From chic St Barths to historic Antigua and volcanic Nevis — the Leewards are the Caribbean’s most varied and elegant chain.
The Leeward Islands curve through the northeastern Caribbean, more sheltered from the trade winds than their Windward neighbours — hence the name. This is the most varied cruising ground in the region: in a single week you can move from the glamour of St Barths to the Georgian harbours of Antigua, the volcanic drama of Nevis and the French-Caribbean charm of Guadeloupe. The sailing balances open passages with sheltered anchorages, and the islands range from chic and cosmopolitan to wonderfully wild — making the Leewards a sophisticated choice for those who want range and elegance in one voyage.
Several of our crewed catamarans sail the Leeward chain, ready to show you its remarkable variety from the deck.
External resources: Visit Antigua & Barbuda
A crewed catamaran is the perfect way to experience the Leewards’ variety. The chain rewards island-hopping — chic one day, historic the next, wild the day after — and a catamaran lets you anchor off the best beaches and slip into harbours large and small. Your crew handles the passages and the local knowledge, from the best table in St Barths to the quietest cove in Les Saintes.
Sophisticated, varied and elegant, the Leewards suit those who want range — glamour and wilderness in a single voyage.
Leeward Islands offers some of the most rewarding sailing in the Caribbean — dramatic islands within reach, trade-wind passages, and anchorages from lively to utterly secluded.
Drop anchor off the Caribbean’s most glamorous harbour, lined with superyachts, designer boutiques and world-class restaurants.
Anchor in English Harbour beside the only working Georgian dockyard in the world, a UNESCO World Heritage site.
A cluster of jewel-like islands with a perfect bay, often called one of the most beautiful in the world.
Anchor off Pinney’s Beach beneath the rainforested peak of Nevis, with old plantation inns to explore ashore.
Sail north to Barbuda for miles of deserted pink-tinged beach and a vast frigatebird sanctuary.
A varied week through the elegant Leeward chain — balancing glamour, history and wilderness, tailored by your crew.
Boarding in Marigot, then a short crossing to St Barths. Anchor in Anse de Colombier — accessible only by sea — for an afternoon swim, then move to Gustavia for dinner ashore.
A morning sail to St Kitts. Tour the colonial Brimstone Hill Fortress, a UNESCO site, then evening on board at Whitehouse Bay.
A relaxed half-day crossing to neighbouring Nevis. Lunch on board off Pinney’s Beach, then ashore for the historic plantation inns and rainforest paths.
Sail south to Antigua’s English Harbour, the heart of Caribbean yachting heritage. Tour Nelson’s Dockyard and dine in the restored Georgian buildings.
A morning passage to Barbuda. Land on the 17-mile pink-sand beach with no other footprints — quite possibly the most pristine of all Caribbean shores.
Lazy morning on Barbuda’s frigate-bird lagoon, then sail back to Antigua’s quieter northern coast. Anchor at Great Bird Island for a final remote swim.
A relaxed return to Falmouth Harbour with a parting brunch at anchor.
Variety. The Leewards pack the Caribbean’s greatest range into one chain — the glamour of St Barths, the Georgian history of Antigua, the volcanic calm of Nevis and the French charm of Guadeloupe. A single week can take you from chic to wonderfully wild.
The Leewards are more sheltered and varied, with a mix of glamorous and historic islands; the Windwards are wilder, lusher and breezier with more dramatic volcanic scenery. The Leewards suit those wanting elegance and range; the Windwards suit those after raw spectacle and adventure.
December to April is prime season — reliable trade winds, warm sun and little rain, and the height of the St Barths social calendar. The June-November hurricane season is avoided.
Most begin in Antigua, a major Caribbean hub with excellent international connections, or sometimes St Maarten. Our team coordinates flights and transfers, and can arrange private aviation.
Absolutely — arriving by yacht is the finest way to experience St Barths. You can anchor off its beautiful beaches, enjoy Gustavia’s restaurants and boutiques, and avoid the island’s limited (and expensive) hotel accommodation entirely.
Yes, particularly with a crewed yacht. The mix of beaches, history and short passages offers something for every age, though some inter-island passages are open water. Our team will tailor the route to suit your party.
Every journey begins with a conversation. Tell us what you have in mind — dates, destinations, group size, experiences — and your Odyssea agent will craft a proposal tailored precisely to you.
An invitation-led membership for travellers who choose the ocean often. Preferred rates on yachts and villas, early access to themed departures, and bespoke journey design from our concierge — reach out to find out more.
“We were greeted warmly by our crew Sarel and Alessandra and treated to a champagne toast to start the charter. We were taken to beautiful bays where we could snorkel, enjoy the beach and the other water sport activities from the boat like paddle boarding. We enjoyed delicious meals and snacks prepared by Alessandra and always had the perfect beverages to accompany. Our accommodations were kept impeccably clean and decorated and we enjoyed restful sleep while aboard. We also enjoyed some shore time in St Barth’s and St Martin. Sarel collaborated with us to fulfill our wishes for the week long trip. My husband and I also had an incredible rendezvous dive trip off the coast of St Barth’s where we saw sharks, turtles, moray eels, and lots of fish! We thoroughly enjoyed the week and the amazing crew. We look forward to the opportunity to sail with them again.”
