Sail to fascinating destinations on The World's Best Small Ship Cruise Line
From £3,129 per person
All fares are displayed in Great British Pound, and pricing is per person based on twin share occupancy unless stated otherwise. Although all due care is taken to keep information as up-to-date as possible, pricing and availability are subject to change without notice: due to varying timing schedules of supplier automated update processes; currency fluctuations; fuel surcharges or government tax & fee changes and may not be guaranteed until paid in full. Gratuities may be an additional onboard charge depending on particular cruise line selected. Please ask your cruise consultant for any clarification of Terms & Conditions.
Pricing is based on departure date 17th Oct 2026
Cruise Highlights
Begin your voyage in Athens, Greece, the cradle of Western civilization and gateway to the Greek Isles.
Discover Monemvasia, a stunning medieval fortress town carved into a rocky island, renowned for its Byzantine charm and cobblestone streets.
Visit Gythion, the picturesque gateway to ancient Sparta and the beautiful Mani Peninsula.
Enjoy a relaxing day at sea, taking advantage of world-class dining, entertainment, and onboard amenities.
Explore Messina (Taormina), Sicily, where you can admire the dramatic landscapes of Mount Etna, ancient Greek theatres, and breathtaking coastal views.
Experience an overnight stay in Sorrento, giving you extra time to explore its charming streets, stunning Amalfi Coast scenery, local cuisine, and nearby attractions such as Pompeii or Capri.
Arrive in Rome, one of the world's most iconic cities, where ancient history, Renaissance masterpieces, and vibrant Italian culture await.
Indulge in authentic Mediterranean cuisine, local wines, and unforgettable coastal experiences throughout your journey.
Experience the perfect blend of ancient history, scenic coastlines, charming seaside towns, and iconic Mediterranean destinations on this unforgettable voyage.
Cruise Overview:

Idyllic islands, charming cobbled villages, spectacular scenery, intriguing history. Capture the heart of the Mediterranean in a single voyage. Each small harbor is especially suited for small ship exploration. Enjoy the best of the region — from the ancient ruins of Sparta and Mystras to the pure indulgence of the Mediterranean lifestyle.
Itinerary highlights

Ship: Wind Star
Cabin: Category B
Sail Date: 17th Oct 2026
Duration: 07 Nights
| Date | Destination | Arrive | Depart |
| 17-Oct-26 | Athens, Greece | 05:00pm | |
| 18-Oct-26 | Monemvasia, Greece | 08:00am | 05:00pm |
| 19-Oct-26 | Gythion, Greece | 08:00am | 04:00pm |
| 20-Oct-26 | At Sea | ||
| 21-Oct-26 | Messina (Taormina), Italy | 08:00am | 02:00pm |
| 22-Oct-26 | Sorrento, Italy | 10:00am | |
| 23-Oct-26 | Sorrento, Italy | 12:00pm | |
| 24-Oct-26 | Rome, Italy | 07:00am |
Why Windstar?
The World's Best Small Ship Cruise Line
All cruise ships let you see the world. Only Windstar’s private yacht style cruises bring's you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.
Your Ship: Wind Star

Wind Star is the yacht that started it all. Commissioned in 1984, this 148-guest sailing icon helped pioneer a new kind of cruising — one with real working sails, that felt more like a private yacht than a regular cruise.
Four decades later, Wind Star still delivers that same elegant yet laid-back atmosphere — now with upgraded amenities and a stunning redesign under our Setting Sails initiative.
This intimate sailing yacht features wide-open teak decks, staterooms with ocean views, an Owner’s Suite, the World Spa by Windstar, a pool with a bar, a hot tub, a water-access marina and much more.
Wind Star also offers multiple dining options — all open seating and complimentary — including our main restaurant Amphora, the full-surface breakfast and lunch buffet Veranda, and our specialty restaurant Candles.
Enquire Now!
All fares are displayed in Great British Pound, and pricing is per person based on twin share occupancy unless stated otherwise. Although all due care is taken to keep information as up-to-date as possible, pricing and availability are subject to change without notice: due to varying timing schedules of supplier automated update processes; currency fluctuations; fuel surcharges or government tax & fee changes and may not be guaranteed until paid in full. Gratuities may be an additional onboard charge depending on particular cruise line selected. Please ask your cruise consultant for any clarification of Terms & Conditions.