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Leeward Islands Sailing Cruise

Join tall ship Star Flyer for this 7-night sailing cruise from St Maarten through the idyllic Leeward Islands, visiting the picturesque Iles de Saintes, glamorous St Barts and historic Antigua

Cruise Only
7 nights from £1950pp

Sailing Holiday
  • Dominica
    Dominica
  • Terre-de-Haut
    Terre-de-Haut
  • St Maarten
    St Maarten
  • Yachts at anchor in St Barts
    Yachts at anchor in St Barts

Call us on 01756 706511 (+44 1756 706511) to discuss this holiday

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Save up to 20%!T&Cs apply

Star Flyer first calls at Nevis, a small, mountainous island full of authentic Caribbean character and ringed with idyllic beaches.

Star Flyer will meet up with Royal Clipper and the ships will sail together to Cabrits, noted for its natural beauty. Stroll around Terre-de-Haut, one of the picturesque islands in the Iles des Saintes group and visit the unspoilt harbour of Des Haies on Guadeloupe.

Explore the historic island of Antigua, home to the historic Nelson's Dockyard and visit glamorous St Barts, which boasts upmarket boutiques and superb restaurants.

S549 Operated by Star Clippers

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Leeward Islands Tall Ship Sailing Cruise Itinerary

  • Day 1 - Philipsburg, St Maarten (Dutch West Indies)

    Embark your ship in Philipsburg. The freeport capital of the Dutch portion of the island sits beside Great Bay, and has local markets and duty free shops.

  • Day 2 - River Bay, Barbuda

    River Bay, a hidden gem on the pristine island of Barbuda, is a natural paradise that encapsulates the Caribbean's unspoiled beauty. This secluded bay is a tranquil haven with its soft, pink-tinged sand and crystal-clear, shallow waters, making it an idyllic spot for swimming and snorkeling. It remains largely untouched by mass tourism, allowing visitors to savor a sense of seclusion and serenity that's increasingly rare in the region. The surrounding lush vegetation and the tranquil sound of gentle waves create a sense of harmony and relaxation. River Bay epitomizes the untouched natural splendor that makes Barbuda a true sanctuary for nature lovers and those seeking a serene escape in the Caribbean.

  • Day 3 - Cabrits, Dominica

    Star Flyer meets Royal Clipper South of Iles des Saintes and the two ships sail together. Dominica is a dream-like island, full of surprises. Glide through a steamy orchid-festooned rainforest in a fascinating boat ride or hike to breathtaking Trafalgar Falls and a bubbling lake.

  • Day 4 - Terre-de-Haut, Iles de Saintes (French West Indies)

    Terre-de-Haut is the largest and one of only two populated islands in the Iles des Saintes group. With a small nod to tourism, the island is an oasis of tranquillity and as part of Guadeloupe, has a relaxed, French air. Browse the local shops, watch the harbour activity from a waterside cafe, or enjoy the superb beaches, snorkelling, diving and other watersports on offer.

     

  • Day 5 - Deshaies, Guadeloupe (French West Indies)

    Set in a glorious bay, Deshaies is an unspoilt glimpse of France in the sunshine of the Caribbean. Nearby is a noted Botanical Garden.

  • Day 6 - Falmouth Harbour, Antigua

    Falmouth Harbour has a busy yacht marina and is a short walk or taxi-ride from the historic Nelson Dockyard in Antigua's English Harbour. Shops and restaurants can be found near the harbour, and Star Clipper offers a tender service to the local sandy beach.

  • Day 7 - Gustavia, St Barts (French West Indies)

    The rocky island of St Barts was a trade port where booty from sea raids was stored or sold. Now it is visited by luxury yachts owned by the world's wealthiest, and the stunning capital of Gustavia has upmarket boutiques and good French restaurants. Inland discover colourful flora and small settlements in the hills and valleys.

  • Day 8 - Philipsburg, St Maarten (Dutch West Indies)

    Disembark your ship in Philipsburg, after a week exploring stunning locations not visited by the large cruise ships.

The Captain reserves the right to alter the itinerary to suit wind and weather conditions.

Price Includes

  • 7-night full board cruise
  • Complimentary tea, coffee and water
  • Use of ship’s watersports and snorkelling equipment
  • We can arrange flights, transfers and hotel stays to suit
  • Port Taxes
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2026 Departures £ price per person based on 2 people sharing

  • December
    • Dec 5th - St Maarten and back - Sailing on: Star Flyer From: £1950
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £1950 Blue Water Price from: £2125 Blue Water Price from: £2320 Blue Water Price from: £2455 Blue Water Price from: £2585 Blue Water Price from: £2895 Blue Water Price from: £3775
    • Dec 19th - St Maarten and back - Sailing on: Star Flyer From: £2005
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £2005 Blue Water Price from: £2185 Blue Water Price from: £2385 Blue Water Price from: £2525 Blue Water Price from: £2660 Blue Water Price from: £2980 Blue Water Price from: £3885

2027 Departures £ price per person based on 2 people sharing

  • January
    • Jan 2nd - St Maarten and back - Sailing on: Star Flyer From: £1950
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £1950 Blue Water Price from: £2125 Blue Water Price from: £2320 Blue Water Price from: £2455 Blue Water Price from: £2585 Blue Water Price from: £2895 Blue Water Price from: £3775
    • Jan 16th - St Maarten and back - Sailing on: Star Flyer From: £2005
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £2005 Blue Water Price from: £2185 Blue Water Price from: £2385 Blue Water Price from: £2525 Blue Water Price from: £2660 Blue Water Price from: £2980 Blue Water Price from: £3885
    • Jan 30th - St Maarten and back - Sailing on: Star Flyer From: £2005
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £2005 Blue Water Price from: £2185 Blue Water Price from: £2385 Blue Water Price from: £2525 Blue Water Price from: £2660 Blue Water Price from: £2980 Blue Water Price from: £3885
  • February
    • Feb 13th - St Maarten and back - Sailing on: Star Flyer From: £2005
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £2005 Blue Water Price from: £2185 Blue Water Price from: £2385 Blue Water Price from: £2525 Blue Water Price from: £2660 Blue Water Price from: £2980 Blue Water Price from: £3885
    • Feb 27th - St Maarten and back - Sailing on: Star Flyer From: £2005
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £2005 Blue Water Price from: £2185 Blue Water Price from: £2385 Blue Water Price from: £2525 Blue Water Price from: £2660 Blue Water Price from: £2980 Blue Water Price from: £3885
  • March
    • Mar 13th - St Maarten and back - Sailing on: Star Flyer From: £2005
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Blue Water Price from: £2005 Blue Water Price from: £2185 Blue Water Price from: £2385 Blue Water Price from: £2525 Blue Water Price from: £2660 Blue Water Price from: £2980 Blue Water Price from: £3885
Map for Leeward Islands Sailing Cruise