I bring a non-playing partner or spouse?
Yes! We offer a non-player rate for partners who wish to join for the accommodations, meals, and social activities without participating in the pickleball clinics and organized play sessions. Please contact us if you're interested.