Just when you’re officially over winter, we’re trading it for Puerto Rican sunshine, warm ocean air, and the girls’ trip we’ll all be craving by February.

Hosted by Pilates Collective founder Rachael and our resident social media maven Sary, this trip is equal parts Pilates retreat, insider adventure, and ridiculously fun long weekend with friends. Sary is Puerto Rican and will be our unofficial local guide - sharing her favorite spots, must-dos, and local gems during our downtime - while Rachael is behind the wheel of our top-down house Jeep, ready for wherever the day takes us.

Think of it as your besties hosting you in a jungle oasis by the beach: later mornings, leisurely breakfasts, beautiful movement, incredible food, a day on the water, a little adventure, and plenty of time left open for the pool, the beach, another coffee, or whatever sounds good in the moment.

And with no passport required and an easy direct flight, it’s the rare getaway that feels like a true escape but still fits into a long weekend. Come with your best friend, sister, daughter, or come solo and leave with new ones. Part Pilates retreat, part elevated girls’ trip, part Puerto Rico insider experience - and exactly the dose of sunshine, connection, and fun we’ll all need come February.

Puerto Rico gives us everything we want from a winter escape - warm sunshine, turquoise Caribbean water, beautiful beaches, incredible food, and a culture that feels vibrant from the moment you arrive. In just a few days, we can experience colorful Old San Juan, swim in the Caribbean, explore the rainforest, eat ridiculously well, and still have plenty of time to simply enjoy being away.

And for an island that feels this far removed from February at home, getting there is incredibly easy. No passport required, no international customs, and easy direct flights from the East Coast make Puerto Rico perfect for a four-night getaway - maximum escape, without needing to take a full week off.

Our mornings start slowly with late-morning mat Pilates by the pool, followed by a fresh, healthy brunch spread prepared by our private chef. No rushing out the door—just a really good workout, sunshine, and breakfast together before the day begins.

We’ll spend an evening wandering the cobblestone streets of Old San Juan, eating our way through the city on a sunset food and walking tour with generous tastings, drinks, local favorites, and time to explore and shop. Another night, we’ll get dressed up and head out for dinner at one of our favorite local restaurants, known for inventive Puerto Rican dishes, craft cocktails, and colorful outdoor dining.

And then there’s our day on the water. We’ll board a luxury catamaran for a day of Caribbean sunshine, snorkeling, swimming, and beautiful beach stops—the kind of day where your only real responsibility is deciding when to jump back in the water.

Afternoons are intentionally ours. Head to the beach, lounge by our private pool, grab a coffee or lunch nearby, explore San Juan, or stay exactly where you are. For anyone craving a little more adventure, we’ll also offer an optional trip to El Yunque National Forest for hiking, swimming, natural waterslides, and a day immersed in Puerto Rico’s tropical rainforest.

We’ll bring it all home on our final evening with a private chef farewell dinner at the Villa —good food, a beautiful setting, and one last night around the table with the girls.

Our Home Base for the Week: A Private Jungle Retreat

For four nights, we’ll have our own private oasis tucked into the lush landscape of El Yunque. Made up of two stunning homes and designed by a renowned Balinese design firm, the property feels straight out of Architectural Digest—bold architecture, tropical textures, handpicked Balinese furniture, original art, and incredible attention to detail throughout.

Outside is where we expect to spend most of our time: a saltwater pool with sweeping ocean views, palms and tropical greenery, an outdoor kitchen, and plenty of beautiful spaces to lounge, gather, or disappear with a book. It’s luxurious without feeling formal—the kind of place where you immediately settle in and stop keeping track of time.

Across the two homes are six spacious bedrooms, each with its own full ensuite bathroom, so everyone has a beautiful private space of their own while still sharing the experience together.

We’re just five minutes from the beach and Luquillo’s famous kiosks, with El Yunque’s waterfalls, swimming holes, and rainforest trails nearby. But this isn’t just where we’ll sleep between adventures. The house is part of the experience—made for slow mornings, long afternoons by the pool, shared meals, late-night conversations, and all the little in-between moments that become some of the best parts of a retreat.

Arrive in sunny Puerto Rico and make your way to our private luxury villa! Settle into your room, unpack, explore the house, and officially switch into vacation mode.

We’ll ease into the weekend with snacks and drinks at the villa, plenty of time to relax by the pool, and a chance to meet the rest of the group.

In the evening, we’ll head out for our Welcome Dinner — the perfect first taste of Puerto Rico and the official start of our girls’ weekend.

Wake up to our first Mat Pilates class, followed by a leisurely chef-prepared brunch at the villa.

After brunch, enjoy some downtime to lounge by the pool, relax at the villa, or get ready for an afternoon in Old San Juan.

We’ll head into the city with plenty of time to wander the colorful streets, shop, grab a coffee or cocktail, and explore on your own before meeting up for our Sunset Old San Juan Food, Cocktail + Walking Tour.

Come hungry — tonight’s tour doubles as dinner!

Start the morning with Mat Pilates, followed by another chef-prepared brunch together.

Then, the day is yours! Join us for an optional adventure into El Yunque Rainforest, the only tropical rainforest in the U.S. National Forest System. Expect hiking, swimming, natural waterslides, and a completely different side of Puerto Rico.

Prefer a slower vacation day? Stay back and relax by the pool, head to the beach, shop, explore San Juan, book a spa treatment, or do absolutely nothing at all. This is your day to make the trip exactly what you need it to be.

The evening is open to explore and enjoy dinner on your own.

Enjoy a slower morning with Mat Pilates, followed by a beautiful chef-prepared brunch at the villa.

Then it’s time for one of the highlights of the trip: our private luxury catamaran day! We’ll spend the afternoon cruising turquoise Caribbean waters, snorkeling, swimming, making beach stops, and soaking up the Puerto Rican sunshine.

After returning to the villa, we’ll freshen up and come together for our private chef-prepared Farewell Dinner — one last night to eat, drink, laugh, and celebrate an incredible weekend together.

Departure Day

Enjoy one last relaxed morning at the villa before packing up and saying goodbye to Puerto Rico.

All guests will depart the villa by 10:00 AM to begin their journey home — sun-kissed, Pilates-ed, and already dreaming about our next adventure together.