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Traveler Tuesday – Patrick Bennett of Uncommon Caribbean

Traveler-Tuesday-on-Misadventures-with-AndiThere have been a lot of great benefits to becoming an AFAR Ambassador, it’s a magazine and a community I believe in, their charitable foundation touches my heart, and the community manager is a dynamo! But one of the best things about it is meeting other ambassadors that I was previously unaware and beginning to explore their “worlds.”

There are so many travel bloggers out there it is impossible to keep up, so I am very thankful to AFAR for exposing me to additional travelers of such high quality. As I continue to do this Traveler Tuesday series I have invited all the AFAR Ambassadors to participate so that you and I can both get to know them a little better.

One of the extraordinary people I have recently had the pleasure of discovering is Patrick Bennett of Uncommon Caribbean.

Traveler Tuesday – Patrick Bennett of Uncommon Caribbean in Anguilla

I have a guilty secret. As a traveler I relish the opportunity to immerse myself into a country's culture and foods, and while I do partake in visiting touristy areas, Mr. Misadventures and I do also seek out spots that will allow us to really get to know a place which usually means getting a little off the beaten path, or at least finding unique experiences when staying on that path.

But there is one spot in the world where I have never done that, and I feel terrible about each and every time I go there.

That place is the Caribbean.

I have been there four times, each time on a cruise and have invested no time in exploring outside of the guardrails of my floating city.

But that is all going to change with my next trip.

Now with Patrick's help, via the blog that he has dedicated to uncovering the true Caribbean I am learning more and more about the wonderful experiences that I can have in this beautiful part of the world and you can too.

But first we'll start by learning a little bit more about Patrick.

Traveler Tuesday – Patrick Bennett of Uncommon Caribbean in Anguilla

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[1] When and how did you become a traveler?

Being born on a tiny island in the Caribbean, it was necessary to “travel” if my parents wanted to stray further than 10 miles in any direction, so I guess you could say I was born a traveler. Island hopping to our family home in Trinidad, or to St. John for family vacations was pretty normal. We even visited Haiti when I was a toddler and a little later, the east coast of the US, Canada, and some of Central America.

Traveler Tuesday – Patrick Bennett of Uncommon Caribbean with son in Anguilla

As I grew older, travel turned more into aimless (penniless) wandering for a while before I was able to scrape enough money together to do “proper” trips again.

But if I have to point to the moment I went from casual to a little obsessed, it would have to be during a month long trek I took across the High Atlas mountains of Morocco. I don't know what it was. Being so far away from humanity, so far away from normal life back in my current home of NYC, or what, but it made me desire cultural connection in a way I never felt before.

Traveler Tuesday – Patrick Bennett of Uncommon Caribbean in Morocco

[2] What is travel to you in 10 words or less?

A journey away from the superficial towards what really matters.

[3] What is your favorite mode of transportation and why?

Without a doubt: Sailing. Unlike many other modes of transportation, it's silent, soothing, and sexy. It embodies a freedom that's simply unattainable through most other means. Yet, it's thoroughly humbling. Sailing with no land in sight never lets you forget that you're but a small part of an infinitely greater whole and that invisible, natural forces like the ones that swell your sails have the real power.

Traveler Tuesday – Patrick Bennett of Uncommon Caribbean Sailing
[4] What do you typically do while traveling by plane?

Drink. Despite all the many miles I've logged in the air, believe it or not, I'm an uncomfortable flyer. In the air I choose my words carefully, never saying “we're going down” instead choosing to use the word “descending.” My palms sweat and I compulsively peer out the window watching for clouds that could spell turbulence. So, I drink, point out that intermittent shakes are just “bumps on the road” to most anyone who'll listen, and count the seconds 'til I'm at my destination. (It's nearly impossible for me to sleep.)

[5] What is your favorite travel memory involving food?

One of my favorite memories involving food has to be from a recent sailing adventure through the Grenadines. It was first light and we'd spent the night in a protected bay off Canouan. I was barely getting my first coffee when a withered, weather-beaten old man in a snorkel and mask swam up to our little boat from out of nowhere.

As I greeted him, he slung a diving bag full of fat Caribbean lobster (no claws like Maine lobster, but with fatter tails) onto the deck stating he'd give us a “fair” price. His fair price turned out to be something closer to half-priced, so for the rest of the trip we had grilled lobster, boiled lobster with pasta, lobster scrambled eggs in the morning and more and more.

Traveler Tuesday – Patrick Bennett of Uncommon Caribbean Lobster

I'm getting hungry just thinking about it.

[6] What is one blogging tip or lesson that you have learned along the way that you can share with my readers?

I'm not sure if it's a tip or a lesson, but what's kept me going over the years is a focus on staying true — to remembering why my brother Steve and I started Uncommon Caribbean in the first place and striving to continue following that North Star. You see, unlike a lot of other travel related blogs, ours almost constantly goes against the grain.

Traveler Tuesday – Patrick Bennett of Uncommon Caribbean & Steve on St Croix

For decades Caribbean travel has been bastardized, Disneyfied, and commoditized. Advertisements show identical white couples on pristine beaches holding fruity drinks regardless of the island being promoted. Or mega-cruise ships promise the Caribbean in fast food sized, artificial bites. Being born and bred West Indians, we knew there was so much more to the story of our home region than what was being told.

The only problem is, a lot of people only want to hear about the kind of Caribbean travel they've come to know and expect. So day after day we set out to swim upstream — expanding the horizons of our readers and hopefully redefining the West Indies as a collection of unique, culturally rich destinations perfect for enriching experiential travel.

[7] Where to next?

The coming months are looking jam packed! We'll be back home in St. Croix twice for Taste of St. Croix plus a video shoot, in the Dominican Republic twice (Samana, Santo Domingo, La Romana), Grenada, sailing again in The Grenadines (heaven on earth), then oddly enough in the former East Germany and finally sailing in the Greek Isles. Phew, I can't wait!

Thanks Patrick! You have inspired me to being building my own Caribbean Wanderlist dedicated to exploring unique experiences.

You can see all of Patricks’s AFAR Highlights and Wanderlists where he shares his experiences all over the world and in the Caribbean on his blog Uncommon Caribbean. Follow the conversation on Twitter as well.

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  1. Very cool!
    I loved visiting Jamaica and am excited to return one day. Although, I am also a little guilty of indulging in touristy areas and being stuck in a resort but I did venture out to Negril where we found a historic light house devoid of any tourists and a cliff jumping spot called The Sands that many tourists don’t visit and opt for the much busier and touristy Rick’s Cafe.
    Will definitely check into Uncommon Caribbean!


  2. Thanks so much for featuring me, Andi! Can’t wait to introduce you to the real Caribbean!

  3. Great interview with Patrick! I agree…as an Ambassador, it’s been really great getting to know the other ambassadors and peek into their lives. When I first went to the Caribbean, I did stay close to the resort. Now I’m not as afraid to go out and venture. The people are incredibly friendly and there are so many stories outside the resorts.

    1. Andi Fisher says:

      @AndiP, between you, Patrick, Charu and Matt Long, I definitely see that!

  4. I’ve really enjoyed learning more about Patrick through this…thanks Andi

    1. Andi Fisher says:

      @Charu, my pleasure! And I know you have had some great experiences in the Caribbean yourself!

  5. I also really enjoyed this interview. Beautiful photos, words that speak from the heart, and a perspective that we need to hear in the travel blogging community. I can’t wait to explore the Caribbean (I’ve never been!) and hope to do so with Patrick’s guidance through his wonderful site and AFAR highlights.

    1. Andi Fisher says:

      @Jenna, I know Patrick’s initiative is really important as so many Americans (including myself) experience the Caribbean from a cruise ship.

  6. Very interesting. Can’t wait to visit the Carribean somaday.