Falling in Love with St. Barths: My First Trip to the Island

by Villa Specialist Kate Olerio

I had been talking about St Barths every day for over a year, learning from other WIMCO Specialists and helping clients plan their vacation. But as a recently promoted Villa Specialist, I had been anxiously awaiting my first trip to the island. I had of course pictured everything in my mind; some things were just as I had expected, and some things were different. But after leaving and reflecting, what I can absolutely understand is why so many people fall in love with this beautiful little island and then return to it year after year.

Good reading material on our flight over with Tradewind…
Good reading material on our
flight over with Tradewind…

For my first trip to St Barths, my traveling companions were fellow colleagues Ben, Johna, Thibault, and Cate Brown (our trip photographer). Besides viewing the villas and hotels in our portfolio, this trip was also set up to experience and learn what the island has to offer each type of client. In addition, my personal goals were to familiarize myself to the different areas, and take it all in so that I could be better prepared to discuss individual villas and our concierge services with our lovely clients.

Cate Brown photographed everything we did, saw, and tasted throughout the entire week. Cate is truly talented and I’m excited to share her photos! We ended each evening by posting pictures to our Instagram accounts of our favorite moments of each day. It was a nice way of recapping with the group on everything we had done. Please fee free to see all my pictures on Instagram, @SBHKate.

We began our trip by flying JetBlue out of Boston and into San Juan, and then Tradewind into St Barths. It was a very quick layover in San Juan and everything went very smoothly. I was excited for the landing in St Barths that I’d heard so much about…it felt like we “floated” onto the landing strip. I’m not entirely sure what I was expecting.

Our home for the first few days, Villa Palm Beach (WV ABV) in Lorient
Our home for the first
few days,
Villa Palm Beach
in Lorient

We arrived at the airport in St Barths just as the sun was setting. We briefly met Guillaume as he was there to greet clients. After picking up our cars we were off to Lorient to our villa for the first three nights, Villa Palm Beach (WV ABV). Walking up the path to this villa, my jaw nearly hit the floor – it was stunning. Being the first WIMCO villa I had ever stepped foot in I think I was very spoiled. The villa has 5 bedrooms, (with one in a back bungalow) and a very large pool and outdoor space. My favorite part was that we were able to hear the waves from the ocean. Our dinner was the delivered Maya’s to Go, which was convenient and left us with plenty of left-overs. After dinner, we headed into Gustavia to Baz Bar to hear some live music. Some of the WSBH staff was next door at Bagatelle, so we went there for a quick drink and more introductions before heading back home.

On our first full day on the island, we began by stopping at the office to meet the rest of the WSBH staff. It was so nice to finally put a face to every name! This was followed by an island tour with a quick stop at Saline beach. I was surprised to see how big the waves were at the beaches on the island – I wasn’t expecting that! For lunch we went to Nikki Beach. I absolutely loved the atmosphere, and the sax player entertainment! We all shared the sushi, calamari, and beef carpaccio. It stood out as one of my favorite lunches of the whole week because of both the food and vibe.

Lunch and a dance party at Nikki Beach, one of my favorites of the trip
Lunch and a dance party
at Nikki Beach,
one of my favorites
of the trip

Monday began with driving out to Grand Fond to meet our hiking tour guide, Helene Bernier. We would be hiking the second highest mountain in St Barths at 276 meters. Throughout the entire hike Helene told us about her family’s history on the island (dating back to the 1600s), as well as interesting facts about the local flora and fauna that we were seeing. For the active client this excursion would be perfect, and the views at the top were incredible. Ask us to arrange this for you on your next trip! I’d also like to thank Ben, Thibault, and Cate for their patience with my fear of spiders during the hike…

After hiking we showered and headed over to Cheval Blanc – Isle de France where we would have lunch followed by a hotel tour. I had a light lobster Caesar salad on their deck overlooking the beach, which is such a lovely spot. That evening was the WIMCO cocktail party, held at Do Brazil that night [Editor’s note: It is now at La Guerite]. While there, I met a repeat clients whom I had helped with earlier that year. It was nice to meet a client in “real life” – and she just loves WIMCO. The party was followed by dinner at Maya’s for our group. I really loved the restaurant’s setting and the visit to our table from the owner, Randy.

At the top of Grand Fond, where we hiked with Helene Bernier
At the top of Grand Fond, where we
hiked with Helene Bernier

Tuesday and Wednesday we toured villas all day (see my villa round up at the bottom of this post!) as well as two more hotels: Le Toiny and Guanahani. We enjoyed lunch at Le Jardin on Tuesday (just around the corner from the WIMCO office), which is a convenient and low-key spot that’s wallet friendly. On Wednesday we lunched at O’Corail—so fun to eat with our feet in the sand. I had a crab tartare.

On Tuesday evening we moved into our new villa for the final nights: Villa Vina (WV VNA) in Vitet. The villa was very comfortable, with great outdoor seating, including the hammock on the porch. That night we enjoyed a private chef’s dinner compliments of Fabulous Feast. The stand out part of this meal for me was the appetizer: the chicken satay with warm peanut sauce – delicious! I really look forward to arranging this type of experience for our guests in the future. It’s so nice to just relax on the deck of the villa and enjoy a lovely meal at home.

Dinner chez nous, with a fabulous catered meal
Dinner chez nous, with a fabulous catered meal

Wednesday evening our group enjoyed a sunset cruise to Colombier beach, compliments of Jicky Marine. We took a ’55 motor yacht out of Gustavia. This was such a memorable part of the week for me, and I would happily recommend this cruise to any client, and we can happily arrange all the details. Dinner following the cruise was my favorite of the week: Tamarin. The setting in the tropical garden was so beautiful and my meal of Tuna with pepper two ways (black pepper encrusted, and with a white pepper sauce) was absolutely delicious. To end the busy day we finished with a drink at Le Ti and caught a glimpse of that evening’s show.

Thursday was more island touring with a stop at Gouverneur beach. When we first came around the corner and down the hill on our way to that beach, the view of the water took my breath away. What a gorgeous beach! I absolutely loved it there and I could have stayed for days and days. On the way back we stopped for a quick snack at Kiki & Mo in the mid afternoon—so easy for a quick bite. Thursday evening we enjoyed a drink and ceviche (four ways!) at Bonito. The coastal-chic atmosphere overlooking Gustavia was perfect. I love to try ceviche any time that it’s on a menu, so I really enjoyed this. After our appetizer, we walked down the hill to Black Ginger for our full dinner. The service we received there was by far the best all week. We let the chef choose for us, so we were able to share and try many different things. I’m not usually a big fan of Thai food, but this dinner really happily surprised me. All the flavors were exceptional.

Mint juleps at Bonito
Mint juleps at Bonito

Friday morning, Cate, Ben, and I took the morning catamaran cruise from Jicky Marine out of Gustavia. We shared the catamaran with two couples, one of which was honeymooning. We snorkeled in beautiful Colombier bay, with Cate using her water-proof camera bag to take pictures the entire time we were in the water. Snorkeling was followed by a leisurely sail back to the harbor where we chatted with the crew. This activity was so perfect to start the day with and I would recommend it to any client who likes to be out on the water. Of course, we can arrange all the details in advance!

After the sail was finished, we drove up into to Lurin for lunch at Sante Fe. The breeze was perfect through the restaurant and I shared the escargot with Ben. My entrée was the mahi mahi burger – the best and most tasty mahi I had all week. That afternoon we did a bit of shopping in Gustavia. I was so happy to visit Fabienne Miot’s jewelry store and buy my fresh water pearl bracelet. For dinner on our last night, we went to Bagatelle in Gustavia. I kept thinking this is a place I would love to bring a big group of my best friends to.

Soaking in the views (and treats) on our excursion to Colombier
Soaking in the views (and treats) on our excursion to Colombier

On Saturday morning Ben and I had the time to visit a few more villas that were unavailable earlier in the week. On our way back from one in Anse de Caye , I said to Ben just as we were rounding the rotary, “I really wish an airplane would land right this second so we could see what it looks like from right here!” – Well, ask and you shall receive. Seconds later just as we stopped at the circle, we turned our heads right and a Tradewind flight came in right above us—so close and so loud! I felt like we could reach out and touch it. This was such a memorable and funny moment of the trip for me, especially since it happened in our final hours on the island. After, we met Cate and Johna at Le Sereno, for a final and wonderful meal at La Gloriette.

Ben really took the time to teach me the island day by day: where we were, what we were passing by, what to look for at villas and hotels. By the end, he was quizzing me on what was what. Thibault arranged so many amazing activities and meals for us to experience. I can’t wait to share these recommendations with our clients.

Laughing with Ben over dinner at L’Esprit
Laughing with Ben over dinner at L’Esprit

Villa Round Up:

WV ABV: Lorient. 5 bedrooms – One of the bedrooms is a bungalow in the back; this bedroom has no view but it is equal in size. Beautiful and modern with lots of outdoor space, and you can hear the waves.

WV VNA: Vitet. 5 bedrooms. Clean, simple, and comfortable – perfect for our group.

WV FLC: Lurin. 3 bedrooms, with a partial view of Gustavia. Great convenient location. The villa has a nice sized infinity pool which attaches to a swim-up bar area.

WV ELA: Flamands beach, 8 bedrooms. Wow! Loved all the white accents and the beach house feel. Right on the beach with a large pool and deck area. Perfect for large groups or families.

WV RIG: St. Jean, 4 bedrooms. Recently updated décor, lovely view. Very comfortable.

WV GIA: Gustavia, 3 bedroom (4th for kids or nanny). Great in town location. The view/ and outdoor area is amazing. This would be a perfect spot to watch the Bucket or another boat race! One of my favorites.

WV GIN: Top of Petite Saline hillside, 5 bedroom. Brand new with absolutely amazing views.

WV TMN: St. Jean. 3 bedrooms. Very exotic feel, with its dark kitchen and living room. Views of St. Jean.

WV JOY: Marigot, 5 bedrooms. Parking garage under the villa, an elevator, movie theater, and pool table in the living room. Beautiful view of Marigot bay.

WV SCA: Marigot, 3 bedrooms. Comfortable with a one-floor layout and views of Marigot bay. Great breeze.

WV YEB: Pointe Milou, 4 bedrooms. An older villa recently remodeled in Pointe Milou. Loved the directions to this villa: “the driveway on the left in the middle of the field of goats.”

These are just a handful of the villas I visited. I’d love to discuss others with you!