Eastern Caribbean • Dec 2027 • 8 nights • Windstar Cruises • Philipsburg

Philipsburg → San José → Jeju → Philipsburg

via Road Bay, Spanish Town (Virgin Gorda), Jost Van Dyke, and 1 more

Wind Surf

8 nights

December 19–27, 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 $3,508, compared with a typical fare of $3,508. This matches the lowest price we've tracked over the past 90 days.

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Wind Surf • December 19, 2027 • departs in about 1 year

Last 90 days

What should you book?

Oceanview is the sweet spot at $3,508.

A suite jumps another $960 ($120/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$3,508

$439/night

Balcony

Unavailable

—

Suite

Insufficient history

$4,468

$559/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), Costa Rica, and Anguilla, and 2 other countries

  • 8 nights
  • 7 ports
  • 1 sea day
  • 5 Masted Motor Sailing Ship-class ship
  • One-way sailing
  • Philipsburg ↔

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Embark port
Disembark port
Port of call

Route

Philipsburg → San José → Road Bay → Jost Van Dyke → Sopers Hole + 4 more

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

    San José, Costa Rica

    Monday, Dec 20, 2027

    Arr 8:00 AM
    Dep 10:00 PM
  3. 3

    At sea

    Tuesday, Dec 21, 2027

  4. 4

    Road Bay, Anguilla

    Wednesday, Dec 22, 2027

    Arr 8:00 AM
    Dep 6:00 PM
  5. 5
    Arr 7:00 PM
    Dep 12:00 AM
  6. 5

    Sopers Hole, Virgin Islands, British

    Thursday, Dec 23, 2027

    Arr 8:00 AM
    Dep 6:00 PM
  7. 6
    Arr 12:00 AM
    Dep 10:00 PM
  8. 7
    Arr 8:00 AM
    Dep 5:00 PM
  9. 8

    Jeju, South Korea

    Sunday, Dec 26, 2027

    Arr 8:00 AM
    Dep 9:00 PM
  10. 9
    Arr 6:00 AM
    Dep 12:00 AM

Embarks in Philipsburg, Sint Maarten (Dutch part) • ends in Philipsburg, Sint Maarten (Dutch part) • 7 ports of call • 1 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 · $3,508

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