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

Philipsburg → San José → Spanish Town (Virgin Gorda) → Philipsburg

via Deshaies, Sopers Hole, Road Bay, Jost Van Dyke

Wind Surf

8 nights

November 20–28, 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 $3,028, compared with a typical fare of $3,028. This matches the lowest price we've tracked over the past 90 days.

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Wind Surf • November 20, 2027 • departs in about 1 year

Last 90 days

What should you book?

Oceanview is the sweet spot at $3,028.

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

$3,028

$379/night

Balcony

Unavailable

—

Suite

Insufficient history

$3,988

$499/night

Prices were last updated about 6 hours ago.

What kind of trip is this?

Port-heavy itinerary with stops in Sint Maarten (Dutch part), Costa Rica, and Guadeloupe, and 2 other countries

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

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Embark port
Disembark port
Port of call

Route

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

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

    At sea

    Sunday, Nov 21, 2027

  3. 3

    San José, Costa Rica

    Monday, Nov 22, 2027

    Arr 8:00 AM
    Dep 10:00 PM
  4. 4

    Deshaies, Guadeloupe

    Tuesday, Nov 23, 2027

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

    Road Bay, Anguilla

    Wednesday, Nov 24, 2027

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

    Sopers Hole, Virgin Islands, British

    Thursday, Nov 25, 2027

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

Oceanview · $3,028

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