Name: 55-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 27646 USD
Availability: InStock
Rating: 4.66 (148 reviews)

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55-Night Caribbean Cruise

Departs Saint Maarten (Phillipsburg), Netherlands Antilles

Sailing Jan 4 - Feb 28, 2026

Windstar Cruises - Wind Surf

4.7148 Reviews

Dates & Pricing

Sail Date

Oceanview

Suite

Sail DateJan 04 - Feb 28, `26

Oceanview

$27,646

Suite

Call Us

Similar Sailings

Cruise Itinerary

Departs Saint Maarten (Phillipsburg), Netherlands Antilles

Sailing Jan 4 - Feb 28, 2026

Day 1

Jan 4

Philipsburg

Sint Maarten

Departs 7:00pm

Day 2

Jan 5

Falmouth Bay

Antigua, Antigua And Barbuda

Arrives 8:00am | Departs 6:00pm

Day 3

Jan 6

Road Bay

Anguilla

Arrives 8:00am | Departs 6:00pm

Day 4

Jan 7

Sopers Hole

Tortola, British Virgin Islands

Arrives 8:00am | Departs 6:00pm

Great Harbour

Jost Van Dyke, British Virgin Islands

Arrives 7:00pm

Day 5

Jan 8

Great Harbour

Jost Van Dyke, British Virgin Islands

Departs 10:00pm

Day 6

Jan 9

Prickly Pear

British Virgin Islands

Arrives 8:00am | Departs 5:00pm

Day 7

Jan 10

Gustavia

Saint Barthélemy, France

Arrives 8:00am | Departs 10:00pm

Day 8

Jan 11

Philipsburg

Sint Maarten

Arrives 6:00am | Departs 7:00pm

Day 9

Jan 12

Basseterre

St. Kitts, St. Kitts And Nevis

Arrives 8:00am | Departs 9:00pm

Day 10

Jan 13

Gustavia

Saint Barthélemy, France

Arrives 8:00am | Departs 10:00pm

Day 11

Jan 14

St. John's

Antigua, Antigua And Barbuda

Arrives 8:00am | Departs 10:00pm

Day 12

Jan 15

îLes Des Saintes

Guadeloupe, France

Arrives 8:00am | Departs 5:00pm

Day 13

Jan 16

Roseau

Dominica

Arrives 8:00am | Departs 4:00pm

Day 14

Jan 17

Mayreau

Saint Vincent And The Grenadines

Arrives 8:00am | Departs 5:00pm

Day 15

Jan 18

Bridgetown

Barbados

Arrives 5:00am | Departs 6:00pm

Day 16

Jan 19

Anse Mitan

Martinique, France

Arrives 9:00am | Departs 11:00pm

Day 17

Jan 20

Castries

St. Lucia

Arrives 8:00am | Departs 4:00pm

Pigeon Island

St. Lucia

Arrives 6:00pm

Day 18

Jan 21

Pigeon Island

St. Lucia

Departs 6:00pm

Day 19

Jan 22

Bequia

Saint Vincent And The Grenadines

Arrives 8:00am | Departs 10:00pm

Day 20

Jan 23

Mayreau

Saint Vincent And The Grenadines

Arrives 8:00am | Departs 6:00pm

Day 21

Jan 24

Saint George's

Grenada

Arrives 7:00am | Departs 2:00pm

Day 22

Jan 25

Bridgetown

Barbados

Arrives 6:00am | Departs 6:00pm

Day 23

Jan 26

Bequia

Saint Vincent And The Grenadines

Arrives 8:00am | Departs 5:00pm

Day 24

Jan 27

Mayreau

Saint Vincent And The Grenadines

Arrives 8:00am | Departs 6:00pm

Day 25

Jan 28

Soufrière

St. Lucia

Arrives 8:00am | Departs 4:00pm

Day 26

Jan 29

At Sea

Day 27

Jan 30

Kralendijk

Bonaire, Netherlands Antilles, Netherlands

Arrives 1:00pm | Departs 10:00pm

Day 28

Jan 31

Willemstad

Curaçao, Curaçao

Arrives 8:00am | Departs 6:00pm

Day 29

Feb 1

Oranjestad

Aruba

Arrives 6:00am | Departs 6:00pm

Day 30

Feb 2

At Sea

Day 31

Feb 3

Cartagena

Colombia

Arrives 8:00am

Day 32

Feb 4

Cartagena

Colombia

Departs 1:00pm

Day 33

Feb 5

San Blas Islands

Panama

Arrives 10:00am | Departs 6:00pm

Day 34

Feb 6

At Sea

Day 35

Feb 7

Bocas Del Toro

Panama

Arrives 7:00am | Departs 3:00pm

Day 36

Feb 8

Colón

Panama

Arrives 8:00am

Day 37

Feb 9

Colón

Panama

Departs 4:00pm

Day 38

Feb 10

Bocas Del Toro

Panama

Arrives 10:00am | Departs 4:00pm

Day 39

Feb 11

San Andrés Island

Colombia

Arrives 1:00pm | Departs 7:00pm

Day 40

Feb 12

At Sea

Day 41

Feb 13

At Sea

Day 42

Feb 14

Coxen Hole

Roatán Island, Honduras

Arrives 9:00am | Departs 5:00pm

Day 43

Feb 15

Belize City

Belize

Arrives 9:00am | Departs 7:00pm

Day 44

Feb 16

Costa Maya

Mexico

Arrives 8:00am | Departs 5:00pm

Day 45

Feb 17

Cozumel

Mexico

Arrives 8:00am | Departs 6:00pm

Day 46

Feb 18

At Sea

Day 47

Feb 19

George Town

Grand Cayman, Cayman Islands

Arrives 8:00am | Departs 6:00pm

Day 48

Feb 20

Cayman Brac

Cayman Islands

Arrives 7:00am | Departs 1:00pm

Day 49

Feb 21

Ocho Rios

Jamaica

Arrives 8:30am | Departs 2:00pm

Day 50

Feb 22

At Sea

Day 51

Feb 23

Santo Domingo

Dominican Republic

Arrives 1:00pm | Departs 10:00pm

Day 52

Feb 24

La Romana

Dominican Republic

Arrives 7:00am | Departs 5:00pm

Day 53

Feb 25

At Sea

Day 54

Feb 26

Great Harbour

Jost Van Dyke, British Virgin Islands

Arrives 8:00am | Departs 10:00pm

Day 55

Feb 27

Prickly Pear

British Virgin Islands

Arrives 8:00am | Departs 5:00pm

Day 56

Feb 28

Philipsburg

Sint Maarten

Arrives 6:00am

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