Five Leeward Island Gems to Explore 🏝️ 💎 🗺️

Five Leeward Island Gems to Explore on a Yacht Charter from Antigua or St. Maarten

Set sail on an unforgettable voyage through the heart of the Caribbean, exploring five hidden Leeward Islands gems. Starting from Antigua or St. Maarten, embark on a journey that weaves through islands rich in history, natural beauty and vibrant marine life. Discover the underwater wonders of Sint Eustatius, the fertile landscapes of Saint Kitts, the lush allure of Nevis, the dramatic peaks of Saba and the resilient spirit of Montserrat. Each island offers a unique blend of culture and adventure, making for an exceptional yachting itinerary through one of the Caribbean’s most captivating regions.

We starting our expedition from the south and the island of Montserrat ~ The Emerald Isle of the Caribbean

Often referred to as the “Emerald Isle of the Caribbean” for its lush green hills and Irish heritage. This unique island shaped by dramatically volcanic activity is a blend of vibrant natural beauty and resilience.

Montserrat’s history took a dramatic turn in 1995 when the Soufrière Hills volcano erupted, covering the southern part of the island, including its capital Plymouth, in ash. The eruptions continued intermittently for years, transforming much of Montserrat into an otherworldly landscape. Today, the southern two-thirds of the island remains an exclusion zone, while the northern part, including the new capital at Little Bay, is open for exploration.

The volcano’s activity has created a surreal but beautiful environment, making Montserrat a must-visit for nature enthusiasts. The Montserrat Volcano Observatory keeps a close eye on any seismic activity so you can enjoy breathtaking views of the volcano and abandoned towns from safe vantage points.

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For those interested in hiking, the island features several trails in light, moderate, difficult to extreme levels. Rich with birdlife and local flora. Montserrat is home to several species near extinction including the Montserrat Oriole, Montserrat Galliwasp, the Mountain Chicken, the Forest Thrush and two bat species — the Yellow-shouldered Bat and White-lined Bat.

The island’s coastline is dotted with beaches in a subdued array of colours, from sparkling black to different shades of grays. Underwater enthusiasts can enjoy scuba diving and snorkeling in pristine waters. Whether you prefer a quiet dive with beautiful coral fishes, reef ridges or adventurous and ‘wild’ dives, Montserrat has it all.

Montserrat’s unique cultural blend of Caribbean and Irish influences, along with its picturesque landscapes and resilient spirit, make it a compelling addition to any Leeward Island yachting itinerary. Just a short sail from Antigua, this island offers a glimpse into the power of nature and the beauty that arises from it.

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We head north to the island of Nevis ~ Land of Beautiful Waters.

Nevis, the smaller sister island of Saint Kitts, is known by many names: Oualie, Dulcina, Nuestra Señora de las Nieves. Each reflects a piece of its rich history and captivating beauty. With the towering 985-meter-high Nevis Peak at its heart, often shrouded in a delicate mist, the island’s lush landscapes are dotted with charming villages, pristine beaches, and well-maintained golf courses.

Nevis has been settled for over 2,000 years, first by the Arawaks and later by the Caribs, before Spanish, Dutch, and English colonial interests took hold. Sighted by Christopher Columbus in 1493, its name “Nuestra Señora de las Nieves” (Our Lady of the Snows) evokes the white clouds often seen encircling the peak.

For the plat lover visit the Botanical Gardens of Nevis are home to a large variety of tropical trees, plants and flowers from around the world. Set in the Montpelier Estate with views of Mount Nevis in the distance, this is one of the finest collections of tropical plants in the Caribbean.

Nevis is blessed with an abundance of geothermal energy and for centuries visitors to the island have enjoyed the hot springs at Bath Village. You can still enjoy the therapeutic benefits of the springs today and visit the site of the the first luxury hotel in the West Indies built in 1778.

The island’s coastlines are lined with beautiful coral reefs, making Nevis an ideal destination for snorkelers and divers. With its relaxed atmosphere and proximity to other Leeward Islands, Nevis offers a tranquil escape that’s perfect for a day’s sail from Montserrat, Antigua, St Barths or St Maarten.

We continue north to Nevis’ sister island, Saint Kitts | Liamuiga ~ Fertile Island

Saint Kitts, formally known as Saint Christopher Island, is a scenic gem in the Leeward Islands chain. The island’s silhouette is shaped by a series of volcanic peaks that form three distinct ranges: the Mount Misery Range, the Verchilds Range, and the Olivees Range. The island’s highest point is the 1,156-meter-tall dormant volcano, Mount Liamuiga, which dominates the landscape with lush green slopes and offers panoramic views from its summit.

Before European colonization, Saint Kitts was home to various indigenous groups, including the Saladoid and Igneri, followed by the Carib people who called it “Liamuiga,” meaning “Fertile Island.” European settlements began in the early 17th century, and by the mid-1600s, both British and French colonies had established their presence, leading to a tumultuous period of shared control.

Today, Saint Kitts is renowned for its verdant rainforests, thriving wildlife, and a host of outdoor adventures. Visitors can explore tropical trails on foot or by zip line, while the surrounding waters provide opportunities for exceptional diving, snorkeling, and other watersports.

Beginner to expert hikers can enjoy lush rainforests walks, shrubed costal paths, rugged, mountainous trails as well as conquering St. Kitts’ tallest peak and walk the rim of the dormant volcano with spectacular views.

If you are a rum lover maybe becoming a certified RumMasters would spark your interest. The cherished tradition of rummaking is alive and well on the island. Explore the blends, walk through the oldest surviving distillery in the Caribbean and get taught everything you need to know and try your creativity at the rum making process to join the island’s community of certified RumMasters.

We cruise farther north to the island of Sint Eustatius ~ Unique Caribbean Beauty

Originally known as Aloi by the indigenous people, the island became Sint Eustatius in 1636 when the Dutch West India Company took possession of the island. The island, well suited for cultivation of tobacco and sugar, together with being a hub for the slave trade became an important island for the Europeans and consequently the island changed hands over 20 times between the Netherlands, Britain, and France over the next centuries before Sint Eustatius became a public body of the Netherlands on 10 October 2010.

Sint Eustatius, locally known as Statia, is 6 miles / 10 km long and approx. 3 miles / 5 km wide. You will find the smaller summits of Signal Hill / Little Mountain and Boven Mountain to the northwest and a 602 meter high dormant volcano, Quill / Mount Mazinga, to the southeast. The flat saddle between the two elevated areas, forms the centre of the island that host the majority of the island’s population and the regional capital Oranjestad.

Without expansive white sandy beaches along its coastlines, the island has remained protected from mass tourism, preserving its natural beauty and serene atmosphere. Discover the rich history and the vibrant marine life within the surrounding underwater marine park, recognized as one of the most spectacular in the Caribbean. These pristine protected coral reefs, walls, volcanic crevices, historical dive sites, wrecks and fantastic wildlife hosts a multitude of dive spots catering for all levels, one to the added to any diver’s to-do list.

We continue our exploration north west to Saba ~ Unspoiled Queen of the Caribbean

The rugged beauty of Saba, the “Unspoiled Queen of the Caribbean,” is a sight to behold. This small island, covering just 13 square kilometers (5 square miles), is the highest point in the Kingdom of the Netherlands, formed by the peak of the dormant Mount Scenery volcano. Saba’s striking landscapes, dense rainforests, and vibrant biodiversity make it a paradise for nature enthusiasts.

Having resolved centuries of territorial disputes, Saba became a part of the Kingdom of the Netherlands through a maritime limits treaty signed in 1978. The island has since embraced ecotourism, attracting adventurers with its world-class scuba diving sites, challenging hiking trails and unique flora and fauna. The surrounding waters are protected by the Saba National Marine Park, ensuring the preservation of its pristine underwater ecosystems.

With its dramatic cliffs, charming villages, and unspoiled nature, Saba promises a truly unique and unforgettable experience for those seeking an off-the-beaten-path destination.

Conveniently situated north west of St Maarten/Saint Martin and Antigua, Saba is an ideal stop for yachting enthusiasts exploring the Leeward Islands.

A down-island cruise starting from St Maarten, with stops in St Barths before exploring the gems of Saba, Statia, St Kitts, Nevis and Montserrat, culminating in Antigua & Barbuda, offers a stunning and diverse cruising experience.

Visit our Leeward destination pages to explore more Leeward island cruising destinations.