A Journey to Remember: A Curated One-Week St Helena Itinerary

When a husband and wife reached out to Destination St Helena to curate their week-long holiday, they were looking for more than just a list of places to visit—they wanted a carefully crafted St Helena itinerary that would allow them to truly experience the island’s unique charm. After a few exchanges of emails, their tailor-made plan was ready. What followed was an unforgettable week filled with discovery, history, nature, and adventure.

Exploring St Helena’s Wild Beauty

Touching down on the island, the couple was immediately struck by the rugged beauty of the cliffs, the rolling green hills, and the dramatic coastline that seemed untouched by time. The warm hospitality of the locals set the tone for the days to come. Their first adventures included an exciting 4x4 tour of St Helena, which allowed them to journey across winding roads into the island’s most remote corners.

One of the highlights was the 4x4 Island Tour with Arron, whom they were highly praising off, funny and overall great guy! Breathtaking views of Sandy Bay beach, enclosed by volcanic cliffs, the beach is raw, untamed, and stunningly beautiful—a perfect introduction to the island’s geology and natural diversity. They enjoyed a peaceful stroll through Plantation Forest, a lush sanctuary of towering trees and offering a completely different side of the island. Perhaps the most heartwarming encounter was meeting Jonathan the Tortoise, St Helena’s most famous resident and the world’s oldest known living land animal. Standing in his presence was like stepping back through centuries of the island’s history.

Following in Napoleon’s Footsteps

History is woven into every stone and path on St Helena, and no visit would be complete without exploring its Napoleonic legacy. The couple followed in the footsteps of the island’s most famous exile, visiting all three of Napoleon’s sites. At Longwood House, they wandered through the very rooms where Napoleon lived during his final years, gaining a tangible sense of history. The Valley of the Tomb offered a place of reflection, its tranquil setting a stark contrast to Napoleon’s turbulent life.

These visits stood out as some of the most profound things to do in St Helena, deepening the couple’s appreciation of the island’s global significance.

Hiking Adventures on the Island

For active travelers, St Helena is a paradise. With a mix of rugged terrain, coastal cliffs, and lush valleys, the island offers hiking experiences that rival some of the best in the world. The couple made the most of their free time by exploring several post box walks—a network of scenic hiking trails unique to St Helena.

They trekked Lot’s Wife Ponds, rewarded with dramatic ocean views and fascinating geological formations. Their hike up to Munden’s and further to the vantage point overlooking Jamestown gave them panoramic views of the historic town nestled between steep cliffs.

Guided hikes added even more depth to their adventure. At Blue Point, one of the most popular trails, the path opened to sweeping views of the ocean and rugged coastline.

High Peak, where low clouds limited visibility but provided an unforgettable lesson in the island’s ever-changing weather. These hikes were more than just physical activities—they were immersive journeys into the island’s character, showcasing its raw beauty and unpredictability.

A Different View: St Helena from the Sea

No visit to St Helena is complete without seeing the island from the ocean. The couple embarked on a marine tour with Seahawk Odyssey, captained by the two Jamies’, which became one of the highlights of their stay. The waters around the island offered an entirely new perspective—jagged cliffs rising dramatically from the sea, secluded coves, and birdlife in abundance.

As if that weren’t enough, a humpback whale appeared at the last moment, creating an unforgettable memory. Watching such a majestic creature against the backdrop of St Helena’s coastline left them both speechless.

We want to give a shout out to Seahawk Odyssey! For their hospitality to our two guests and for the photos sent to use for this blog post.

Culinary Delights and Local Life

St Helena’s charm lies not only in its landscapes and history but also in its people and food. The couple immersed themselves in the island’s social side, joining locals and travelers for the famous Wednesday fish fry—an event that blends fresh fishy cuisine with lively community spirit. They also dined at Anne’s Place, a restaurant known for its welcoming atmosphere and popularity with visitors. But the culinary highlight of their stay was undoubtedly the Blue Lantern Restaurant, where they enjoyed a meal crafted with care and creativity.

Originally, their final dinner at Blue Lantern was meant to cap off their holiday before their Saturday flight. However, when their flight was delayed, Destination St Helena quickly stepped in to rebook them for another evening. Instead of stress, the couple experienced yet another memorable night, proving how flexibility and local support can turn unexpected changes into cherished moments.

Why Choose a Curated St Helena Itinerary

By the end of their journey, the couple will take away just how much they had experienced in a single week. From Jonathan the Tortoise to Napoleon’s legacy, from dramatic hikes to marine adventures, and from cozy local meals, they discovered the island’s many layers. A week on St Helena can feel like a month’s worth of experiences, each day offering something new and remarkable.

What made their trip truly special, however, was the curation. Instead of piecing together activities on their own, they enjoyed the seamless flow of a carefully designed St Helena itinerary created by local St Helenian who know the island intimately. This allowed them to maximize their time, balance relaxation with adventure, and uncover both the highlights and hidden gems.

From knowing contacts within each restaurant or service provider and quick access to them, this is what makes us easy to work with and plan a stay on St Helena.

For travelers seeking their own adventure, entrusting your journey to Destination St Helena ensures that you don’t just tick off a list of attractions—you immerse yourself in the island’s stories, landscapes, and culture. Whether your passion is history, hiking, wildlife, or simply soaking up the rhythm of island life, the top things to do in St Helena are waiting to be discovered.

Plan Your Own St Helena Adventure

Inspired by this journey? Let Destination St Helena curate your own unforgettable itinerary. Whether you’re drawn to historic landmarks, breathtaking hikes, marine adventures, or local dining, we’ll design a personalized plan that lets you experience the very best of the island.

📩 Get in touch today to start planning your St Helena itinerary and discover the top things to do in St Helena—crafted just for you.