Eastern Caribbean • Feb 2027 • 7 nights • Windstar Cruises • Philipsburg

Philipsburg → Sopers Hole → Road Bay → Philipsburg

via Jost Van Dyke, Spanish Town (Virgin Gorda)

Wind Surf

7 nights

February 27–March 6, 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 $3,253, compared with a typical fare of $3,253. This matches the lowest price we've tracked over the past 90 days.

Loading...

Wind Surf • February 27, 2027 • departs in 5 months

Last 90 days

What should you book?

Oceanview is the sweet spot at $3,253.

A suite jumps another $840 ($120/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$3,253

$465/night

Balcony

Unavailable

—

Suite

Insufficient history

$4,093

$585/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), Virgin Islands, British, and Anguilla

  • 7 nights
  • 5 ports
  • 2 sea days
  • 5 Masted Motor Sailing Ship-class ship
  • Philipsburg ↔

Loading map...

Embark port
Disembark port
Port of call

Route

Philipsburg → Sopers Hole → Jost Van Dyke → Spanish Town (Virgin Gorda) → Road Bay + 1 more

Expand full itinerary
  1. 1
    Arr 1:00 PM
    Dep 7:00 PM
  2. 2
    Arr 8:00 AM
    Dep 6:00 PM
  3. 2
    Arr 7:00 PM
    Dep 12:00 AM
  4. 3
    Arr 12:00 AM
    Dep 10:00 PM
  5. 4
    Arr 7:00 AM
    Dep 5:00 PM
  6. 5

    At sea

    Wednesday, Mar 3, 2027

  7. 6

    Road Bay, Anguilla

    Thursday, Mar 4, 2027

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

    At sea

    Friday, Mar 5, 2027

  9. 8
    Arr 6:00 AM
    Dep 12:00 AM

Embarks in Philipsburg, Sint Maarten (Dutch part) • ends in Philipsburg, Sint Maarten (Dutch part) • 5 ports of call • 2 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 · $3,253

Booking link not available

Book on Cruisebound