Hiking trails
Choose a route from approximately 2 to 5 km through the landscape around St. Helene.
Beyond the port dayRoatan's East End
Windward Historic Trails
Follow the history. Experience the place.
Custom day journeys and extended stays through St. Helene, New and Old Port Royal, and Camp Bay, created by renowned Bay Islands historian and author Matthew Harper for travelers who want to understand the East End through its landscapes, communities, and stories.
For visitors staying on Roatan and island residents
The distance and unhurried format make this experience unsuitable for cruise port days. Every visit is custom-arranged as a dedicated day trip or extended stay.
Day trips and overnight stays
Plan your adventure
Guided day trip
Prices in USD for the whole group.
- 1–2 guests
- $650
- 3–6 guests
- $780
Both group sizes include the same experience.
Request a day tripIncluded in your day trip
- Round-trip boat transport
- One local guide and one historian
- A midday meal, snacks and drinks throughout the day in a jungle palapa
- Forest hiking and exploration of two caves
- Snorkeling at Rambler, with an overview of Old and New Port Royal history
Stay overnight and explore for two days
Starting from $800 USD
Starting price for a group of 1–2 guests.
Includes an overnight stay, two days of exploring, lunch and dinner, plus breakfast the following day. Matthew will confirm accommodation details, availability and the final price for your visit.
Request an overnight stayBefore your visit
A dedicated East End visit
Day trips and overnight stays are for guests staying on Roatan and island residents. The distance and pace make these trips unsuitable for cruise port days.
Walking and cave exploration
Hiking routes range from approximately 2 to 5 km. Tell Matthew about your group's walking ability, children's ages and dietary needs so he can arrange a suitable route.
Confirm your arrangements
Ask Matthew to confirm your boat departure point, hotel transport, trip times, equipment and accommodation. Agree payment, weather and cancellation arrangements before confirming your visit.
Built around your interests
Three regions. One custom journey.
This is not a fixed bus itinerary. Windward Historic Trails connects the history of the East End with guided exploration, local meals, water experiences, and time in communities rarely reached by conventional tours.
Day journeys Overnight stays Custom routes
Historian · Author · Columnist
Meet Matthew Harper
Matthew Harper is a Bay Islands historian, author and columnist who has published books and magazine articles since 1990.
He considers the East End the epicentre of Roatan's history. His expeditions and writing reflect a longstanding passion for its people, places and stories, the same curiosity he brings to Windward Historic Trails.
Matthew is currently working on a nonfiction book about the pre-Columbian peoples of the Bay Islands, expected in early 2027.
Plan a visit with Matthew
St. Helene
Explore beyond the road's end.
Walk, snorkel, fish, and share a meal in a part of the Bay Islands where the rhythm is still set by the sea. Choose the experiences and pace that fit your group, with local knowledge leading the way.
Guided cave exploration
Select a suitable difficulty level and explore with expert guides, supported by historical and archaeological commentary.
Fishing hamlets
Visit small communities on Helene in the company of local guides who know the island firsthand.
Local Creole meals
Make local food part of the journey, prepared and shared close to its source.
Secluded snorkeling
Snorkel selected East End spots away from Roatan's busiest visitor areas.
Fish with local experts
Head out with knowledgeable local fishers, then cook and enjoy your catch.
A little closer to Saint Helene.
Choose forest walks, caves, community visits or time on the water. Matthew will help match the route and cave difficulty to your group, with activities confirmed for your dates.
Stay on Saint Helene
Let the day become a stay.
Follow the wooden walkway into the trees and settle into a cozy forest cabin overlooking the Caribbean. An overnight or extended stay leaves time to explore Saint Helene at your own pace.
Pair your stay with guided walks, local Creole meals, snorkeling or fishing. Matthew will confirm the accommodation, meals, activities and price with you before booking.
Ask Matthew about a stayNew and Old Port Royal
History told where it happened.
Explore the ancient Indigenous cultures of the Bay Islands, then travel by sea and ashore through places tied to conflict, navigation, settlement, and strategic English interest across the seventeenth and eighteenth centuries.
1000 BC to 1500 AD
The ancient peoples of the Bay Islands
Learn about the ancient Indigenous cultures that inhabited the Bay Islands prior to the European conquests. Who were these peoples? What was their connection with the limestone caves?
1650
The battle of Old Port Royal
Retrace the confrontation between Spanish conquistadores and a joint force of Pech Indians and English logwood cutters, approaching the story by sea and then ashore, and learn about the aftermath and the demise of the Pech.
18th century
A strategically important coast
Discover areas that drew English military interest and hear how the coastline shaped movement, defense, and control.
1782
The battle of New Port Royal
Explore the battle of New Port Royal in 1782, more than a century after the 1650 conflict at Old Port Royal.
At sea
Wrecks and maritime stories
Learn about the Rambler, Cay Comfort, and a nearby pre-Columbian wreck, with snorkeling in the area when conditions and the selected route allow.
Camp Bay area
Wild coast. Comfortable stay.
Hike within the Port Royal Nature Reserve, swim at Camp Bay Beach, and settle into an East End stay with the freedom to self-cater or arrange a local guest chef.
Stay in Camp Bay
Caulfields Cottage
This well-appointed Camp Bay beach house takes its name from Colonel James Caulfield, identified in the project's historical notes as the first English commanding officer of the Islands in 1742.
Overnight or extended stay
Self-catering or local guest chef
Camp Bay Beach nearby
Made to fit the journey
Combine Camp Bay with St. Helene or Port Royal, or make the coastline and nature reserve the focus of your stay.
Stories from the East End
A closer look
Visit Santa Elena on film and hear Matthew share stories of St. Helene, Rose Hall and Never Stain Bight.
Dream Ferries · Episode 3
Roatan Alternativo: Santa Elena
Watch on YouTube
ARC+ News · Stories with Matthew Harper
St. Helene's shrine and plundered gold
Watch on YouTube
ARC+ News · Stories with Matthew Harper
Rose Hall and Never Stain Bight
Watch on YouTubePlan with Matthew Harper
Your East End journey starts here.
Tell Matthew your dates, guest count, preferred regions, and whether you are considering a day journey or overnight stay. He will confirm the route, accommodation, timing, and price personally.
1. Your visit2. Review & send3. Request sent