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Leeward Islands Cruise

  • Departure DateSat 13th Feb 2027
  • Star Clippers Star Flyer
  • 7 Night Cruise From Philipsburg
  • Cruise Only From £1,999 pp
  • Get A Quote

Itinerary

  • Philipsburg, St Maarten
  • Charlestown, Nevis
  • Iles Des Saintes
  • Cabrits
  • Terre de Haut, Ile des Saintes
  • Deshaies, Guadeloupe
  • Falmouth Harbour,Antigua
  • Gustavia, Saint Barthelemy
  • Philipsburg, St Maarten

What's Included

  • Authentic, Natural Sailing Experiences
  • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
  • Complimentary Water Sports

Prices from pp

TypeInteriorOcean ViewBalcony
Cruise Only
£1,999
£2,379
£2,979

Single Cruise Only prices available from £2,919
Cruise Only - price based on cruise only, call to add flights from your regional airport.

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Call Us Free On

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Day 1 - Philipsburg, St Maarten

Arrive: Sat 13 February 2027 / Depart: Sat 13 February 2027

The smallest island in the world shared by two countries, St. Martin/St. Maarten is big on shopping. Whether you go Dutch in Philipsburg or prefer Marigot's French touch, you're always welcome.

Day 2 - Charlestown, Nevis

Arrive: Sun 14 February 2027 / Depart: Sun 14 February 2027

Nevis is the kind of place you wish they wouldn't write about because you'd like to keep it all to yourself. The island is dotted with old sugar plantations, some of them now turned into charming inns, many with interesting histories. Dominated by the perilously steep cliffs of Mt. Scenery, this small Dutch island didn't even have a road around it until 1951. But the diving is definitely out of this world.

Day 3 - Iles Des Saintes

Arrive: Mon 15 February 2027 / Depart: Mon 15 February 2027

Day 3 - Cabrits

Arrive: Mon 15 February 2027 / Depart: Mon 15 February 2027

Dominica is a dream-like island, full of surprises. From Star Clipper’s anchorage in remote Prince Rupert Bay, the steep mountainsides and lush jungle-like beauty might remind you of a Rousseau landscape. Glide through a steamy orchid-festooned rain forest in a fascinating boat ride up the winding Layrou River. Alternatively, hike to breathtaking Trafalgar Falls and a bubbling lake.

Day 4 - Terre de Haut, Ile des Saintes

Arrive: Tue 16 February 2027 / Depart: Tue 16 February 2027

Les Saintes is a thoroughly entrancing group of islands lying off Guadeloupe. You'll enjoy the superb beaches, snorkelling, diving and other watersports on offer.

Day 5 - Deshaies, Guadeloupe

Arrive: Wed 17 February 2027 / Depart: Wed 17 February 2027

Guadeloupe looks like a butterfly from the air. Its giant wings are actually two islands, separated by the Rivière Salée, a natural salt water channel. Basse Terre, the southern or leeward part of Guadeloupe, is lush and rugged, dominated by La Soufrière. A stream of boiling water gushes from the top of the 4,800-ft. mountain, reminding you that this volcano is not dormant, but very much alive.

Day 6 - Falmouth Harbour,Antigua

Arrive: Thu 18 February 2027 / Depart: Thu 18 February 2027

The dockyards, marinas, old inns, venerable pubs and convivial crowds of sun-tanned yacht crews might remind you a bit of Newport or Annapolis, because this is the epicenter of the Caribbean yachting world. English Harbour, just south of where Royal Clipper docks in Falmouth, is probably one of the most atmospheric ports you’ll ever encounter. It was here that a soon-to-be-famous Royal Navy Captain set up his base in 1785. Today, every faded pink brick and weather-worn bollard of Nelson’s Dockyard evokes the presence of the greatest naval Commander in history.

Day 7 - Gustavia, Saint Barthelemy

Arrive: Fri 19 February 2027 / Depart: Fri 19 February 2027

In its elegant little capital of Gustavia, French joie de vivre is tempered by Swedish spic and span neatness. Diversions include duty-free shopping in exquisite boutiques, beautiful beaches, excellent dining and people-watching.

Day 8 - Philipsburg, St Maarten

Arrive: Sat 20 February 2027 / Depart: Sat 20 February 2027

The smallest island in the world shared by two countries, St. Martin/St. Maarten is big on shopping. Whether you go Dutch in Philipsburg or prefer Marigot's French touch, you're always welcome.

Star Flyer From Star Clippers

ROMANCE THE WIND ABOARD A TALL SHIP. They are the stars of the sea. Star Clipper and Star Flyer are as fleet as the wind and as graceful as swans. These are true clipper ships reflecting their proud heritage in every inch of their polished brass and gleaming brightwork. Step aboard these unique vessels and discover a new age of sail, where the traditions of the past are happily married to the comforts and amenities of the present day. Star Clipper and Star Flyer are modern cruise ships in every way, created for luxury-loving passengers who also love the traditions and romance of the legendary era of sailing ships. Star Clipper and Star Flyer are both 360 feet long and each carries just 170 guests in pampered comfort. Life aboard is blissfully relaxed, much like traveling on a private yacht. You’ll never feel confined on Star Clipper or Star Flyer. Each ship offer spacious accommodations and expansive teak decks with ample space and not one, but two swimming pools. In fact, you’ll find that these ships offer more outdoor space per passenger than most conventional cruise ships. The décor of Star Clipper and Star Flyer is reminiscent of the grand age of sail. Antique prints and paintings of famous sailing ships please the eye, while teak and gleaming mahogany rails are richly reminiscent of Star Clippers’ proud nautical heritage. All Star Clippers ships feature open-seating dining in an elegantly appointed dining room, our convivial indoor-outdoor Tropical Bar and Piano Bar, and an Edwardian style library where a Belle Époque fireplace glows with a warmth that reflects the friendliness and enthusiasm of Star Clippers’ hospitable officers and crew.

Ship Cabins

Category 1

Deluxe Deck Cabin. Two lower beds convert to double bed. Minibar. Bathroom with whirlpool bath. Cabin doors open onto deck.

Category 2

Larger Outside Cabin. Twin/double or triple beds. Bathroom with shower.

Category 3

Outside Cabin Twin, double or triple beds. Bathroom with shower.

Owners Cabin

Deluxe Outside Cabin. Double bed. Sitting area. Minibar. Bathroom with whirlpool bath.
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Filter Results

    Leeward Islands

    Star Clippers

    Luxury

    Star Flyer 05 December 2026 7 nights

    Itinerary: Philipsburg - Charlestown - Iles Des Saintes - Cabrits - Terre de Haut - Deshaies - Falmouth Harbour - Gustavia - Philipsburg

    • Authentic, Natural Sailing Experiences
    • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
    • Complimentary Water Sports

    Cruise Only from

    • Interior £1,949pp
    • Ocean View £2,319pp
    • Balcony £2,889pp

    more details

    Leeward Islands

    Star Clippers

    Luxury

    Star Flyer 02 January 2027 7 nights

    Itinerary: Philipsburg - Charlestown - Iles Des Saintes - Cabrits - Terre de Haut - Deshaies - Falmouth Harbour - Gustavia - Philipsburg

    • Authentic, Natural Sailing Experiences
    • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
    • Complimentary Water Sports

    Cruise Only from

    • Interior £1,949pp
    • Ocean View £2,319pp
    • Balcony £2,889pp

    more details

    Leeward Islands

    Star Clippers

    Luxury

    Star Flyer 16 January 2027 7 nights

    Itinerary: Philipsburg - Charlestown - Iles Des Saintes - Cabrits - Terre de Haut - Deshaies - Falmouth Harbour - Gustavia - Philipsburg

    • Authentic, Natural Sailing Experiences
    • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
    • Complimentary Water Sports

    Cruise Only from

    • Interior £1,999pp
    • Ocean View £2,379pp
    • Balcony £2,979pp

    more details

    Leeward Islands

    Star Clippers

    Luxury

    Star Flyer 30 January 2027 7 nights

    Itinerary: Philipsburg - Charlestown - Iles Des Saintes - Cabrits - Terre de Haut - Deshaies - Falmouth Harbour - Gustavia - Philipsburg

    • Authentic, Natural Sailing Experiences
    • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
    • Complimentary Water Sports

    Cruise Only from

    • Interior £1,999pp
    • Ocean View £2,379pp
    • Balcony £2,979pp

    more details

    Leeward Islands

    Star Clippers

    Luxury

    Star Flyer 27 February 2027 7 nights

    Itinerary: Philipsburg - Charlestown - Iles Des Saintes - Cabrits - Terre de Haut - Deshaies - Falmouth Harbour - Gustavia - Philipsburg

    • Authentic, Natural Sailing Experiences
    • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
    • Complimentary Water Sports

    Cruise Only from

    • Interior £1,999pp
    • Ocean View £2,379pp
    • Balcony £2,979pp

    more details

    Leeward Islands

    Star Clippers

    Luxury

    Star Flyer 13 March 2027 7 nights

    Itinerary: Philipsburg - Charlestown - Iles Des Saintes - Cabrits - Terre de Haut - Deshaies - Falmouth Harbour - Gustavia - Philipsburg

    • Authentic, Natural Sailing Experiences
    • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
    • Complimentary Water Sports

    Cruise Only from

    • Interior £1,999pp
    • Ocean View £2,379pp
    • Balcony £2,979pp

    more details

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    Filter Results

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      Star Clippers

      Luxury

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      Itinerary: Philipsburg - Road Bay - Jost Van Dyke - Soper’s Hole - Spanish Town - Basseterre - South Friar's Beach - Gustavia - Philipsburg

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      • Ocean View £2,329pp
      • Balcony £2,919pp

      more details

      Leeward Islands

      Star Clippers

      Luxury

      Star Flyer 07 March 2026 7 nights

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      • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
      • Complimentary Water Sports

      Cruise Only from

      • Interior £1,959pp
      • Ocean View £2,329pp
      • Balcony £2,919pp

      more details

      Treasure Islands

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      • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
      • Complimentary Water Sports

      Cruise Only from

      • Interior £1,959pp
      • Ocean View £2,329pp
      • Balcony £2,919pp

      more details

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      • Complimentary Water Sports

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      • Complimentary Water Sports

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      • Complimentary Water Sports

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      • Complimentary Water Sports

      Cruise Only from

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      more details

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      • Complimentary Water Sports

      Cruise Only from

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      • Balcony £3,069pp

      more details

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      • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
      • Complimentary Water Sports

      Call us now on 0800 197 8050

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      • Passengers can get Involved with Sailing the Ship, Climbing the Crows Nest and Pulling the Ropes.
      • Complimentary Water Sports

      Cruise Only from

      • Interior £2,079pp
      • Ocean View £2,459pp
      • Balcony £3,069pp

      more details

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