Eastern Caribbean • Mar 2028 • 21 nights • Windstar Cruises • Philipsburg

Philipsburg → San José → Funchal, Madeira → Lisbon

via Jost Van Dyke, Philipsburg, Sopers Hole, Road Bay, and 1 more

Wind Surf

21 nights

March 12–April 2, 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 $4,168, compared with a typical fare of $4,278. This matches the lowest price we've tracked over the past 90 days.

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Wind Surf • March 12, 2028 • departs in over 1 year

Last 90 days

What should you book?

Oceanview is the sweet spot at $4,168.

A suite jumps another $2,090 ($100/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$4,168

$198/night

Balcony

Unavailable

—

Suite

Insufficient history

$6,258

$298/night

Prices were last updated about 6 hours ago.

What kind of trip is this?

View itinerary profile →

Balanced itinerary with stops in Sint Maarten (Dutch part), Costa Rica, and Virgin Islands, British, and 2 other countries

  • 21 nights
  • 8 ports
  • 13 sea days
  • 5 Masted Motor Sailing Ship-class ship
  • Atlantic crossing
  • Philipsburg → Lisbon

Loading map...

Embark port
Disembark port
Port of call

Route

Philipsburg → San José → Jost Van Dyke → Sopers Hole → Jost Van Dyke + 5 more

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

    San José, Costa Rica

    Monday, Mar 13, 2028

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

    At sea

    Tuesday, Mar 14, 2028

  4. 4

    Jost Van Dyke, Virgin Islands, British

    Wednesday, Mar 15, 2028

    Arr 7:00 PM
    Dep 12:00 AM
  5. 4

    Sopers Hole, Virgin Islands, British

    Wednesday, Mar 15, 2028

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

    Road Bay, Anguilla

    Saturday, Mar 18, 2028

    Arr 8:00 AM
    Dep 10:00 PM
  9. 8
    Arr 6:00 AM
    Dep 4:00 PM
  10. 9

    At sea

    Monday, Mar 20, 2028

  11. 10

    At sea

    Tuesday, Mar 21, 2028

  12. 11

    Funchal, Madeira, Portugal

    Wednesday, Mar 22, 2028

    Arr 8:00 AM
    Dep 5:00 PM
  13. 12

    At sea

    Thursday, Mar 23, 2028

  14. 13

    Lisbon, Portugal

    Friday, Mar 24, 2028

    Arr 8:00 AM
    Dep 12:00 AM

Embarks in Philipsburg, Sint Maarten (Dutch part) • ends in Lisbon, Portugal • 8 ports of call • 13 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 · $4,168

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