The Over The Moon Guide to a Piña Colada–Filled Bachelorette Weekend in Puerto Rico

By Shayna Seid

Looking for somewhere to bond with your bridal party on a bachelorette weekend? With beautiful beaches, tropical rainforests, delicious cuisine, locally-made spirits, and lively music—and no need for a passport or an international phone plan—search no further than Puerto Rico. And who knows, a bridesmaid may even find her destination wedding venue too!

Celebs like J. Lo, Bad Bunny, Joan Smalls, and Ricky Martin call the U.S. territory home, and now that Frontier Airlines has just launched new non-stop flights from several U.S. cities to Puerto Rico, it’s never been easier to reach the tropical paradise. From NYC, it’s less than four hours until you touchdown in the capital, San Juan. Pack your bikinis, pareos, and sunglasses because we’re going to Puerto Rico!

When To Go

The Caribbean island sees beautiful weather in the winter with temperatures hovering around 80-degrees with little chance of rain. Prices will be at their lowest in summer, specifically in August and September (because that’s peak hurricane season), and the best beach days are seen from the beginning of winter through July. If your group has their sights on the swells, winter is the best time to paddle out to catch waves.

Where To Stay

O:live Boutique Hotel

With a luxe, earthy ambiance, Olive Boutique Hotel in San Juan is situated by the natural reserve of the Condado lagoon. This property is best suited for a laid-back group of ladies who want to a chill environment and to be pampered before hitting the town.

Photo: Caribe Hilton

Caribe Hilton

If you like Piña Coladas. . .you’ll absolutely flip out for this hotel. Conrad Hilton opened his first hotel outside of the continental U.S. in San Juan in 1946, and it’s famously credited for being the birthplace of the famous pineapple and coconut cream drink. In 1954, Caribe Hilton bartender Ramón “Monchito” Marrero won a cocktail competition with his concoction made of rum, coconut cream, and pineapple juice, and the Piña Colada was born (and back then, it was not blended)! In 1978, the tropical beverage was declared the official drink of the island.

After you’ve enjoyed a daily Piña Colada, lounge with your besties by the beach or one of the many pools on a cabana or get pampered at Zen Spa Océano. With three complete wings of rooms, you’ll be sure that no matter how large your party is, they’ll be able to stay together.

And while the hotel features a Starbucks, make sure to get a more authentic Puerto Rican breakfast at Ice Cream & Cookie Co. (yes, just trust us). The chefs are also excellent at accommodating dietary restrictions and preferences—we were treated to an amazing vegan meal here.

Condado Ocean Club

For a livelier bachelorette, book your stay at the adults-only Condado Ocean Club in San Juan. Lay out with your pals by the infinity pool, pop bottles in a private cabana, or dip your toes in the salty sea waters just steps below THE DECK. Weekends and evenings have their own lively vibe with an alluring lineup of exclusive parties and rising guest DJs.

The St. Regis Bahia Beach Resort

Situated between the El Yunque National Forest and Espíritu Santo River State Preserve, The St. Regis Bahia Beach Resort is set on 483 pristine acres and two miles of secluded beach with stunning views of the Atlantic Ocean. It’s the most tried-and-true luxury experience for a bachelorette in Puerto Rico. And if your group likes appreciates a pleated skirt and the game of golf, book a tee time at the expertly-designed 18-hole course and then a relaxing treatment at the Iridium Spa.

Where To Eat & Drink

Bar Cero Punto Dos

Founded by artists Yiyo Tirado y Karlo Andrei Ibarra, Bar 0.2 is part art gallery, part lively bar/lounge. With rotating installations and various DJ sets, find metropolitan, art-appreciating locals and travelers alike here and dance and cheers together to your road to the altar.

Café Lucero

For an authentic meal after exploring the coastal town and beaches of Ponce (pon-say), get a table at Café Lucero. The restaurant’s owner also operates a 216-acre coffee farm in the nearby mountains—which you can also take a tour of—so you know the caffeine will perk you up like only a Puerto Rican roast can after being out in the sun. We recommend ordering the croquetas de bacalao as an appetizer and sharing the chicken stuffed with cassava and yellow potatoes wrapped in bacon with guava sauce and brandy. It’s safe to say, you’ll miss out, if you only order a salad.


If you appreciate vintage glassware, Mad Men vibes, and good cocktails and food, you’ll fall head over heels for this female-owned gin lounge in Caguas. Inspired by the founder’s parents’ love of hosting gatherings in their New York City apartment in the ’60s, the menu matches the ambiance with unexpected classics like Beef Wellington, Chicken à la King, and creme brûlée. It’s a great place for drinks before going out dancing or for a delicious dinner. This establishment also prides itself on being LGBTQ+-friendly; we love an ally.

El Grifo

Vegans, rejoice! El Grifo is rooted in plant-based culture, local production, and sustainable planning, located in Caguas, Puerto Rico. Chef and Co-Owner Loumiry Sanchez created a beautiful menu of vegan fare that even a carnivore would enjoy.

La Pícara

Owned by Chef Xiomara Marquez, this buzzing gem would easily fit it in in the Manhattan restaurant scene and reservations are highly recommended. Be sure to order the signature namesake cocktail, La Pícara, and the espresso martini-esque Carajillo Pícara—if you’re lucky, the amazing bar director, Nicole Fas, will mix your drinks. For bites, you must order the Marcilla wontons, the salmon poke served on edible spoons, and the Cubanito roll. It’s an energetic place to get the night started at.

What To Do

Cacao Tour at Semila

For a unique experience, drive to Barceloneta to the tropical farm Semila, founded by Decenia Vega. There, you’ll tour the grounds, learn how cacao is grown, and sample edible flora and fauna along the way. Then, you’ll get to taste the finished product, chocolate, paired with wine, spirits, and Puerto Rican coffee. It’s a fun, lively, outdoor experience that has something for everyone in a breathtaking landscape, nestled in-between the tropical jungle.

Don Q Rum Tour at El Castillo

Rum fans will absolutely drink up the Don Q rum tour at Museo Castillo Serrallés in Ponce, which can also be a hired as a wedding venue. The old mansion sits on two-and-a-half acres and was built in the ’30s by Juan Eugenio Serrallés, the son of Juan Serrallés, who founded of Destilería Serrallés, which made—you name it—rum. The actual house is stunning with indoor courtyards and European-style interiors and even features a little atelier, where a bridal gown, vintage dresses, and wedding photos are on display—a highlight of the tour for us.

Once you’ve learned all the names of the sprawling sugar and rum-producing family during the tour, you get to learn how to distill the latter. Silvia Santiago, the first female master blender in Puerto Rico, makes sure every barrel of rum is exquisite and perfect for the palate. And finally, you and your gals will get to mix your own cocktails—one of those being the famous Piña Colada.

Frutos Del Guacabo

In Manatí, stop at the farm Frutos Del Guacabo to tour their grounds, where they grow local greens, herbs, and more and raise goats, sheep, and horses. Treat your organic-obsessed group to a delicious and true farm-to-table experience with a private meal here. If you’re bringing a city crowd here, be sure to feed and milk the goats for a truly unforgettable day.

What To Pack

Now that you’ve booked your flight and have your itinerary filled with enough activities, it’s time to pack. For luxe, personalized merch that will live long after the bachelorette, browse our collection of custom sweatshirts, printed itineraries, bucket hats, baseball caps, reusable cups, tumblers, koozies, and more that feature crests matching the location, theme, or the bride-to-be herself. And for easy, breezy bridal and bridal party looks, shop our collection of spring and summer styles that will no doubt complement all of the Piña Coladas.