A Photo Diary of the Boss Women Retreat St. Maarten

It finally happened. I successfully concluded the first Boss Women Retreat for women over 35, who like me are interested in Caribbean travel, networking, adventure, exploring, de-stressing and learning how to unleash their passion.

4 amazing women joined me on St. Maarten, the location for the first retreat. I was touched by their excitement to be a part of something I created. Something that began with a “what if” suddenly became a reality and all I had to do was push away my own insecurities and fears of failure. The girls all had to do the same. Jumping on a plane to meet people they have never met before, on an island they’re not completely familiar with was hard enough. They also had to deal with the nay-sayers, and those around them who spoke doubts into their heads. What if this is a scam? What if the other women don’t like you? What if you don’t like the others?

In retrospect their fears were greater to overcome than mine. All that could go wrong for me was hosting an empty retreat on my home island and initially, when the deadline approached and there were only 4 applicants, I thought I had failed. Until I realized that this was an amazing opportunity to get to know 4 new people in an intimate environment where everyone could really get to know each other and learn from one another.

Dawn brought knowledge, Karina brought style, Kim brought perseverance and Melinda brought determination. I was in awe of each one of these ladies, their stories and their plans for success.

Day 1 – Arrival Day

We had started a chat group on Whatsapp a month before the first day of the retreat, so that everyone could start getting acquainted. But we all know that chatting in an app is very different than actually meeting one another in real life. The air was thick with anticipation on arrival day. Would she look like she does in her pictures? Is she really as funny as she is in the chat group?

We gelled instantly. It was like we knew each other for years prior to this day. We claimed our beds and started to unpack, all the time busily chatting and sipping on adult beverages. Before we knew it, it was time to get dressed for dinner. We all piled into the mini van we rented for the 5 days and set out to Pineapple Pete’s, a restaurant well known for their service and large menu filled with yummy choices. Cocktails, great food and conversation ensued.

Day 2 – Adventure and Bar Hopping

Day two was a special day. It was the day we were gonna put our courage to the test, separate the girls from the women, so to say. We drove to Rainforest Adventures St. Maarten, known for the steepest zip line in the Caribbean, called the Flying Dutchman. Some of us have fear of heights, while others were just a bit nervous about the prospect of plunging into nothingness. Yet, we were all super excited, like kids about to go on a Disney ride.  We nervously took our seats on the chairlift and up and up we went, all the way to very top of the Sentry Hill.

Once at the top it took some of us some convincing to actually come flying down that hill strapped to a seat of some sort. At the end we all did it. We zipped down that steep hill and experienced the most exhilarating sense of freedom in the 2.2 minutes it took us to reach the bottom.

That night we celebrated at the Rusty Rocket, the bar I own with my husband James. Burgers and drinks were in order after our bonding experience at Rainforest Adventures. High on adrenaline and life itself, we bar hopped, ending up at a piano bar where oddly enough there was a Soca band playing and we danced the night away till the wee hours of the night.

Day 3 – Planes so low you can touch them

Day 3 was supposed to be about exploring the island but the night and excitement of the day before took its toll and we made a group decision to visit the island’s most famous beach to see the planes land and head back to the quiet of our villa and brainstorm in the pool instead.

We worked on our picture taking skills and our tans on the white sandy beach of Maho Beach. Once back at our little villa we made a light lunch and sat at the table discussing our dreams, goals and aspirations. A few hours in the pool was next before it was time to get ready for another delicious dinner.

Day 4 – An island escape within an island retreat

Sunday was the most exciting day of the retreat. It was the day we headed to neighboring island Anguilla. We were joined by three local business women, personal friends of mine, who also wanted to experience this outing and meet other boss women like themselves.

Our day in Anguilla was much like the island itself, magical. We rented a van and I drove us to some of my favorite beaches on the island. Beaches so beautiful, they look like pictures ripped out of a magazine. Lunch with live music on the beach got all of us in the island mood and the trip to the natural arch in Anguilla proofed to be as amazing as I thought it would be. A stop for one last dip at Mead’s Bay before catching the ferry back to St. Maarten was the perfect end to our little island escape.

Day 5 – Picture Perfect Shopping Day

The last day of the retreat was here. It all went by so quickly. After another wonderful breakfast made by Dawn, the designated chef in the group we all headed to Philipsburg for some souvenir hunting and some picture perfecting. Philipsburg is vey colorful and made it easy to get some amazing shots for our social media platforms.

Lunch was in my most favorite area of the island, Grand Case. We had great local food at the Lolo’s before I introduced the girls to my absolute favorite spot in the world for pictures, under a rustic pier in Grand Case.

An afternoon in the pool at the villa was just what the doctor ordered. We brainstormed some more and made plans to advance our businesses, blogs and ideas. That night we were joined by my friend Cynthia who made us a fabulous last dinner. It was the perfect way to end 5 days of empowerment, de-stressing, networking and friendship.

Find out which Caribbean island the Boss Women Retreat is headed to next. Click here.