Windstar Cruises luxury itinerary

Star Pride October 22-November 1 2027 Cruise & Offers

BOSTON, MA to SAN JUAN

VoyagePR20271022-10D DatesOctober 22-November 1 2027 Duration10 nights ShipStar Pride

Review the complete published itinerary, source-status notes, suite guidance, and current offer assistance with Deluxe Cruises.

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Star Pride October 22-November 1 2027 route map from BOSTON, MA to SAN JUAN
Star Pride · Voyage PR20271022-10D · BOSTON, MA to SAN JUAN · local schematic map based on the published itinerary sequence

October 22-November 1 2027 ยท Voyage PR20271022-10D

Ports & shore experiences

Each destination is shown once. Select a destination to reveal every published call date and time, its voyage-specific overview, and exact shore experiences currently listed for this departure.

7 destination panels · 6 verified voyage-specific shore experiences · 4 panels with planning notices

Official voyage overview

Embark on a voyage from the East Coast to San Juan with an overnight in St. George’s, Bermuda. Indulge in the luxury of multiple sea days, where you’ll have uninterrupted relaxation. Explore the UNESCO World Heritage Site of St. George’s, Bermuda. Take in the charming streets lined with colonial buildings, visit the iconic St. Peter's Church, one of the oldest Anglican churches in the Western Hemisphere, and discover the fascinating history at the Bermuda National Trust Museum. For nature enthusiasts, St. George's offers stunning coastal views, and Tobacco Bay provides an opportunity for snorkeling in crystal-clear waters teeming with marine life. Arrive in the historic and vibrant city of San Juan, Puerto Rico. Traverse the cobblestone streets of Old San Juan, visit ancient forts, and immerse yourself in the rich local culture. From colonial charm to lively markets, San Juan welcomes you with a blend of history and Caribbean flair.

October 22, 2027 BOSTON, MA United States · Departure 17:00 · 2 listed experiences

About BOSTON, MA

BOSTON, MA is a Windstar destination in United States within the Caribbean sailing region. Across the current published program, locally focused experience themes include City Tour With Transfer To Airport & City Tour With Transfer To Windstar Hotel. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.

Shore experiences currently listed

  • Boston, City Tour With Transfer To Airport (Easy) — Easy activity
  • Boston, City Tour With Transfer To Windstar Hotel (Easy) — Easy activity

Published call times

  • October 22, 2027 · Embarkation · Departure 17:00
October 23, October 24, October 28 & October 29, 2027 Sea Days International waters · No separately published port call

Published sea days aboard Star Pride

The official Windstar timetable names no port call on October 23, October 24, October 28 & October 29, 2027. These dates are grouped once as Sea Days; no onboard activity, route detail, or shore program has been inferred.

Shore planning

No shore experience applies to these Sea Days. Windstar's daily onboard program is confirmed aboard and is not estimated on this page.

Published call times

  • October 23, 2027 · No separately published port call
  • October 24, 2027 · No separately published port call
  • October 28, 2027 · No separately published port call
  • October 29, 2027 · No separately published port call
October 25-26, 2027 HAMILTON Bermuda · 2-day overnight call

About HAMILTON

HAMILTON is a Windstar destination in Bermuda within the Caribbean sailing region. Across the current published program, locally focused experience themes include Crystal Cave Discovery, Harrington Sound ECO Cruise & VIP Sunset Sail. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.

Shore planning

No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.

Published call times

  • October 25, 2027 · Arrival 08:45 · Departure 23:59 · Overnight stay
  • October 26, 2027 · Departure 07:00 · Overnight stay
October 26-27, 2027 ST GEORGE'S BERMUDA Bermuda · 2-day overnight call · 2 listed experiences

About ST GEORGE'S BERMUDA

ST GEORGE'S BERMUDA gives this stage of the itinerary its individual destination focus. George’s, Bermuda. George’s, Bermuda. This context places the destination within the Caribbean route; exact call times and any experiences published for this sailing are listed below.

Shore experiences currently listed

  • St. George's, St George's Heritage Walking Tour (Moderate) — Moderate activity
  • St. George's, Crystal Caves Discovery Tour (Moderate) — Moderate activity

Published call times

  • October 26, 2027 · Arrival 10:00 · Departure 23:59 · Overnight stay
  • October 27, 2027 · Departure 12:00 · Overnight stay
October 30, 2027 GUSTAVIA, ST. BARTHELEMY Saint Barthelemy · Arrival 10:00 · Departure 22:00

About GUSTAVIA, ST. BARTHELEMY

GUSTAVIA, ST. BARTHELEMY is a Windstar destination in Saint Barthelemy within the Caribbean sailing region. Across the current published program, locally focused experience themes include St. Barts: Intimate Island Tour, Jet Ski & Sailing Catamaran to St Barth Nature Reserve. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.

Shore planning

No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.

Published call times

  • October 30, 2027 · Arrival 10:00 · Departure 22:00 · Watersports platform scheduled
October 31, 2027 VIRGIN GORDA/PRICKLY PEAR, BVI British Virgin Islands · Arrival 08:00 · Departure 18:00 · 2 listed experiences

About VIRGIN GORDA/PRICKLY PEAR, BVI

VIRGIN GORDA/PRICKLY PEAR, BVI is a Windstar destination in British Virgin Islands within the Caribbean sailing region. Across the current published program, locally focused experience themes include Highlights & Bath Tour & Snorkel Adventure. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.

Shore experiences currently listed

  • Virgin Gorda: Highlights & Bath Tour (Moderate) — Strenuous activity
  • Virgin Gorda: Snorkel Adventure (Moderate-Strenuous) — Moderate-Strenuous activity

Published call times

  • October 31, 2027 · Arrival 08:00 · Departure 18:00
November 1, 2027 SAN JUAN Puerto Rico · Arrival 07:00

About SAN JUAN

SAN JUAN gives this stage of the itinerary its individual destination focus. Embark on a voyage from the East Coast to San Juan with an overnight in St. Arrive in the historic and vibrant city of San Juan, Puerto Rico.

Shore planning

No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.

Published call times

  • November 1, 2027 · Arrival 07:00 · Disembarkation

Published timetable status: Official Windstar itinerary entries and voyage-specific shore experiences are combined without estimating destinations, call times, experience names, or activity levels. Synthetic midnight continuation placeholders from the source are suppressed.

Please note: Shore-experience names, activity levels, availability, and schedules can change before departure. Confirm the final program with Deluxe Cruises closer to sailing. No excursion prices or cruise-line links are included on this page.

A closer look at this sailing

BOSTON, MA to SAN JUAN aboard Star Pride

On October 22-November 1 2027, Star Pride sails 10 nights from BOSTON, MA to SAN JUAN. The published route brings together HAMILTON, ST GEORGE'S BERMUDA, creating a specific progression of ports for travelers comparing destination variety and voyage pace.

This route includes an official day-by-day schedule and published port times. The source lists 8 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.

For PR20271022-10D, Deluxe Cruises can compare suite availability, deck location, current fares, eligible promotions, and available amenities. Request a personalized review before reserving so the ship, suite, timing, and complete value fit your plans.

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Luxury cruise planning summary

Star Pride October 22-November 1 2027: is Voyage PR20271022-10D right for you?

This 10-night voyage aboard Star Pride sails BOSTON, MA to SAN JUAN, with calls including Sea Days, HAMILTON, ST GEORGE'S BERMUDA, and GUSTAVIA and 1 published sea day. Voyage PR20271022-10D matches the latest verified voyage-search dataset used by this website. Before reserving, ask Deluxe Cruises to compare accommodations, deck location, inclusions, current availability, and any family, medical, dietary, or accessibility arrangements for this exact departure.

Best for
Travelers considering a 10-night BOSTON, MA to SAN JUAN aboard Star Pride, including Sea Days, HAMILTON, ST GEORGE'S BERMUDA, and GUSTAVIA.
Why Deluxe Cruises
Personal guidance for Voyage PR20271022-10D, including accommodation, deck location, itinerary, inclusion, and special-request comparisons.
Before you book
Confirm current availability, exact itinerary details, accommodation benefits, applicable preferred-rate opportunities, and documented guest requirements.

Questions travelers ask

Why book Star Pride Voyage PR20271022-10D with Deluxe Cruises?

Deluxe Cruises provides personal planning for Voyage PR20271022-10D, including accommodation and deck-location comparisons, current availability and preferred-rate guidance, and help documenting family, medical, dietary, or accessibility requests before departure.

What should travelers compare for Voyage PR20271022-10D?

For the October 22-November 1 2027 BOSTON, MA to SAN JUAN, compare the published schedule, accommodation category and location, included services, current availability, and any special requirements before you reserve.

How do I request a personalized luxury cruise quote?

Email info@deluxecruises.com, call +1-702-501-7105, or use WhatsApp +1-702-900-9975 and mention Voyage PR20271022-10D to request a personalized quote from Deluxe Cruises.

What are Star Pride's verified headline statistics?
312Guests
200Crew
6Guest decks
522 ftLength
12,995 GRTGross tonnage
What clothes should I bring for this October itinerary?

Deluxe Cruises packing guidance for this October warm-weather itinerary

  • Pack lightweight breathable clothing, swimwear, strong sun protection, and a light rain layer for tropical showers.
  • Bring secure non-slip walking shoes plus suitable beach or water footwear where the published activities and local conditions call for it.
  • Add a light wrap or sweater for air-conditioned interiors and breezy evenings, and review local customs before visits to religious or community sites.

Windstar Cruises dress guidance

  • Windstar has no formal nights. Daytime dress is relaxed resort wear, while dinner in the main evening restaurants calls for casually elegant clothing.
  • Published evening examples include slacks or non-distressed jeans with a collared, button-down or polo shirt, or a blouse, skirt, casual dress or sundress. Reserve shorts, T-shirts, hats and flip-flops for daytime.

Packing suggestions are Deluxe Cruises editorial guidance; the cruise line's final documents and the weather forecast control the last check.

What services and amenities are available aboard Star Pride?
  • Published fleet experiences include open-seating dining, lounges, 24-hour room service from a limited menu, World Spa by Windstar, pools or whirlpools and an Open Bridge when operational.
  • Dining venues, watersports platforms, pools, spa spaces, entertainment and included services differ between Wind Class sailing yachts, Star Plus all-suite yachts and the newer Star Class yachts.

Venues, hours, inclusions, equipment, and operating conditions can vary by ship and sailing. Deluxe Cruises will reconfirm the details for this departure.

What fitness, sports, or wellness facilities does Star Pride have?
  • Watersports-platform access, swimming and paddle activities depend on sea state, weather, anchorage, local rules and the captain's approval.

Class schedules, age rules, treatment access, operating hours, and equipment availability are confirmed for the exact ship and voyage.

What accommodation features and services can Star Pride guests expect?
  • Wind Class sailing yachts publish ocean-view staterooms and suites without a fleetwide private-veranda promise. Star Plus yachts are all-suite, while Star Seeker and Star Explorer publish suites with private verandas or infinity windows among their categories.
  • Room size, window or veranda, bed arrangement, bath, accessibility and amenities differ by yacht, category and room number; use the exact deck plan before reserving.

Review the exact room or suite number, category, deck position, layout, and benefits for Voyage PR20271022-10D before reserving.

Can children and babies sail aboard Star Pride?
  • Windstar cannot accommodate children under eight years old. A guest under 21 must be accompanied in the room by a parent, guardian or chaperone who is at least 21.
  • Windstar does not publish a fleetwide supervised children's program or babysitting service. Shore operators can impose separate age and participation limits, and minors require direct adult supervision.
  • A guest may not board if she will have entered the 24th week of pregnancy when travel with Windstar begins. Notify Windstar early and confirm current documentation requirements.

For Voyage PR20271022-10D: do not assume a supervised program, babysitting, crib, or child-specific service unless it is confirmed for this sailing.

How does Star Pride handle special needs, medical arrangements, and accessibility?
  • Notify Windstar at booking and complete its Guest Accommodation Request Form. Current guidance requests advance notice for interpreters, equipment, oxygen, dialysis supplies and other services, with timing depending on the request.
  • Guests normally bring an approved wheelchair or scooter; size, weight and storage can prevent acceptance, and crew cannot lift guests or heavy devices. Standard rooms are not barrier-free.
  • Modified suites are published on Star Pride, Star Breeze and Star Legend, but features are limited. Gangways, tenders, stairs, ports and shore transport can restrict access, and personal daily care is not provided.
  • Windstar states that its yachts do not have full medical services. Serious emergencies are referred ashore, and evacuation at sea or from a tender or remote port may be delayed or infeasible.
  • Carry a medical summary and adequate medication, and arrange oxygen, dialysis supplies, sharps or refrigerated medication in advance through the accessibility process. Not every request can be accommodated.

Important: access varies by accommodation, gangway, pier, tender, shore transport, and operating conditions. Document needs when requesting the booking and reconfirm them before travel.

What is the smoking policy aboard Star Pride?
  • Smoking and vaping are prohibited in every stateroom, suite and indoor public space, including restaurants and corridors. They are permitted only in designated outside-deck smoking areas.

Designated locations and onboard rules can change. Follow the policy, posted signs, and crew instructions in force for the voyage.

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