Travel, Travel Stories

4 Countries, 5 Days & 160 Cousins: An Island-Hopping #TravelFamily

June 6, 2014

Imagine island hopping between 4 of the most beautiful and exclusive islands in the Caribbean, with private beaches, deluxe yachts and the most beautiful water you’ve ever seen. Then imagine you don’t have to plan a single piece of your vacation. No flight stalking, no customs clearance drama, no Hotwire Hustling for a better hotel rate. Nada. Β Every detail is handled Olivia Pope style, and all you have to do is show up at JFK on time (that’s actually the hard part cause LAWD that 5:30 AM flight had me on that #OpenMouthLeaningIntoTheAisle struggle bus).

It almost seems like there’s a catch, right? I had the same question my first time traveling with the OHPsalms “Travel Family” but it’s really that simple, and the group’s organizer, Omar Hamilton, spends nearly a full year taking care of these details so the group can relax and have a great time.

Last year when I first heard they were called the “travel family” I was skeptical though. Like, “aww that’s cute, but what makes ya’ll family?” And who goes on these trips anyway? Why have I never heard of them? Does everybody come back? Am I gonna end up on a milk carton?

However, after last year’s trip to Curacao I totally understood.Β While the trip can get pretty live at times (the “booze cruise” was like a straight up Trinidad carnival boatride!), at the end of the day it really does feel like you’re traveling with a bunch of cousins. I’ll admit your first trip feels like freshman year in high school, all awkward cause everybody seems to know each other. But by the end of the trip you be all like “Ayo son, sign my yearbook!” and stuff because you have all these new friends and memories from your adventures together.

This year was the 10 Year Anniversary of the trip and while it was only my 2nd one, it felt like they took the experience to the next level. Below is a run down of the islands we visited and some tips for anyone interested in planning their own island-hopping adventure!

ohpsalms_stmaartenST. MAARTEN

St. Maarten was our home base for the trip. We stayed at the Sonesta Great Bay all-inclusive resort and the view from the rooms each morning (pictured above) was breathtaking. The daily buffet had a wide range of options, but the star of the culinary show was their jerk chicken served poolside daily that will make you lick your fingers in public. Twice. The staff at Sonesta was also super friendly and accommodating to our group of over 160, simply looking the other way during a few turn up moments by the pool at their “quiet resort” #PoolsideTwerk #TurntUpTammy

For those looking to hang out, there’s definitely plenty to do on the island, with enough nightlife to have a bachelorette/bachelor type of weekend. Several nightclubs, (and strip clubs for the fellas), shopping malls and other attractions to keep you busy, with easy access to other islands nearby via ferry.

OHPsalms Travel Family AnguillaANGUILLA

The water here was unbelievable. Like, I would take photos and go to add filters on Instagram, only to find the original was flawless as is. These photos are the ones I’m still weeping over at my desk Β in New York. With perfect blue waves and pristine white sand I just….I mean….. *holds back ugly cry*

My favorite beach from the entire trip was Sandy Island, a private island accessibly only by boat that we traveled to on our “Booze Cruise” that Sunday. At only 150 yards long, it’s super tiny but was perfect for the group to take over for the day. We enjoyed lunch complete with grilled lobster, played football and volleyball, sunbathed, took some amazing sunset photos and indulged ourselves in what felt like a once in a lifetime experience. In my next life when I’m rich and fancy I’ll definitely be taking my yacht out to Sandy Island on weekends.

OHPsalms_StBarth2ST. BARTHS

I was actually surprised at how much this island reminded me of Paris! It’s shamelessly expensive with lots of designer shopping for their wealthy clientele. I kinda sorta got my feelings hurt at the Louis Vuitton store though (why nobody told me their bags are a few months rent! I was like how much is a wallet? Ya’ll got a layaway plan?)

As far as the beaches go, here’s a tip: Skip the typical American destinations like Nikki Beach, and head over to Shell Beach for lunch at Do Brazil. When you’re done, take a dip in the clear, turquoise water in front of the restaurant. It’s so serene and untouched here, perfect for a lovers adventure and a little skinny dipping if you dare πŸ™‚


Overall, the OHPsalms island-hopping trip left me craving more of “the good life” and reinforced my desire to pile my pennies and have a vacation home one day on a Caribbean island (possibly St. Kitts).Β Complete with a chef and a personal captain for my private yacht to take me out to Sandy Island on weekends, it’s gonna be amazing and you are all invited to the house anytime!

*checks bank account*

Um, so yeah….for now I’ll have to settle for my mini-getaways, and as often as I can get them planned for me with groups like this, I’ll keep traveling and can at least narrow down my options for where me and my Heathcliff will eventually settle down at our vacation home and finger-licking jerk stand on the beach πŸ™‚

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  • Reply Jarrell June 9, 2014 at 1:20 am

    How does one join the festivities???

  • Reply Chantaya August 1, 2014 at 8:24 pm

    This is amazing! How can I get more info about joining!

  • Reply L Thompson September 3, 2016 at 4:01 am

    What is the price like? And do they go the different places each time? I wanna do the Curaçao trip! (Crying Face)

  • Reply L Thompson September 3, 2016 at 4:20 am

    What is the price like? And do they go to different places each time? I wanna do the Curaçao trip! (Crying Face)

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