Windstar Cruises luxury itinerary

Star Pride October 22-November 8 2027 Cruise & Offers

BOSTON, MA to SAN JUAN

VoyagePR20271022-17D DatesOctober 22-November 8 2027 Duration17 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 8 2027 route map from BOSTON, MA to SAN JUAN
Star Pride · Voyage PR20271022-17D · BOSTON, MA to SAN JUAN · local schematic map based on the published itinerary sequence

October 22-November 8 2027 ยท Voyage PR20271022-17D

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.

11 destination panels · 17 verified voyage-specific shore experiences · 6 panels with planning notices

Official voyage overview

Sail from the North Atlantic into the heart of the Caribbean on an extended journey shaped by island character and days unrushed at sea. Take advantage of rare overnights in Bermuda’s historic towns before continuing toward San Juan’s timeless fortresses and colorful shoreline. You’ll also have two full days to experience Gustavia and Virgin Gorda, giving you more time to enjoy their beaches, cafés, and sheltered bays. From there, explore quiet anchorages in the Virgin Islands, snorkel pristine bays, and wander small-ship harbors like Jost Van Dyke and Virgin Gorda.

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. Take advantage of rare overnights in Bermuda’s historic towns before continuing toward San Juan’s timeless fortresses and colorful shoreline. 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 & November 4, 2027 GUSTAVIA, ST. BARTHELEMY Saint Barthelemy · 2 published calls

About GUSTAVIA, ST. BARTHELEMY

GUSTAVIA, ST. BARTHELEMY gives this stage of the itinerary its individual destination focus. You’ll also have two full days to experience Gustavia and Virgin Gorda, giving you more time to enjoy their beaches, cafés, and sheltered bays. This context places the destination within the Caribbean route; exact call times and any experiences published for this sailing are listed 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
  • November 4, 2027 · Arrival 07:00 · Departure 22:00 · Watersports platform scheduled
October 31 & November 7, 2027 VIRGIN GORDA/PRICKLY PEAR, BVI British Virgin Islands · 2 published calls · 2 listed experiences

About VIRGIN GORDA/PRICKLY PEAR, BVI

VIRGIN GORDA/PRICKLY PEAR, BVI gives this stage of the itinerary its individual destination focus. You’ll also have two full days to experience Gustavia and Virgin Gorda, giving you more time to enjoy their beaches, cafés, and sheltered bays. From there, explore quiet anchorages in the Virgin Islands, snorkel pristine bays, and wander small-ship harbors like Jost Van Dyke and Virgin Gorda.

Shore experiences currently listed

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

Published call times

  • October 31, 2027 · Arrival 08:00 · Departure 18:00
  • November 7, 2027 · Arrival 08:00 · Departure 17:00
November 1 & November 8, 2027 SAN JUAN Puerto Rico · 2 published calls

About SAN JUAN

SAN JUAN gives this stage of the itinerary its individual destination focus. Take advantage of rare overnights in Bermuda’s historic towns before continuing toward San Juan’s timeless fortresses and colorful shoreline. This context places the destination within the Caribbean route; exact call times and any experiences published for this sailing are listed 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

  • November 1, 2027 · Arrival 07:00 · Departure 19:00
  • November 8, 2027 · Arrival 07:00 · Disembarkation
November 2, 2027 CRUZ BAY, ST. JOHN U.S. Virgin Islands · Arrival 08:00 · Departure 18:00 · 4 listed experiences

About CRUZ BAY, ST. JOHN

CRUZ BAY, ST. JOHN is a Windstar destination in U.S. Virgin Islands within the Caribbean sailing region. Across the current published program, locally focused experience themes include Cinnamon Beach Getaway, Lind Point Trail Eco Hike & Trunk Bay Snorkeling Experience. 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

  • St. John, Trunk Bay Snorkeling Experience — Moderate activity
  • St. John, Island tour Featuring Annaberg Ruins — Easy activity
  • St. John, Cinnamon Beach Getaway — Moderate activity
  • St. John, Lind Point Trail Eco Hike — Moderate activity

Published call times

  • November 2, 2027 · Arrival 08:00 · Departure 18:00
November 3, 2027 BASSETERRE, ST. KITTS Saint Kitts and Nevis · Arrival 08:00 · Departure 17:00 · 7 listed experiences

About BASSETERRE, ST. KITTS

BASSETERRE, ST. KITTS is a Windstar destination in Saint Kitts and Nevis within the Caribbean sailing region. Across the current published program, locally focused experience themes include Snorkel Safari, St Kitts Quad ATV Adventure & Island History & Rum Tasting. 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

  • Basseterre: Snorkel Safari (Moderate) — Moderate activity
  • Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
  • Basseterre: Sky Safari Zipline Adventure (Strenuous) — Strenuous activity
  • Basseterre, Brimstone Hill Fortress & Fairview Great House — Easy-Moderate activity
  • Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts (Easy) — Easy activity
  • Basseterre, Nevis Panoramic and Beach Tour (Easy-Moderate) — Easy-Moderate activity
  • Basseterre, Island History & Rum Tasting — Moderate activity

Published call times

  • November 3, 2027 · Arrival 08:00 · Departure 17:00
November 5, 2027 PHILIPSBURG, ST. MAARTEN Sint Maarten · Arrival 08:00 · Departure 22:00

About PHILIPSBURG, ST. MAARTEN

PHILIPSBURG, ST. MAARTEN is a Windstar destination in Sint Maarten within the Caribbean sailing region. Across the current published program, locally focused experience themes include America's Cup Sailboat Racing with Transfer to Airport, America's Cup Sailboat Racing with Transfer to Windstar Hotel & Post Island Tour with Transfer to 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 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 5, 2027 · Arrival 08:00 · Departure 22:00
November 6, 2027 GREAT HARBOUR, JOST VAN DYKE British Virgin Islands · Arrival 09:00 · Departure 22:00

About GREAT HARBOUR, JOST VAN DYKE

GREAT HARBOUR, JOST VAN DYKE gives this stage of the itinerary its individual destination focus. From there, explore quiet anchorages in the Virgin Islands, snorkel pristine bays, and wander small-ship harbors like Jost Van Dyke and Virgin Gorda.

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 6, 2027 · Arrival 09:00 · Departure 22:00 · Watersports platform scheduled

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 8 2027, Star Pride sails 17 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 15 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.

For PR20271022-17D, 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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Contact Deluxe Cruises before you reserve

Ask a specialist to compare the itinerary, suite category, current fare, inclusions, eligible promotions, and available amenities.

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Request detailed information for Star Pride PR20271022-17D.

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Luxury cruise planning summary

Star Pride October 22-November 8 2027: is Voyage PR20271022-17D right for you?

This 17-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 PR20271022-17D 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 17-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 PR20271022-17D, 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 PR20271022-17D with Deluxe Cruises?

Deluxe Cruises provides personal planning for Voyage PR20271022-17D, 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 PR20271022-17D?

For the October 22-November 8 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 PR20271022-17D to request a personalized quote from Deluxe Cruises.

What is included and not included on Star Pride Voyage PR20271022-17D?

For the October 22-November 8, 2027 BOSTON, MA to SAN JUAN sailing aboard Star Pride: Cruise-only fares publish accommodation, onboard meals and entertainment, including specialty dining, 24-hour room service, the signature barbecue and welcome champagne. Wi-Fi, selected beer, wine and cocktails and gratuities are included only with an All-Inclusive fare or package or a qualifying promotion, not with every cruise-only booking. Spa, shore excursions and personal services can cost extra. The exact fare and booking confirmation control.

What bed is provided for a child or third guest on Star Pride Voyage PR20271022-17D?

For the October 22-November 8, 2027 BOSTON, MA to SAN JUAN sailing aboard Star Pride: Selected Star Plus suites publish third-guest capacity, but the current verified guide does not name the sleeping surface. Deluxe Cruises will confirm the exact suite number and will not assume a sofa bed, rollaway, Pullman or berth. Deluxe Cruises will confirm the exact room and occupancy before booking.

Are shore excursions included on Star Pride Voyage PR20271022-17D, and can Deluxe Cruises help with alternatives?

For the October 22-November 8, 2027 BOSTON, MA to SAN JUAN sailing aboard Star Pride: Windstar shore excursions are optional and charged separately unless the exact booking states otherwise. Watersports-platform access and the Open Bridge are conditional onboard features, not shore-excursion inclusions. Each tour and booking term must be checked. If a preferred shore experience is not included, Deluxe Cruises can compare independent alternatives and check whether a lower price or better value is available than booking through the cruise line. Availability and savings vary and are confirmed before purchase.

How does Internet and Wi-Fi work aboard Star Pride for Voyage PR20271022-17D?

For the October 22-November 8, 2027 BOSTON, MA to SAN JUAN sailing aboard Star Pride: Wi-Fi is included only with an All-Inclusive fare or package or a qualifying promotion, not every cruise-only fare. The published package permits up to two connected devices; coverage, speed and uninterrupted performance are not guaranteed. The exact booking confirmation controls.

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 PR20271022-17D 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 PR20271022-17D: 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.

Where can I review cruise travel insurance information?

Visit the Deluxe Cruises Cruise Travel Insurance page to prepare for a quote and compare optional protection with Travel Insured.

You can also search the Deluxe Cruises Cruise-Line Travel Insurance Directory for cruise-line-specific plan companies, insurer or administrator contacts, available policy-document links, and published pre-existing-condition purchase guidance. Plan terms and availability can change; the policy or certificate issued for your state controls.

Ask Deluxe CruisesView Suites & Deck PlansEmail a cruise specialist
Ready to reserve Star Pride October 22-November 8 2027?

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