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St Barts harbor view

Leeward Islands

Roundtrip St Maarten - Example 8 Day Cruise aboard Star Flyer
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Sail roundtrip from Philipsburg, St. Maarten, on this 8-day Caribbean cruise aboard the Star Flyer. Explore the dual-nation culture of St. Maarten before visiting Charlestown, Nevis. Discover historic sugar plantations and charming inns on this secluded island. Navigate to Cabrits, Dominica, to experience the orchid-filled rainforest via boat ride or hike to Trafalgar Falls and the bubbling lake. Visit Terre-de-Haut, Iles des Saintes, known for superb beaches, snorkeling, and water sports. Experience Falmouth Harbor, Antigua, the epicenter of the yachting world, and explore the historic Nelson's Dockyard. Stop in Gustavia, St. Barts, and relax on pristine beaches. Disembark in St. Maarten. Cover the Leeward Islands' diverse history, volcanic geography, and marine life.
Beautiful beach in DominicaView from the beaches of Philipsburg, St. MaartenThe Southeast Peninsula of Saint Kitts with Nevis in the BackgroundPanorama of Les SaintesCaribbean landscapes and harborsBeach, harbor and village of Terre-de-HautRelax on the beaches of St. MaartenSt Barts harbor view
Highlights
  • Explore Nevis to see historic sugar plantations and charming inns
  • Tour Dominica rainforests to see wild orchids via boat ride
  • Snorkel Terre-de-Haut to see superb beaches and clear blue waters
  • Visit Falmouth Harbour to see the famous Nelson's Dockyard ruins
Activity Level: Variable
Activity options vary depending on destination and operator. Activity level is determined by the range and intensity of activities you choose to participate in. Discuss with your Trip Planner which options are best for you.
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Full Itinerary

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Day 1: Philipsburg, St. Maarten | Embark

As the smallest landmass shared by two nations, St. Martin and St. Maarten present big shopping opportunities. Visitors may choose between the Dutch culture of Philipsburg and the French ambiance of Marigot, both of which offer a welcoming environment.

Day 2: Charlestown, Nevis

Consider Nevis the kind of secluded sanctuary you might prefer to keep entirely to yourself. Explore an island dotted with historic sugar plantations, many now transformed into charming inns with fascinating stories. On the neighboring Dutch island, gaze up at the perilously steep cliffs of Mt. Scenery—a rugged landscape that lacked a perimeter road until 1951—and experience diving that is truly out of this world.

Day 3: Sail with Royal Clipper South of Iles des Saintes | Cabrits, Dominica

Star Flyer meets Royal Clipper South of Iles des Saintes and the two ships sail together.

Dominica is a dream-like island, full of surprises. Glide through a steamy orchid-festooned rainforest in a fascinating boat ride or hike to breathtaking Trafalgar Falls and a bubbling lake.

Day 4: Terre-de-haut, Iles des Saintes

Les Saintes is a thoroughly entrancing group of islands lying off Guadeloupe. Enjoy the superb beaches, snorkeling, diving and other watersports on offer.

Day 5: Deshaies, Guadeloupe

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

The dockyards, marinas, old inns, venerable pubs, and convivial crowds of sun-tanned yacht crews - this is the epicenter of the Caribbean yachting world. 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, St.Barts

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 | Disembark

  • 1 Breakfast
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.

Disembark after breakfast and continue your independent trip back home.

Ship/Hotel

Star Flyer

Star Flyer, Star Clipper Interior
Star Flyer/Star Clipper Bar

Dates & Prices

My Preferred Start Date

Deals

Wave Offer 30294
Book your 2026 or 2027 cruise before February 28, 2026, and receive an air credit of up to $500 per cabin.
  • 11+ Nights: $500 per cabin
  • 7–10 Nights: $400 per cabin
  • 5–6 Nights: $300 per cabin
This offer is valid for new bookings on select 2026-2027 sailings in cabin categories 2–6 only. Subject to availability and cannot be combined with other promotions. Additional restrictions may apply. Please contact us for details.
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Reduced Single Supplement 30316
Solo travelers: Book now and enjoy a reduced single supplement of 25% in cabin categories 2–3, and no single supplement in cabin categories 4–6 on select 2026–2027 sailings. This promotion is valid for new bookings, is capacity-controlled, and may be withdrawn at any time without notice. Additional restrictions may apply. Please contact us for details.
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Per person starting at
$2,010 2-3 travelers
Star Flyer Category 6 Cabin
Category 6
Located on the Commodore Deck, 4 Inside Staterooms (no portlight) have upper and lower Pullman style bunk beds, ample closet and storage space, a private bathroom with shower, and a sitting area with desk, vanity, and seating. All staterooms have their own thermostat-controlled air-conditioning, telephone, private safe, and hairdryer.
Star Flyer, Star Clipper Cabin Category 5
Category 5
Located on the Clipper & Commodore Decks, 6 Outside Staterooms w/porthole (#139,136,300,301,342,345), with Portlight, with raised Fixed Double Bed (43 inches (1.09 m) off the floor / raised about 4-feet off the ground and steps/stairs are provided in order to reach bed) Ample closet and storage space, private bathroom with shower, and a sitting area with desk, vanity, and seating. All staterooms have their own thermostat-controlled air-conditioning, telephone, television with DVD player, private safe, and hairdryer. 2 Inside Staterooms (Inside/no porthole = cabin 404 & 406) feature Two Twin beds that convert to a double (no portlight) ample closet and storage space, private bathroom with shower, and a sitting area with desk, vanity, and seating. All staterooms have their own thermostat-controlled air-conditioning, telephone, television with DVD player, private safe, and hair dryer. The inside Category 5 is also equipped with an additional Pullman bed (upper bunk) to accommodate a third guest/child.
Star Flyer, Star Clipper Cabin 4
Category 4
Located on the Commodore Deck, 20 Outside Staterooms with 1 Portlight, two twin beds that convert to a double, ample closet and storage space, a private bathroom with shower, and a sitting area with desk, vanity, and seating. All staterooms have their own thermostat-controlled air-conditioning, telephone, television with DVD player, private safe, and hairdryer. Some staterooms are equipped with additional bedding (upper Pullman-upper bunk bed) to accommodate a third guest.
Star Flyer, Star Clipper Cabin Category 3
Category 3
Located on the Clipper & Commodore Decks, 20 Outside Staterooms with 1 Portlight, two twin beds that convert to a double, ample closet and storage space, private bathroom with shower, and a sitting area with desk, vanity, and seating. All staterooms have their own thermostat-controlled air-conditioning, telephone, television with DVD player, private safe, and hairdryer. Some staterooms are equipped with additional bedding (upper Pullman-upper bunk bed) to accommodate a third guest
Star Flyer, Star Clipper Cabin Category 2
Category 2
Located on the Clipper Deck, 24 Outside Staterooms with 1 Portlight, two twin beds that convert to a double, ample closet and storage space, a private bathroom with shower, and a sitting area with desk, vanity, and seating. All staterooms have their own thermostat-controlled air-conditioning, telephone, television with DVD player, private safe, and hairdryer. Some staterooms are equipped with additional bedding (upper Pullman-upper bunk bed) to accommodate a third guest.
Star Flyer, Star Clipper Cabin Category 1
Category 1
Located on the Main & Sun Decks, 8 Outside Staterooms (with 1 Window + 1 Portlight) located on the Main deck - have a full windowed door leading to the main deck, two lower beds that convert into a double-sized bed, ample closet and storage space, private bathroom with whirlpool tub and shower, and a living area with desk, vanity, and sofa. All deluxe staterooms have their own thermostat-controlled air-conditioning, mini bar, telephone, television with DVD player, private safe, hairdryer, bathrobes.
Star Flyer Owner's Cabin
Owner's Cabin (Double)
Located on the Clipper Deck, Cabin with 4 Portlights, one fixed double-sized bed, ample closet and storage space, private bathroom with whirlpool tub and shower, and a spacious living area with desk, vanity, and wrap-around sectional sofa. All suites have their own thermostat-controlled air-conditioning, mini bar, telephone, television with DVD player, private safe, hairdryer, bathrobes. Cabin Stewart service and complimentary mini-bar (an exception to champagne)

Notes

Single supplement: A single supplement fare is available at 150% of the published cruise fare for categories 2-6. It is available at 200% for category 1 cabins, Deluxe Suites, and Owner's Suites. Single space is capacity controlled and may not be available on all departures.
Included
  • 7 Breakfasts, 6 Lunches, 7 Dinners
  • 7 Nights Accommodations
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • Port Fees
  • All meals and snacks (open seating) including: Coffee and tea are available 24 hours a day. Different juices are included only for breakfast.
  • Ocean transportation to remote ports.
  • Complimentary snorkeling, kayaks, paddle boarding, water-skiing, windsurfing, and sunfish sailing (subject to weather conditions and local authorities).
Excluded
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)
  • Gratuities
  • Visa
  • All transfers to/from the boat from airports.
  • Laundry services 
  • Medical services
  • Shore Excursions
  • Alcoholic drinks and sodas.

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The trip might have been the absolute best of our lifetime (thus far). We particularly want to commend our guide Peter in the Guilin area-he was so incredibly attentive, energetic, enthusiastic-and absolutely dedicated to ensuring that our meals were 100% vegetarian.
Jack Charney

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