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Itinerary & Ports
date
port
arrive
depart
Dec 19 Sat
7:00 PM
 
Dec 20 Sun
12:00 PM
7:00 PM
 
Dec 21 Mon
9:00 AM
5:00 PM
Dec 22 Tue
10:00 AM
10:00 PM
Dec 23 Wed
8:00 AM
6:00 PM
 
Dec 24 Thu
8:00 AM
4:00 PM
 
Dec 25 Fri
At Sea
Dec 26 Sat
7:00 AM
11:59 PM
 
Dec 27 Sun
8:00 AM
5:00 PM
Dec 28 Mon
8:00 AM
6:00 PM
 
Dec 29 Tue
8:00 AM
5:00 PM
Dec 30 Wed
7:00 AM
11:59 PM
Jan 1 Fri
12:01 AM
1:00 AM
Jan 1 Fri
1:00 PM
9:00 PM
Jan 2 Sat
7:00 AM
 
SAT DEC 19
TO 7:00 PM San Juan

day 1 San Juan, Puerto Rico


San Juan, Puerto Rico
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan. 
SUN DEC 20
12:00 PM TO 7:00 PM St. Maarten

day 2 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.
MON DEC 21
9:00 AM TO 5:00 PM Les Saintes

day 3 Les Saintes, Guadeloupe


Les Saintes, Guadeloupe
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
TUE DEC 22
10:00 AM TO 10:00 PM Bequia

day 4 Bequia, St. Vincent & the Grenadines


Bequia, St. Vincent & the Grenadines
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces. 
WED DEC 23
8:00 AM TO 6:00 PM St. George's

day 5 St. George's, Grenada


St. George's, Grenada
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must. 
THU DEC 24
8:00 AM TO 4:00 PM Pigeon Island

day 6 Pigeon Island, St. Lucia


Pigeon Island, St. Lucia
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
SAT DEC 26
7:00 AM TO 11:59 PM San Juan

day 8 San Juan, Puerto Rico


San Juan, Puerto Rico
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan. 
SUN DEC 27
8:00 AM TO 5:00 PM Virgin Gorda

day 9 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.
MON DEC 28
8:00 AM TO 6:00 PM St. Maarten

day 10 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.
TUE DEC 29
8:00 AM TO 5:00 PM Little Bay

day 11 Little Bay, Montserrat, BWI


Little Bay, Montserrat, BWI
Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
WED DEC 30
7:00 AM TO 11:59 PM Gustavia

day 12 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 JAN 1
12:01 AM TO 1:00 AM Gustavia

day 14 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 JAN 1
1:00 PM TO 9:00 PM Jost Van Dyke, Great Harbour

day 14 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. 
SAT JAN 2
7:00 AM TO San Juan

day 15 San Juan, Puerto Rico


San Juan, Puerto Rico
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan. 

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