Eastern Caribbean • Dec 2026 • 7 nights • Windstar Cruises • Philipsburg

Philipsburg → Road Bay → Spanish Town (Virgin Gorda) → Philipsburg

via Jost Van Dyke, Sopers Hole

Wind Surf

7 nights

December 19–26, 2026

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 $3,638, compared with a typical fare of $3,638. This matches the lowest price we've tracked over the past 90 days.

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Wind Surf • December 19, 2026 • departs in 2 months

Last 90 days

What should you book?

Oceanview is the sweet spot at $3,638.

A suite jumps another $840 ($120/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$3,638

$520/night

Balcony

Unavailable

—

Suite

Insufficient history

$4,478

$640/night

Prices were last updated about 4 hours ago.

What kind of trip is this?

View itinerary profile →

Port-heavy itinerary with stops in Sint Maarten (Dutch part), Anguilla, and Virgin Islands, British

  • 7 nights
  • 5 ports
  • 2 sea days
  • 5 Masted Motor Sailing Ship-class ship
  • Round-trip sailing
  • Philipsburg ↔

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Embark port
Disembark port
Port of call

Route

Philipsburg → Road Bay → Jost Van Dyke → Sopers Hole → Jost Van Dyke + 2 more

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

    At sea

    Sunday, Dec 20, 2026

  3. 3

    At sea

    Monday, Dec 21, 2026

  4. 4

    Road Bay, Anguilla

    Tuesday, Dec 22, 2026

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

    Jost Van Dyke, Virgin Islands, British

    Wednesday, Dec 23, 2026

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

    Sopers Hole, Virgin Islands, British

    Wednesday, Dec 23, 2026

    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
    Arr 6:00 AM
    Dep 12:00 AM

Embarks in Philipsburg, Sint Maarten (Dutch part) • ends in Philipsburg, Sint Maarten (Dutch part) • 5 ports of call • 2 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 · $3,638

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