INFO: A Gay Guy's Guide to Tobago Island
Chances are you've heard of the nation of Trinidad & Tobago but only have a fleeting idea of where it's located or what there is to do there. T&T is a relatively well known Caribbean nation but is often over overlooked as a travel destination. Other places like Jamaica, the Dominican Republic, or the Bahamas overshadow these dual islands which sit just under 7 miles from Venezuela at their closest point. Despite its small size T&T is actually one of the world's wealthiest nations per capita, even ranking within the Top 40 in the 2010 survey of world economies. While oil is the biggest industry by far in the nation, tourism still ranks in the top three. Still, the number of visitors and overall impact of tourism on the islands is far less than in other Caribbean locales. A little digging into travel circles on the internet will reveal that crime is relatively high on the islands and there have been a few sad incidents in the past decade involving tourists being robbed, attacked, or raped while visiting which pop up when researching travel to this island nation. With promoting tourism not a big priority and stories of crime often filling the space remaining, T&T isn't exactly the region's next hot spot. Even among people who are slowly (or break-neck quickly) trying to visit every country in the world, most seem to document their time in the nation as a long layover in the capital city of Port of Spain before heading on to other Caribbean or South American destinations.
Sunset over Buccoo Bay, a popular spot for diving and dining on Tobago.
For those that do find themselves in T&T, they're likely spending their time on the first "T" - Trinidad. Making up over 93% of the nation's territory and 95% of the country's population, Trinidad dominates the relationship between the two islands on many fronts. When I made the decision to spend a few day here most of my research lead me toward things to do and see on the main island, so much so that I started to ask "Is there anything on Tobago at all?" Digging around for a bit revealed that despite being only a few miles apart, the atmosphere and culture on Tobago is quite different than her sister isle. Tobago may be smaller than Trinidad but packs a pretty powerful tourism punch and is apparently quite popular with German and British visitors. There are even direct flights to Tobago island from Europe (though some make stops on the way).
Tobago is considered much calmer, much tamer, and much safer than Trinidad and the significantly smaller population and crime statistics on the island support that assertion. Due to its British colonial past the nation has quite a multicultural demographic makeup with the descendants of African slaves and Indian indentured servants making up 47% and 35% of the population respectively. Smaller groups of mixed race, Europeans, and Asians (mostly Chinese) make up the remainder. However on Tobago itself the vast majority of residents are descendants of African slaves, with only small communities of colonial European and Indians present.
The little bit of research I did online was enough to pique my curiosity and soon enough I had booked a $25 one way flight from Port of Spain (where my plane ticket was depositing me) to the little isle of Tobago. Honestly I thought there wasn't a more poetic and proper way to explore one of the Caribbean's most overlooked nations than by exploring its most overlooked island. I spent several days on the island, slowly making my way to various points of interest and mixing it with time laying on the beach or quietly reading a book near the seashore. If you were in rush you could probably see most of the island's major sights in a single day since it's not very large, but I would encourage you to take your time here. Tobago is known as the more back and relaxed island when contrasted with Trinidad, so embrace the vibe.
Buckle up and make sure the gas tank is full as we hit the gas on this guide to the little island paradise of Tobago!
As I mentioned in the introduction, Trinidad & Tobago has a rather poor safety reputation. When you Google topics like "safest Caribbean destinations" or "Trinidad and Tobago safety" you'll likely encounter a variety of articles noting how T&T struggles with controlling both violent and property crimes within its borders. The good news for you as a visitor is two fold - crime on the island is not often targeted at visitors (though it does still happen) and Tobago has a much lower level of crime than its more populous, bigger sister isle. That being said, there are still things to be aware of when you visit and ways to make yourself more likely to enjoy your time on the island without an incident.
The locals can be reserved but are friendly if you take the initiative to engage with them first. They're more than willing to share information on areas on the island to avoid or give you tips on parts of towns to avoid to remain safe and secure. I'd highly recommend talking to someone at your guesthouse, hotel, or the owner/manager of your AirBnB to get the local perspective on the safety landscape.
Common sense is key with any travel destination, not just Tobago. Avoid doing things that make you or your property easy targets. Don't wear expensive jewelry, don't leave valuables in your car while you're lounging at a beach, don't walk around alone in isolated areas late at night, etc.
If you've rented a car and are doing a self-drive exploration of the island be aware that traffic moves slow and with road conditions relatively poor you're unlikely to be moving very fast in most places on the island. Sometimes people will see you and attempt to flag you down to speak with you. While this often will end with a request for money, it's best to avoid stopping for anyone in these situations.
Be cautious when wandering around some of the more quiet beaches and corners of the island. While generally you'll be just fine, there have been isolated incidents of visitors being robbed or attacked when exploring areas of the island where they're completely alone. Tobago's population is small and even at some of the bigger locations on the island I was the only visitor anywhere to be seen.
On the flip side, here's a list of things I think you should be completely fine doing that I've seen some people (in my very humble and not legal opinion) warn visitors against:
You really don't need to hire a driver or tour guide to safely see the island. Does it make it convenient and less difficult for you? Yup. But it shouldn't be considered mandatory for visitors. You can definitely safely rent your own car and explore the island on your own as long as you take some of the common sense precautions mentioned above and can deal with some less than text book driving habits by locals.
Visiting events or concerts such as Sunday School (discussed below) can be done with little concern as long as you don't drink too much and have a safe way to getting home.
You don't need to stay at a compound hotel to be safe on Tobago, you can definitely stay at a guesthouse or rent a local house/villa. While many of the hotel properties on neighboring Trinidad are walled off from the population out of an abundance of caution, don't let that convince you it's necessary on Tobago. I had a perfectly lovely stay at a guesthouse with a rickety gate in Bucco where I wandered through every street in town without incident.
Overall the main takeaway for general safety on Tobago (more on LGBTQ-specific safety at the end of the post) is pretty much the same as any other place - make smart decisions about how you're exploring and you're very unlikely to encounter any issues during your stay. I felt much safer over the several days I spent in Tobago than I do sometimes in my home city of Chicago.
Being such a small island means there's a rather limited list of options for arriving. For most visitors its going to mean routing to the nation's biggest airport just outside of the capital of Port of Spain before continuing onward to Tobago. Piarco International Airport has a decent level of connectivity to major cities in the region and further afield. Major carriers bringing passengers into Port of Spain include Air Canada and WestJet (Toronto), American Airlines (Miami), British Airways (London Gatwick), JetBlue (Ft. Lauderdale, New York JFK), and United Airlines (Newark, Houston). Caribbean Airlines is the national airline of Trinidad & Tobago and operates a hub in Port of Spain. It is currently the largest airline in the Caribbean. They offer the most options into Port of Spain with major entry points from Ft. Lauderdale, Miami, New York JFK, Orlando, and Toronto. Note that Caribbean runs frequent shuttle flights between Port of Spain and Tobago and the fare is standard for all flights (currently $30 USD, up $5 from when I took it). If you're looking to visit, I suggest pricing flights directly to Tobago AND to Port of Spain to see if you can get a better deal one way or the other since the price of flights between the two is capped and airlines can often build in a premium to fly directly to a hard-to-reach locale.
I've flown with Caribbean Airlines four times in the past and have had mixed results. Service on all flights was good to excellent. Food/snacks provided were standard for just about any airline in the world. My biggest issue was a major delay on a flight to New York on my way home from Guyana (see THIS and THIS) that was poorly communicated and handled by the airline.
If you'd like to fly directly into Tobago and avoid the Port of Spain connection (which isn't too difficult logistically but can be frustrating as the airport isn't very efficiently operated), you can look at the twice a week (seasonal) British Airways flight from London Gatwick (with a stop in Antigua), Germany's Condor (Frankfurt), or the weekly Sunday Caribbean Airlines service from New York JFK.
Of course being an island there are also options to arrive by sea. Do you have a yacht or small sailing vessel? Good for you. I don't, so the logistics of sailing your own boat into Tobago are beyond me. Google is your friend. For the rest of us, there's always the public ferry option from Trinidad. The Port Authority of Trinidad operates fast and standard ferry service from Port of Spain to Scarborough several times per day. Tickets range from $5-$8 USD depending on which boat you take. Schedule and fare information for the ferry is updated on the Port Authority's website (LINK). If you're looking to take the ferry immediately after arriving in Trinidad note that the airport is located outside of the city proper and it can take some time to get to the port. The Port Authority asks passengers to arrive two hours prior to departure as well (your mileage may vary with this though!)
This will a pretty short section since I would recommend only two options to visitors on Tobago - renting a car for yourself or hiring a driver to take you around.
Unfortunately the public transportation network on Tobago is relatively non-existent. There are a handful of buses and mini-bus routes crisscrossing the island but they are very infrequent which means you'd be doing quite a lot of waiting around for a ride if you wanted to use this method. Walking to explore is an option once you've gotten to an area or town, but despite being a small island it is still way too big to be considered walkable. Keep your footwork for spot to spot sightseeing and use a car to get between places.
Just your average roadside view on Tobago.
As I hinted at above, renting a car and self-driving is a very viable option on Tobago. Rental cars are generally not brand new but are serviceable. I saw quite a few SUVs with visitors behind the steering wheels while exploring. Road conditions on the highway on the island were good though the state of roads inland and crisscrossing Tobago were much more hit and miss. Locals appeared to drive fast (relatively speaking), even on the hills and blind curves inland, so use caution if you're doing it on your own.
If you're averse to driving in a foreign country then hiring a driver is your next best option. Online travel agencies offering day tours around the island range from about $100-$300 per day depending on which agency you look at and how many people will be joining you. You may be able to save a good amount of money by asking your hotel or guesthouse staff to connect you with someone they know and trust to take you around and you're likely to be able to set your own itinerary vs. the packaged routing many tour companies offer.
WHEN TO GO
On the whole and with a little bit of luck, Tobago can be a year-round destination but there are indeed better times than others to visit. January through March seems to the be the undisputed best time of year to visit with the least rain and most sunshine. After March and up through November there is a varying level of rain that is likely to fall, with some timeframes seeing intermittent showers to others with full day downpours. On the whole temperatures in Tobago stay consistently in the 80 degree Fahrenheit range, so that's a consistent offering to look forward to on your visit. I don't typically recommend people avoid visiting places during rainy season as I often find the rain will only happen during small portions of the day and the vegetation is at its most vibrant and lush. It's all about what you value and how much rain will ruin your plans.
Tobago's $100 million dollar goat racing facility.
If you're looking to visit to experience a local event or unique tradition you can always angle your visit during Carnival (the Monday and Tuesday before Ash Wednesday) or over the Easter holiday when Tobago hosts one of the world's oldest and biggest goat races!
WHAT TO SEE
For such a tiny island Tobago packs quite a scenic punch, and despite having several days on the island to explore I didn't end up seeing all of the sights I had on my list prior to leaving, so keep in mind this list is admittedly incomplete. I don't really feel comfortable telling you to see something (for example Argyle Falls and the Main Ridge Forest Preserve) that are listed as great things to do on the island if I haven't seen it myself. Hopefully you can use this as a jumping off point in your research on how to spend your time on the island!
A small town on the north shore of the island, Bucco is best known as the start and end point for many boat tours. The nearby coral reef is one of the island's biggest attractions and many glass-bottom boats leave from Bucco in the morning for a full day of exploring the surrounding waters. The reef has a shallow water level above it which lends itself to floating and frolicking with ease. Locals have coined the term "the nylon pool" to describe the appearance of the reef's water. Honestly I'm not the biggest fan of swimming in open water. Actually it terrifies me, so needless to say I didn't really partake in these in-water festivities but I can tell you from observation on the boat that this was a very popular way to spend a day on Tobago and the boats were constantly picking up and dropping off sunburnt UK tourists. Even if you don't like open water swimming or snorkeling, sitting on on the boat and enjoying the Caribbean is a lovely way to spend a day. If water adventures are your thing, make this a priority.
If you're more like me and prefer to not have fish and sharks potentially nibbling on your nethers in the ocean, Bucco actually isn't without some things to keep you entertained for a few hours. The other big draw to Bucco is a weekly party called "Sunday School". As the name so easily implies it happens every Sunday night along Bucco's waterfront and depending on the time of year can draw huge crowds of local and tourist party-goers. Early in the evening the party starts with steelpan bands giving a low key soundtrack as the sun sets and the evening starts to take hold. If you're a more laid back partier this is probably your ideal niche as it's prime time for a few drinks and some light dancing. Eventually the entertainment takes a turn and the steelpan bands make an exit and the loud speakers come out, blasting soca music until the wee hours of the night. This is a rowdier, more dance oriented portion of the evening so come prepared if you show up later at night.
If you happen to be staying in Bucco (like I was), you should be aware that Sunday School is LOUD and there is absolutely nothing you or your hotel/guesthouse can do about it. I've been warned about loud events disrupting people when I've traveled in the past to other destinations but have always been fine. Sunday School was the one time I've ever been really impacted by how loud everything was and I did in fact struggle to get to sleep. The event goes until the wee hours of the morning so even if you are enjoying the festivities unless you're willing to be up till dawn you'll need to deal with sleeping through the noise at some point. Note that if you want to enjoy some of the music during the daylight hours and you happen to be staying in Bucco, you can often hear some of the local steelpan bands practicing for a few hours if you wander around the very small town.
Because of Sunday School and the number of people coming into town for the boat tours, Bucco is also a relatively popular place for a meal for those on the southern end of Tobago. Note that the handful of restaurants that are open for dinner are quite expensive, with one person's meal costing between $25 - $75 USD depending how much you order and whether you want alcohol along with your meal. I didn't properly research the dining options prior to booking my stay at a guesthouse in town and ended up really frustrated with how much food cost me the first two evenings. After that I ended up eating huge lunches while out on the island or buying extra food during the day to eat in my room at night. Still, the views from many of the restaurants at sunset is quite lovely.
FORT JAMES & THE GRAVE OF BETTY STIVEN
Nestled along a slab of the Great Courland Bay, Fort James is located in one of the island's oldest colonial towns - Plymouth. The town is a little hamlet of houses and churches occupying a lovely swath of land along the turquoise waters of the Caribbean. Originally serving as a barracks, over time the fort grew in importance as shipping and trade activity in the area increased. In 1777 a four gun battery was placed at the fort by the British, only for the French to capture the area a few years later.
The fort eventually returned to British hands and now enjoys relative peace and quiet in the age of independence. In all honesty Fort James is a rather unimpressive site, not worth going out of your way to see. The Great Courland Bay area, however, is a nice little stretch of land to relax while perhaps enjoying a self-catered booze and brunch though. And if you're in the area already, might as well swing by to view the historic landmark.
Another quirky site in Plymouth is the grave of Betty Stiven. This is one of those oddities that locals seem to love to torment visitors with by bringing them and then questioning them over and over about what they think the riddle on her grave means. Spoiler alert - no one actually knows what the mysterious inscription at the bottom of her grave means. A quick survey of people nearby revealed one person insisting she married her husband while he was drunk, another told me she was a witch who used magic to ensnare a man into a vegetative state, and another who insisted she lost her virginity to a man and that meant they were married. Again, not a particularly compelling site but worth seeing if you're nearby and like a bit of mystery.
MOUNT DILLON LOOKOUT
A nice little manicured and landscaped park land jutting out over western Tobago, Mount Dillon Lookout is a lovely place to stop to stretch your legs and get a view of the coast and lush greenier the island has to over. Relatively empty, the Lookout has multiple places to sit down and take in the beauty all around you. Palm trees, tropical flowers that pop with color, and a nice look down on the popular Castara Bay.
It's not a massive area with hiking trails for miles into the surrounding hills but it does give you a little bit of space to explore and walk a bit. I suggest walking through the area a bit to find a quiet bench to sit down and take it all in for an hour while you breath in the ocean breeze and admire the tropical vibes. Mount Dillon Lookout is a cute little stop along the road on your way to what is likely your real destination if you find yourself in this part of Tobago island, which is .....
Perhaps my favorite place on the entire island of Tobago. Castara Bay is a gorgeous strip of sand and water that is half-tourist relaxation spot and half locals living life. You'll find a variety of things going on at any given time of the day ranging from fisherman pulling in the day's catch to a comfortable rope hammock being rented out for a quick afternoon snooze next to the ocean. Honestly at first it was a little bit of thrown off by the vibe here because it seemed to be serving so many functions at once. Castara's Grindr profile lists it as versatile and it's not lying!
Just go with the flow though. Locals are living life while working and shopping at the handful of stores that dot the shore line. Visitors are walking up and down the water line or laying down on the sand. The hills are dotted with luxury rental homes where the handful of visitors are most likely living during their stay.
Kids spend the day running around in various stages of undress playing in the surf or climbing around on the boats sitting in the sand. The one above was named "O Fish L Business", which is a pun I can get behind. Regardless, Castara Bay was probably the most relaxing place I spent time while on Tobago. There are other beaches around the island that I'll discuss below but this one has the right mix of amenities and solitude that made it worth considering for an extended day of rest and relaxation.
Englishman's Bay is another beach relaxation option for those making their way around Tobago island. Unlike Castara, this one is considerably quieter in terms of both local and tourist traffic. The entire time I was at Englishman's Bay I was either entirely alone or at most had two other people far off at the other end of the beach from where I was. While Castara has a handful of restaurants and stores selling snacks, food, and sundries to locals and visitors the only business open at Englishman's Bay is the small trinket stand with a mini-eatery pictured above.
I'm relatively self-conscious when it comes to taking selfies when I travel but Englishman's Bay was one of the few places on the island I was confident no one would see me raise the camera and snap a few photos.
One of the down sides of this is that you have relatively few options in terms of picking up snacks or amenities during a long day, but you can always self-cater whatever it is you're looking to have for the day. You're trading off the nearby commerce and subsequent body count for the pristine quiet and solitude being offered.
Sadly due to its isolated vibe Englishman's Bay has been the location of a few negative stories from tourists saying they were approached on the beach by a local and targeted for crime. I read one account online of a man who said his wife and he were strolling the beach and were approached as they reached their car by a man wielding a large knife asking for money. Fortunately for me the only threat I encountered while visiting was the cuteness of this cow which distracted me as we drove down toward the bay from Castara. Still, if you choose this location for its isolation remember that it comes with risk as well.
If you're on Tobago and making your way across the island visiting various sites, you're more than likely to find yourself in Scarborough once or twice. The island's administrative capital and largest "city", the area has some of the highest concentrations of food and shopping you'll find on the isle outside of Crown Point. While many of the smaller communities have stores you can pick up supplies from, some of the more obscure items you may want on the island are best sourced in Scarborough. One example? Sunscreen. I stupidly forgot to pack any on this trip and ended up burning up like a beautiful, juicy lobster on my first two days on the island because none of the small stores anywhere I stopped had any on hand. It was only on day three when I ended up in Scarborough that I was able to slip into a store and find some Banana Boat. It was largely too late for my skin by then but it saved me on the rest of my stay.
The biggest attraction in the area from a tourism perspective is likely Fort King George. Unlike the fort in Plymouth, this one is rather sizable and has quite a few colonial era buildings which you can explore. The fort is also home to the Tobago Museum, housed in one of the restored barracks buildings. The site is located on top of a hill overlooking the surrounding city and has a picturesque view of the southern coastline of Tobago island including Rockly Bay.
If Englishman's Bay was a little too remote and Castara Bay was just the right amount of solitude and commerce, Pigeon Point is the over commercialized answer to both. Officially called the Pigeon Point Heritage Park, this is essentially a private beach with all the amenities and crowding of a mini-Waikiki. Even though it's owned by the government of Tobago, an entry free for all visitors is mandated which plays into the "elite beach" feel that is really played up to make things feel high-end and exclusive. Once you've paid the fee you're given a wristband to denote you're allowed access (the type of wrist band you get at college bars or a foam party) and can frolick freely up and down the property.
The beach is super clean and gives you access to a variety of amenities just steps away. There's plenty of shaded canopies and beach chairs that you can rent by the hours or day, and the entire beach is dotted with shops selling sandwiches, snacks, water, soda, and plenty of booze to let you really enjoy the tropical party vibe. The beach is surprisingly not overrun by foreign visitors, as there seems to be a solid mix of overseas tourists mixed with wealth Trinis and Tobagonians. There's even a handful of companies offering boat excursions and other water sport activities for you to partake in should the desire arise. As I mentioned before my money is still on Castara as the most evenly balanced place on Tobago to spend some time on a beach. But if you're the type that loves easy access to all of life's comforts, Pigeon Point is where you'll want to spend your time. The beach is indeed quite beautiful and you'll never be far from a beer or burger.
WHAT TO EAT
Speaking of beer and burgers .... if that's all you're consuming on Tobago, you're making very poor choices. With the Caribbean surrounding the tiny island you can bet fresh seafood plays pretty heavily into the dining options here. Throw in the multicultural melting pot that is the islands with influences from Africa, India, Amerindian, Chinese, and European residents and you've got a culinary hotpot of flavor waiting to be discovered. While T&T are two different island and do in fact feature a bit of their own unique dishes and treats, for the purpose of this guide I'll focus a bit more broadly and include things you might find on both islands.
CRAB AND DUMPLINGS
One of the dishes most associated with the island of Tobago itself, crab and dumplings was one of the great joys of dining out during my trip. It reminded me a bit of Singapore's infamous chili crab in a way with its saucy crab shells cracking open and the sweet crab meat tickling the back of my throat.
Crab and dumplings is exactly what it sounds like - a bit of crab and a bit of dumplings. Like any recipe there are variations of presentation styles and ingredients. The basics are this though: shell-on crab tossed in a savory curry sauce crafted from chili peppers, garlic, and creamy coconut milk with simple flour dumplings to sop up the delightful dish. Whether at a small stand on the side of the road or a fine dining establishment, you're likely to find some variation of the dish on the menu on the island of Tobago. What do I mean by variation? Take the above photo. The dish was pared down to an appetizer where the dumplings are stuffed with crab and the curry sauce thrown over the top. Not traditional but delicious nonetheless.
Doubles is the dish you've most likely heard about prior to arriving in Trinidad & Tobago, the island's culinary trademark if you will. While the dish can be found in other corners of the Caribbean (and beyond), T&T stakes their claim to fame on this little slab of heaven. Consisting of two flat pieces of fried bread called bara and topped with a curried chickpea mixture (channa), this meal is snack-sized and typically eaten in the morning or early afternoon. I've mentioned multiple times that the islands feature a massive Indian population and this dish is pretty much India on a plate.
While the dish is messy enough on its own, you can customize the sloppy mixture with additional sauces and chutneys when available. My favorite additions were Scotch bonnet pepper sauce (considerably more potent than your typical jalapeno and better known as the heat behind Jamaican jerk) or a sweet and runny tamarind glaze. You can't miss a meal of doubles since every other person on the island will ask you if you've tried it, and they're ubiquitously sold at just about every roadside stand and restaurant shack you'll encounter. Do yourself a favor and try them so you can experience how delicious they are and to ensure you have a satisfactory answer for everyone that will ask you about them!
To quote a Trini friend of mine who once expressed shock when they saw me eating this dish - "What do you know bout callaloo!?"
Needless to say my trip to Tobago wasn't my first experience with callaloo, but that doesn't mean I didn't enjoy it while I was visiting either. Made largely with okra and taro greens (called dasheen) in Trinidad, the dish derives from West Africa and is made throughout the Caribbean islands with a variety of greens. Typical additional ingredients include coconut, coconut milk, crab, fish, Scotch bonnets, and a variety of other seasonings. Thrown in a pot and reduced to a stew-like consistency, the dish is generally a side to a meal or used as sauce/gravy.
Note that callaloo is also used colloquially to describe the greens used in the dish themselves, so take care when requesting this dish to ensure you get the lovely stewed mixture and not a plate full of uncooked plants.
This blog has a multitude of focal points and one of those is definitely the unique experiences and concerns LGBT travelers have while on the road in the world. Trinidad & Tobago is a relatively LGBT-friendly destination when compared to many other Caribbean islands but is still far from a safe haven. Let's dig a little into some fast LGBT facts on T&T:
Same-sex intercourse was addressed in April of this year (2018) when the High Court ruling the country's antiquated buggery law unconstitutional. The country is still working through the logistics and debate of actually removing the laws though.
There are currently no LGBTQ community protections in employment, commerce, or against hate speech.
Same-sex marriage and subsequent rights (marriage recognition, adoption) are not recognized in T&T.
There is no legal right for transgender individuals to change their legally recognized gender.
Like many former British colonies (see my guide to Georgetown, Guyana for reference), T&T is struggling to shake off the legal frame work against LGBTQ communities that were left behind when they gained independence in 1962. But as mentioned above, progress is being made! Just a few months ago the country's High Court declared the "buggery" laws criminalizing same-sex sexual activity unconstitutional. While the ruling was greeted with glee by the LGBTQ community and human rights groups, it should be noted there was still strong opposition expressed by many religious groups in T&T and many vowed to fight the progressive social tide. For LGBTQ travelers that are not citizens, it's technically illegal to enter Trinidad & Tobago. Section 8 of the Immigration Act actually bans entry into the country for "homosexuals or persons living on the earnings of homosexuals". The law was famously invoked by the Anglican Church in 2007 in an attempt to ban Elton John from performing a scheduled concert. The attempt failed and Sir Elton performed as scheduled, so needless to say the enforcement of this law is in practice pretty much zero from what I can find online. And clearly they let my homosexual ass into the country, so there's that. Still, it's important to know before you go.
So while steps are being taken to advance equality in the nation, much work still needs to be done from a legal standpoint.
Socially the nation is considered one of the most open to LGBT communities and travelers in the Caribbean region, though that isn't saying a lot. In 2010 a public poll showed support for same-sex marriage was at a dismal 15.4%. On the other hand a 2013 poll showed 78% of respondents felt discrimination against the LGBTQ community was unacceptable and 56% stated they were accepting or at least tolerant of the community. So clearly this is a complicated and evolving dynamic in the nation. A visitor will likely not have any issues while touring though exercising caution and discretion in public situations would likely be wise. If you're in the country and find yourself needing assistance with an issue or incident, consider contacting the Coalition Advocating for the Inclusion of Sexual Orientation (CAISO), a leading T&T based LGBT nonprofit based in the capital Port of Spain.
Like many countries where the LGBTQ community is less than protected and accepted, there are relatively few friendly venues for enjoying a night out. There are bars catering to the community but they often open and close with little notice or consistency, meaning your best bet is to find a local that can tell you where the party is during your stay. Unfortunately most of the country's gay life is centered on Trinidad which means if you're on the smaller Tobago you're pretty much out of luck in terms of a gay bar to drink the night away. Pride has been celebrated for over 20 years now but the festivities are often indoors and quietly advertised, so quite different than the loud and vivacious parades you'll find in the US, Europe, or parts of Asia. As with most places on the globe, you're much more likely to find acceptance and safety as an LGBTQ visitor in larger urban centers than in rural areas, which means the entire island of Tobago would require one to be relatively cautious in interactions and openness.
Locals and visitors alike can use gay social apps such as Grindr, Scruff, and Hornet without any interference by the government or telecom companies. Due to the social climate many locals do not use face pictures in their profiles or may opt to use a fake photo. On the island of Tobago the population is small and scattered so unless you're basing yourself in the highly populated areas in Scarborough or Crown Point you're unlikely to find anyone near you. You'll likely find a handful of locals eager to chat with visitors or a scattering of foreign visitors visiting for the scuba options around the island. Tobago itself is charming and fun because of the laid back vibe and smaller population, so if meeting locals from the LGBTQ community or even other LGBTQ travelers is high on your list of priorities you may want to consider the bigger Trinidad for your trip.
Long story short - Trinidad & Tobago is one of the Caribbean's better options for LGBTQ travelers but is still a destination where one would need to exercise caution about being open about your life and what behavior you engage in/exhibit while in public.
And that's a wrap on my guide to Tobago island, though it oven detoured into a general discussion on Trinidad & Tobago itself. As I mentioned above I think T&T is often overlooked as a destination in the Caribbean as many of its neighbors are more well known for their pristine beaches and package hotel deals. If that's your thing, have at it! But Tobago in particular offers a fun little escape into a quiet little corner of island life. Deserted beaches, delicious local cuisine, and relatively few selfie-sticks bumping into you as you make your way across the island are all things that make the trip worthwhile. For LGBTQ travelers its one of the Caribbean's more accepting destinations though caution should still be practiced and it is far from a welcoming destination like Paris or Berlin. I hope you'll consider a stop on Tobago during your next jaunt to the Caribbean!