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 Boston, USA 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 17-night cruise like?

A 17-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 17-night Star Collector: Bermuda & Caribbean Island Explorer from Boston, USA, Oct 22, 2027

Windstar Cruises · Star Pride · Oct 22, 2027 – Nov 08, 2027

Visit Boston, USA, Hamilton, Bermuda, St George's Bermuda, Gustavia, St. Barthelemy , Virgin Gorda / Prickly Pear, British Virgin Island and 5 more ports

Departure Boston, USA

Return San Juan

Duration 17 Nights

From $5700 pp

Itinerary

Day 1

Boston, USA 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

Hamilton, Bermuda Arrives 8:45 AM · Departs 11:59 PM
Day 5

Hamilton, Bermuda Arrives 12:00 AM · Departs 7:00 AM
Day 5

St George's Bermuda Arrives 10:00 AM · Departs 12:00 AM
Day 6

St George's Bermuda Arrives 12:00 AM · Departs 12:00 PM
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

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

Virgin Gorda / Prickly Pear, British Virgin Island Arrives 8:00 AM · Departs 6:00 PM
Day 11

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

Cruz Bay, St. John, Virgin Islands (u.S.) Arrives 8:00 AM · Departs 6:00 PM
Day 13

Basseterre, St. Kitts Arrives 8:00 AM · Departs 5:00 PM
Day 14

Gustavia, St. Barthelemy Arrives 7:00 AM · Departs 10:00 PM
Day 15

Philipsburg, St. Martin Arrives 8:00 AM · Departs 10:00 PM
Day 16

Jost Van Dyke, Great Harbour Arrives 9:00 AM · Departs 10:00 PM
Day 17

Virgin Gorda / Prickly Pear, British Virgin Island Arrives 8:00 AM · Departs 5:00 PM
Day 18

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 $5700

Balcony $10205

Suite $14540

Ports of Call

Boston, USA
Hamilton, Bermuda
St George's Bermuda
Gustavia, St. Barthelemy
Virgin Gorda / Prickly Pear, British Virgin Island
San Juan
Cruz Bay, St. John, Virgin Islands (u.S.)
Basseterre, St. Kitts
Philipsburg, St. Martin
Jost Van Dyke, Great Harbour

About This Cruise

17-night Windstar Cruises Star Pride cruise from Boston, USA to Hamilton, Bermuda, St George's Bermuda, Gustavia, St. Barthelemy and Virgin Gorda /…

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 Boston, USA 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 17-night cruise like?: A 17-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.