Maho Bay, famous for its abundance of sea turtles, is just a one-mile paddle from Cinnamon Bay Campground.JOSHLASKIN.COM/The Globe and Mail
As the ferry pushed farther from the harbour, the buildings of Saint Thomas receded to tiny smudges of colour on the horizon. Ahead, the rolling green hills of Saint John emerged from the Caribbean Sea. They appeared, at first glance, nearly untouched.
Despite being the smallest of the three main U.S. Virgin Islands, Saint John’s allure was immediately apparent. White sand beaches dotted the island’s perimeter, broken only by sections of craggy coastline and tracts of forest. I envisioned a destination filled with mega-resorts and 15-deck cruise ships, but was surprised to find a landscape that more closely resembled a tropical version of the Appalachian Mountains.
I’ve always been drawn to adventurous vacation destinations that allow me to explore new landscapes and cultures, travelling to places such as Peru or Spain to rock-climb, backpack and meet locals in dingy bars. The idea of a Caribbean vacation – sipping overly sweet cocktails on a beach while hiding from the realities of life – wasn’t appealing.
But after admiring photos of hiking trails that meandered along rugged coastline and reading about the island’s culture, history and opportunities to connect with nature, I decided to give Saint John a chance.
Like much of the Greater Antilles, Saint John’s first major settlement was by the Arawakan-speaking Taino people, who occupied the island from around 700 A.D. until the mid-15th century.
The craggy coastline around Saint John is perfect for snorkeling and viewing wildlife.Josh Laskin/The Globe and Mail
In 1718, Denmark laid claim to Saint John. Plantations that grew sugar cane, cotton and tobacco sprang up across the island’s interior thanks to the colonizers’ exploitation of African slaves. Eventually, the focus in sugar cane, the most profitable export, became the island’s main product. The familiar story of foreign meddling, slavery and revolts continued for the next century, shaping the cultural landscape. Then, in 1917, as a World War raged across the ocean, the United States purchased Saint John from Denmark to establish a military presence in the region.
In 1952, philanthropist Laurance Rockefeller visited the island for the first time and was inspired by its beauty. Rockefeller and the non-profit conservation organization Jackson Hole Preserve purchased and donated 5,000 of the island’s 12,500 acres to the U.S. federal government to create Virgin Islands National Park.
Today, nearly 60 per cent of the island is designated a national park, preserving its natural beauty, the remnants of the Taino culture and the history of those who came after them.
“Saint John is unique,” says Ernest Matthias, a fifth-generation Saint Johnian who runs the watersports program at Cinnamon Bay Campground, one of the island’s few public accommodations. “There is really good nature and hiking here, but it’s also more laid back and quiet than the other islands.”
Tourists began flocking to Saint John in 1935 when the West Indian Company opened a hotel at Caneel Bay, on the island’s northwest corner. Rockefeller purchased the plantation-turned-resort nearly two decades later, transforming it into an elite destination that attracted the world’s wealthiest. Hurricanes Irma and Maria decimated Caneel Bay in 2017, and the debate about whether or not the once-flourishing resort should reopen is ongoing.
The Cinnamon Bay Loop Trail is steeped in history, with several plantation ruins to explore along the way.Josh Laskin/The Globe and Mail
When I arrived in June of 2024, there were no obvious signs of destruction. Deer picked along the walkways at Cinnamon Bay Campground, unbothered by human activity, while blue land crabs burrowed into the mud as I approached. That night, as I lay in the oversized canvas “glamping tent,” which felt more like a screened-in hotel room, my resistance to vacationing in tropical destinations dissipated. Just outside, the sounds of crashing waves mixed with calls from unfamiliar birds. I was already starting to enjoy myself. But I wasn’t quite ready to admit it.
On the first full day, our group kayaked 1.5 kilometres to Maho Bay, known for its diverse sea life, and spent a few hours snorkelling. Moored sailboats bobbed in the sheltered cove as a dozen tourists swam, face-down, to see the sea turtles poking around on the sea floor.
After hours in the water, we recovered at Trunk Bay Beach, where I ordered the shrimp burger – a must-try menu item – at the snack bar. It wasn’t quite the authentic Saint Johnian curried goat or stewed oxtail I was hoping for, but I was already two for two on eating fresh seafood during the trip, which was fine by me.
We spent the rest of the day cruising around the islands on a catamaran, sipping homemade Painkillers – a rum cocktail that makes it easy to forget you’re drinking booze – and hanging around Cruz Bay. Drinking on a boat without fishing gear isn’t typically my cup of tea, but thinking about the next day’s hike made it a bit more palatable. I might’ve even enjoyed it.
The next morning, after waiting out a rain squall and grabbing a quick egg breakfast at the campground’s Rain Tree Cafe, we headed to the 5 km Reef Bay trail and started our descent through subtropical forest to the ocean below. Landmarks along the trail told stories of the island’s past, from petroglyphs left by the Taino to sugar plantation ruins, a reminder of the dark era of slavery. But it told personal stories, too.
After a day of exploring, La Tapa in Cruz Bay, Saint John is a popular stop to wind down with cocktails.Josh Laskin/The Globe and Mail
“My grandpa was born here,” Matthias said, smiling as he stood in the middle of a stone square that suggested a house once stood there. “He was born in 1901, right here on this trail.”
Matthias continued to point out various plants, mentioning how the Saint Johnian people have used them for centuries.
We passed one final ruin before emerging onto a vacant beach, bookended by a rocky coastline, accessible only by foot or boat. My usual beach-hating self enjoyed sitting still, admiring the turquoise water, while waiting for the boat that would pick us up and take us into town. Knowing we had to swim a few hundred metres to the boat – it couldn’t be put directly on the beach – was anxiety-inducing owing to my lackluster swimming abilities, but I suppose I was looking for an adventure.
That night in my tent, after scarfing down a plate of stewed goat, a monsoon swept across the campground. Torrents of rain poured off the canvas. I decided to embrace it – it was the beginning of the rainy season, after all.
With scant cell service and no WiFi at the campsite, I was forced to let my mind wander, an art form nearly lost in a world of constant connectivity. I was exhausted from the day’s adventures. I listened to the rain and read a book that had been collecting dust for the past few weeks. It reminded me of why I had grown to love the outdoors in the first place, and in the end, all it took was a trip to the tropics.
If you go
Saint Thomas is the main hub for air travel to the U.S. Virgin Islands. Canadians can fly into U.S. airports, including Miami, Charlotte, Atlanta and Fort Lauderdale for connections. Once on Saint Thomas, there is regular ferry service from Red Hook, which is just 18 km from the airport and can be reached by taxi. The 20-minute ferry departs daily, every hour until 11:30 pm.
Virgin Islands National Park has over 20 hiking trails, from accessible boardwalks that meander through the Cinnamon Bay Sugar Plantation ruins to rugged trails such as the Reef Bay Trail. Cellular connectivity can be sparse on the island.
For something different, Love City Excursions offers boat charters to various destinations throughout the islands and can be a great off-day activity between hikes. lovecityexcursions.com
Accommodation can be found at Airbnb’s, the Gallows Point Resort and a Westin Saint John, which offers resort villas. The Cinnamon Bay Beach and Campground is on a pristine beach and offers glamping tents, basic tent sites and cottages, plus two restaurants. It’s just 15 minutes from the restaurants, cafes and attractions of downtown Cruz Bay. cinnamonbayvi.com
If nightlife is what you’re looking for, the nearby island of Saint Thomas is a better bet, but Cruz Bay, Saint John’s biggest town, has its fair share of bars and restaurants. The 1864 restaurant, named after its geographic co-ordinates, is a great option for higher-end seafood dishes. La Tapa, which offers a unique take on Mediterranean cuisine in addition to bay views, is another high-end option. Gwen’s Place and Heading East Bar and Grill are both great options for local dishes.
The writer was a guest of Cinnamon Bay Beach and Campground. It did not review or approve the story before publication.
Editor’s note: A previous version of this article incorrectly referred to Rainforest Cafe at Cinnamon Bay Campground. The correct name is Rain Tree Cafe. This version has been updated.