YACHTSMAN'S CARIBBEAN

  • Wind Surf
  • 7 days
  • Philipsburg to Philipsburg
Itinerary & Ports
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Yachtsman's Caribbean

  • Wind Surf
  • 7 days
  • Philipsburg to Philipsburg

date
port
arrive
depart
Dec 9 Fri
7:00 PM
Dec 10 Sat
8:00 AM
11:59 PM
Dec 11 Sun
12:01 PM
1:00 PM
Dec 12 Mon
8:00 AM
6:00 PM
Dec 12 Mon
7:00 PM
11:59 PM
Dec 13 Tue
12:01 AM
3:00 PM
Dec 13 Tue
6:00 PM
11:59 PM
Dec 14 Wed
12:01 AM
5:00 PM
Dec 15 Thu
10:00 AM
6:00 PM
Dec 16 Fri
6:00 AM
FRI DEC 9
TO 7:00 PM Philipsburg

day 1 Philipsburg, St. Maarten


Philipsburg, St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
SAT DEC 10
8:00 AM TO 11:59 PM Gustavia

day 2 Gustavia, St. Barthélemy


Gustavia, St. Barthélemy
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by. 
SUN DEC 11
12:01 PM TO 1:00 PM Gustavia

day 3 Gustavia, St. Barthélemy


Gustavia, St. Barthélemy
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by. 
MON DEC 12
8:00 AM TO 6:00 PM Soper's Hole

day 4 Soper's Hole, Tortola, B.V.I.


Soper's Hole, Tortola, B.V.I.
Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime sunset Sail Away and cruise that glides along Sir Francis Drake Channel and on through “The Narrows.” 
MON DEC 12
7:00 PM TO 11:59 PM Jost Van Dyke, Great Harbour

day 4 Jost Van Dyke, Great Harbour, B.V.I.


Jost Van Dyke, Great Harbour, B.V.I.
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. An overnight stay gives you ample time to visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar yacht aglow in the harbor. 
TUE DEC 13
12:01 AM TO 3:00 PM Jost Van Dyke, Great Harbour

day 5 Jost Van Dyke, Great Harbour, B.V.I.


Jost Van Dyke, Great Harbour, B.V.I.
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. An overnight stay gives you ample time to visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar yacht aglow in the harbor. 
TUE DEC 13
6:00 PM TO 11:59 PM Virgin Gorda

day 5 Virgin Gorda, Prickly Pear Beach, B.V.I


Virgin Gorda, Prickly Pear Beach, B.V.I
A beautiful coral reef wavers just beneath you as your yacht makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
WED DEC 14
12:01 AM TO 5:00 PM Virgin Gorda

day 6 Virgin Gorda, Prickly Pear Beach, B.V.I


Virgin Gorda, Prickly Pear Beach, B.V.I
A beautiful coral reef wavers just beneath you as your yacht makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
THU DEC 15
10:00 AM TO 6:00 PM Falmouth Harbour

day 7 Falmouth Harbour, Antigua


Falmouth Harbour, Antigua
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches to midnight to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
FRI DEC 16
6:00 AM TO Philipsburg

day 8 Philipsburg, St. Maarten


Philipsburg, St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

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