What is included in the cruise fare?

Standard cruise fares include your cabin, onboard meals at main dining venues, most non-specialty entertainment, use of pools and common facilities, and transport between ports of call. Gratuities, specialty dining, alcoholic drinks, shore excursions and onboard spa services are typically billed separately.

How far in advance should I book this cruise?

For popular sailings, booking 6–12 months ahead typically gives the best cabin selection and fares. Last-minute discounts can appear 30–60 days before departure when the cruise line wants to fill remaining cabins on Wind Surf.

What documents do I need to board?

Most international itineraries require a passport valid for at least six months beyond your return date. Closed-loop sailings that depart and return to the same U.S. port from Lisbon, Portugal may accept a government-issued photo ID plus a certified birth certificate for U.S. citizens — always verify with the cruise line.

Can I change or cancel my booking?

Change and cancellation policies depend on Windstar Cruises's fare type and how close you are to departure. Refundable deposits typically allow changes up to the final-payment date without penalty; closer to sailing, cancellation fees scale up. Review the specific fare rules before booking.

What is a 23-night cruise like?

A 23-night cruise balances relaxing sea days with active port days. You can expect a mix of onboard programming — dining, entertainment, spa and fitness — and multiple shore excursions from Wind Surf. Pack for both formal nights and casual deck days.

Wind Surf 23-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing from Lisbon, Portugal, Nov 5, 2027

Windstar Cruises · Wind Surf · Nov 05, 2027 – Nov 28, 2027

Visit Lisbon, Portugal, Funchal, Jost Van Dyke, Great Harbour, Philipsburg, St. Martin, Gustavia, St. Barthelemy and 5 more ports

Departure Lisbon, Portugal

Return Philipsburg, St. Martin

Duration 23 Nights

From $4813 pp

Itinerary

Day 1

Lisbon, Portugal Arrives 12:00 AM · Departs 5:00 PM
Day 2

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 3

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 4

Funchal Arrives 8:00 AM · Departs 3:00 PM
Day 5

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 6

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 7

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 8

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 9

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 10

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 11

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 12

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 13

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 14

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 15

Jost Van Dyke, Great Harbour Arrives 8:00 AM · Departs 6:00 PM
Day 16

Philipsburg, St. Martin Arrives 6:00 AM · Departs 7:00 PM
Day 17

Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 PM
Day 18

St. John's, Antigua Arrives 8:00 AM · Departs 10:00 PM
Day 19

Deshaies, Guadeloupe Arrives 7:00 AM · Departs 5:00 PM
Day 20

Road Bay, Anguilla Arrives 8:00 AM · Departs 6:00 PM
Day 21

Soper'S Hole, Tortola, B.V.I. Arrives 8:00 AM · Departs 6:00 PM
Day 21

Jost Van Dyke, Great Harbour Arrives 7:00 PM · Departs 11:59 PM
Day 22

Jost Van Dyke, Great Harbour Arrives 12:00 AM · Departs 10:00 PM
Day 23

Virgin Gorda / Prickly Pear, British Virgin Island Arrives 8:00 AM · Departs 5:00 PM
Day 24

Philipsburg, St. Martin Arrives 6:00 AM · Departs 7:00 AM

Cabin Prices

Prices as of 2026-10-19.

Prices per person, based on double occupancy in USD.

Ocean View $4813

Suite $7228

Ports of Call

Lisbon, Portugal
Funchal
Jost Van Dyke, Great Harbour
Philipsburg, St. Martin
Gustavia, St. Barthelemy
St. John's, Antigua
Deshaies, Guadeloupe
Road Bay, Anguilla
Soper'S Hole, Tortola, B.V.I.
Virgin Gorda / Prickly Pear, British Virgin Island

About This Cruise

23-night Windstar Cruises Wind Surf cruise from Lisbon, Portugal to Funchal, Jost Van Dyke, Great Harbour, Philipsburg, St. Martin and Gustavia, St.…

Cruise Line Windstar Cruises

Ship Wind Surf

Frequently asked questions

What is included in the cruise fare?: Standard cruise fares include your cabin, onboard meals at main dining venues, most non-specialty entertainment, use of pools and common facilities, and transport between ports of call. Gratuities, specialty dining, alcoholic drinks, shore excursions and onboard spa services are typically billed separately.
How far in advance should I book this cruise?: For popular sailings, booking 6–12 months ahead typically gives the best cabin selection and fares. Last-minute discounts can appear 30–60 days before departure when the cruise line wants to fill remaining cabins on Wind Surf.
What documents do I need to board?: Most international itineraries require a passport valid for at least six months beyond your return date. Closed-loop sailings that depart and return to the same U.S. port from Lisbon, Portugal may accept a government-issued photo ID plus a certified birth certificate for U.S. citizens — always verify with the cruise line.
Can I change or cancel my booking?: Change and cancellation policies depend on Windstar Cruises's fare type and how close you are to departure. Refundable deposits typically allow changes up to the final-payment date without penalty; closer to sailing, cancellation fees scale up. Review the specific fare rules before booking.
What is a 23-night cruise like?: A 23-night cruise balances relaxing sea days with active port days. You can expect a mix of onboard programming — dining, entertainment, spa and fitness — and multiple shore excursions from Wind Surf. Pack for both formal nights and casual deck days.