- Home>
- Windstar Cruise & Stay holidays
Windstar Cruise & Stay holidays
19 results
At The Cruise Line, we offer a collection of exclusive Windstar cruise and stay packages designed to help you experience some of the world's most captivating destinations in a more seamless and rewarding way. Combining flights, overseas transfers, handpicked hotel stays and a Windstar yacht voyage, these holidays take care of every detail from the moment you leave home.
Whether you're sailing the Greek Islands aboard Wind Spirit, exploring the Dalmatian Coast on Wind Surf, or discovering the Canary Islands and Madeira under sail, our packages give you additional time to enjoy each destination before or after your cruise. Many itineraries also feature stays in iconic cities such as Venice, Rome and Tenerife, allowing you to experience more of the places you visit.
As the UK's leading Windstar Cruises specialist, we've worked closely with the cruise line for many years and carefully selected the itineraries we believe offer the very best combination of destination, value and yacht-style cruising.
You'll find details of our latest Windstar cruise and stay holidays below. If you'd like more information or would prefer us to tailor an itinerary around your plans, call our Voyage Consultants on 0800 008 6677.
19 results

Carnival of Venice: Winter Italy and the Dalmatian Coast Fly-Cruise
30 Jan '27
8 nights
Star Explorer
Dep: Venice
Arr: Civitavecchia
A golden Adriatic sunset trail
Journey through the Eastern Mediterranean for eight nights aboard Star Explorer, from Zadar's sea organ sunsets to Dubrovnik's walls and Naples' volcanic skyline.

Europe's Winter Riviera Fly-Cruise
7 Feb '27
7 nights
Star Explorer
Dep: Civitavecchia
Arr: Barcelona
Meet the Riviera's quieter season
Slow down for seven nights aboard Star Explorer, tracing a winter route from Rome to Barcelona through Livorno, Genoa and Nice.

Beach Fun & Sun: A Remote Caribbean Getaway from St. Maarten with Island Stay
10 Feb '27
11 nights
Wind Surf
Dep: Philipsburg
Arr: Philipsburg
Bespoke Cruise & Stay
Handpicked cruise, hotel stays and tours pair together for more of the journey, with your Voyage Consultant shaping every detail to your taste.

Beach Fun & Sun: A Remote Caribbean Getaway from St. Maarten with Island Stay
24 Feb '27
11 nights
Wind Surf
Dep: Philipsburg
Arr: Philipsburg
Bespoke Cruise & Stay
Handpicked cruise, hotel stays and tours pair together for more of the journey, with your Voyage Consultant shaping every detail to your taste.

Europe's Winter Riviera Fly-Cruise
4 Mar '27
7 nights
Star Explorer
Dep: Barcelona
Arr: Civitavecchia
A slower way through three cities
Settle in rather than rush through. Allow two full days for each of Barcelona, Nice and Livorno, your flight out already taken care of, over seven nights aboard Star Explorer via Genoa to Rome.

Winter Italy and the Dalmatian Coast Fly-Cruise
19 Mar '27
8 nights
Star Explorer
Dep: Venice
Arr: Civitavecchia
Dalmatian walls meet Sicilian cobblestones
Land in Venice during its quieter season, then thread south through Zadar's Roman ruins and Dubrovnik's walls to Sicily's Messina and Naples over eight nights aboard Star Explorer.

No-Fly Cruise: Tulip Season in Holland & Belgium with Amsterdam Stay and Tour
20 Apr '27
9 nights
Star Pride
Dep: Amsterdam
Arr: Amsterdam
Bespoke Cruise & Stay
Handpicked cruise, hotel stays and tour pair together for more of the journey, with your Voyage Consultant shaping every detail to your taste.

No-Fly Cruise: Tulip Season in Holland & Belgium with Amsterdam Stay and Tour
27 Apr '27
10 nights
Star Pride
Dep: Amsterdam
Arr: London Tower Bridge
Bespoke Cruise & Stay
Handpicked cruise, hotel stays and tour pair together for more of the journey, with your Voyage Consultant shaping every detail to your taste.

Autumn Colours of Southern Japan: Intimate Small-Ship Cruise with Stay
21 Oct '27
16 nights
Star Seeker
Dep: Tokyo
Arr: Kobe
An intimate voyage into golden Japan
Frame an intimate Star Seeker voyage through Takamatsu's Ritsurin Garden and Karatsu's pine forest with three nights in Tokyo and two in Osaka.
