YACHTSMAN'S CARIBBEAN

  • Wind Surf
  • 7 days
  • St. Maarten to St. Maarten
From $ 2,499 pp
Itinerary & Ports
date
port
arrive
depart
Dec 29 Sat
7:00 PM
Dec 30 Sun
7:00 AM
12:30 PM
Dec 30 Sun
3:00 PM
11:59 PM
Dec 31 Mon
12:01 AM
6:00 AM
Dec 31 Mon
9:00 AM
11:59 PM
Jan 1 Tue
12:01 AM
5:00 AM
Jan 1 Tue
9:00 AM
6:00 PM
Jan 2 Wed
At Sea
Jan 3 Thu
8:00 AM
10:00 PM
Jan 4 Fri
8:00 AM
10:00 PM
Jan 5 Sat
6:00 AM
SAT DEC 29
TO 7:00 PM St. Maarten

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.
SUN DEC 30
7:00 AM TO 12:30 PM Road Town

day 2 Road Town, Tortola, British Virgin Islands


Road Town
Situated on lovely horseshoe-shaped Road Harbour, Road Town offers a variety of shops along the harbor’s edge, including the charming Crafts Alive Village, a collection of small shops offering a variety of local crafts and the Village Cay Complex with restaurants and bars full of local flavor.  Other sites to see include Main Street, The Old Government House and Waterfront Drive.
SUN DEC 30
3:00 PM TO 11:59 PM Norman Island

day 2 Norman Island


Norman Island
One of the islands reputed to be inspiration for Robert Lewis Stevenson’s Treasure Island, Norman Island is today, uninhabited and privately owned. It is popular for its three water level caves found at the base of cliffs near Bight that are ideal for snorkeling. The only permanent inhabitants here are wild goats, but you can find fun dining on the only two restaurants on this hidden island.
MON DEC 31
12:01 AM TO 6:00 AM Norman Island

day 3 Norman Island


Norman Island
One of the islands reputed to be inspiration for Robert Lewis Stevenson’s Treasure Island, Norman Island is today, uninhabited and privately owned. It is popular for its three water level caves found at the base of cliffs near Bight that are ideal for snorkeling. The only permanent inhabitants here are wild goats, but you can find fun dining on the only two restaurants on this hidden island.
MON DEC 31
9:00 AM TO 11:59 PM Jost Van Dyke, Great Harbour

day 3 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. 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 ship aglow in the harbor. 
TUE JAN 1
12:01 AM TO 5:00 AM 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. 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 ship aglow in the harbor. 
TUE JAN 1
9:00 AM TO 6:00 PM Virgin Gorda

day 4 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 ship 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 JAN 3
8:00 AM TO 10:00 PM Falmouth Harbour

day 6 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 JAN 4
8:00 AM TO 10:00 PM Gustavia

day 7 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. 
SAT JAN 5
6:00 AM TO St. Maarten

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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