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 Legend.

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 14-night cruise like?

A 14-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 Legend. Pack for both formal nights and casual deck days.

Star Legend 14-night Star Collector: Lovely Leewards from San Juan, Dec 27, 2027

Windstar Cruises · Star Legend · Dec 27, 2027 – Jan 10, 2028

Visit San Juan, St. George's, Bequia, Grenadines, Mayreau, Grenadines, Les Saintes, Guadeloupe and 7 more ports

Departure San Juan

Return San Juan

Duration 14 Nights

From $4434 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 7:00 PM
Day 9

Cruz Bay, St. John, Virgin Islands (u.S.) Arrives 8:00 AM · Departs 6:00 PM
Day 10

Gustavia, St. Barthelemy Arrives 7:00 AM · Departs 10:00 PM
Day 11

Basseterre, St. Kitts Arrives 8:00 AM · Departs 5:00 PM
Day 12

Philipsburg, St. Martin Arrives 8:00 AM · Departs 10:00 PM
Day 13

Jost Van Dyke, Great Harbour Arrives 9:00 AM · Departs 10:00 PM
Day 14

Virgin Gorda / Prickly Pear, British Virgin Island Arrives 8:00 AM · Departs 5:00 PM
Day 15

San Juan Arrives 7:00 AM · Departs 12:00 AM

Cabin Prices

Prices as of 2026-10-19.

Prices per person, based on double occupancy in USD.

Ocean View $4434

Balcony $6814

Suite $10384

Ports of Call

San Juan
St. George's
Bequia, Grenadines
Mayreau, Grenadines
Les Saintes, Guadeloupe
Marigot Bay
Cruz Bay, St. John, Virgin Islands (u.S.)
Gustavia, St. Barthelemy
Basseterre, St. Kitts
Philipsburg, St. Martin
Jost Van Dyke, Great Harbour
Virgin Gorda / Prickly Pear, British Virgin Island

About This Cruise

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

Cruise Line Windstar Cruises

Ship Star Legend

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 Legend.
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 14-night cruise like?: A 14-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 Legend. Pack for both formal nights and casual deck days.