Authentic sailing experience
Feel the power of wind in the sails and take part in a real sea adventure – without commercial gimmicks and crowds of tourists.
Round trip from Philipsburg · 4–11 December 2027
4 December 2027 – 11 December 2027
7 nights
Philipsburg, St. Maarten
Star Flyer
from~€997/ person
Operator price: £855
Approximate conversion using the ECB reference rate from 28 August 2026. The operator's final charge may differ.
Route
St. Maarten - St. Maarten
Port
Philipsburg, St. Maarten
A tall ship cruise is more than a journey - it's an experience that stays with you for a long time
Why choose a Tall Ship cruise?
I want to set sail →Closeness to nature and peace
Immerse yourself in a world where time flows slower, and the only sound is the rush of waves and the crack of lines.
Cruises for everyone
Whether you have sailing experience or are taking your first steps on deck – you'll find a cruise tailored to your expectations and abilities.
Diversity of routes and ships
From short Baltic cruises to multi-week transatlantic voyages. Choose a cruise that fits your rhythm and dreams.
Check the voyage itinerary
Arriving in Philipsburg, you are greeted by a bright Caribbean shoreline, calm turquoise water, and a busy harbour backed by low green hills. Nearby, the town is known for its long seafront, colorful streets, and relaxed island atmosphere that blends beach life with the energy of a cruise port.
Arriving by ship at Charlestown, you are welcomed by a low, sunlit waterfront backed by green hills and the broad silhouette of Nevis Peak rising inland. Nearby, the town has a calm Caribbean feel, with Georgian-era buildings, quiet streets, and beaches and old plantation landscapes within easy reach.
Arriving at Cabrits, you are greeted by a lush, volcanic coastline, calm bay waters and a quieter, more remote corner of Dominica than the island’s larger ports. Nearby, the Cabrits peninsula and the old hilltop fort offer striking views over Prince Rupert Bay, with dense tropical greenery all around.
Approaching Terre-de-Haut by sea, you are met by one of the loveliest bays in the Lesser Antilles, with bright water, green hills and a compact village of colourful houses gathered around the harbour. Nearby, quiet streets, small beaches and hilltop views give the island an easy, sunlit Caribbean atmosphere.
Deshaies is a small, relaxed harbour on Guadeloupe’s lush northwest coast, where fishing boats, green hills and calm Caribbean water create an easygoing tropical atmosphere. Arriving by ship, you get a lovely view of the sheltered bay and waterfront village, with beaches and rainforest scenery nearby rather than right at the quay.
Falmouth Harbour on Antigua opens onto a broad, sheltered bay lined with green hills, marinas, and a lively yachting scene. Arriving by ship, you get a taste of the island’s relaxed Caribbean atmosphere, with historic English Harbour and scenic coastal viewpoints close by.
Arriving in Gustavia, you are greeted by a compact Caribbean harbour framed by green hills, bright waterfront buildings, and a lively mix of yachts and ferries. Just beyond the port, the town’s boutiques, cafés, and hillside viewpoints give St. Barts its polished yet relaxed island atmosphere.
Arriving in Philipsburg, you are greeted by a bright Caribbean shoreline, calm turquoise water, and a busy harbour backed by low green hills. Nearby, the town is known for its long seafront, colorful streets, and relaxed island atmosphere that blends beach life with the energy of a cruise port.
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Places you'll visit
Philipsburg, St. Maarten
Arriving in Philipsburg, you are greeted by a bright Caribbean shoreline, calm turquoise water, and a busy harbour backed by low green hills. Nearby, the town is known for its long seafront, colorful streets, and relaxed island atmosphere that blends beach life with the energy of a cruise port.
Charlestown, Nevis
Arriving by ship at Charlestown, you are welcomed by a low, sunlit waterfront backed by green hills and the broad silhouette of Nevis Peak rising inland. Nearby, the town has a calm Caribbean feel, with Georgian-era buildings, quiet streets, and beaches and old plantation landscapes within easy reach.
Cabrits, Dominica
Arriving at Cabrits, you are greeted by a lush, volcanic coastline, calm bay waters and a quieter, more remote corner of Dominica than the island’s larger ports. Nearby, the Cabrits peninsula and the old hilltop fort offer striking views over Prince Rupert Bay, with dense tropical greenery all around.
Terre-de-Haut, Îles des Saintes
Approaching Terre-de-Haut by sea, you are met by one of the loveliest bays in the Lesser Antilles, with bright water, green hills and a compact village of colourful houses gathered around the harbour. Nearby, quiet streets, small beaches and hilltop views give the island an easy, sunlit Caribbean atmosphere.
Deshaies
Deshaies is a small, relaxed harbour on Guadeloupe’s lush northwest coast, where fishing boats, green hills and calm Caribbean water create an easygoing tropical atmosphere. Arriving by ship, you get a lovely view of the sheltered bay and waterfront village, with beaches and rainforest scenery nearby rather than right at the quay.
Falmouth Harbour, Antigua
Falmouth Harbour on Antigua opens onto a broad, sheltered bay lined with green hills, marinas, and a lively yachting scene. Arriving by ship, you get a taste of the island’s relaxed Caribbean atmosphere, with historic English Harbour and scenic coastal viewpoints close by.
Gustavia, St. Barts
Arriving in Gustavia, you are greeted by a compact Caribbean harbour framed by green hills, bright waterfront buildings, and a lively mix of yachts and ferries. Just beyond the port, the town’s boutiques, cafés, and hillside viewpoints give St. Barts its polished yet relaxed island atmosphere.
Frequently asked questions about tall ship cruises and sailing ships
Many leisure and introductory voyages accept guests without sailing experience. Training and expedition voyages may require active participation, minimum ages or a particular level of mobility. Check the operator's conditions for the exact voyage before booking.
Start with the operator's joining instructions because space, dress rules and required equipment vary by ship. Soft luggage, layered clothing, a waterproof outer layer, sun protection and operator-approved non-slip footwear are common recommendations. Ask a medical professional about suitable seasickness precautions if needed.
Choose a cruise on the Cruise Tall Ships site, click the offer and go to the operator's booking page. We do not charge fees – we connect you directly with the cruise organizer.
Choosing a tall ship cruise is more than just booking a vacation; it is an invitation to experience the timeless romance of the sea. Unlike modern, crowded cruise liners, a traditional sailing vessel offers an intimate atmosphere where the sound of the wind in the canvas replaces the hum of engines. Taking part in such a unique voyage allows you to connect with maritime heritage while enjoying the comforts of a modern leisure cruise. Whether it’s the thrill of seeing the horizon from a wooden deck, the spectacular sight of a full press of sail, or the chance to visit hidden coastal gems inaccessible to larger ships, a tall ship voyage offers a sense of freedom that is simply unmatched. It is the perfect choice for travelers seeking authenticity, tranquility, and a truly luxury sailing experience that stays with them long after they return to shore.
Tall ships cruises take place on many waters: Baltic, North Sea, Atlantic, Caribbean, Mediterranean and others. Each offer indicates the region and route.
Safety rules, vessel certification, briefings and required equipment depend on the ship, flag state, route and operator. Review the operator's current safety information and ask them directly about certification or accessibility before booking.
Follow our website and newsletter – we regularly add new cruises and news. You can also subscribe to the newsletter to receive information about offers.
Swimming requirements vary by operator and voyage. Do not assume that a life jacket removes an operator's swimming or mobility requirement; confirm the conditions for the specific departure.
