Travel, Working Mom

Chicly Geeky Guide to Tobago

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This is a sponsored post, though all ideas, images, and opinions are my own.


Tobago is one of those places on Earth where you feel like you have stepped out of reality and into a post card. The raw power of nature is all around you, flowing from waterfalls into rivers that merge with the sea like lifeblood coursing through the very heart of the island.  Trinidad is rumored to be the setting for Robert Louis Stevenson’s Treasure Island, and was a stop over for real pirates for years.  Many locals still believe that there is treasure buried on the island, waiting to be discovered.  After a single visit, I can see why they believe it is there, and haven’t found it.  The island has everything, breathtaking beaches, mountainous vistas that overlook secret bays, and lush rain forest – each of which could be holding tight to long buried secrets.

My stay based at the Magdalena Grand Beach Resort for a conference I was attending. The conference is based on the work some colleagues and I have been doing in Belize as we developed their quality assurance system.  For several days the leading experts in Caribbean Quality Assurance in Higher Education from their respective countries gathered to share ideas, reflect, and learn from each other.  CANQATE (Caribbean Area Network for Quality Assurance in Tertiary Education) is held annually, and I strongly suspect that there is no bad host country location in this particular network.  But on one day when I didn’t have to report to the opening ceremony until late in the day, I made the most of my time and did a little exploring.

My first stops were at a famous tomb.  Yep, I was thrilled to head straight to Plymouth to the tomb of Mrs. Betty Stivren.  This tomb is important for the riddle on the epitaph.  “She was a mother without knowing it, and wife without telling her husband, except for her sweet indulgences to him.”  There are a few interpretations, but two of them particularly stood out to me.  Keep in mind that Betty had a legal husband, and by all accounts was married to him in a typical manner until her death.  Betty is suspected to have been a slave of mixed descent as slavery was still practiced in Tobago at that time.  She met an overseer that she was taken with and late one evening, when he payed her a visit, she got him intoxicated and had a wiley priest marry them while he was in no state to object.  Because this relationship was based on the aforementioned “kind indulgences” she became pregnant.  Unfortunately before she was far enough along to know she was to be a  mother, she died.  The girl had some spunk in this version.

Another local had a different view on how this riddle could be interpreted, with a little more culturally relevant spin to the locals than the previous one, and a little darker meaning.  Unlike Trinidad, Tobago’s culture is primarily influenced by it’s African roots.  The West Indies were a popular location for cotton, indigo and sugar cane to grow – and for the French, English, and Dutch – who were constantly fighting over control of the island (it changed hands more than 30 times!) they needed laborers to work the plantations.  In traditional culture, you are always connected to the first person you have a sexual encounter with – consensual or not in Betty’s case.  In this version she was still thought to have been a slave, and still thought to be the concubine of an overseer.  This interpretation reflects the brutality of captivity.  Betty was taken as a mistress by one of the overseers or land owners, though she did marry another resident of the plantation (another slave).  Because Betty’s cultural beliefs connected her to this overseer, he was her husband without knowing it.  Betty became impregnated and either died before or during childbirth, never knowing the joys of Motherhood.  She was only 23.

After paying my respects to Mrs. Stivren, I ventured to Adventure Farms, the home of a local gentleman that is a hummingbird sanctuary.  The trees are laden with fruit for the various birds as if they are Christmas trees waiting for the holidays!  The birds were absolutely stunning.  We saw Trinidad Mot Mots, Copper Rumped Humming Birds, Emerald Humming Birds, and a variety of other species, but the one that caught my attention was a White Necked Jacobin.  He was a stunning sapphire blue with a white chest and emerald accents.  I was captivated by these amazing birds.  The sun reflected off their feathers in a rainbow of colors and hues that were jewel like as they fed and flitted.  The owner brought additional food out, then range a little bell and the birds swarmed!  He has them trained in a very Pavlovian way!

By the time my guide picked me up the rains had settled into the area.  Analisia from Gail’s Exclusive Tour Services. Limited arrived in their classic lime green shirt to lead me on the remainder of my adventures.  Analisia’s smile and warm personality were a little sunshine on a rainy day.  She and her husband Willie (our driver) took me up terrifyingly winding roads with ease and professionalism.  They seem to know everyone on the island!  I felt more like I had been adopted by locals than had arranged a tour.  It was the most laid back and inviting tour I have ever experienced.

We began by stopping to view some smaller water falls that were occurring because of recent rains, and continued on to Castera via our little windy path.  We stopped at Little Englishman’s Bay and Englishman’s Bay on our way to Castara bay.  They took me to two different beaches near Castera, a small and very casual fishing village where the locals greeted even me, a complete stranger, with genuine hellos and smiles.  I walked along small sandy beaches surrounded by craggy cliffs and rocky jetties as huge waves cast spray violently into the air over sea bound boulders.  The rocks are not just any rocks.  Large chunks of volcanic rock, rose quarts, quarts, and blueish purple limestone wash on the shore and lay on the beaches like jewels sparkling in the sun.  I couldn’t help but pick up a few to bring back to Tiny and Teeny so that they too could see the natural wonder of this wild and untamed shore.

My lunch was provided by L and H restaurant in Castera, where we ate on a breezy veranda, seated just off the beach.  The brightly yellow painted building is inviting in color and in smell!  I got to try a local favorite – macaroni pie.  This is a lot like the American macaroni and cheese, but a baked version bound by egg that is a lot more dense but absolutely delicious.  If I had to commit suicide by carbohydrates, this would be my weapon of choice.  Warm, cheesy, and delicious, it was the perfect side to my fresh vegies, rice, and fried chicken.  Woah!  I was full, and so very happy after that meal

Analisia led me on a walk down the beach where women were cooking their bread in a earthen oven.  Twice a week, the women of the village heat up the massive oven, and all come to socialize and bake their bread for the next few days.  These women have it down to a science.  Holy moly!

The bread was light and fluffy, with a whole wheat dough that was earthy and just slightly sweet.  They let me sample a coconut tart that the ladies had made – this bread is shaped in perfect crescents stuffed with spiced coconut was a treat!  I was so full that I couldn’t eat it all there, so they wrapped it up for me to take back to the hotel for later that night.  Is it too late to change my mind on that death by carb weapon?  I may still have some thinking to do.  The oven fascinated me.  Bread isn’t known to be the easiest thing in the world to get to come out properly, so for these women to cook it as the women in this village had for generations was captivating.  Nigel, the gentleman who was manning the oven showed me the banana leaves that they set each loaf on and slide it into the oven – they then cover it with leaves as well.  The oven is massive!  It sort of reminded me of something that an old witch would bake parts of her ginger bread house and maybe the occasional errant children in.  You could see the heat pouring out of the front door as the oven was working its magic – rippling out in shimmery waves, bathing me in the yeasty aroma of hand made bread.

As we walked through the village streets, it became clear why this would be a hot spot for tourists who wanted to get away from it all.  There are very few touristy shops, vendors, or commercial elements in this village – it exists now as it has for generations – therein being the appeal.  There were no groups of people rushing hurriedly past, all on their cell phones, no pollution or smog.  There were only locals, fishermen resting after being up before dawn and already having put in a full day’s work before most of us go to lunch.  This is one of those rare places that still exist where you can rent a small villa or room in a local B and B, spend a week, and take life long friendships home with you when you leave.

After Castera, we began to make our way back to Scarborough, the largest of the communities on the island.  We came through the center of the island on our return so that we could venture into some of the smaller, more rural villages.  Lovely pastel houses dotted the communities which were small and quaint.  We stopped for a quick coconut water – chopped fresh on the side of the street.  The cool, refreshing waters were lovely on a hot afternoon.  Then I really got a treat!  The very imposing, yet sweetly smiling man with the machete quartered the coconut and chopped off a small sliver of shell for me to use as a spoon.  They then taught me how to eat the jelly from the middle of the coconut like a pro!  Seriously, I was a total boss at coconut jelly eating.  They only laughed a little at me, which I count as a major win.

In Scarborough, Fort King George was built by the British during one of their occupations.  The Fort is situated on the Atlantic side of the island (bigger waves here, but also some SERIOUS under tows – be careful if you swim) on the Atlantic side of the island – I preferred the Caribbean side for swimming – the waters were much more calm and swimmable.


The Fort was perched on the cliff with sweeping views of the area, and had all of the things that you would imagine – powder magazine ,barracks, look outs and court yard.  This fort also had a charming museum with artifacts from the varied cultural backgrounds of both the controlling forces as well as the enslaved on the island.  The museum was small, but laid out well and was curated so that you got a sense of the individual cultures that influenced modern day Tobago.  The fort also has in intake prison (quite interesting) and the original cemetery.

The grounds are immaculately kept – which is why we stumbled on a pop up wedding while we were visiting.  Could you imagine getting married in a location as stunningly beautiful as this?  Well you can!  Tobago is the perfect place for a destination wedding.  The fort allows couples to bring a photographer and take their wedding photos in the airy arches of the red brick and limestone grounds.


This beautiful couple and their guests were kind enough to give me permission to snap a few photos of the wedding party and use them to share their joy with all of you!

This is one sharp dressed, father of the bride (she was glowing, by the way!)

If I weren’t already married to my own Prince Charming (he watched the kids for a week so that I could attend my conference – now doubt that he’s the real deal!) I could certainly see myself making Fort King James my personal wedding goal!  What do you think?  Should I set that as a renewal of the vows goal for our 15th anniversary in a few years?

The views and beaches were breathtaking.  The food, oh my!  But most of all, the thing that struck me the most during my time in both Trinidad and Tobago were the people.  They called me by name, didn’t look at me as just another tourist, and made me feel like a local.  The experiences I had during my stay will stay with me forever.  I am already looking forward to bringing my family back to Trinidad and Tobago so that they, too, can have the personal experiences and connection to each community that I was able to experience.  I can’t help but feel like this was no accident, and that Gail’s Tours operates with experiences in mind, not just their bottom line.  I was treated like a princess (I’ve always thought of myself as one anyway) and even passed by Analisia at the airport.  She remembered my name and wished me safe travels (I don’t know how I missed her in her Gail’s Tours green shirt – yes I do, I was running my mouth to a colleague).

I will say that shopping is limited in many places, a few crafts and craft stands dotted the beaches and country side, but they were not nearly as prevalent as they were in many touristy areas.


The feeling that I was true guest in the community and the personal touches and comfort extended to me during the tours (a cooler of water, snacks, meals and even towels for the beaches!) made my tour an experiential adventure.  I didn’t have to think of anything!  I guarantee you, the next time I return to Trinidad or Tobago, I’ll book with the same amazingly attentive service – they have certainly gained my confidence and trust, and as someone who travels internationally a lot, and encounters travel glitches, to not only want to book them again, but to trust Gail with my family’s memories is high praise.

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  1. Who knew so many wonderful things in a relatively unknown (at least to me) world.

    1. Momleficent says:

      I know. Trinidad and Tobago were so different than I thought they would be. I underestimated the culture and individuality each island would have!

    2. I know! I wonder why they are not more publicized? Honestly, I’m glad they weren’t though, it was so amazing to be on those beaches without a ton of other people.

  2. O.K…. this is now officially on my Bucket List. I vaguely remember Trinidad and Tobago stamps from my long distant youth, but had totally forgotten about the island, Your descriptions, stories and pictures have made me wat to go visit and discover this place for myself.

    1. Momleficent says:

      It was such an amazing experience for me! I would love to take my family back to see the things I did – and of course read Robinson Crusoe on the way down!

  3. Your description (and picture) of the coconut brought back so many memories of my own childhood in my native Guatemala. My parents used to buy us coconuts to drink all the time. Tobago looks like a lovely place to visit!

    1. Momleficent says:

      It is beautiful. Guatemala is pretty lovely as well. I loved my time in Flores, and would love to go to Antigua!

  4. It sounds like you had a wonderful time seeing so many wonderful sites. I especially enjoyed Mrs. Betty’s riddle!

    1. Momleficent says:

      I did too! That was so interesting to me. I read about it in Atlas Obscura’s new book and knew I had to go when I got to the island! It was worth the trip, especially to hear Analisa’s take on the riddle.

  5. Wow! You sold me on Tobago! It sounds like another world, another beautiful world, that is. Though I loved the gorgeous nature scenes, the interesting sites and delicious foods, your conclusion caught my heart. That you were treated with such a personal connection, adopting you, calling you by name, treating you like a local, that is hospitality from the heart. No wonder you hope to take your family back to Trinidad and Tobago someday. I hope to do the same!

    1. It was staggeringly beautiful. I think that Tiny (10) and Teeny (3) would love to run wild on the beaches!

  6. My husband and I have been deciding where to travel next. Would have never thought of this place, but now it’s on the list! Love the idea of stepping into a postcard!

    1. Oh my, try to spend time on both islands. Trinidad had a TON of culture and different things to experience, and Tobago was a really chill, get away from it all kind of place. Both have their place!

  7. You did such a wonderful job sharing the details of your trip, I would love to visit. The scenery, the food but mostly the people seem absolutely wonderful. Thank you for sharing.

    1. The people were one of the highlights of my trip – they were just so warm and friendly. As a female who travels alone a good bit, safety is always a concern. Never once did I feel unsafe.

  8. This looks like a wonderful place to visit. I could see myself visiting this area in the future.

    1. Sarah, it is amazing. This is one of those places that you will want to visit time and time again.

  9. Sounds like you had an amazing experience, thank you for sharing! I especially like the wedding photos – weddings are such a great way to really get a sense of the culture of a different place. I could feel the sense of relaxation and serenity you experienced on this trip, something we all need to soak in on occasion!

    1. Getting to photograph the happy couple was such a special treat, and to be invited in as a perfect stranger was not something I would have ever had happen here in the states. The bride’s dress was beautiful!

  10. Dear Carlise!

    I’ve not been to Tobago, but it looks nice 🙂

    Those are some beautiful pictures of the couple.

    Edna Davidsen

    1. I especially loved the father of the bride. You could see how proud of his daughter he was. He was just adorable – and especially dapper with his gloves and hat. He was adorable.

  11. Wow, beautiful! Thanks for the tour! Those coconut tarts look amazing. I had a student who had grown up in Trinidad and told me that she loved to visit Tobago. Now I can definitely understand why!

    1. Momleficent says:

      Me too! I loved the culture and communities in Trinidad, but Tobago had some really amazing features as well. I don’t know which one would be my favorite.

  12. Awesome post. Sounds like a fun adventure!

    1. Momleficent says:

      It was amazing! I really enjoyed delving into the cultures of the islands!

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