Eastern Caribbean • Dec 2027 • 15 nights • Windstar Cruises • Philipsburg

Philipsburg → Jeju → Spanish Town (Virgin Gorda) → Philipsburg

via Roseau, Jost Van Dyke, Terre-de-Haut (Les Saintes), and 4 more

Wind Surf

15 nights

December 12–27, 2027

Recommendation

Not enough history yet

We need more price history before making a confident recommendation.

  • ✓ Oceanview prices are at a 90-day low.

Why we're recommending this

Oceanview pricing is $5,145, compared with a typical fare of $5,145. This matches the lowest price we've tracked over the past 90 days.

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Wind Surf • December 12, 2027 • departs in about 1 year

Last 90 days

What should you book?

Oceanview is the sweet spot at $5,145.

A suite jumps another $1,500 ($100/night).

We would wait for more cabin-specific pricing history before making a stronger call.

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$5,145

$343/night

Balcony

Unavailable

—

Suite

Insufficient history

$6,645

$443/night

Prices were last updated about 6 hours ago.

What kind of trip is this?

View itinerary profile →

Port-heavy itinerary with stops in Sint Maarten (Dutch part), South Korea, and Dominica, and 4 other countries

  • 15 nights
  • 11 ports
  • 4 sea days
  • 5 Masted Motor Sailing Ship-class ship
  • Pacific crossing
  • Philipsburg ↔

Loading map...

Embark port
Disembark port
Port of call

Route

Philipsburg → Jeju → Roseau → Terre-de-Haut (Les Saintes) → Philipsburg + 7 more

Expand full itinerary
  1. 1
    Arr 1:00 PM
    Dep 7:00 PM
  2. 2

    Jeju, South Korea

    Monday, Dec 13, 2027

    Arr 8:00 AM
    Dep 5:00 PM
  3. 3

    Roseau, Dominica

    Tuesday, Dec 14, 2027

    Arr 8:00 AM
    Dep 4:00 PM
  4. 4

    At sea

    Wednesday, Dec 15, 2027

  5. 5
    Arr 12:00 PM
    Dep 6:00 PM
  6. 6

    At sea

    Friday, Dec 17, 2027

  7. 7

    At sea

    Saturday, Dec 18, 2027

  8. 8
    Arr 6:00 AM
    Dep 7:00 PM
  9. 9

    San José, Costa Rica

    Monday, Dec 20, 2027

    Arr 8:00 AM
    Dep 10:00 PM
  10. 10

    At sea

    Tuesday, Dec 21, 2027

  11. 11

    Road Bay, Anguilla

    Wednesday, Dec 22, 2027

    Arr 8:00 AM
    Dep 6:00 PM
  12. 12

    Sopers Hole, Virgin Islands, British

    Thursday, Dec 23, 2027

    Arr 8:00 AM
    Dep 6:00 PM
  13. 12
    Arr 7:00 PM
    Dep 12:00 AM
  14. 13
    Arr 12:00 AM
    Dep 10:00 PM
  15. 14
    Arr 8:00 AM
    Dep 5:00 PM
  16. 15

    Jeju, South Korea

    Sunday, Dec 26, 2027

    Arr 8:00 AM
    Dep 9:00 PM
  17. 16
    Arr 6:00 AM
    Dep 12:00 AM

Embarks in Philipsburg, Sint Maarten (Dutch part) • ends in Philipsburg, Sint Maarten (Dutch part) • 11 ports of call • 4 sea days

The ship

Wind Surf

Wind Surf is a small ship in Windstar Cruises' fleet.

Guests
376
Built
1990
Tonnage
14,745 GT
Ship details →

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Oceanview · $5,145

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