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Round trip from Philipsburg · 28 November – 5 December 2026 – Main voyage image

Round trip from Philipsburg · 28 November – 5 December 2026

28 November 2026 – 5 December 2026
7 nights
Philipsburg, St. Maarten
Star Flyer
from~€1,178/ person

Operator price: £1,010

Approximate conversion using the ECB reference rate from 27 August 2026. The operator's final charge may differ.

Places available
Visit operator's page

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?

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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.

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

Photo: Clavius66, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Philipsburg_and_the_Great_Bay,_Sint_Maarten,_Caribbean.jpg)

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.

Photo: unknown author, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Anguilla_Prickly-Pear.jpg)

Road Bay opens onto a bright, low-lying coastline with pale beaches, clear turquoise water, and a relaxed Caribbean feel. From the anchorage or quay, you are close to the small seaside settlement and nearby stretches of sand that give this part of Anguilla its calm, unhurried atmosphere.

White Bay welcomes ships with a brilliant curve of white sand, clear turquoise water, and low green hills that give this corner of Jost van Dyke its relaxed Caribbean feel. From the anchorage, the shoreline looks idyllic and unhurried, with beaches and coastal views nearby rather than a busy port scene.

Sopers Hole is a small, sheltered harbour on Tortola, known for calm turquoise water, low green hills and a relaxed Caribbean feel. From the quay you step straight into a compact waterfront area, while nearby coves, coastal views and the island’s winding roads invite a slower look at the western end of the British Virgin Islands.

Sea day
Photo: 4m1g0, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Waves_In_A_Coru%C3%B1a_(206975629).jpeg)

The Bight lies on the broad inlet by A Coruña, where busy harbour waters meet low green shores and open views across the bay. Arriving by ship, you get a sense of Galicia’s Atlantic character—working waterfronts, changing light, and nearby coastal scenery rather than a compact old town right at the quay.

Photo: Photo by Not home (talk); Not home at en.wikipedia, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St.-Jago-de-la-Vega.JPG)

Arriving here, you get a taste of Galicia’s Atlantic character: a working harbour, green hills, and a rugged coastline shaped by changing light and weather. Nearby, the city of A Coruña offers broad seafront views, lively streets, and long urban beaches that give the area an open, maritime feel.

Photo: ESA/NASA, Public domain, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Martinique-de-haut_(cropped).jpg)

This stop has the feel of a quiet Atlantic shoreline, with open sea views, sandy stretches and a relaxed coastal atmosphere rather than a busy city waterfront. From the landing area, the appeal is in the nearby beach and the surrounding coast, where you can enjoy fresh sea air, broad horizons and an easygoing island mood.

Photo: giggel, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St._Kitts,_Karibik_-_Marina_in_Basseterre_-_panoramio.jpg)

Arriving in Basseterre, you are met by a bright Caribbean waterfront backed by green hills and the low-rise capital of St Kitts spreading just beyond the harbour. Nearby, visitors can look out for the town’s historic core and the island’s lush volcanic scenery, with a warm, easygoing atmosphere that feels both lively and relaxed.

Photo: Fred Hsu on en.wikipedia, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:2016_02_FRD_Caribbean_Cruise_South_Friars_Bay_S0767183.jpg)

South Friars Bay offers a quiet arrival on the sheltered waters of Southampton Water, with busy shipping lanes, mudflats, and low green shoreline giving the area a distinctly maritime character. From here, the nearby coast and villages feel calm and residential, while the wider Southampton and Solent waterfront lies within easy reach.

Photo: digitalfilmphoto, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Gustaviaphare2.jpg)

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.

Photo: Clavius66, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Philipsburg_and_the_Great_Bay,_Sint_Maarten,_Caribbean.jpg)

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.

Photo: Clavius66, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Philipsburg_and_the_Great_Bay,_Sint_Maarten,_Caribbean.jpg)
Photo: Clavius66, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Philipsburg_and_the_Great_Bay,_Sint_Maarten,_Caribbean.jpg)

Road Bay, Anguilla

Road Bay opens onto a bright, low-lying coastline with pale beaches, clear turquoise water, and a relaxed Caribbean feel. From the anchorage or quay, you are close to the small seaside settlement and nearby stretches of sand that give this part of Anguilla its calm, unhurried atmosphere.

Photo: unknown author, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Anguilla_Prickly-Pear.jpg)
Photo: unknown author, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Anguilla_Prickly-Pear.jpg)

White Bay, Jost van Dyke

White Bay welcomes ships with a brilliant curve of white sand, clear turquoise water, and low green hills that give this corner of Jost van Dyke its relaxed Caribbean feel. From the anchorage, the shoreline looks idyllic and unhurried, with beaches and coastal views nearby rather than a busy port scene.

Sopers Hole

Sopers Hole is a small, sheltered harbour on Tortola, known for calm turquoise water, low green hills and a relaxed Caribbean feel. From the quay you step straight into a compact waterfront area, while nearby coves, coastal views and the island’s winding roads invite a slower look at the western end of the British Virgin Islands.

The Bight

The Bight lies on the broad inlet by A Coruña, where busy harbour waters meet low green shores and open views across the bay. Arriving by ship, you get a sense of Galicia’s Atlantic character—working waterfronts, changing light, and nearby coastal scenery rather than a compact old town right at the quay.

Photo: 4m1g0, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Waves_In_A_Coru%C3%B1a_(206975629).jpeg)
Photo: 4m1g0, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Waves_In_A_Coru%C3%B1a_(206975629).jpeg)

Spanish Town

Arriving here, you get a taste of Galicia’s Atlantic character: a working harbour, green hills, and a rugged coastline shaped by changing light and weather. Nearby, the city of A Coruña offers broad seafront views, lively streets, and long urban beaches that give the area an open, maritime feel.

Photo: Photo by Not home (talk); Not home at en.wikipedia, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St.-Jago-de-la-Vega.JPG)
Photo: Photo by Not home (talk); Not home at en.wikipedia, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St.-Jago-de-la-Vega.JPG)

Beach, Martinique

This stop has the feel of a quiet Atlantic shoreline, with open sea views, sandy stretches and a relaxed coastal atmosphere rather than a busy city waterfront. From the landing area, the appeal is in the nearby beach and the surrounding coast, where you can enjoy fresh sea air, broad horizons and an easygoing island mood.

Photo: ESA/NASA, Public domain, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Martinique-de-haut_(cropped).jpg)
Photo: ESA/NASA, Public domain, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Martinique-de-haut_(cropped).jpg)

Basseterre

Arriving in Basseterre, you are met by a bright Caribbean waterfront backed by green hills and the low-rise capital of St Kitts spreading just beyond the harbour. Nearby, visitors can look out for the town’s historic core and the island’s lush volcanic scenery, with a warm, easygoing atmosphere that feels both lively and relaxed.

Photo: giggel, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St._Kitts,_Karibik_-_Marina_in_Basseterre_-_panoramio.jpg)
Photo: giggel, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:St._Kitts,_Karibik_-_Marina_in_Basseterre_-_panoramio.jpg)

South Friars Bay

South Friars Bay offers a quiet arrival on the sheltered waters of Southampton Water, with busy shipping lanes, mudflats, and low green shoreline giving the area a distinctly maritime character. From here, the nearby coast and villages feel calm and residential, while the wider Southampton and Solent waterfront lies within easy reach.

Photo: Fred Hsu on en.wikipedia, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:2016_02_FRD_Caribbean_Cruise_South_Friars_Bay_S0767183.jpg)
Photo: Fred Hsu on en.wikipedia, CC BY-SA 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:2016_02_FRD_Caribbean_Cruise_South_Friars_Bay_S0767183.jpg)

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.

Photo: digitalfilmphoto, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Gustaviaphare2.jpg)
Photo: digitalfilmphoto, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Gustaviaphare2.jpg)

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.

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