Eastern Caribbean • Dec 2027 • 13 nights • Windstar Cruises • Philipsburg

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Philipsburg → Jeju → Sopers Hole → Philipsburg

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

Wind Surf

13 nights

December 27, 2027–January 9, 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 $4,280, compared with a typical fare of $4,280. This matches the lowest price we've tracked over the past 90 days.

Wind Surf • December 27, 2027 • departs in about 1 year

Last 90 days

What should you book?

Oceanview is the sweet spot at $4,280.

A suite jumps another $1,235 ($95/night).

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

Other cabin categories

Interior

Unavailable

—

Oceanview

Insufficient history

$4,280

$329/night

Balcony

Unavailable

—

Suite

Insufficient history

$5,515

$424/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), South Korea, and Dominica, 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 → Jeju → Roseau → Terre-de-Haut (Les Saintes) → Philipsburg + 5 more

Expand full itinerary

1

Philipsburg, Sint Maarten (Dutch part)

Monday, Dec 27, 2027

Arr 1:00 PM

Dep 7:00 PM
2

Jeju, South Korea

Tuesday, Dec 28, 2027

Arr 8:00 AM

Dep 5:00 PM
3

Roseau, Dominica

Wednesday, Dec 29, 2027

Arr 8:00 AM

Dep 4:00 PM
4

At sea

Thursday, Dec 30, 2027
5

Terre-de-Haut (Les Saintes), Guadeloupe

Friday, Dec 31, 2027

Arr 12:00 PM

Dep 6:00 PM
6

At sea

Saturday, Jan 1, 2028
7

At sea

Sunday, Jan 2, 2028
8

Philipsburg, Sint Maarten (Dutch part)

Monday, Jan 3, 2028

Arr 6:00 AM

Dep 7:00 PM
9

Road Bay, Anguilla

Tuesday, Jan 4, 2028

Arr 8:00 AM

Dep 6:00 PM
10

At sea

Wednesday, Jan 5, 2028
11

Jost Van Dyke, Virgin Islands, British

Thursday, Jan 6, 2028

Arr 8:00 AM

Dep 10:00 PM
12

Spanish Town (Virgin Gorda), Virgin Islands, British

Friday, Jan 7, 2028

Arr 8:00 AM

Dep 5:00 PM
13

Sopers Hole, Virgin Islands, British

Saturday, Jan 8, 2028

Arr 8:00 AM

Dep 6:00 PM
14

Philipsburg, Sint Maarten (Dutch part)

Sunday, Jan 9, 2028

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 →

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Oceanview · $4,280

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