YACHTSMAN'S CARIBBEAN

  • Wind Surf
  • 7 days
  • St. Maarten to St. Maarten
From $ 2,499 pp Pick Your Perk
Itinerary & Ports

Yachtsman's Caribbean

  • Wind Surf
  • 7 days
  • St. Maarten to St. Maarten

date
port
arrive
depart
Feb 6 Sat
7:00 PM
 
Feb 7 Sun
8:00 AM
6:00 PM
Feb 8 Mon
8:00 AM
6:00 PM
Feb 8 Mon
7:00 PM
11:59 PM
Feb 9 Tue
12:01 AM
3:00 PM
Feb 9 Tue
6:00 PM
11:59 PM
Feb 10 Wed
12:01 AM
5:00 PM
Feb 11 Thu
8:00 AM
10:00 PM
Feb 12 Fri
8:00 AM
5:00 PM
 
Feb 13 Sat
6:00 AM
 
SAT FEB 6
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 FEB 7
8:00 AM TO 6:00 PM Road Bay

day 2 Road Bay, Anguilla


Road Bay, Anguilla
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
MON FEB 8
8:00 AM TO 6:00 PM Soper's Hole

day 3 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 FEB 8
7:00 PM 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 FEB 9
12:01 AM TO 3:00 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. 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 FEB 9
6:00 PM TO 11:59 PM Virgin Gorda

day 4 Virgin Gorda, B.V.I.


Virgin Gorda, B.V.I.
A beautiful coral reef wavers just beneath you as your ship makes the break into the heart of Spanish Town, the Yacht Harbor Marina, Located to the south of Spanish Town 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 FEB 10
12:01 AM TO 5:00 PM Virgin Gorda

day 5 Virgin Gorda, B.V.I.


Virgin Gorda, B.V.I.
A beautiful coral reef wavers just beneath you as your ship makes the break into the heart of Spanish Town, the Yacht Harbor Marina, Located to the south of Spanish Town 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 FEB 11
8:00 AM TO 10:00 PM Gustavia

day 6 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. 
FRI FEB 12
8:00 AM TO 5:00 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 into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
SAT FEB 13
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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