A week in TOBAGO


Tobago is quite simply, Paradise. From liming with locals, to a music and dance fueled visit to Sunday School, the local way of life is infectious. If you can't slow down and get on island time here, I'm not sure you can anywhere.

Duration: One week

Tobago exceeded all of our expectations. Sure, it’s an island paradise located in the Caribbean, but we found so much more than that in the incredible kindness of the people, the omnipresence of music, and the wild and undeveloped natural beauty. (Tobago hosts the Western hemisphere’s oldest protected rainforest). We stayed at Castara Retreats and I wouldn’t stay anywhere else, it truly made our entire experience. In an age of Airbnbs (which we use frequently), there are a few hotels that are so dream-inspiring that you find yourself planning an entire trip to a place just because of them. Most of the time, these fantasies are fueled by 5 star, huts over water in the Maldives, break the bank style places, but occasionally, a reasonably priced hotel looks so special that fantasy and reality combine. Castara’s ‘eco lodge’ approach is that place. Our trip came about because of cheap flight deals from SF to Trinidad, combined with our discovery of Castara Retreats, and we plan to return to this hotel again in the future. After a week in Tobago, we are partial to Castara Beach (which is far away from the parts of the island frequented by day trippers, cruise ships, and big boats), and this little hotel deeply embedded in the local community. The website claims you’ll get a taste of ‘the real Tobago’ and we found this to be absolutely true (many hotels claim this but Castara really delivers). The heart of the hotel is the legendary manager Porridge and his wife Jeannell who grew up in Castara, and help arrange every detail of your stay from taxi rides to excursions (all in partnership with local operators and friends). We found that by the end of the week, we knew a dozen locals, we’d spent time in their homes for harvest festival parties, at dance parties, and on the beach, and we were already planning our next visit from the plane ride home.

  • Sight Seeing 70% 70%
  • Food 70% 70%
  • Ease of Transportation 70% 70%
  • Chill Factor and likelihood we’ll be back 100% 100%

Liming: You don’t come to Tobago to do a ton of activities. Yes you can scuba dive, you can go out on a boat, you can join a bird watching tour or a nature walk, you can watch turtles hatch and scramble to the sea, and we did do a few of these things. But the sooner you slow down, spend an entire afternoon on the beach listening to impromptu drum circles, shoot the shit with locals and accept an invite to a beach barbeque, the sooner you’ll get what Tobago is all about. Liming is a way of life here, and if you get onboard with that, you’ll start wondering why anyone would choose to live otherwise. Don’t try to schedule a million activities, don’t get frustrated when things don’t start on time, and do embrace the random opportunities and invitations as they come. We had our most memorable experiences when we relaxed our ‘plans’, and went with the flow.

Each morning at Castara we woke up to the sound of humming bird wings thrumming around the feeder on our deck, with a view of the peaceful beach below. We would head down to Cheno’s coffee shop, the local breakfast gathering place, to say hi to people and figure out any local news. (They sometimes knew when barbeques or music events were happening in Castara). We spent days sunbathing on Castara beach, drinking rum punch in plastic takeaway cups from Cascreole Bar & Beach Club (so refreshing but they do sneak up on you) and by late afternoon drummers, various musicians, and occasional limbo dance offs would get started down the beach at Boathouse, which is where we spent a few late afternoons. It looks like they host official drum nights, and I definitely wouldn’t miss this. I think what we stumbled upon was a bit more impromptu and the friends we made here were local people we spent time with the rest of the week.

For dinner we would head back up to Castara for happy hour (2 for 1 cocktails from 5-6pm) in their beautiful bar and restaurant Caribbean Kitchen overlooking the sea. The food is fantastic; the flavors are locally inspired, and it’s a big enough menu that you can come back each evening and not order the same thing. My vegetarian friend swore the black bean burger was the best she’s ever had anywhere in the world, and the Jamaican jerk fish and griddled prawns didn’t disappoint. The cocktails are more sophisticated than your average rum punch (though we loved average rum punch), and worth paying a bit more for.


Bird watching, rain forest exploring, and house parties with locals:

Tobago is famous for its variety of birds; both in the Tobago bird sanctuary, and in the Tobago rain forest (the oldest protected forest in the Western Hemisphere). We had never gone bird watching before and aren’t particularly interested in birds, but took a ‘when in Rome’ approach, and decided to organize a walk. We were too late to reserve Newton George, the island’s preeminent bird expert, so Porridge and Jeanell arranged a nature walk with Darlington Chance which ended up being one of the most suprising and enjoyable days we’ve ever had on holiday.

From the moment he picked us up, Darlington gave us an education in every aspect of Tobago life; animal and human. A few minutes into our drive, we passed a car on the side of the road surrounded by half a dozen other cars and a group of twenty people standing by the vehicle. It turned out there had been a minor car accident, and in Tobago we learned, you would never drive by someone in distress and not stop and help out. Even if twenty other people were already there. As we stopped to chat to people Darlington knew about what had happened, we watched car after car come around the corner, immediately pull over, get out, and begin chatting and joining the others. We would see variations of this unselfish, community kindness throughout the week.

When we knew there was no danger, we continued on to the Main Ridge Forest Reserve on the upper reaches of the island. Darlington slowly ambled through the forest, pointing out moving leaves that revealed fiery ants beneath, and varieties of ferns and flora, along with legends of some of his greatest sightings. We didn’t see monkeys or snakes, or any ‘exotic’ animals, and yet Darlington’s calm wonder, and his passion for every element of the forest, from leaf, to ant, to red billed tropic bird was infectious. His presence is calming, the pace is slow and relaxed, and I would almost describe it as a meditative nature walk. If you want to race around, check birds off a list, and get pictures of rare sightings to show people back home, this probably isn’t the tour for you. If you want to relax, spend time with someone who truly loves plants and animals, and has spent his entire life learning about them and respecting them, and you want to learn about Tobago and its rhythms, then Darlington is your man.

After walking through the rain forest, Darlington told us there were a few harvest festivals going on, and asked if we’d like to go to a village to enjoy the local festivities. Each village has its own harvest festival date, and its a time when everyone cooks huge amounts of food, fires up massive speakers and soundsystems, and its one big open house where you go from place to place eating food, drinking drinks, listening to music, and chatting with friendly people. We went to several houses with Darlington where we were served crab, goat stew, handed cold beers, and welcomed as if we’d known people our entire lives. At some houses we sat around in chairs, talking with people who wanted to tell us all the places they’d travelled to, and warned us to be careful when we went back to Trinidad, in other homes we stood in crowded hallways swaying to loud music in true house party fashion. Some hosts refused to let us leave without giving us more food to go, and by the end of the day we had a small collection of tupperware filled with goat stews. Seeing the enormous speakers that were set up at litle homes sprinkled throughout the quiet villages in Tobago was just one example of the primacy of music here. People blasted their speakers off the front patios of their homes where music reverberated for miles around. If you come to Tobago, I would highly recommend checking the harvest festival calendar, and perhaps arranging an excursion with Darlington to go for a truly local experience. 

Sunday School: one of the most popular island-wide parties is known at Sunday School, a vibrant street party with music that kicks off every Sunday evening. It begins with a steel drum performance, which is impressive and a nice opportunity to hear this famous style of music, although as we discovered, it’s more prevalent in Trinidad than in Tobago. Tobago has more of an African drumming tradition, and we saw more of this later in the evening, after the DJ took over and the dance floor was packed with people dancing to the popular Soca music (a mix of Calypso with catchy lyrics and hard percussive beats). If you want to read more about the music and history of both Trinidad and Tobago, this is a good resource.  But if you want to really experience it, then spend a few days hanging and making friends on the beach where people play their own drums, at harvest house parties where they blast Soca from the speakers, and at Sunday School where they get down to both. This could have been overwhelming if we didn’t know so many people by the end of the week. Porridge arranged transportation from Castara (it’s on the opposite end of the island), and we felt looked after by him and his team who know people across the island. We ran into a bunch of our beach friends from Castara and had a fun night dancing and hanging out with them. Sunday School gets packed and can feel overwhelming, particularly later at night. I wouldn’t go alone, and I would definitely organize transportation through Porridge, make friends with the other lodge guests who are going so you have people to watch out for, and go for the first half of the night with the steel drums and some DJ Soca music. 

Pigeon Point and Nylon Pool: On our final day in Tobago, we went to Pigeon Point, the more touristy part of the island, to catch a glass bottom boat out to the infamous Nylon Pool. The water is crystal clear and beautiful, and shallow like a swimming pool, and the Cool Runnings boat makes for a fun few hours. Interestingly, a lot of the tourists on our trip were just over from Trinidad to enjoy the crystal waters of Tobago. That said, after the calm, idyllic paradise of Castara, Pigeon Point feels busy and touristy with large hotels and day-trippers. I wouldn’t have wanted to spend more time here than an afternoon, and the busy boat excursion, while beautiful, had us relishing the quiet time ‘off the beaten path’ in Castara.

A few final tips: We’ve seen frequent cheap flight deals from San Francisco to Trinidad (via Houston), which was the impetus for our trip. From there, it’s a short hop on Caribbean Air over to Tobago, and there are flights almost every hour. We were advised NOT to take the ferry, which can be subject to rough seas, and take much longer. We spent a couple days in Trinidad in Port of Spain, and visiting the Caroni swamp, but after our amazing time in Tobago, we wished we’d spent more of our time there. Trinidad frequently comes up on numerous travel advisory lists as unsafe. While our trip was without incident, we did feel stressed out and a bit restricted in our movements in Trinidad as a result. Many of the warm, open people we met in Tobago advised us to be careful in Trinidad (although some of that might have been a small island vs. big city mentality). I think if you were to devote more time to Trinidad in its own right, get out of Port of Spain, and perhaps go to the Asa Wright Nature Centre, then you can have an enjoyable time in Trinidad. If you don’t have much time to get out of Port of Spain, and are merely book ending Tobago connections, then I would spend as little time as possible and fly straight through to maximize time in Tobago. 

Next time I’m in Tobago, I will definitely go diving in Speyside. The biodiversity in Tobago is legendary, and far less touristy than other diving destinations. I will also be sure to organize turtle watching, as Tobago is the world’s premier places to see turtles hatch on the beach at night, and make their perilous first journey into the sea. It’s a site I’ve always wanted to witness, and I’ll prioritize this on my next trip. 


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