GRAND CARIBBEAN HOLIDAY

  • Wind Surf
  • 15 days
  • Philipsburg to Philipsburg
Itinerary & Ports
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Grand Caribbean Holiday

  • Wind Surf
  • 15 days
  • Philipsburg to Philipsburg
select departure date:

date
port
arrive
depart
Dec 23 Fri
7:00 PM
Dec 24 Sat
8:00 AM
11:59 PM
Dec 25 Sun
At Sea
Dec 26 Mon
8:00 AM
6:00 PM
Dec 26 Mon
7:00 PM
11:59 PM
Dec 27 Tue
12:01 PM
3:00 PM
Dec 27 Tue
6:00 PM
11:59 PM
Dec 28 Wed
12:01 PM
5:00 PM
Dec 29 Thu
8:00 AM
10:00 PM
Dec 30 Fri
6:00 AM
7:00 PM
Dec 31 Sat
8:00 AM
11:59 PM
Jan 1 Sun
8:00 AM
5:00 PM
Jan 2 Mon
8:00 AM
5:00 PM
Jan 3 Tue
8:00 AM
4:00 PM
Jan 4 Wed
8:00 AM
6:00 PM
Jan 5 Thu
8:00 AM
10:00 PM
Jan 6 Fri
8:00 AM
10:00 PM
Jan 7 Sat
6:00 AM
FRI DEC 23
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 24
8:00 AM TO 11:59 PM Falmouth Harbour

day 2 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.
MON DEC 26
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 26
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 27
12:01 PM 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 27
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 28
12:01 PM 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 29
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. 
FRI DEC 30
6:00 AM TO 7:00 PM 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.
SAT DEC 31
8:00 AM TO 11:59 PM Falmouth Harbour

day 9 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.
SUN JAN 1
8:00 AM TO 5:00 PM Barbuda

day 10 Barbuda, Barbuda


Barbuda, Barbuda
This picturesque island is what most cruisers are looking for but won’t find, because most cruise ships don’t stop here. (They can’t.) Life here is sleepy, laid-back, unspoiled — pick your adjective. There are a few ruins from plantation days, but mostly the entertainment is of the do-it-yourself variety: watching plumes of white spray splash up from the reef, collecting conch shells, or if you’re feeling ambitious, a trip to the Frigate Bird Sanctuary to watch the giant-winged avians harass other seabirds for their catches like the man o’ wars they’re nicknamed for. The only thing that can be really called grand (aside from the island’s beauty) is the 20-mile stretch of pink sand beach that greets us when we arrive.
MON JAN 2
8:00 AM TO 5:00 PM Roseau

day 11 Roseau, Dominica


Roseau, Dominica
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trios Pitons National Park, a UNESCO World Heritage Site. 
TUE JAN 3
8:00 AM TO 4:00 PM Pigeon Island

day 12 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.
WED JAN 4
8:00 AM TO 6:00 PM Les Saintes

day 13 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.
THU JAN 5
8:00 AM TO 10:00 PM Basseterre

day 14 Basseterre, St. Kitts


Basseterre, St. Kitts
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site. 
FRI JAN 6
8:00 AM TO 10:00 PM Gustavia

day 15 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 7
6:00 AM TO Philipsburg

day 16 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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