Antigua

When we select a destination, we aren't simply looking for beautiful beaches or great pickleball courts. We're looking for a place where every part of the week works together. Antigua gives us that.The mornings are dedicated to purposeful coaching in a setting that's easy to enjoy. The afternoons invite you to slow down, explore the island, relax by the water, or simply enjoy time with the women you've spent the morning laughing and learning alongside.Pineapple Beach Club offers the kind of relaxed, adults-only atmosphere that lets the week unfold naturally. Nothing feels rushed. Nothing feels crowded. For us, the destination should never compete with the experience. It should make the experience even better. That's why we chose Antigua.

No two women arrive in Antigua with exactly the same goals. Some come to improve their game. Others come to recharge, meet new friends, or finally take the trip they've been talking themselves out of for years. By the end of the week, most discover they found a little of everything.Here's a glimpse of how your week unfolds.Arrival DayYour week begins the moment you arrive at Pineapple Beach Club. After settling into your room, you'll have time to relax, explore the resort, and start meeting the women you'll be sharing the week with. Before long, conversations begin, laughter starts to fill the air, and what began as a group of strangers starts feeling like something much more familiar.Purposeful MorningsEach morning is dedicated to purposeful pickleball. With up to four hours of reserved court time, you'll learn through live play, real-game situations, thoughtful coaching, and meaningful feedback. We focus on helping you better understand the game, make smarter decisions, improve your positioning, strengthen your partnership skills, and build confidence that carries into every match you play long after the retreat ends.With only sixteen women and two coaches, you'll receive individual attention while still enjoying the energy of learning together.Afternoons at Your PaceThe afternoons are yours. Relax beside one of the pools. Walk the beach. Schedule a spa treatment. Explore the island. Read a book overlooking the Caribbean. Grab lunch with new friends or simply enjoy doing absolutely nothing.Some afternoons become adventures. Some become conversations you'll remember long after the trip ends. Both are exactly what they're supposed to be.Evenings Worth Lingering OverAs the sun begins to set, everyone naturally comes back together. Dinner becomes more than a meal. It's where stories are shared, victories are celebrated, and friendships grow a little deeper each evening. No schedules to rush through. No pressure. Just great food, beautiful surroundings, and women who simply enjoy being together.One Signature AdventureOne evening we'll head to Shirley Heights, one of Antigua's most iconic destinations. With panoramic views of English Harbour, Caribbean music filling the air, and one of the island's most beautiful sunsets, it's the kind of experience that reminds you why you said yes to the trip in the first place.Before You Know It...By the end of the week, you'll leave with more than a stronger pickleball game. You'll leave with greater confidence, meaningful friendships and a different perspective on what a pickleball retreat can be.

Coaching with PurposeUp to four hours of reserved court time each morningSmall-group coaching with Becki Wheeler and Laura OuelletteLive play with real-time coaching and feedbackStrategy, positioning, partner movement, and court awarenessShot selection and smarter decision-makingIndividual attention in a supportive small-group settingOrganized play designed around the groupYour Antigua ExperienceSix nights at Pineapple Beach ClubAdults-only resort (ages 16+)All-inclusive accommodations, including:Unlimited meals, snacks, and alcoholic and non-alcoholic beveragesAccess to the resort’s restaurants and barsThree pools and a beautiful white-sand beachEvening entertainmentComplimentary resort activities and non-motorized water sportsLooking to treat yourself? The Orchid Steakhouse offers an optional premium dining experience for guests who choose to enjoy a special evening during their stay.Island ExperiencesRound-trip transportation between the airport and resortTime to enjoy the resort and explore AntiguaRound-trip transportation and admission to Shirley Heights, with time to enjoy the breathtaking views, local atmosphere, and optional food and beveragesThe 16 Society DifferenceWe aren't trying to host the biggest event. We're creating an experience where every woman feels welcomed, encouraged, and included.Limited to only sixteen womenTwo experienced coachesIndividual attentionSmall-group learningGenuine connectionThe best weeks are the ones where you never have to think about what's next. You simply enjoy where you are. That's exactly how we designed this one.

Investment begins at $3,950.Several accommodation options are available to fit different preferences and budgets. Complete room selections, pricing, and current availability are shown during the reservation process.A $1,150 non-refundable deposit secures your place.The remaining balance is divided into convenient scheduled payments, due on or before September 15, 2026 and December 10, 2026.Included: Six nights accommodations, adults-only all-inclusive accommodations, meals and beverages, coaching, reserved court time, airport transfers, Shirley Heights excursion, resort amenities, The 16 Society experience.Not Included: Airfare, travel insurance, optional spa services, personal purchases, activities outside the published itinerary.Life doesn't always go according to plan. We strongly encourage every guest to purchase comprehensive travel insurance.Because this experience is intentionally limited to just sixteen women, availability is often determined by who reserves first, not who decides later.