“Honey, do you want to come with me to a bike race in Tobago?”

“Sure! Where’s Tobago?”

“It’s an island in the Caribbean. All we have to do is pay for your airfare. The team is paying for mine and our lodgings for the week.”

Team Rio Grande:

Aaron had been racing for the Rio Grande Cycling Team, based in Boulder, CO, for six months before the Tobago trip offer was presented. The team had given Aaron the chance to road race in New Mexico, Arizona, and California, but the Tobago trip was the first time I was given an invite to travel with the team. I knew most of the racers from weekend trips to Boulder for team building events and local races, and I was pleased to discover that the team captain’s girlfriend would be travelling to Tobago as well. It wasn’t exactly my vision of a perfect beach vacation, but it was practically a free week in the Caribbean. So, we packed our bags, eagerly anticipating Tobago’s blue waters and tropical island vibe.

Getting to Tobago:

If you’ve never flown with a bicycle, let me tell you, it is quite the adventure. Not only did we have to drag our wheelies through the airport, we also had to push this enormous box containing Aaron’s disassembled bike. The only relief from this excessive luggage burden came when we finally dropped the bags and bike box off at the check-in counter. In fact, we were so happy to no longer have to drag the bike box around that we were happy to pay the exorbitant luggage fees. Now, imagine that scene with a team of seven cyclists and seven enormous bike boxes struggling to navigate the airport. I’m sure it was quite the comical sight.

We flew out of Miami International Airport and arrived in the early evening in Port of Spain, Trinidad. Unfortunately, it took hours, literally, for us to clear customs. By the time we collected all the bike boxes, we had missed our connecting flight to Tobago, which as it turned out was the last flight of the day.

As all travelers inevitably experience, flexibility was forced upon us and we had to stay the night at a hotel in Port of Spain. Our room was about average in every way with the exception of a giant puddle in the middle of the floor which we had to leap over every time we wanted to use the bathroom. But, hey, it could have been worse and it was only for one night.

The next day we finally arrived in Tobago and checked into our beach front apartment in Store Bay. We immediately threw on our swimsuits, abandoned the bike boxes, and dove into the crystal clear, delightfully warm Caribbean Sea. The long, tedious two days of travel were worth it!

Road Cycling in Tobago:

Our first few days in Tobago took on a comfortable routine. We spent the early part of the days at the bike races, Aaron riding and me supporting the team by handing out water bottles in the feed zone, a random spot on the side of the road along the race route. Once the race was over for the day, we headed back to Store Bay and spent the afternoon at the beach.

Since we were in the Caribbean, the weather was hot and humid making water bottles a hot commodity. The value of these water bottles skyrocketed when we discovered the scarcity of bike shops on the island. In other words, lost cycling bottles tossed aside during the races could not easily be replaced. In the feed zone it was a mad scramble to get new bottles to the riders and at the same time collect the discarded empties before another team made off with them.

The most dramatic event of the race series occurred when Aaron’s front wheel shattered after going off-road in the middle of a particularly sharp turn and riding over razor-sharp coral reef rock. He flew over the handlebars and got some gnarly road rash, but the incident led to an interview with ESPN and the resulting bragging rights.

Day Tour Around Tobago:

One day in between cycling races, we had a free day at leisure that we decided to use to tour the island. We hired Denis, a local driver from the hotel next door to our apartment, and asked him to take us to the best spots around the island.

 We started our tour early in the morning with a stop at Denis’ house to meet his family and pick up a few essential snacks for the road. We learned that he was skipping work at his government job to drive us around the island but that it was “no problem” because his buddy was covering for him. I guess we paid more than enough for it to be worth the risk.

 Next, we headed to Fort James, a small military base in Plymouth left over from Tobago’s colonial era. We also visited the tombstone of Betty Stiven, a local grave famous for its mysterious epitaph indicating that “She was a Mother without knowing it and a Wife without letting her Husband know it, except by her kind indulgences to him…”.

While pondering this unusual legacy, we drove north into a particularly dense bit of jungle to visit an abandoned sugarcane plantation. The rainforest had made excellent progress in reclaiming the plantation’s man-made structures. Tropical plants of a stunning variety crawled over every surface. The wooden floorboards and walls were thick with slime, making walking a treacherous endeavor. I slipped and lost my balance at least three times, careening wildly and desperately reaching for anything that would stop my fall.

The baroness of the forgotten plantation was both beautiful and sad, evoking feelings of immense loneliness. It was not difficult to imagine the plantation, newly built and at the height of its production, but today we were surrounded only by ghosts and the jungle they left behind.

We continued our tour of the island at Englishman’s Bay, a gorgeous beach cove that we had all to ourselves. We walked the length of the beach hand-in-hand sipping on Carib, a local beer, and congratulating ourselves on the wise idea of exploring the entire island.

The next stage of our journey took us into the heart of the Main Ridge Forest Reserve, an area of rainforest that runs through the center of the island and has been legally acknowledged as a preservation site since 1776. Our destination was Argyle Falls, a beautiful waterfall with a refreshing natural swimming pool at the end of an easy stroll.

For lunch, we dined on freshly caught seafood at Jemma’s Tree House Restaurant in Speyside. The shrimp were to die for and the view of the ocean was unparalleled. With our bellies full we drove to the easternmost point of Tobago to visit Pirate’s Bay, a beach that Denis claimed was the best beach on the island. To get there we navigated some of the steepest, curving roads I have ever seen. In one section, the road’s grade averaged 22% for more than two miles! As we traversed these twisting, mountain-hugging roads, we were blown away that such roads even existed in the middle of the rainforest. Little did we know that Aaron would be traveling the same crazy roads the next day via bicycle.

When we arrived at Pirate’s Bay, we knew the chaotic drive was worth the effort. Denis parked the car on the edge of a cliff and led us down a winding staircase down to the beach, a narrow strip of sand surrounded by rocky cliffs on one side and calm blue ocean on the other. We couldn’t see any signs of civilization, save for a few sail boats lazily rocking back and forth in the water. To us, Pirate’s Bay embodied the ideal combination of seclusion and beauty, perfect for fostering a romantic afternoon.

We tossed our belongings in the golden sand and gleefully dove into the water. As we swam, we took in our surroundings in wonder, grateful that our local guide had shared this slice of paradise with us.

Top Tip from our Day Tour of Tobago:

We highly recommend hiring local guides and drivers to explore a new destination. They provide a wealth of insight into their culture and, of course, know all the best beaches, viewpoints, and eateries.

-Annie, Your Friend at Orange Backpack Travel