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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 £1695pp

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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Exclusive 11-night fly-cruise and stay package from £4099pp!Includes 7-night cruise, 3-night hotel stay and return flights from the UK, departs 18 Feb 2026

Save up to 20% PLUS exclusive Blue Water extra £50pp discount!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

Price Does Not Include

  • Flights and transfers - please contact us for a quote.
  • Port Charges
  • Optional excursions
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2025 Departures £ price per person based on 2 people sharing

  • December
    • Dec 13th - St Maarten and back - Sailing on: Star Flyer From: £1695
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Brochure Price from: £1745 Brochure Price from: £1915 Brochure Price from: £2105 Brochure Price from: £2240 Brochure Price from: £2365 Brochure Price from: £2670 Brochure Price from: £3530
      Blue Water Price from: £1695 Blue Water Price from: £1865 Blue Water Price from: £2055 Blue Water Price from: £2190 Blue Water Price from: £2315 Blue Water Price from: £2620 Blue Water Price from: £3480
    • Dec 27th - St Maarten and back - Sailing on: Star Flyer From: £1805
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Brochure Price from: £1855 Brochure Price from: £2035 Brochure Price from: £2235 Brochure Price from: £2380 Brochure Price from: £2515 Brochure Price from: £2840 Brochure Price from: £3750
      Blue Water Price from: £1805 Blue Water Price from: £1985 Blue Water Price from: £2185 Blue Water Price from: £2330 Blue Water Price from: £2465 Blue Water Price from: £2790 Blue Water Price from: £3700

2026 Departures £ price per person based on 2 people sharing

  • January
    • Jan 10th - St Maarten and back - Sailing on: Star Flyer From: £1750
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Brochure Price from: £1800 Brochure Price from: £1975 Brochure Price from: £2170 Brochure Price from: £2310 Brochure Price from: £2440 Brochure Price from: £2755 Brochure Price from: £3640
      Blue Water Price from: £1750 Blue Water Price from: £1925 Blue Water Price from: £2120 Blue Water Price from: £2260 Blue Water Price from: £2390 Blue Water Price from: £2705 Blue Water Price from: £3590
    • Jan 24th - St Maarten and back - Sailing on: Star Flyer From: £1750
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Brochure Price from: £1800 Brochure Price from: £1975 Brochure Price from: £2170 Brochure Price from: £2310 Brochure Price from: £2440 Brochure Price from: £2755 Brochure Price from: £3640
      Blue Water Price from: £1750 Blue Water Price from: £1925 Blue Water Price from: £2120 Blue Water Price from: £2260 Blue Water Price from: £2390 Blue Water Price from: £2705 Blue Water Price from: £3590
  • February
    • Feb 7th - St Maarten and back - Sailing on: Star Flyer From: £1750
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Brochure Price from: £1800 Brochure Price from: £1975 Brochure Price from: £2170 Brochure Price from: £2310 Brochure Price from: £2440 Brochure Price from: £2755 Brochure Price from: £3640
      Blue Water Price from: £1750 Blue Water Price from: £1925 Blue Water Price from: £2120 Blue Water Price from: £2260 Blue Water Price from: £2390 Blue Water Price from: £2705 Blue Water Price from: £3590
    • Feb 21st - St Maarten and back - Sailing on: Star Flyer From: £1750
      Cat 6 Cat 5 Cat 4 Cat 3 Cat 2 Cat 1 Owners Suite
      Brochure Price from: £1800 Brochure Price from: £1975 Brochure Price from: £2170 Brochure Price from: £2310 Brochure Price from: £2440 Brochure Price from: £2755 Brochure Price from: £3640
      Blue Water Price from: £1750 Blue Water Price from: £1925 Blue Water Price from: £2120 Blue Water Price from: £2260 Blue Water Price from: £2390 Blue Water Price from: £2705 Blue Water Price from: £3590

Price Information

  • Guaranteed Single - from £1745-£1930
  • Third Person - from £555-£680
  • Port Charges - £135pp
  • Please note prices are updated regularly from a third party price feed and may fluctuate from those shown. Please contact us for latest prices
Map for Leeward Islands Sailing Cruise