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 Star Pride.

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 San Juan 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 21-night cruise like?

A 21-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 Star Pride. Pack for both formal nights and casual deck days.

Star Pride 21-night Star Collector: Windward Islands, Spanish Cities & Costa Rica from San Juan, Nov 22, 2027

Windstar Cruises · Star Pride · Nov 22, 2027 – Dec 13, 2027

Visit San Juan, St. George's, Bequia, Grenadines, Mayreau, Grenadines, Les Saintes, Guadeloupe and 11 more ports

Departure San Juan

Return Puerto Caldera, Costa Rica

Duration 21 Nights

From $7460 pp

Itinerary

Day 1

San Juan Arrives 12:00 AM · Departs 7:00 PM
Day 2

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

St. George's Arrives 9:00 AM · Departs 10:00 PM
Day 4

Bequia, Grenadines Arrives 8:00 AM · Departs 10:00 PM
Day 5

Mayreau, Grenadines Arrives 8:00 AM · Departs 5:00 PM
Day 6

Les Saintes, Guadeloupe Arrives 10:00 AM · Departs 5:00 PM
Day 7

Marigot Bay Arrives 8:00 AM · Departs 3:00 PM
Day 8

San Juan Arrives 7:00 AM · Departs 5:00 PM
Day 9

Isla Catalina, Dominican Republic Arrives 10:00 AM · Departs 9:00 PM
Day 10

Santo Domingo Arrives 7:00 AM · Departs 3:00 PM
Day 11

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

Cartagena, Colombia Arrives 2:30 PM · Departs 11:59 PM
Day 13

Cartagena, Colombia Arrives 12:00 AM · Departs 1:30 PM
Day 14

Panama Canal, Panama Arrives 8:00 AM · Departs 5:00 PM
Day 15

Colon, Panama Arrives 7:00 AM · Departs 6:00 PM
Day 16

Panama Canal, Panama Arrives 4:00 AM · Departs 6:00 PM
Day 16

Fuerte Amador, Panama Arrives 10:00 PM · Departs 11:59 PM
Day 17

Fuerte Amador, Panama Arrives 12:00 AM · Departs 5:00 PM
Day 18

At Sea Arrives 12:00 AM · Departs 12:00 AM
Day 19

Isla Parida, Panama Arrives 8:00 AM · Departs 6:00 PM
Day 20

Puerto Jimenez (Golfo Dulce), Costa Rica Arrives 8:30 AM · Departs 5:00 PM
Day 21

Quepos, Costa Rica Arrives 6:00 AM · Departs 6:00 PM
Day 22

Puerto Caldera, Costa Rica Arrives 6:00 AM · Departs 12:00 AM

Cabin Prices

Prices as of 2026-10-19.

Prices per person, based on double occupancy in USD.

Ocean View $7460

Balcony $10190

Suite $15545

Ports of Call

San Juan
St. George's
Bequia, Grenadines
Mayreau, Grenadines
Les Saintes, Guadeloupe
Marigot Bay
Isla Catalina, Dominican Republic
Santo Domingo
Cartagena, Colombia
Panama Canal, Panama
Colon, Panama
Fuerte Amador, Panama
Isla Parida, Panama
Puerto Jimenez (Golfo Dulce), Costa Rica
Quepos, Costa Rica
Puerto Caldera, Costa Rica

About This Cruise

21-night Windstar Cruises Star Pride cruise from San Juan to St. George's, Bequia, Grenadines, Mayreau, Grenadines and Les Saintes, Guadeloupe Compare…

Cruise Line Windstar Cruises

Ship Star Pride

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 Star Pride.
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 San Juan 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 21-night cruise like?: A 21-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 Star Pride. Pack for both formal nights and casual deck days.