Eastern Caribbean • Jan 2028 • 13 nights • Windstar Cruises • Philipsburg

Philipsburg → Road Bay → Terre-de-Haut (Les Saintes) → Philipsburg

via Jost Van Dyke, Roseau, Spanish Town (Virgin Gorda), and 3 more

Wind Surf

13 nights

January 3–16, 2028

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 $4,085, compared with a typical fare of $4,085. This matches the lowest price we've tracked over the past 90 days.

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Wind Surf • January 03, 2028 • departs in about 1 year

Last 90 days

What should you book?

Oceanview is the sweet spot at $4,085.

A suite jumps another $975 ($75/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$4,085

$314/night

Balcony

Unavailable

—

Suite

Insufficient history

$5,060

$389/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), Anguilla, and Virgin Islands, British, and 3 other countries

  • 13 nights
  • 8 ports
  • 4 sea days
  • 5 Masted Motor Sailing Ship-class ship
  • Philipsburg ↔

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Embark port
Disembark port
Port of call

Route

Philipsburg → Road Bay → Jost Van Dyke → Spanish Town (Virgin Gorda) → Sopers Hole + 5 more

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

    Road Bay, Anguilla

    Tuesday, Jan 4, 2028

    Arr 8:00 AM
    Dep 6:00 PM
  3. 3

    At sea

    Wednesday, Jan 5, 2028

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

    Sopers Hole, Virgin Islands, British

    Saturday, Jan 8, 2028

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

    Jeju, South Korea

    Monday, Jan 10, 2028

    Arr 8:00 AM
    Dep 5:00 PM
  9. 9

    Roseau, Dominica

    Tuesday, Jan 11, 2028

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

    At sea

    Wednesday, Jan 12, 2028

  11. 11
    Arr 12:00 PM
    Dep 6:00 PM
  12. 12

    At sea

    Friday, Jan 14, 2028

  13. 13

    At sea

    Saturday, Jan 15, 2028

  14. 14
    Arr 6:00 AM
    Dep 12:00 AM

Embarks in Philipsburg, Sint Maarten (Dutch part) • ends in Philipsburg, Sint Maarten (Dutch part) • 8 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 →

Oceanview · $4,085

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