Adventures of Annie, Sarah and the 1%

Fast forward to 1:00pm on Day 3. Annie, my dad and I slept for about 4 hours after the Jovert and it was time to get the party started again! My mom, total trooper and general party gal, was ready to get her carnival on. French braids, stretchy pants and some road sodas were all we needed to be back in the mood. The whole downtown was flooded with people, bands, floats, bars and music. Thanks to our sweet location, we were there within minutes and enjoying great bands, adorable kids and seriously drunken carnivalers.





Annie and I went off to do our own thing and make some new friends. Several rounds in we meet a guy from NY who graduated from Ithaca when I was a baby. It’s a Small World After All should probably be the anthem for traveling… you can always find some sort of connection. Stephen owned a house on the island with his wife and their cousin and friend were in town visiting. Annie and I had hit our hyper-sassy point of the day and served as the entertainment for the group. Pam, the wife was SHOCKED that we were vacationing with my parents. (Clearly she had not had a JOD breakfast sandwich.) A little later my parents came into the bar and I introduced Pam. She repeatedly told them she could not believe that I was their daughter or that I was 26 or that I was allowed to be charge of children (her drunken interpretation of what my job was.) The afternoon went on. Pam decided that Stephen needed to give me my own TV show.They asked us if we wanted to leave the bar and come with them to their house for a pool party?  My first reaction…um, no, weird, you’re strangers… But in the end we decided yes, why not? As long as we could make it back into to town for the fireworks that night.

Along the way to Steve and Pam’s house (our brand new friends) we had to stop at Caneel Bay to pick up their cousin and friend’s luggage. FYI – Caneel Bay is a private resort that Brad Pitt and Angelina Jolie have stayed at. Fancy. What were we getting ourselves into here?? On we went, heading up the coast and we pulled up to a GIANT wrought iron gate. Steve clicked a button to opened it and we continued to drive down a really long, private road. We stopped at the end of the point where there was a panoramic view of the Caribbean Ocean. We had pulled up in front of the biggest house I have ever seen. At this point I decided well.. if they’re crazy murderers and they’re gonna kill us there isn’t much I can do about it now, so I might as well enjoy myself! I mean, this had to be at least a million dollar house, right? Fresh drinks in hand we started one of several tours we ended up taking through the house. The kitchen was a great room, at least two stories high. Every surface, appliance and piece of furniture seemed brand new. The pantry was bigger than my bedroom. The bathroom was fully stocked with anything a guest might need. The house was built on a curve, as almost a semi circle so that every room has a wall of windows to enjoy the perfect view of the ocean. There was a secret garden. There was a hammock room with a sand floor and double hammocks. The pool had a grotto and a lazy river. There were multiple layers of decks with sitting areas and fire pits. This place was insane.

I walked outside to the pool and there was Pam, clad in a neon yellow bikini. “SARAHHHHHHHHHH! Get in the pool! Come swimming with me!!” Sorry Pam, no suit, no swim. What’s that Pam, you’re offering me one of your neon colored bikinis? No, Pam, that’s NOT gonna work. We lounged around outside the house for a while, took a few more tours of the different wings, made a DiGiorno frozen pizza and then proceeded to dropped it top down on the floor. Whoops. Steve took out a monster bottle of Patron and I was somehow talked into having some. All the while Annie and I were nothing if not classy saying things like… You guys have A LOT of money. Let’s talk about it. Or.. How do you get this rich? How do I get this rich? What do you DO? But we didn’t really get any answers.

Steve mentioned that he paid for the fireworks in town so we might as well go see them. My initial thought was BS, you bought the fireworks? Then I realized it was probably true. They were stupid rich. We headed back and somewhere along the drive before arriving in town I stopped speaking in English and switched over to drunken gibberish. Annie decided to take us home in a taxi before we realized that my parents had the house key. We were locked out. I immediately went to sleep to on the floor of the front porch but Annie decided she could MacGyver her way inside. All the while my parents were still in town, partying like rock stars. I did a bit of time traveling through this next part but according to Annie we went down the steep back steps, up steps to the pool and climbed a fence. Yup, I climbed a fence. I can only image how awesome that must have looked. I went back to sleep, this time in a chaise lounge that was about 3 inches from the side of the pool. Another awesome choice. Annie wanted to sit on the big, wide pool steps and put her feet in the water. That would have worked great except that the steps were on the opposite side of the rather large pool from where Annie thought they were. Annie fell in. Another thing I would have loved to have seen! She managed to pull herself out and while there were several other chaises available she went to sleep on the teeny tiny porch swing.

My parents came home and my Mom found my purse on the front porch where I’d taken my little nap. She and my Dad went through the house looking for us and finally found me sleeping it off by the pool. My mom was worried that my chaise lounge was so close to the edge of the pool and was convinced I would fall in the pool and drown, so she woke me up. Apparently that led to a lot of “No.. I don’t want to get up! FINE! Fine, I’m up! Are you happy now??” I clearly did not appreciate having my sleep interrupted. My parents were worried that I’d lost Annie but once my dad started calling her name she popped right up from the porch swing and shouted “I’M HERE!” Yet another hilarious moment for those of us able to remember it.

The recovery period took about a day and half. Not my most graceful state. Shots of tequila are my nemesis which is why I typically shy away from them but apparently I had been feeling invincible. Turns out, I was mistaken. My stomach was highly vincible. People should really use that poison liquor’s proper pronunciation (to-kill-ya).

The next day (while being made fun of for feeling awful) we recapped the story for my parents. I asked my dad how much he thought the house was worth. He told us that the most expensive house on the island was just on the market for 32 million so it was probably a 10 million house or something like that. Later that day we went for a drive on North Shore Road and all of the sudden Annie and I saw the house! I played paparazzi and took some pictures. Sadly, we hadn’t taken any the night before. When we pointed out the house my dad asked us if we were sure? We were, even I didn’t forget, that was our play house for the night. You guessed it.. we had been at the 32 million dollar house! For the Real Housewives of NY fans, the housewives had a photo shoot there at some point.  I had undershot my million dollar estimate of the place by just a little.


Going off with strangers for a pool party (without even having bathing suits) was probably not the smartest decision we ever made but they were super nice and now we can say that we’ve partied in a mega mansion! Pam and I exchanged numbers so I later apologized for bailing once we got to town and thanked them for a fun night. Pam graciosly said Annie and I were crazy and fun, no need for apologies! My mom kept referring to them as “going slumming” in town and being bored. We were two loudmouth, fun girls who provided the rich folks with a distraction. It was definitely weird that Steve wouldn’t tell us his last name or job because he didn’t want us to google him. Annie is super sleuth though and two days later she figured it out. Steve is the owner of a very profitable investment banking firm in NY and among other things he owns a television network in the Caribbean. He really could have given me my own show if he’d listened to Pam.

We considered seeing if they wanted to hang out again but decided once was kinda creepy enough. I spent my final day in St. John, after Annie had gone home, hanging out with my parents. All of sudden we hear “SARAHHHHHHHHH!!! You look gorgeous!! Come hang out with us!!” It was the rich girls coming into town for the night. Once again they were shocked I was with my parents which I found hilarious. I had an early flight and without my wing woman I just wasn’t looking for another crazy night. That was the point when I noticed what I had thought was a Jeep was actually a brand new, top of the line Land Rover. Because those come cheap, right?

Ok, so going off with strangers is obviously not the smartest thing to do. That said.. we made it out unscathed and now Annie and I can check ‘party in a mega mansion’ off our bucket list. Oh St. John.. I never know what you’ll have in store.


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