EXCLUSIVE OFFER

7-night Leeward Islands Cruise

Roundtrip St. Maarten (Philipsburg)

Voyage Overview

Embarkation
St. Maarten (Philipsburg)
Disembarkation
St. Maarten (Philipsburg)
Destination Highlight

The island of St. Martin is divided between French St. Martin in the north and Dutch St. Maarten in the south. Although the cultural flow transcends any borders, each side manages to retain its own distinct flavor. This 37-square-mile island promises beautiful vistas, first-rate water sports and stunning beaches. Philipsburg is the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

About the 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.


Daily Itinerary
Dec 05, 2026 - St. Maarten (Philipsburg)

The island of St. Martin is divided between French St. Martin in the north and Dutch St. Maarten in the south. Although the cultural flow transcends any borders, each side manages to retain its own distinct flavor. This 37-square-mile island promises beautiful vistas, first-rate water sports and stunning beaches. Philipsburg is the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

Dec 06, 2026 - Charlestown

Charlestown is a Caribbean town with remnants of the Colonial era. It’s the capital of the island of Nevis of Saint Kitts and Nevis in the West Indies. The town was developed as early as the 17th century by the British building Fort Charles and mounting 26 cannons to protect its harbor. The British had a lucrative sugar trade much profitable than that of North America. Historical figure Anthony Hamilton, the first US Secretary of Treasury was born and raised in Charlestown. 

Travelers visiting Charlestown can tour the Nelson Museum, Philatelic Bureau or Museum of Nevis History. Visitors can either horseback ride by the beach or relax by it under the Caribbean sun!

Dec 07, 2026 - Iles des Saintes

Pastoral and far off the beaten track, the Saintes are a cluster of eight islands off the southern coast of Guadeloupe. In Bourg, the charming hamlet on Terre-de-Haut, the largest isle, you can wander peaceful streets past small houses, then follow the narrow road out of town through fields and hills to a sweeping strand of secluded beach.

Dec 07, 2026 - Cabrits, Dominica

Dominica's majestic, mountainous landscape towers above the two oceans surrounding the island: the ruggedly beautiful Atlantic to the east and the calm and romantic Caribbean on the west.

Dec 08, 2026 - Terre-de-Haut, Guadeloupe

The largest of the Les Saintes islands, off the southern coast of Guadeloupe, Terre-de-Haut is a tropical paradise.  Its calm waters provide an excellent environment for snorkeling.  Rent a moped and explore the island, visit the 19th century penitentiary turned museum at Fort Napoleon or simply relax on the sandy shores of Terre-de-Haut.
 

Dec 09, 2026 - Deshaies, Guadeloupe

Deshaies is a beautiful island commune in the French region of Lesser Antilles. The beaches are are very popular here and excellent for swimming. The Botanical park is also a highlight of the island. Additionally, residents keep up a small handcraft industry, and wooden souvenirs can be purchased in shops.

Dec 10, 2026 - Falmouth Harbour, Antigua

Falmouth Harbour is on the south coast of Antigua close to Nelson' Dockyard in English Harbour. Falmouth is a quiet village surrounded by sugar plantations and mills with the main historic building of interest being St. Paul's Church which dates back to the 17th Century. On the eastern side of the bay visitors will find excellent shops, restaurants, and a marina.  Falmouth offers a host of beaches including Windward beach which is considered a sun bathers paradise.

Dec 11, 2026 - Basseterre, St. Kitts

Basseterre, St. Kitts’ capital, still shows signs of colonial architecture. However, its setting against the emerald green hills ensures a distinct Caribbean ambiance. Many travelers agree Basseterre is one of the prettiest of the Caribbean’s small capitals.

Dec 11, 2026 - South Friar's Bay, St. Kitts

Located on the Southeast Peninsula, South Friar's Bay is a great swimming beach with a long stretch of golden sand and calm waters. This Caribbean beach, which is a favorite for both tourists and locals, is perfect for watersports, especially snorkeling. It is also a great spot for a beach picnic or party. South Friar's Bay is home to Godfather's, Sunset and Shipwreck Beach Bars - which provide refreshments for all visitors.

Dec 12, 2026 - St. Maarten (Philipsburg)

The island of St. Martin is divided between French St. Martin in the north and Dutch St. Maarten in the south. Although the cultural flow transcends any borders, each side manages to retain its own distinct flavor. This 37-square-mile island promises beautiful vistas, first-rate water sports and stunning beaches. Philipsburg is the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

Stateroom Options

Owner's Cabin - Deluxe Outside Stateroom
Owner's Cabin - Deluxe Outside Stateroom (Cat Owners)
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Size: 22 sq. mt.

  • Double bed
  • Sitting area
  • Minibar
  • Bathroom with whirlpool bath

Owner's Cabin - Deluxe Outside Stateroom
Owner's Cabin - Deluxe Outside Stateroom (Cat Owners Cabin)
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Size: 22 sq. mt.

  • Double bed
  • Sitting area
  • Minibar
  • Bathroom with whirlpool bath

Deluxe Outside Stateroom
Deluxe Outside Stateroom (Cat 1)
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Size: 14.5 sq. mt.

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

Large Outside Stateroom
Large Outside Stateroom (Cat 2)
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Size: 12 sq. mt.

  • Twin/double or triple beds
  • Bathroom with shower

Outside Stateroom
Outside Stateroom (Cat 3)
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Size: 11 sq. mt.

  • Twin, double or triple beds
  • Bathroom with shower

Outside Stateroom
Outside Stateroom (Cat 4)
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Size: 11 sq. mt.

  • Two lower beds, double bed or triple berth
  • Bathroom with shower

Outside Stateroom
Outside Stateroom (Cat 5)
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Size: 11 sq. mt.
  • Raised double bed, two lower beds or triple berth
  • Bathroom with shower

Inside Stateroom
Inside Stateroom (Cat 6)
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Size: 8 sq. mt.
  • Upper/lower berths
  • Bathroom with shower

Included Amenities

Exclusive Bonus:
  • $150 per Couple Shipboard Credit
  • 7-night cruise
  • All meals on board the ship
  • Complimentary water sports including snorkeling, sunfish sailing, water skiing and windsurfing

Additional Departure Dates for This Itinerary

Select an upcoming departure below to view availability or lock in exclusive Signature Travel Network perks.

Jan 02, 2027
7-night Leeward Islands Cruise
7 Nights • Star Flyer • Roundtrip St. Maarten (Philipsburg)
Signature PerksSpecial Rate
Jan 16, 2027
7-night Leeward Islands Cruise
7 Nights • Star Flyer • Roundtrip St. Maarten (Philipsburg)
Signature PerksSpecial Rate
Jan 30, 2027
7-night Leeward Islands Cruise
7 Nights • Star Flyer • Roundtrip St. Maarten (Philipsburg)
Signature PerksSpecial Rate
Feb 13, 2027
7-night Leeward Islands Cruise
7 Nights • Star Flyer • Roundtrip St. Maarten (Philipsburg)
Signature PerksSpecial Rate
Feb 27, 2027
7-night Leeward Islands Cruise
7 Nights • Star Flyer • Roundtrip St. Maarten (Philipsburg)
Signature PerksSpecial Rate

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Starting From
Call for Rates
Rates listed are per person based on double occupancy, cruise-only in U.S. Dollars, and include Port Charges. Rates are time sensitive and maybe withdrawn at any time without notice. Valid for residents of North and Latin America only.

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The Vincent Vacations Advantage
Signature Travel Network Member
  • Best Price Guarantee: Exact same price or lower than booking directly with the cruise line.
  • Signature Exclusive Perks: Up to $500 Onboard Spending Credit, Specialty Dining & Welcome Wine on qualifying voyages.
  • Dedicated Certified Specialist: Direct advisor phone line, stateroom selection advice & automated price monitoring.
  • Zero Agency Fees: 100% complimentary white-glove planning & VIP booking service.
Already booked direct within 30-60 days? Transfer for free & claim up to $500 bonus OBC →
Trip Summary
Ship Name Star Flyer
Departure Date December 05, 2026
Duration 7 Nights
Offer ID 1629461
Ship Facts
Built 1991
Guests 170
Crew 72
Call Vincent Vacations: 1 (888) 883-0460

Offer Highlights

  • Duration: 7 Nights
  • Supplier: Roundtrip St. Maarten (Philipsburg)
  • Destination: Roundtrip St. Maarten (Philipsburg)
  • Starting Rate: Call for Rates

Frequently Asked Questions

Rates listed are per person based on double occupancy, cruise-only in U.S. Dollars, and include Port Charges. Rates are time sensitive and maybe withdrawn at any time without notice. Valid for residents of North and Latin America only.All fares are quoted in US Dollars.

You can book this offer directly through Vincent Vacations by clicking the 'Request a Free Quote' button or calling our travel agency at 1 (888) 883-0460 to speak with a travel specialist.

Verified Guest Reviews

4.8 out of 5
Based on verified reviews for Roundtrip St. Maarten (Philipsburg)

Satisfied Traveler
Recent Guest
"Booking this trip through Vincent Vacations was incredibly seamless. The vacation arrangements by Roundtrip St. Maarten (Philipsburg) were top notch!"
Rates listed are per person based on double occupancy, cruise-only in U.S. Dollars, and include Port Charges. Rates are time sensitive and maybe withdrawn at any time without notice. Valid for residents of North and Latin America only.

All fares are quoted in US Dollars.