Windstar Cruises
263 sailings with Windstar Cruises day-by-day itineraries
Windstar Cruises Travel Agent
Book With a Cruise Specialist
Waterways Cruise is a cruise specialist travel agency that helps clients plan and book Windstar Cruises cruises to Anguilla, Antigua and Barbuda, Aruba, Barbados, Belgium, Bermuda, Bonaire, BVI and more. Our advisors know Windstar Cruises' ships, itineraries and onboard experience first-hand, so you get expert guidance, access to exclusive rates, and one dedicated point of contact from booking through the day you sail.
Why Book With Waterways Cruise?
Four decades of expertise, one dedicated advisor, and every detail handled, from your front door to the gangway and back.
Cruise Concierge
A dedicated advisor who learns your name, your travel style and your preferences, then stays with you from the first conversation to the day you return home. Not a call center. Never a stranger.
100% Custom‑Built
No cookie-cutter packages. Flights, hotels, transfers and shore days are designed from scratch around how you actually like to travel, then refined until the trip feels like yours.
40+ Years in Travel
Founded by J. Richard, a four-decade veteran of the travel industry, and focused solely on premium river and ocean cruising. Decades of ship and itinerary knowledge go into every recommendation.
Book With Total Confidence
A travel agency that is a proud member of Signature Travel Network, CLIA, ASTA and IATA.
16 Days One-Way from Philipsburg St Maarten to Lisbon
Wind Surf
24 Days One-Way from Philipsburg St Maarten to Tarragona
Wind Surf
Created by the Waterways Cruise content team and reviewed and fact-checked by J. Richard, Sr. Cruise Travel Agent and Founder of Waterways Cruise.
Published May 16, 2026 · Last updated October 31, 2026
Fares, availability and itineraries change often. Confirm current details with your cruise line or a Waterways Cruise agent before you book.
Cruise Disclosure
Good to know: Prices are quoted per person based on double occupancy and include all applicable taxes and fees. Availability and prices can change quickly, so please continue through the booking process to confirm the latest availability and pricing before you pay.
We work hard to make sure everything on this website is accurate and up to date. However, some information may be incomplete or inaccurate, including details supplied by third parties or otherwise outside our control, and we cannot be held responsible for such errors. We work with 41 cruise line operators, that are providing cruises on 585 ships visiting 1,731 ports across 7,194 unique cruises, creating 13,822 itineraries. This is a great deal of data to continually update daily from our suppliers. If a pricing error, misrepresentation, or omission occurs, we reserve the right to adjust the pricing, correct the information, or cancel or decline any booking made in error, with notice to you. Thank you for your understanding!