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, Jan 31, 2028

Windstar Cruises · Star Legend · Jan 31, 2028 – Feb 14, 2028

Visit San Juan, Cruz Bay, St. John, Virgin Islands (u.S.), Gustavia, St. Barthelemy , Philipsburg, St. Martin, Basseterre, St. Kitts and 7 more ports

Departure San Juan

Return San Juan

Duration 14 Nights

From $4014 pp

Itinerary

Day 1

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

Cruz Bay, St. John, Virgin Islands (u.S.) Arrives 8:00 AM · Departs 6:00 PM
Day 3

Gustavia, St. Barthelemy Arrives 7:00 AM · Departs 10:00 PM
Day 4

Philipsburg, St. Martin Arrives 8:00 AM · Departs 10:00 PM
Day 5

Basseterre, St. Kitts Arrives 8:00 AM · Departs 5:00 PM
Day 6

Jost Van Dyke, Great Harbour Arrives 9:00 AM · Departs 10:00 PM
Day 7

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

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

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

St. George's Arrives 9:00 AM · Departs 10:00 PM
Day 11

Bequia, Grenadines Arrives 8:00 AM · Departs 10:00 PM
Day 12

Mayreau, Grenadines Arrives 8:00 AM · Departs 5:00 PM
Day 13

Les Saintes, Guadeloupe Arrives 10:00 AM · Departs 5:00 PM
Day 14

Marigot Bay Arrives 8:00 AM · Departs 3:00 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 $4014

Balcony $6184

Suite $9544

Ports of Call

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

About This Cruise

14-night Windstar Cruises Star Legend cruise from San Juan to Cruz Bay, St. John, Virgin Islands (u.S.), Gustavia, St. Barthelemy , Philipsburg, St.…

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.