Windstar Cruises luxury itinerary
Star Pride October 20-28 2026 Cruise & Offers
BOSTON, MA to SAN JUAN
Review the complete published itinerary, source-status notes, suite guidance, and current offer assistance with Deluxe Cruises.
October 20-28 2026 · Voyage PR20261020-8D
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.
5 destination panels · 13 verified voyage-specific shore experiences · 2 panels with planning notices
Official voyage overview
Embark on a wellness voyage with Debbie Dixon, a yoga teacher, life coach and inspirational speaker. Once at sea, you’ll have daily chances to rejuvenate your being with meditation, breathwork and yoga — and engage in transformational talks focused on mental, physical and spiritual health, designed to deepen your personal growth. Ashore in Bermuda, you’ll stroll the UNESCO site of St. George’s, as a palette of pastel-colored buildings and azure waters evoke a sense of serenity. Immerse yourself in history, from the imposing silhouette of St. Peter's Church to the architectural marvel of the Town Hall. Refresh yourself with specially crafted elixirs to enhance your wellness journey, or enjoy the juice cleanse and healthy food options available to restart your health through nutritious meals.
October 20, 2026 BOSTON, MA
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 20, 2026 · Embarkation · Departure 17:00
October 21, October 22, October 26 & October 27, 2026 Sea Days
Published sea days aboard Star Pride
The official Windstar timetable names no port call on October 21, October 22, October 26 & October 27, 2026. 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 21, 2026 · No separately published port call
- October 22, 2026 · No separately published port call
- October 26, 2026 · No separately published port call
- October 27, 2026 · No separately published port call
October 23-24, 2026 HAMILTON
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 experiences currently listed
- Hamilton, Harrington Sound ECO Cruise — Moderate activity
- Hamilton, Glass Bottom Snorkel & Sightseeing (Easy-Moderate) — Easy-Moderate activity
- Hamilton, Crystal Cave Discovery — Easy-Moderate activity
- Hamilton, Quintessential Island Drive (Easy) — Easy activity
- Hamilton, VIP Sunset Sail (Easy-Moderate) — Easy-Moderate activity
Published call times
- October 23, 2026 · Arrival 08:45 · Departure 23:59 · Overnight stay
- October 24, 2026 · Departure 07:00 · Overnight stay
October 24-25, 2026 ST GEORGE'S BERMUDA
About ST GEORGE'S BERMUDA
ST GEORGE'S BERMUDA gives this stage of the itinerary its individual destination focus. Ashore in Bermuda, you’ll stroll the UNESCO site of St. 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, Crystal Caves Discovery Tour (Moderate) — Moderate activity
- St George's, Old Town Train — Easy activity
- St. George's, Colonial St. George's Sightseeing Trip (Easy) — Easy activity
- St Georges, Electric E Trike - Explore St. Georges — Moderate-Strenuous activity
- St. George's, Harrington Sound ECO Cruise (Moderate) — Moderate activity
- St. George's, St George's Heritage Walking Tour (Moderate) — Moderate activity
Published call times
- October 24, 2026 · Arrival 10:00 · Departure 23:59 · Overnight stay
- October 25, 2026 · Departure 07:00 · Overnight stay
October 28, 2026 SAN JUAN
About SAN JUAN
SAN JUAN is a Windstar destination in Puerto Rico within the Caribbean sailing region. Across the current published program, locally focused experience themes include Half Day Private SUV with Guide, Old San Juan Fortress & City Walking Tour with Transfer to & Bacardi Rum Tour & Tasting- With Transfer to Airport. 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 28, 2026 · 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 20-28 2026, Star Pride sails 8 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 6 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
Personalized cruise planning with Windstar Cruises
Ask Deluxe Cruises about Star Pride Voyage PR20261020-8D
Considering the October 20-28, 2026 Star Pride sailing, Voyage PR20261020-8D? A Deluxe Cruises specialist can verify this itinerary's current status and availability and assist with stateroom or suite selection and deck location, fare and inclusion comparisons, eligible offers, available amenities, and personalized planning.
We may have access to eligible pricing and amenities that are not displayed online. Before placing a deposit, ask us to compare a current like-for-like offer and review the value we can confirm for your requested sailing with Windstar Cruises.
Comparable offers must be current and verifiable for the same ship or program, departure, accommodation category, fare terms, and inclusions. All fares, offers, and amenities are subject to eligibility, availability, and terms set by Windstar Cruises.