Windstar Cruise & Stay holidays
6 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.
6 results
Classic Italy & Dalmatian Coast with Venice stay
- 17 Aug '26
9 nights 
Wind Surf
Dep: Venice
Arr: Rome
Exclusive to The Cruise Line
Includes return flights from the UK, private overseas transfers, one-night stay in Venice with breakfast, and 8-night Mediterranean cruise aboard Wind Surf.
Enchanting Greece & the Amalfi Coast from Rome with Stay
- 27 Aug '26
- 7 nights
- Wind Spirit
- Dep: Rome
- Arr: Athens
Exclusive to The Cruise Line
Includes return flights from the UK, private overseas transfers, one-night pre-cruise stay in Rome, and a seven-night Mediterranean cruise aboard Wind Spirit with all meals onboard.
Enchanting Greece & the Amalfi Coast from Rome with Stay
- 18 Sep '26
- 7 nights
- Star Legend
- Dep: Rome
- Arr: Athens
Exclusive to The Cruise Line
Includes return flights from the UK, private overseas transfers, a one-night stay in Rome, and a six-night Mediterranean cruise aboard Star Legend with all meals onboard.
Yachtsman's Harbors of the Rivieras from Rome with Stay
- 24 Oct '26
- 6 nights
- Wind Surf
- Dep: Rome
- Arr: Barcelona
Exclusive to The Cruise Line
Includes return flights from the UK, private overseas transfers, one-night stay in Rome, and a five-night Mediterranean cruise aboard Wind Surf.
Hidden Gems of the Canary Islands & Madeira with Tenerife Stay
- 25 Nov '26
- 12 nights
- Wind Spirit
- Dep: Santa Cruz de Tenerife
- Arr: Santa Cruz de Tenerife
Exclusive to The Cruise Line
Includes return flights from the UK, private overseas transfers, 2-night pre-cruise stay in Santa Cruz de Tenerife, and a 10-night Canary Islands cruise aboard Wind Spirit.
Dreams of Tahiti with Papeete Stay
- 1 Dec '26
- 12 nights
- Star Breeze
- Dep: Papeete, Tahiti
- Arr: Papeete, Tahiti
Exclusive to The Cruise Line
Includes return flights from the UK, private overseas transfers, pre- and post-cruise stays at the InterContinental Tahiti Resort & Spa, and a seven-night cruise aboard Star Breeze.