1300 052 966

Philipsburg, St. Maarten to Oranjestad

  • 4 Jan ‘26
  • 28 nights
  • Departing from Philipsburg
  • Wind Surf
  • Inside price from
    Call for price
  • Outside price from
    $9,099*/pp
  • Balcony price from
    Call for price
  • Suite price from
    $11,899*/pp

YOUR ITINERARY

Philipsburg, St. Martin - Falmouth, Antigua - Road Bay, Anguilla - Soper'S Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I - Jost Van Dyke, B.V.I - Virgin Gorda, B.V.I - Gustavia, St. Barthelemy - Philipsburg, St. Martin - Basseterre, St. Kitts - Little Bay, Montserrat, Bwi - Gustavia, St. Barthelemy - Les Saintes, F.W.I. - Roseau, Dominica - Pigeon Island, St.Lucia - Bridgetown, Barbados - Anse Mitan, Martinique - Castries, St. Lucia - Pigeon Island, St.Lucia - Pigeon Island, St.Lucia - Bequia, Grenadines - Mayreau, Grenadines - St Georges, Grenada - Bridgetown, Barbados - Man-o-War Bay, Charlotteville, Tobago - Mayreau, Grenadines - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba

Leaflet | © OpenStreetMap contributors © CARTO
Date
Port
Info
Arrive
Depart
Day 1
4th Jan 2026
Philipsburg, St. Martin

Philipsburg is the capital of Sint Maarten, the Dutch side of t...

Arrive
Depart
19:00
Day 2
5th Jan 2026
Falmouth, Antigua

Surrounded by many abandoned sugar mills, the small village o...

Arrive
08:00
Depart
18:00
Day 3
6th Jan 2026
Road Bay, Anguilla
Arrive
08:00
Depart
18:00
Day 4
7th Jan 2026
Soper'S Hole, Tortola, B.V.I.

Soper’s Hole Marina is arguably one of the most picturesq...

Arrive
08:00
Depart
18:00
Day 4
7th Jan 2026
Jost Van Dyke, B.V.I

Inviting beaches and tiny shops selling local treasures wel...

Arrive
19:00
Depart
Day 5
8th Jan 2026
Jost Van Dyke, B.V.I

Inviting beaches and tiny shops selling local trea...

Arrive
Depart
22:00
Day 6
9th Jan 2026
Virgin Gorda, B.V.I

The most chic resorts of the British Virgin Isles are...

Arrive
08:00
Depart
17:00
Day 7
10th Jan 2026
Gustavia, St. Barthelemy

Gustavia is the main town and capital of the island of S...

Arrive
08:00
Depart
22:00
Day 8
11th Jan 2026
Philipsburg, St. Martin

Philipsburg is the capital of Sint Maarten, the Dutch si...

Arrive
06:00
Depart
Day 9
12th Jan 2026
Basseterre, St. Kitts

Basseterre, set against the irresistible backdrop of ...

Arrive
08:00
Depart
21:00
Day 10
13th Jan 2026
Little Bay, Montserrat, Bwi

Little Bay is a town under construction, intended to be ...

Arrive
08:00
Depart
18:00
Day 11
14th Jan 2026
Gustavia, St. Barthelemy

Gustavia is the main town and capital of the island ...

Arrive
08:00
Depart
23:00
Day 12
15th Jan 2026
Les Saintes, F.W.I.

The Îles des Saintes, or Les Saintes, are dependency i...

Arrive
08:00
Depart
17:00
Day 13
16th Jan 2026
Roseau, Dominica

Roseau is the capital of the Caribbean island nation of D...

Arrive
08:00
Depart
17:00
Day 14
17th Jan 2026
Pigeon Island, St.Lucia

The twin towers of the Pitons, two volcanic peaks rising to...

Arrive
07:00
Depart
16:00
Day 15
18th Jan 2026
Bridgetown, Barbados

An infectiously happy island, with beautiful beac...

Arrive
05:00
Depart
18:00
Day 16
19th Jan 2026
Anse Mitan, Martinique

This is the Caribbean of days gone by – deep blue wat...

Arrive
09:00
Depart
23:00
Day 17
20th Jan 2026
Castries, St. Lucia

Castries is the capital of the island nation of St. Luc...

Arrive
08:00
Depart
16:00
Day 17
20th Jan 2026
Pigeon Island, St.Lucia

The twin towers of the Pitons, two volcanic peaks rising t...

Arrive
18:00
Depart
Day 18
21st Jan 2026
Pigeon Island, St.Lucia

The twin towers of the Pitons, two volcanic peaks...

Arrive
Depart
18:00
Day 19
22nd Jan 2026
Bequia, Grenadines

Life in Bequia revolves around the sea. Walk through the pret...

Arrive
08:00
Depart
22:00
Day 20
23rd Jan 2026
Mayreau, Grenadines

In the north of Mayreau is Salt Whistle Bay, a per...

Arrive
08:00
Depart
18:00
Day 21
24th Jan 2026
St Georges, Grenada

St. George’s is the capital city of the Car...

Arrive
07:00
Depart
14:00
Day 22
25th Jan 2026
Bridgetown, Barbados

An infectiously happy island, with beautiful beaches, balmy ...

Arrive
06:00
Depart
18:00
Day 23
26th Jan 2026
Man-o-War Bay, Charlotteville, Tobago

The large, horseshoe-shaped Man of War Bay is frin...

Arrive
08:00
Depart
17:00
Day 24
27th Jan 2026
Mayreau, Grenadines

In the north of Mayreau is Salt Whistle Bay, a perfect half m...

Arrive
08:00
Depart
18:00
Day 25
28th Jan 2026
Soufriere, St. Lucia

Soufrière is a town on the West Coast of Saint Lucia,...

Arrive
08:00
Depart
16:00
Day 27
30th Jan 2026
Kralendijk, Bonaire

Kralendijk is the capital of Bonaire, a Dutch island ...

Arrive
13:00
Depart
22:00
Day 28
31st Jan 2026
Willemstad, Curacao

The people of the Netherlands established a tradi...

Arrive
08:00
Depart
18:00
Day 29
1st Feb 2026
Oranjestad, Aruba

When it comes to the Caribbean, many islands are bles...

Arrive
06:00
Depart
18:00

YOUR SHIP - The Wind Surf

On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Description

On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Relaxation

Hot Tubs
Massage
Spa
Whirlpool

Recreational

Library
Outdoor Pool

Food and Drink

Bar
Compass Rose
Degrees
Poolside Bar
Terrace Bar
Veranda

STATEROOMS

    suite

    outside

ENQUIRE TO BOOK THIS CRUISE https://cruiseabout.cruiseappy.com/wp-content/uploads/2024/01/1586160270.png

Thank you!

Thank you for your enquiry. We look forward to helping you find the perfect cruise experience.

Thank you for your secured booking deposit request. We will be in touch shortly to confirm your booking.

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Traveller information

2
  • Adults
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
Children (under 18yrs)
  • Children (under 18yrs)
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
Infants (under 2yrs)
  • Infants (under 2yrs)
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
Number of staterooms
  • Number of staterooms
  • 1
  • 2
  • 3
  • 4
Stateroom Type
  • Stateroom Type
  • Inside
  • Oceanview
  • Balcony
  • Suite

Additional information

Call 1300 052 966 or enquire to book this cruise

If you have any questions, please call 1300 052 966