There are many ways we island girls can experience loneliness on a rock. Sometimes it’s for the more obvious reason of mere distance from friends and family. Other times, it’s something that can be hard to place. We have friends whose company we enjoy, but there’s still somehow a hole in our rock life. For me, it’s always been a lack of people in this small place who share my soul interests – those passions that are the core of who I am, the biggest of which is writing.

The Women Who Live on Rocks community has long been an island life support group of sorts for me and thousands of others, but I’ve always wanted to find more ways for us to connect not just online, but in person. Then, this past August 2016, I received a photo message from two women who write for this site: Jen of Drinking the Whole Bottle and Riselle of The Traveling Island Girl. Riselle, who lives in St. Maarten, was on a trip to the Dominican Republic and reached out to Jen who lives there to see if they could meet up, having only known each other through Women Who Live on Rocks. An hour or so later, they’d felt like they’d known each other for years and were reaching out to me with an idea hatched over cocktails: we needed to meet up for a retreat; a “ROCKtreat” those clever brains of theirs announced.

The island girl meet-up that started it all…

Because I’m always ready for anything that sounds even remotely fun, and because it’s been a long running dream of mine to host an island girls’ retreat, I said yes (I think it may have even been a HELL YES) immediately. And just like that, we set to work making it happen.

I decided to focus this first retreat around island writers who are building their own brands of sorts. I wanted it to be formatted as a type of mastermind/skill-sharing retreat where we would not only play, but work on our writing goals together as well. I invited a small group of women who were in similar stages in their writing pursuits who I hoped would gel in personality too.

Though I have known many of these women through their writing and via online interactions over the last year or more, it was still a bit of a wild card. I mean, 10 women who’ve never met sharing a house and spending basically 24 hours a day with each other for 4 days? It sounds like the premise of a reality show. Or, in the words of Brittany of Windtraveler, “This could have been a dumpster fire in a hurry.” But it wasn’t. It was better than I could have ever imagined. The farthest thing from a dumpster fire, in fact. The immaculate, sparkly kitchen of Mr. Clean, perhaps? Yes. That level of magic. But with tequila.

I selected San Juan, Puerto Rico as our retreat’s destination. With 10 attendees all flying in from different islands, it was the perfect centrally-located hub that made travel more affordable for all of us. We rented a historic villa in Old San Juan that had plenty of bedrooms, group meeting space for our daily Roundtable Sessions, and was walking distance from bars and restaurants galore.

So how did we spend our time, you ask?

Let’s just say, island girls went rogue. Freed from our tiny rocks, we dusted off what clothes we had that didn’t have holes or stains on them, stayed up far later than our typical bedtimes, and some of us even donned heels (yes, heels) once or twice (and are all beyond thankful to be barefoot again; that shit is painful).

We had some amazing sponsors for this trip who welcomed us into their city with open arms. Puerto Rico knows hospitality and has mucho to offer island girls escaping their wee islands. We all agreed by the end – this place, though an island itself, is the perfect cure for Rock Fever. Here’s a little taste of what we got up to:

We invented a signature cocktail for our ROCKtreat: “Spa Water” at Greengos Caribbean Cantina. Their ingenious cucumber-infused tequila with some soda water (for hydration, obviously) made for a refreshing Mexican-style happy hour party that kicked our weekend off with a bang. This bar was so freaking fun, we even went back on our one free night for another helping of their signature nachos and yes – much, much more tequila. (If you’re on St Thomas, they also have a location there and a new one on the way in St. John – lucky USVI!)

Most of us have little to no shopping options on our rocks, so we were itching for some retail therapy. We shopped our booties off at the fabulous new Mall of San Juan. They heard island girls were coming so they started our mall marathon off with some much needed carb-loading at Il Nuovo Mercato – an inventive new Italian marketplace where they make everything fresh and to-order. As you can imagine – we oohed and ahhed over all the locally-sourced produce (Would you look at that arugula, ladies!). Next, we popped the champagne to kick off the shopping fun with a sneak preview of this year’s summer fashion at Nordstrom, educated ourselves on all things delicious at Oil and Vinegar, and treated our sun-worn skin to facials at Lush. Then, they set us free into the mall wilderness and we hunted out the goods. Oh, we how we hunted…

One thing this group of island foodies was looking forward to most was sampling the creative cuisine of Puerto Rico. Who better to dine with than one of Puerto Rico’s best, most famous chefs, Mario Pagan. We savored (and I mean, savored – I seriously wanted to lick my cauliflower soup bowl) a memorable tasting menu at the Mario Pagan Restaurant. The talented (and handsome, it was unanimously agreed upon) chef even came out to take selfies with us after the meal. This place is a must visit if you’re ever in San Juan.

Because most of us live on quiet little islands where we’re normally in bed by 10pm, some late night playtime was in order. La Placita de Santurce is the street party of street parties – complete with jello shots. As an island girl who lives on a rock with a population of just 3,000, spending an evening out roaming the streets with around that many people at once was invigorating, to say the least.

“Joy will take you further.”

You can’t keep island girls away from the water for long, even in a city. After a day in the mall, the outdoors were calling. We paddle-boarded around the Condado lagoon with the super fun team at VIP Adventures. They’ve set themselves up in a special spot with views of the city to one direction and the Caribbean sea the opposite. The icing on this enchanting day was definitely our run-in with two social manatees, who kept popping up to join in the laughs with their new island buddies.

Among all the activities, it was a priority to us to make time each day to put our heads together. After all, brainstorming with fellow island creatives was the draw that pulled us all to Puerto Rico in the first place. Having this many writers in one spot doesn’t happen for us on our home rocks very often, so we embraced it. We set aside a couple of hours each day to chill in the villa for our “Roundtable Sessions” – we shared knowledge, experience, opinions, ideas, and so much more. It’s because of these – and our newfound friendships – that we all left this retreat feeling both inspired and energized to continue pursuing our goals/dreams/passions.

Continuing in our Old San Juan explorations, we ducked into the quaint entrance to Pirilo Pizza Rustica and were blown away by what we found inside. Upstairs is a historically renovated space that was so charming, most of us were ready to move in and make it our bedroom, pirate-style. We gorged ourselves on some of the most creative pizza we’ve ever had (the one with the hidden truffle-oiled mushrooms under the cheese was a fan favorite). The traditional sangria with their special twist – a pie-crust-like garnish made of almonds – kept us all well-ahem-hydrated. It’s safe to say that a group of 10 island women can put down a shocking amount of gourmet pizza when they’re coming from places they know they won’t be able to get gourmet pizza again for a looonnng time.

No trip to San Juan is complete without a visit to the iconic El San Juan Hotel. You could easily spend an entire evening just people-watching and dancing in their classic lobby bar where the live music always seems to be jamming. To start our night out, we did cocktail hour and dinner at Caña, a beautiful restaurant on property that specializes in locally sourced, earth-conscious dining prepared by Puerto Rican Chef Juliana Gonzalez. From the tamarind margaritas to the vibrant dishes with a local twist, we had a blast chatting over our family-style meal and could have sat in that gorgeous space for hours. But we had dancing to do!

The rest of our night was spent in the bumping, glam Club Brava. It had been a long time since any of us had been in a proper nightclub, so we went all out – champagne bottles were flowing and we danced until we were dripping in so much sweat, you’d think it was your average island day at noon running errands.

Sundays are for brunching, no matter where you are in the world, right? Our post-club night Sunday morning was spent on a rooftop by one of Isla Verde’s most popular beaches at The Water Beach Club. Mimosa glasses were clinked, blue views and sea breezes refreshed our foggy heads (and sore feet), and a filling brunch was gobbled up. Plates were passed around and the mac n’ cheese with shrimp in a cast iron skillet was the winner – though with all the unique dishes we ordered, it really was tough to choose. Before we left, we made sure we dug our toes in the San Juan sand, for you can take an island girl off the beach for a couple of days, but you can’t keep her away long!

To wrap up our time in Puerto Rico with a bang (because island women know how to make an exit), we even managed to set a bar on fire at San Juan’s speakeasy, La Factoria. This place was cooler than cool (Secret bars! Salsa dancing!), though I do question their faith in drunk people’s capacity to be trusted with flaming shots… (Not to worry – no island girls or bars were harmed in the fire.)

–   –   –

I’m beyond grateful to all of the island girls who said YES to the very first Women Who Live on Rocks retreat. It’s not every day that you meet 9 strangers who turn into lifetime friends in a flash. That’s some island wizardry, for sure.

As for the future, I’d love to host more meet-ups and retreats to give more island women the opportunity to connect like this. Perhaps they won’t all be centered around writing and branding, who knows. What I do know is that I’ve already received a ton of interest from women who’d like to attend the next event (and islands who’d like to host it!). So I better get on it, right?

Custom cards for attendees designed by Drawing a Blank Cards

Are you someone who would be interested in participating in a future meet-up, retreat, or other social event for island gals? Have any ideas as to the type of event you’d like to attend? Leave a note in the comments below or on our Facebook page – I’d love your input!

In the meantime, you can find more pictures of the retreat (and zoom in on the ones in this post) on Instagram under #ROCKtreatPR and subscribe to the attendees’ websites, listed below, for additional upcoming articles covering the retreat:

Jennifer Legra, Dominican Republic: Drinking the Whole Bottle
Riselle Celestina, St. Maarten: The Traveling Island Girl
Mariah Moyle, The Bahamas: Out Island Life
Brittany Meyers, Tortola, BVI: Windtraveler
Claudia Hanna, Cyprus: Live Like a Goddess
Liz Wegerer, Bonaire: The Adventures of Island Girl; Island Girl Writing
Lizzy Yana, St. Thomas, VI: Island Lizzy
Jennifer Morrow, Puerto Rico: Jen There Done That
Sherri DeWolf, Key West: Deeply Creative; Island Jane

Written By:

Current Rock of Residence:

Virgin Gorda, BVI

Island Girl Since:


Originally Hails From:


Chrissann’s home rock in the British Virgin Islands feels bigger to her than it actually is. Though after spending five years on a teensy one acre island, the current 13-mile long rock she’s residing on now IS ginormous, at least by comparison. As with everything in the tropics, it’s all about perspective.

Once upon a time she used to care about things like matching her purse to her pumps but these days, any activities that require a bra and shoes go under careful, is-this-even-worth-it consideration. If island life has taught her anything at all, it’s that few things are more rewarding than time spent in the pool with a cocktail in hand.

As the Editor in Chief of this site, she spends her days working from home with her blue-eyed sidekick, Island Dog Diego, writing, editing, and cultivating content in the hopes of bringing some laughter and lightness to her fellow island souls. She recently published her first children’s book, When You’re a Baby Who Lives on a Rock, and is pretty pumped to share it with all of the island mamas out there. Her days off are typically spent boating, hiking, and meeting up with the neighborhood’s imperious roadside goats, who she shamelessly bribes into friendship. While normalcy was never listed as one of her special skills, Caribbean life may indeed be responsible for new levels of madness. She attributes at least a smidge of her insanity to the amount of time she spends talking to drunk people.

If you’re somehow still reading this and feel inclined to find out more about this “Chrissann” of which we speak, you can also take a gander at her eponymous website or follow her daily escapades on Instagram @womanonarock.

Want to read more posts by this writer? Click here.

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