No Avoya Fees on Cruises or Tours. Book, change, or cancel without paying any Avoya fees. Plus, our Low Price Guarantee! No Avoya Fees on Cruises or Tours. Click Here!

An Independent Agency in
the Avoya Travel Network

Speak To A Vacation Planner Now

9202778152

Call

Cheryl Skinner: 920-277-8152

Avoya Customer Care: 800-788-0970

Call

Speak To A Vacation Planner

9202778152

No Avoya Fees on Cruises or Tours. Book, change, or cancel without paying any Avoya fees. Plus, our Low Price Guarantee! No Avoya Fees on Cruises or Tours. Click Here!

28 Night Caribbean Cruise

28-Night Caribbean Cruise

Departs Saint Maarten (Phillipsburg), Netherlands Antilles

Sailing Jan 4 - Feb 1, 2026

Windstar Cruises - Wind Surf

4.7 (148)

Prices from

$15,895

28-Night Caribbean Cruise

Name: 28-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 15895 USD
Availability: InStock
Rating: 4.66 (148 reviews)

Windstar Cruises - Wind Surf

Speak To A Vacation Planner

9202778152 920-277-8152

Unlock Avoya Member pricing for free to see if you qualify for special deals.

Cruise prices are constantly changing click here to get live pricing.

Oceanview

From

$15,895

Suite

Call Us

Cruise Itinerary

Departs Saint Maarten (Phillipsburg), Netherlands Antilles

Sailing Jan 4 - Feb 1, 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

Ship Reviews

4.7 (148)

* All reviews are by verified customers that have traveled by booking through a travel agent in the Avoya Network

View All Reviews

customers say

Windstar's Wind Surf receives overwhelmingly positive reviews for its attentive service, excellent food, and unique itineraries that visit smaller, less crowded ports. Guests consistently praise the crew's friendliness and professionalism, the ship's cleanliness, and the intimate, relaxed atmosphere. Some areas for improvement include the ship's aging facilities, expensive excursions and extras, and inconsistent internet service. Overall, most guests highly recommend Wind Surf and look forward to sailing with Windstar again.

AI-generated from the text of customer reviews

select to learn more