Our Leinster Bay and Waterlemon Cay adventure packed some of the best variety of any day in St. John. We started by exploring the historic Annaberg Sugar Plantation, then followed the shoreline of Leinster Bay before climbing the Johnny Horn Trail to the Guardhouse and Windy Hill Great House ruins – two of the best overlooks of our entire trip. From crumbling stone ruins high above brilliant turquoise water, we could look across Leinster Bay, Waterlemon Cay and the surrounding islands, making the steep detours completely worth it. We finished with our most adventurous snorkel of the trip at Waterlemon Cay, giving us a day that combined meaningful history, hiking, spectacular panoramic views and underwater exploration – easily one of our favorite adventures of our St. John trip.

🗓️ Itinerary: Annaberg + Leinster Bay + Waterlemon Cay

This plan came from our September 16, 2026 adventure.

• 🚙 8:00 AM – Leave villa 
• 🅿️ 8:30 AM – Park at Annaberg Sugar Plantation
• 🏛️ 8:30 AM – Explore Annaberg Sugar Plantation (~30 min, walk by windmill, sugar factory & ruins)
• 🥾 9:00 AM – Start Leinster Bay Trail (~1 mi, ~30 min each way, ~2 mi RT)
• 🥾 9:20 AM – Take Johnny Horn Trail spur to Guardhouse ruins (~0.1 mi, ~5 min, steep climb)
• 📸 9:25 AM – Explore Guardhouse ruins and Waterlemon views through arch ruins (~15 min)
• 🥾 9:40 AM – Continue Johnny Horn Trail to Windy Hill ruins (~0.4 mi, 10 min, steep climb)
• 📸 9:50 AM – Explore Windy Hill Great House ruins with stunning overlook (~15 min)
• 🥾 10:15 AM – Descend to Leinster Bay & continue to end of the beach (~0.7 mi, ~15 min, descent and rocky beach)
• 🤿 10:30 AM – Snorkel to Waterlemon Cay (~60 min, swim across the deeper section from the end of the beach and explore the reef along the south side of the cay)
• 🥾 11:30 AM – Hike back to Annaberg along Leinster Bay Trail (~1.1 mi, 30 min)

💡 Tips: When Life Gives You Waterlemon

• 🌅 Start Early: The shoreline portion of Leinster Bay Trail is relatively easy, but the Johnny Horn Trail spurs are steeper and the day gets much hotter as the sun climbs.
• 👟 Wear Shoes, Not Just Flip-Flops: You’ll want decent footwear if you’re adding the steep climbs to the Guardhouse and Windy Hill ruins.
• 🩱 Hike in Your Swimsuit: This adventure is half hiking and half snorkeling, so wearing your swimsuit underneath your hiking clothes makes the transition much easier.
• 💧 Carry Plenty of Water: There aren’t services along the trail, and combining hiking with a long snorkel makes this a more substantial outing than the mileage alone suggests.
• 🤿 Bring Snorkel Gear: Waterlemon was our most adventurous snorkel in St. John and the main reason to carry the extra gear along the trail. We left ours near the Johnny Horn Trail junction while we climbed to the Guardhouse and Windy Hill ruins, then picked it back up on our way to Waterlemon rather than hauling it up and down.
• 🥾 Don’t Skip the Ruin Spurs: The short, steep climbs to the Guardhouse and Windy Hill ruins gave us some of our favorite views of the entire trip and turned an otherwise mostly flat shoreline hike into a much more interesting adventure.
• 🌊 Respect the Current: Waterlemon Cay is surrounded by deeper, moving water. We snorkeled along the south side of the cay rather than attempting to circle the entire island, avoiding the stronger current on the Tortola-facing side.
• 🪸 Don’t Stand on the Reef: The water becomes shallow around portions of the cay, but stay horizontal and avoid touching or standing on coral. We found one very small sandy area where we could regroup after the swim out to the cay.
• 📷 Bring a Waterproof Camera: Between the ruins, overlooks, shoreline and reef, this was one of our most photogenic days in St. John.

🏚️ Annaberg Sugar Plantation: Survival & Freedom Across the Narrows

Before starting our hike to Leinster Bay, we explored the remarkably well-preserved ruins of Annaberg Sugar Plantation, where interpretive signs helped bring the site’s difficult history to life. Annaberg grew into a major sugar plantation under James Murphy, with its windmill and sugar factory completed in 1805 and hundreds of enslaved Africans forced to perform the dangerous work of growing, crushing and processing sugar cane. Today you can explore the remains of the windmill, sugar factory, bake house, oven, and other plantation structures while learning how the operation once worked. One of the most powerful parts was the view across the narrow channel toward the British Virgin Islands – after Britain abolished slavery there in 1834, enslaved people on St. John could see islands where freedom was less than two miles away, and some attempted to escape across the water from nearby Leinster Bay. Annaberg’s story also continued after emancipation: George Francis, who was born enslaved at Annaberg, later became a landowner and purchased Annaberg and Leinster Bay for $100 following the devastating 1867 earthquake and hurricane. The combination of extensive ruins, detailed exhibits and beautiful views made Annaberg much more interesting than we expected and added important context to the landscape we were about to hike through.

🔄 360 Photo: Click and drag to look around

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🥾 Leinster Bay Trail + Johnny Horn

From Annaberg, we followed the Leinster Bay Trail along the shoreline, with Waterlemon Cay visible offshore for much of the route and plenty of wildlife along the way. We spotted a Great Blue Heron hunting along the rocky shore and several goats wandering right onto the beach – one of which apparently managed to bite into my trail mix despite by backpack being zipped. The Leinster Bay portion was relatively easy and mostly flat, following the rocky coastline toward Waterlemon Cay. Things changed considerably when we turned onto the Johnny Horn Trail, where short but steep climbs led us above the bay to the Guardhouse and Windy Hill Great House ruins. Those detours added most of the elevation to the hike, but they also delivered some of the best panoramic views of our entire St. John trip, making Johnny Horn every bit as memorable as the shoreline trail below.

📈 Hiking Stats

Time: 1:08 moving, 1:54 elapsed with photo and ruin stops
Distance: ~3.4 miles total
~2.4 miles round trip on Leinster Bay Trail
~1.0 mile Johnny Horn Trail spur to the Guardhouse and Windy Hill ruins
Difficulty: Easy along Leinster Bay; moderate on steep Johnny Horn
Terrain: Mostly flat shoreline trail with rocky sections, followed by short, steep climb to the ruins
Directions: Park at Annaberg and follow Leinster Bay Trail along the shoreline (~1 mile). Take Johnny Horn Trail uphill to the Guardhouse ruins (~0.1 mile), continue toward Windy Hill (~0.4 mile), then descend back to Leinster Bay and follow the shoreline toward Waterlemon Cay (~0.7 mile). Return the same way to Annaberg (~1.1 mile).
Additional Resources: Garmin Data: Leinster Bay Trail + Johnny Horn, Leinster Bay Return, AllTrails: Leinster Bay Trail, Johnny Horn Trail

🏚️ Guardhouse Ruins: Framing Waterlemon

Our first detour up the Johnny Horn Trail was a short but steep climb to the Danish Guardhouse ruins, and the payoff was phenomenal. Built at strategic Leinster Point, the guardhouse once overlooked the Fungi Passage and the Narrows and was reportedly armed with cannons. Today, the crumbling stone arch perfectly frames Waterlemon Cay and the brilliant turquoise water below, becoming one of our favorite photo spots of our entire St. John trip.

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🎥

🌴 Windy Hill Ruins: Worth the Extra Climb

We thought the Guardhouse view would be hard to beat, but then we kept climbing to Windy Hill – also known as the Murphy Great House – and found the most sweeping panorama! The hilltop estate was associated with James Murphy, who controlled Annaberg and neighboring plantations around the turn of the 19th century, and its commanding location overlooks an enormous stretch of the surrounding islands and sea. From the ruins, we could see Waterlemon Cay directly below, Mary Point and Whistling Cay, Great and Little Thatch islands, Tortola and the British Virgin Islands stretching across the horizon. Of course, simply admiring the view wasn’t enough for Scott and Justin – they decided to climb onto the crumbling ruins for an even better vantage point while the rest of us held our breath and hoped they wouldn’t disappear into the ruins below. 😬 Questionable decision-making aside, Windy Hill gave us some of the most spectacular views of our entire St. John trip and was absolutely worth the extra climb.

🔄 360 Photo: Click and drag to look around

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🎥

🤿 Waterlemon Cay: Our Most Adventurous Snorkel

Waterlemon Cay was our most advanced and adventurous snorkel in St. John. Reaching the reef requires swimming across deeper water from the end of Leinster Bay, making it a noticeably bigger commitment than our other snorkels. Once we reached the cay, we found a very small sandy area where we could regroup and get a picture before exploring the reef along the south side, where the shallower water brought us closer to coral, gorgonians and reef fish. We deliberately didn’t circle the entire cay because of the stronger currents on the Tortola-facing side.