British Virgin Islands and Lesser Antilles: Dominica, Guadeloupe, Antigua & St Kitts
Leeward Islands Christmas Cruise
When the sun sinks into the sea and steeps the sky in colours no evening repeats.
Interested in this voyage?
Personal advice, no call centre - a reply within 24 hours.
Leeward Islands from/to Philipsburg
9 nights under white sails aboard the Star Flyer, from Philipsburg and back. The voyage takes you through the Caribbean with volcanic peaks, colonial fortresses and unspoilt bays. Steady north-easterly trade winds turn every leg between the islands into a true sailing passage.
Ports of call
- Charlestown
- Îles des Saintes
- Cabrits National Park
- Deshaies
- Terre-de-Haut
- Falmouth Bay
- Gustavia
- Road Bay
- Basseterre
- South Friars Bay
Life on board
The Star Flyer is a classic fully rigged ship with four masts and 16 sails, 170 guests, sporty and unhurried in atmosphere, no dress code, open seating and two pools. Guests are welcome to climb the rigging with the crew or take the helm.
Route Highlights
- Charlestown (Nevis): Birthplace of US founding father Alexander Hamilton, Georgian colonial architecture
- Îles des Saintes: Archipelago south of Guadeloupe, voted one of the world’s most beautiful bays by Parisian geographers
- Cabrits National Park (Dominica): Fort Shirley from the 18th century set in the heart of the rainforest
- Falmouth Bay (Antigua): Nelson’s Dockyard as a UNESCO World Heritage Site, the only surviving Georgian naval dockyard in the world
- Gustavia (Saint-Barthélemy): Swedish heritage in the island’s only deepwater harbour, a chic meeting place
- Basseterre (St. Kitts): Capital with the UNESCO World Heritage Site Brimstone Hill Fortress from the 17th century
Early booking advantage: Voyages in 2027 fill quickly - premium cabins are often reserved 18-24 months in advance. An early booking enquiry is non-binding and secures your preferred cabin category.
The Route
Philipsburg
9 nights
Philipsburg
How the route could go:
-
Philipsburg (Sint Maarten) · Embarkation
Philipsburg is the capital of Dutch Sint Maarten - the smallest land mass shared by two nations. Front Street with its duty-free shops and the aeroplane beach bar near Princess Juliana Airport are Caribbean attractions of a very special kind. On the French side of the island, Saint-Martin, life is celebrated with French savoir-vivre: excellent French cuisine meets Caribbean joie de vivre.
-
Charlestown (Nevis)
Charlestown is the capital of the island of Nevis and the birthplace of US Founding Father Alexander Hamilton. Colonial stone architecture, Pinney's Beach and the hot springs at the foot of Nevis Peak shape the island.
-
Îles des Saintes (Guadeloupe)
The Îles des Saintes are regarded as the most authentic piece of France in the Caribbean: whitewashed houses with blue shutters, fresh tuna, crystal-clear anchorages. Here, time stands still.
-
Cabrits National Park (Dominica)
Cabrits National Park on Dominica covers tropical forest, wetlands and the restored 18th-century ruins of Fort Shirley. Dominica, the "Nature Island of the Caribbean", is one of the least touristically developed countries in the region. Dominica is the only Caribbean island where the indigenous people survived: the Kalinago still live in the Kalinago Territory on the east coast. The national bird, the Sisserou parrot (Imperial Amazon), is found nowhere else on earth and features on the national flag. On this green island people keep a particularly deep connection with nature.
-
Deshaies (Guadeloupe)
Deshaies in the north-west of Guadeloupe is one of the most charming small harbours in the Caribbean. Colourful wooden houses, a weekly market and the botanical garden "Jardin Botanique de Deshaies" - known from the TV series "Death in Paradise" - define the village.
-
Terre-de-Haut (Îles des Saintes)
Terre-de-Haut is the main island of the Îles des Saintes - a Provençal fishing village transposed to the Caribbean, with boulangeries, small harbours and Fort Napoléon high above the sea.
-
Falmouth Bay (Antigua)
Off the southern coast of Antigua in the eastern Caribbean lies the sheltered Falmouth Bay, one of the region's most renowned yachting grounds. Each April, it hosts Antigua Sailing Week, a leading classic yacht regatta worldwide, next to historic Nelson's Dockyard.
-
Gustavia (St. Barth)
Gustavia is the capital of Saint-Barthélemy and is regarded as the "Côte d'Azur of the Caribbean". The small natural harbour, surrounded by international boutiques, gourmet restaurants and elegant yachts, blends relaxed island feel with European refinement.
-
Road Bay (Anguilla)
Road Bay (also Sandy Ground) is the main anchorage on Anguilla's west coast, famous for fresh lobster grilled right by the water. Lively beach bars and the historic salt-drying site in the hinterland make the place authentically Caribbean.
-
Basseterre (St Kitts)
Basseterre is the capital of Saint Kitts and one of the best-preserved colonial cities in the English-speaking Caribbean. Brimstone Hill Fortress, the "Gibraltar of the Caribbean", has been a UNESCO World Heritage Site since 1999.
-
South Friars Bay (St Kitts)
South Friars Bay lies on the quiet south-eastern coast of Saint Kitts, sheltered by hills and the South East Peninsula. The bay is known for its calm water and relaxed beach-bar atmosphere.
-
Philipsburg (Sint Maarten) · Disembarkation
The route of a sailing voyage may change without giving rise to mutual claims.
Shore Excursions
Selected highlights at the ports on this route. Water sports – kayaking, snorkelling, paddleboarding, windsurfing – are complimentary directly from the ship. Shore excursions are bookable on board.
Gustavia
- Luxury boutiques & harbour sundowners
- Gouverneur & Saline beaches
Charlestown
- Botanical Gardens of Nevis
- Alexander Hamilton's birthplace
- Four Seasons Resort Beach
Îles des Saintes
- Walk to Fort Napoléon
- Snorkelling at Pain de Sucre bay
Deshaies
- Deshaies Botanical Garden
- Grande Anse beach
Basseterre
- Brimstone Hill Fortress (UNESCO World Heritage)
- Sugar cane train ride
Philipsburg
- Aeroplane beach bar at Maho Beach
- Duty free shopping on Front Street
Destination
Star Flyer
Star Flyer was in 1991 the first ship of the Star Clippers fleet - proof that commercial sailing cruises need not be nostalgia. Four-masted barquentine, 16 sails, 166 guests: travel under sail without compromising on comfort.
In the Caribbean, Star Flyer sails through the Grenadines and the Windward Islands - waters with constant wind and islands that reveal their full magic only under sail.
The Ship
Cabins
Owner Suite
Double bed and sitting area, minibar and bathtub. Note: low ceiling and steps at the entrance.
Category 1
Two single beds convertible to a double, minibar, bathtub and direct deck access.
Category 2
Double bed or two beds convertible to a double, some cabins with a third berth, shower bathroom.
Category 3
Double bed or two beds convertible to a double, some cabins with a third berth, shower bathroom. Cabins on the Clipper Deck are slightly smaller than those on the Commodore Deck.
Category 4
Double bed or two beds convertible to a double, some cabins with a third berth, shower bathroom.
Category 5
Raised double bed or two beds convertible to a double, some cabins with a third berth, shower bathroom.
Category 6
Bunk beds, shower bathroom.
Deck plan · Star Flyer
Cabin prices
Prices per person in double cabin (suites: based on double occupancy), all-inclusive. Subject to availability.
| Category | Price p.P. | Status | |
|---|---|---|---|
| Innenkabine, Kat. VI | € 3.255 | Available | Enquire |
| Innen-/Aussenkabine, Kat. V | € 3.560 | Available | Enquire |
| Aussenkabine, Kat. IV | € 3.880 | Available | Enquire |
| Aussenkabine, Kat. III | € 4.100 | Available | Enquire |
| Aussenkabine, Kat. II | € 4.310 | Available | Enquire |
| Deluxe Aussenkabine, Kat. I | € 4.820 | Available | Enquire |
| Deluxe Aussenkabine, Eigner Kabine | € 6.300 | Available | Enquire |
Prices as of: 14.08.2026
Standard inclusions of the ship voyage
On board
- Cabin in booked cabin category
- Full board
- Beverages with meals: tap water in carafes, coffee and tea, and juices (breakfast only)
- Water sports (except diving)
- Port fees
- Regular cabin cleaning
Not included
- Onboard beverages
- Shore excursions
- Travel to/from ship
- All alcoholic beverages, soft drinks, bottled water, cocktails and coffee/tea creations outside regular meal times
- Personal expenses such as laundry, telephone, etc.
- Travel cancellation insurance and additional travel/health insurance
- Gratuities (voluntary - recommended 10 EUR per person per day)
Frequently asked questions
How do I book this voyage?
Send us a non-binding enquiry via the form on this page. Our team replies personally within 24 hours with availability, cabin options and a tailored offer. No enquiry fee, no upfront payment.
What is included in the price?
The base price per person (twin cabin) includes the cabin in your chosen category, full board, all port fees and the onboard programme. Flights and transfers are quoted separately. 9 nights from EUR 3.255 p.p.
How many guests sail on the Star Flyer?
A maximum of 166 guests - extraordinarily intimate compared to standard cruise ships. The high crew-to-guest ratio ensures personal attention throughout the voyage.
Can the itinerary change?
Yes - all itineraries are subject to weather, port availability and the captain's decisions. This is part of the charm of small-ship cruising: flexibility allows for unexpected discoveries.
Are there specials for early bookers or solo travellers?
Yes. Early bookers receive discounts for timely booking. Solo travellers often benefit from a reduced or waived single supplement. Simply mention your preferences in the enquiry.
Is my booking protected?
Yes. As a German tour operator, ivent-sailing provides a travel protection certificate (Reisesicherungsschein) under German law. Your payment is fully insured.
What about flights and transfers?
We arrange flights and transfers on request as part of your personal offer. This allows us to find the best connections for your specific departure date and home airport.
Are there shore excursions?
Yes. All cruise lines offer shore excursions - from guided cultural tours to nature experiences. The concepts vary by fleet. We are happy to provide details on available excursions for your chosen voyage.
What water sports and activities are available?
Depending on the ship and route: snorkelling, kayaking, stand-up paddling, diving, and Zodiac landings (on expedition voyages). Many ships have a marina platform for direct access to the water. We will be happy to tell you exactly what is available on your voyage.
Non-binding enquiry
Your enquiry reaches a person familiar with this voyage and ship.
