Yacht Charter in the Leeward Islands

Exploring the Leeward Islands

Travelling the Leeward Islands on a luxury yacht charter gives you the freedom to island hop, experiencing multiple destinations and cultures in one trip.
To help you plan your perfect escape, we’ve listed some of the best places you can reach on your Leeward Islands yacht charter below.

Places to visit

Spanning some 300 miles, the Leeward Islands invite you to discover what a true tropical paradise can be. From lush green mountains to water as clear as the eye can see, here in the Leeward Islands you will discover that there is more than meets the eye.

St. Barts (St. Barthélemy)

One of the Leeward Islands’ most stylish spots is St. Barts, known for its striking natural beauty and laid-back atmosphere. The landscape here features cascading green hills that lead down to vibrant blue bays with over 20 beautiful beaches. On land, you can soak up the charm of the capital, Gustavia, which features French architecture, upscale shopping districts and a bustling marina. You can also enjoy art galleries, cafes and refined bars. 

Visit St. Jean and Nikki Beach for a vibrant social scene and beach clubs, or head to Saline and Gouverneur for a wilder, untouched beach experience. Colombier, only accessible by boat or hike, is also one of the Caribbean’s most peaceful coves.  Enjoy snorkelling and diving at the many coral reefs surrounding St. Barts, where you can spot sea turtles or enjoy a range of watersports. Alternatively, enjoy the many events and celebrations the island has to offer, such as the St. Bart Bucket Regatta.

If you like the sound of the upscale charm and beach culture of St. Barts, you would also love a US Virgin Islands yacht charter. With beautiful surroundings, boutique shipping and elegant dining, you can enjoy even more if you choose to extend your trip.

Antigua

A popular starting point for a Leeward Islands yacht charter is Antigua. Its major harbours, easy international connections and central location make it the perfect place to sail between all the main islands.
Antigua is also famous for its endless beaches, with up to 365 (one of each day of the year). You can escape to the powdery white sands, hidden coves, and calm, reef-protected shores.  Favourite beaches include Dickenson Bay, Half Moon Bay, and Jolly Beach. Here you can indulge in perfect conditions for swimming, snorkelling, and sun lounging. Alternatively, head to the famous English Harbour where you can enjoy boutiques, waterfront restaurants, and centuries of maritime history.  At the centre lies Nelson’s Dockyard, a beautifully restored Georgian naval base and UNESCO World Heritage Site. 

For adventure seekers, you can hike coastal trails, wander rainforest paths to Mount Obama, or snorkel colourful reefs at Cades Reef. You could even meet the island’s famous stingrays at Stingray City. 

Antigua is also home to the North Sound Marine Park, a protected area with mangrove forests, coral reefs, and diverse marine life. It’s an excellent location for underwater exploration, birdwatching or kayaking. 

Barbuda

For a more tranquil, remote experience, visit the less-populated island of Barbuda. It is known for its untouched landscapes, pink beaches, and relaxed atmosphere.

Some of the Caribbean’s most pristine beaches can be found here, such as the famous 11-mile stretch of Pink Sand Beach (named after the pink and white sands).  You can also explore the calm turquoise waters and coral reefs, which offer excellent snorkelling, diving, and fishing opportunities. For wildlife fans, head to the Codrington Lagoon to see one of the world’s largest frigate bird sanctuaries, or head inland to discover Darby’s Cave. This major sinkhole sheltered a miniature rainforest of ferns and palms, as well as wild deer, roaming horses, and quiet coastal trails perfect for biking or exploring.

Barbuda has long been a favoured spot for those seeking a private escape (including Princess Diana in the 1990s).

St. Kitts and Nevis

If you want to combine stunning natural landscapes with uplifting Caribbean experiences, you can take a trip to the twin volcanic islands of St. Kitts and Nevis.  The terrain here is a fascinating mix of dramatic mountain peaks, lush rainforests and golden coastlines. 

St. Kitts offers historic sights, like the UNESCO-listed Brimstone Hill Fortress, as well as rugged hiking trails and striking black-and-gold beaches (due to its volcanic terrain). Here you can climb Mount Liamuiga, explore rainforest zip-lines, or dive the coral reefs. You can also enjoy lively beach bars and restaurants in the island’s villages.  By contrast, Nevis is considered a quieter area, perfect for a slow-paced, relaxing break. It offers boutique hotels, natural hot springs, and historically important areas. 

Visitors can explore colonial-era Charlestown, visit the birthplace of Alexander Hamilton, or unwind on Pinney’s Beach. These islands pair adventurous days with elegant nights, from candlelit dinners and rum punches to authentic Caribbean evenings spent under the stars.

Anguilla

Anguilla is a small British Overseas Territory, located in the northern area of the Leeward Islands. It offers travellers an ideal blend of white sandy beaches, clear turquoise waters, and a tranquil atmosphere.

With its flat coral landscape, you can enjoy stunning views, secluded cays and excellent conditions for snorkelling or paddleboarding. There are also more than 30 beautiful, crowd-free beaches.  Beyond the beaches, Anguilla offers natural wonders to explore, such as the Fountain Cavern National Park. Here you will find ancient cave systems and impressive diving sites, such as Meppel Reef. 

The culture here is wonderfully laid-back, with world-class restaurants, champagne lounges and beachfront bars to enjoy. 

Montserrat

Montserrat is a small yet dramatic island, known for its green landscapes, Irish heritage, and the powerful volcanic forces that earned it the nickname “The Emerald Isle of the Caribbean.”  The island is dominated by the Soufrière Hills Volcano, whose eruptions in the 1990s reshaped much of the terrain. Today, Montserrat offers an authentic, nature-rich experience far from typical tourist areas.

Its forested hills, waterfalls, and protected parks are home to unique wildlife, including the Montserrat oriole and the mountain chicken frog.  Its coastlines feature dramatic dark-sand beaches and the island’s lone white-sand gem at Rendezvous Bay. Adventurers can enjoy kayaking along volcanic shores, hiking jungle trails, and diving in pristine reefs.

Culturally, Montserrat has been shaped by African and Irish influences, which are celebrated during St. Patrick’s Week. This major festival honours the island’s heritage and its historic 17 March slave uprising.

To get your next yacht charter adventure started, speak to our booking team today. Fill in our enquiry form, give us a call on +44 (0) 1489 557 755 or email info@princessyachtcharter.com.

Culture and history

Visit Nelson’s Dockyard (Antigua)
Experience the UNESCO-listed Georgian naval base in English Harbour. Its restored buildings, museum exhibits, and historic significance make it a top attraction for history and sailing enthusiasts.

Explore Brimstone Hill Fortress (St. Kitts)
Enjoy sweeping panoramic views at this hilltop colonial fortress, one of the best-preserved in the region.

Discover Nevis’ plantation heritage (Nevis)
Gain insight into the colonial and Caribbean history of the area by visiting sites like Alexander Hamilton’s birthplace, New River Estate, and Hermitage Plantation.

Events and Festivals

Celebrate at island festivals
Enjoy events such as Antigua Carnival, Nevis Culturama, and Montserrat’s St. Patrick’s Festival. Experience the culture and variety on offer through their music, dance, and island traditions.

Beaches and Coastline

Beaches
Enjoy endless beaches
Relax at some of the Caribbean’s best beaches in Antigua and Anguilla. Antigua, with its “365 beaches,” includes favourites like Dickenson Bay and Half Moon Bay, while Anguilla offers luxurious, tranquil shores at Shoal Bay and Meads Bay.

Beach Clubs
Experience Nikki Beach, the world-famous beach club known for cocktails, loungers, and stylish seaside dining

Water activities
Dive world-class reefs and wrecks
Explore exceptional diving sites like Saba Marine Park and Statia’s Charlie Brown wreck, or snorkel in Anguilla and St. Barts. Discover the turtles, coral reefs, and marine life among the clear waters.

Hiking
Climb Mount Liamuiga (St. Kitts) or Mount Scenery (Saba), trek Nevis Peak (Nevis), or explore Statia’s Quill crater to experience iconic summits, rainforests, ecosystems and spectacular views

Nature
Visit Barbuda’s frigate bird sanctuary

See the Caribbean’s largest frigate bird colony at Barbuda’s protected lagoon. This is a rare wildlife spot, great for nature lovers.
If you love the opportunity to snorkel and enjoy calm, clear waters full of marine life, consider a Bahamas yacht charter. Here you can visit wild coastlines and snorkelling sanctuaries, enjoying the area’s natural beauty.

Cuisine and Nightlife

Antigua
Dine right on the beach at Fort James, Pigeon Point or Ffryes Beach, with standout spots such as Beachlimerz, Catherine’s Café, or Dennis Beach Bar.

St. Barts
Enjoy gourmet French-Caribbean cuisine at Villa Marie, harbourfront restaurants in Gustavia, and chic beach clubs along St. Jean and Shell Beach.
Dine and dance at La Guérite, where upscale dining turns into lively nightlife.

Anguilla
Try flavourful Caribbean dishes at Ocean Club Cabana Bar & Grill, The Flamingo Café, and many relaxed beach bars serving lobster and grilled seafood.
One of Anguilla’s most celebrated restaurants is Blanchards, where you can indulge in fine dining or enjoy beachfront meals at Straw Hat or Sandy Island Beach Bar.

St. Kitts & Nevis
Enjoy classic seafood favourites at lively beach spots such as The Shiggidy Shack on Frigate Bay for lobster dinners, or Mango and Fisherman’s Village for regional seafood dishes.

Plan your trip

A luxury yacht charter is all about discovering new destinations, and having the right travel details in advance helps you enjoy every moment.
To make planning easier, we’ve gathered the essential information you need for a Leeward Islands yacht charter below.

Seasons
The best time to charter a yacht in the Leeward Islands is from December to April, when the weather is warm, dry, and comfortable, with average temperatures of 26°C to 29°C.
Avoid travel between June and November, as this is hurricane season, bringing higher humidity, increased rainfall, and a greater risk of storms.

Currency
The East Caribbean Dollar (XCD) is used on the main islands (Antigua, Barbuda, St. Kitts, Nevis, Anguilla, Montserrat). However, the US Dollar is also widely accepted.

Languages
English is the predominant language throughout the Leeward Islands.
French is the official language in St. Barts and French Saint Martin, but English is widely spoken in tourist areas.
Dutch is spoken on the St. Maarten side, while Creole dialects and Spanish may also be heard among local communities.

How to charter a yacht in The Leeward Islands

Ready to discover the delights of the Leeward Islands on a luxury yacht charter? Booking your trip with Princess Charter is quick and easy.

Just tell us when you’d like to travel and who’s coming along, and we’ll take care of the rest. From designing a custom itinerary to choosing your ideal yacht, our dedicated team will ensure every detail of your trip is perfect.

To start your adventure, you can fill in our enquiry form, give us a call on +44 (0) 1489 557755 or email info@princessyachtcharter.com, and we can get planning.

FAQ

What do I need to know before booking a Leeward Islands yacht charter?
Simply decide when you want to travel, who will be joining you, and the destinations you’d like to explore. The Princess Charter team will handle everything else, crafting a bespoke itinerary, selecting the perfect yacht, and arranging your crew.

How do I secure my booking for a yacht charter in the Leeward Islands?

Reach out to our booking team, and we’ll begin organising your trip. You can get in touch via our enquiry form, call us on +44 (0) 1489 557 755, or email info@princessyachtcharter.com. 

How do I find the right yacht for a Leeward Islands yacht charter?

Once we understand your travel plans, we’ll recommend the most suitable yacht from our luxury fleet.

Why choose Princess Yacht Charter for my charter?

With over 50 years of experience, we know that exceptional charters come down to the details. Our yachts offer unmatched comfort and privacy, while our expert crews and dedicated support ensure a flawless, unforgettable experience.