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Stroll along the beautiful beaches of the Caribbean

Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - Example 21 Day Cruise aboard Star Flyer
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Embark on a 21-day cruise aboard the Star Flyer. Begin in Philipsburg with access to the island's Dutch and French sides. Spend 18 days at sea and enjoy relaxing lounges and open-deck pools. Visit Ponta Delgada in the Azores, a historical Atlantic hub with preserved 16th- and 17th-century architecture. Conclude in Malaga, Spain, known for its Moorish landmarks including the Alcazaba and nearby Alhambra Palace in Granada. This itinerary blends open-water sailing with cultural discovery across the Atlantic.
An aerial view of the city MalagaImmerse yourself in the spectacular charm of the Atlantic OceanColorful shores of the AzoresOcean viewsSunset over PhilipsburgRelax on the beaches of St. MaartenAdmire sun-soaked MalagaStroll along the beautiful beaches of the Caribbean
Highlights
  • Explore Philipsburg’s Dutch side with a vibrant Caribbean atmosphere
  • Experience Marigot’s French style and open-air seaside markets
  • Unwind poolside while crossing the Atlantic with steady trade winds
  • Visit Ponta Delgada’s historic churches and leafy island landscapes
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

The world's smallest island divided between two nations, St. Martin/St. Maarten offers a major shopping experience. Choose the Dutch charm of Philipsburg or the French flair of Marigot—either way, you're warmly received.

Day 2-13: At Sea

Each Star Clippers ship offers a traditional and elegant way to see the world. Feel the wind fill the sails and gently carry you from one gorgeous destination to the next. During your time on board, you can choose to relax on a sun lounger or cool off in one of the pools on the top deck, while more adventurous passengers may enjoy the opportunity to climb the rigging or even have a go at steering the ship. Alternatively, you can wander the interior areas of the ship and discover relaxing lounges, and a peaceful library.

Day 14: Ponta Delgada, Azores

The Azores have long played host to transatlantic yachtsmen, traders and explorers. It stands on the pretty green and fertile island of Sao Miguel. 16th and 17th century economic growth saw the construction of lavish palaces and churches, many still surviving.

Day 15-20: At Sea

Each Star Clippers ship offers a traditional and elegant way to see the world. Feel the wind fill the sails and gently carry you from one gorgeous destination to the next. During your time on board, you can choose to relax on a sun lounger or cool off in one of the pools on the top deck, while more adventurous passengers may enjoy the opportunity to climb the rigging or even have a go at steering the ship. Alternatively, you can wander the interior areas of the ship and discover relaxing lounges, and a peaceful library.

Day 21: Malaga, Spain | Disembark

  • 1 Breakfast
Malaga's fortress palace of the Alcazaba and the Castillo de Gibralfaro are splendid examples of Moorish architecture. But it is in Granada that you can see the most romantic and magnificent expression of the Arabesque style in the glorious Alhambra Palace.

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

  • Mar 21, 2026from $3,420
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Star Flyer Category 6 Cabin
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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
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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
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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
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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
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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
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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
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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
  • 20 Breakfasts, 19 Lunches, 20 Dinners
  • 20 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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Our guide and driver were very good with their knowledge and were very helpful with our questions. It was a very pleasant visit that would have been impossible to do on our own. Hotels and restaurants were fantastic. The special places we got to go to, like the kitchens, were great. Enjoyed the entire trip!
Meyer Smolen

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