Lisbon → Funchal, Madeira → Jost Van Dyke → Philipsburg

Wind Surf

15 nights

November 5–20, 2027

Jibhop recommendation

Okay to book
Moderate confidence

Prices are close to their usual levels across cabin categories.

  • ✓ Oceanview prices are at a 90-day low.
  • ✓ Overall pricing is close to typical.

What should you book?

No cabin is an amazing value right now.

The oceanview is closest to its usual price, but no tracked cabin looks attractively priced.

All cabin categories

Interior

Unavailable

—

Oceanview

About average

$2,580

$172/night

Balcony

Unavailable

—

Suite

About average

$4,380

$292/night

Prices were last updated about 5 hours ago.

Price history

Why we're recommending this

Oceanview pricing is $2,580, compared with a typical fare of $2,580. This matches the lowest price we've tracked over the past 90 days.

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Wind Surf • November 05, 2027 • departs in about 1 year

Last 90 days

What kind of trip is this?

Sea-day focused itinerary with stops in Portugal, Virgin Islands, British, and Sint Maarten (Dutch part)

Embarks in Lisbon, Portugal • ends in Philipsburg, Sint Maarten (Dutch part) • 2 ports of call • 12 sea days

  • 15 nights
  • 2 ports
  • 12 sea days
  • 5 Masted Motor Sailing Ship-class ship
  • Atlantic crossing
  • Lisbon → Philipsburg

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Embark port
Disembark port
Port of call

Route

Lisbon → Funchal, Madeira → Jost Van Dyke → Philipsburg

Expand full itinerary
  1. 1

    Lisbon, Portugal

    Friday, Nov 5, 2027

    Arr 1:00 PM
    Dep 5:00 PM
  2. 2

    At sea

    Saturday, Nov 6, 2027

  3. 3

    Funchal, Madeira, Portugal

    Sunday, Nov 7, 2027

    Arr 8:00 AM
    Dep 3:00 PM
  4. 4

    At sea

    Monday, Nov 8, 2027

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

    Philipsburg, Sint Maarten (Dutch part)

    Wednesday, Nov 10, 2027

    Arr 6:00 AM

The ship

Wind Surf

Wind Surf is a small ship in Windstar Cruises' fleet.

Guests
376
Built
1990
Tonnage
14,745 GT
Ship details →