Eastern Caribbean • Jan 2027 • 7 nights • Windstar Cruises • Philipsburg

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

via Jost Van Dyke, Sopers Hole

Wind Surf

7 nights

January 30–February 6, 2027

Recommendation

Not enough history yet

We need more price history before making a confident recommendation.

  • ✓ Oceanview prices are 7% above their usual range.

Why we're recommending this

Oceanview pricing is $3,323, compared with a typical fare of $3,096.

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Wind Surf • January 30, 2027 • departs in 4 months

Last 90 days

What should you book?

Oceanview is the sweet spot at $3,323.

A suite jumps another $525 ($75/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$3,323

$475/night

Balcony

Unavailable

—

Suite

Insufficient history

$3,848

$550/night

Prices were last updated about 5 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

    Road Bay, Anguilla

    Sunday, Jan 31, 2027

    Arr 8:00 AM
    Dep 6:00 PM
  3. 3
    Arr 7:00 PM
    Dep 12:00 AM
  4. 3
    Arr 8:00 AM
    Dep 6:00 PM
  5. 4
    Arr 12:00 AM
    Dep 10:00 PM
  6. 5
    Arr 8:00 AM
    Dep 10:00 PM
  7. 6

    At sea

    Thursday, Feb 4, 2027

  8. 7

    At sea

    Friday, Feb 5, 2027

  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 · $3,323

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