Transpacific • Dec 2027 • 15 nights • Windstar Cruises • Philipsburg

Philipsburg → San José → Terre-de-Haut (Les Saintes) → Philipsburg

via Road Bay, Roseau, Sopers Hole, Philipsburg, and 3 more

Wind Surf

15 nights

December 19, 2027–January 3, 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 $5,370, compared with a typical fare of $5,370. 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 $5,370.

A suite jumps another $1,500 ($100/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$5,370

$358/night

Balcony

Unavailable

—

Suite

Insufficient history

$6,870

$458/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 Anguilla, and 4 other countries

  • 15 nights
  • 11 ports
  • 4 sea days
  • 5 Masted Motor Sailing Ship-class ship
  • Pacific crossing
  • Philipsburg ↔

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Embark port
Disembark port
Port of call

Route

Philipsburg → San José → Road Bay → Sopers Hole → Jost Van Dyke + 7 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

    Sopers Hole, Virgin Islands, British

    Thursday, Dec 23, 2027

    Arr 8:00 AM
    Dep 6:00 PM
  6. 5
    Arr 7:00 PM
    Dep 12:00 AM
  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 7:00 PM
  11. 10

    Jeju, South Korea

    Tuesday, Dec 28, 2027

    Arr 8:00 AM
    Dep 5:00 PM
  12. 11

    Roseau, Dominica

    Wednesday, Dec 29, 2027

    Arr 8:00 AM
    Dep 4:00 PM
  13. 12

    At sea

    Thursday, Dec 30, 2027

  14. 13
    Arr 12:00 PM
    Dep 6:00 PM
  15. 14

    At sea

    Saturday, Jan 1, 2028

  16. 15

    At sea

    Sunday, Jan 2, 2028

  17. 16
    Arr 6:00 AM
    Dep 12:00 AM

Embarks in Philipsburg, Sint Maarten (Dutch part) • ends in Philipsburg, Sint Maarten (Dutch part) • 11 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 · $5,370

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