A unique culture on every island

Leeward Islands

View over the bay of Antigua, Leeward Islands, Caribbean

A favourite with yachtsmen for centuries, the Leeward Islands are a beguiling mix of untouched islands and luxury holiday hotspots. Discover welcoming local cultures or escape to enchanting natural sites, from volcanoes and dive reserves to palm-fringed paradise beaches.

This is an example of an eight day yacht charter itinerary for the Leeward Islands. Itineraries are created individually for every client based around personal preferences and how you want to spend your time onboard.

Aerial view of the bay of Antigua, Caribbean
Day 1


Welcome to Island Life

Board your charter yacht in Falmouth Harbour on the beautiful island of Antigua. Falmouth Harbour is a stone’s throw away from the famous Nelson's Dockyard, an old British colonial naval station. Spend the afternoon exploring the dockyard with a local guide, then take a trip up the mountain to Shirley Heights for a fantastic sunset. Later, arrive at Carlisle Bay on the south western tip of the island, and enjoy the wellbeing spa and fine dining at the luxury Carlisle Bay resort.
Soufriere volcano, Montserrat, Leeward Islands, Caribbean
Day 2


Volcano Experience

Cruise to Montserrat and anchor in Rendezvous Bay on the north-west side of the island for a day of watersports and exploring. With few visitors, this bay is pristine and free of development. Two thirds of Montserrat was engulfed in ash when the Soufriere volcano erupted in 1995, and much still remains submerged. It has been slowly coming back to life and offers a unique tranquillity and friendly locals. Visit the volcano or the partially buried city of Plymouth, the Caribbean's answer to Pompeii.
St Kitts beach and hills, Leeward Islands, Caribbean
Day 3

St Kitts

Tee Off in Style

Enjoy an early morning cruise to the unspoilt island of St Kitts, with pristine beaches and historical sites such as Brimstone Hill Fortress and National Park. For golf enthusiasts, St Kitts is home to the 18 hole Royal St Kitts Golf Course, right on the water’s edge. Tie up overnight in Christophe Harbour, a new marina set in a natural harbour.
Nevis island, Leeward Islands, Caribbean
Day 4


Nature Escape

After a short sail, arrive on Nevis. Explore the island's stunning plantation houses reimagined into luxury hotels. Take the strenuous climb up Nevis Peak to be rewarded with sweeping views over Antigua, Montserrat and other islands. Wander the Asian-inspired Botanical Gardens. Nevis is also perfect for horseback riding on the beach or hiking trails before the sun is high in the noonday sky.
St Martin, view over the landscape and water at sunset, Leeward Islands, Caribbean
Day 5

St Maarten

Holland Meets France

St. Martin is the French side of the island also known as Sint Maarten to those from The Netherlands. Take your choice of either culture in Caribbean style, with pretty beaches on the French side, substantial marinas on the Dutch side and everything from casinos to fine dining in between. Watersports are an option here too.
Anguilla beach, Leeward Islands, Caribbean
Day 6


Laid Back Life

Anguilla, to the north, is a fantastic place to spend a beach day. This exclusive island attracts far fewer crowds than you’ll find on Sint Maarten, as well as some higher-end restaurants. Save some time after sunset to visit The Dune for live reggae and rum punch with Bankie Banx, Anguilla's answer to Bob Dylan.
St Barths harbour, Leeward Islands, Caribbean
Day 7

St Barths

Hello Saint-Tropez

On to St. Barths, the Saint-Tropez of the Caribbean. Gustavia Harbour is your entry point to fine shops, boutiques and restaurants. Send the kids snorkelling while you browse the Cartier, Hermes, Louis Vuitton and more along the waterfront streets. Harborfront cocktails are a must.
View over Antigua at sunset, Leeward Islands, Caribbean
Day 8



Wake in Antigua and enjoy a leisurely breakfast and some last-minute souvenir shopping in Nelson’s Dockyard before disembarking.
Local Time