Windstar Cruises to Mediterranean | Mediterranean Cruises

Roundtrip

8-Night Mediterranean Cruise

$5,299

Windstar Cruises – Star Legend

85 Reviews

Date:

Oct 03, 2026 View Other Dates

Ports:

Piraeus (Athens) → Kusadasi → Kavalla → Thessaloniki → Volos → Skopelos → Piraeus (Athens)

Departs Oct 03, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,299

Roundtrip

7-Night Mediterranean Cruise

$5,299

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 03, 2026 View Other Dates

Ports:

Piraeus (Athens) → Mykonos → Kusadasi → Patmos → Santorini → Monemvasia → Nafplio → Piraeus (Athens)

Departs Oct 03, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,299

16-Night Mediterranean Cruise

$7,599

Windstar Cruises – Star Legend

85 Reviews

Date:

Oct 03, 2026

Ports:

Departs Oct 03, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$7,599

8-Night Mediterranean Cruise

$4,199

Windstar Cruises – Wind Surf

145 Reviews

Date:

Oct 07, 2026

Ports:

Rome (Civitavecchia) → Sorrento → Giardini Di Naxos → Kotor → Dubrovnik → Trogir → Rovinj → Venice

Departs Oct 07, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$4,199

Roundtrip

7-Night Mediterranean Cruise

$5,299

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 10, 2026 View Other Dates

Ports:

Piraeus (Athens) → Mykonos → Kusadasi → Patmos → Santorini → Monemvasia → Nafplio → Piraeus (Athens)

Departs Oct 10, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,299

8-Night Mediterranean Cruise

$4,299

Windstar Cruises – Star Legend

85 Reviews

Date:

Oct 11, 2026 View Other Dates

Ports:

Piraeus (Athens) → Delphi → Corinth Canal → Santorini → Bodrum → Kusadasi → Mykonos → Myrina → Istanbul

Departs Oct 11, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$4,299

7-Night Mediterranean Cruise

$3,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Oct 15, 2026 View Other Dates

Ports:

Piraeus (Athens) → Monemvasia → Gythion → Messina → Sorrento → Rome (Civitavecchia)

Departs Oct 15, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$3,399

10-Night Mediterranean Cruise

$4,199

Windstar Cruises – Wind Surf

145 Reviews

Date:

Oct 15, 2026

Ports:

Venice → Rovinj → Split → Dubrovnik → Kotor → Giardini Di Naxos → Sorrento → Rome (Civitavecchia)

Departs Oct 15, 2026 from Venice, Italy

Up to 2 deals including an Avoya Exclusive

From

$4,199

15-Night Mediterranean Cruise

$5,399

Windstar Cruises – Wind Surf

145 Reviews

Date:

Oct 15, 2026

Ports:

Departs Oct 15, 2026 from Venice, Italy

Up to 2 deals including an Avoya Exclusive

From

$5,399

23-Night Mediterranean Cruise

$8,399

Windstar Cruises – Wind Surf

145 Reviews

Date:

Oct 15, 2026

Ports:

Departs Oct 15, 2026 from Venice, Italy

Up to 2 deals including an Avoya Exclusive

From

$8,399

7-Night Mediterranean Cruise

$3,399

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 17, 2026

Ports:

Piraeus (Athens) → Monemvasia → Gythion → Messina → Sorrento → Ponza → Rome (Civitavecchia)

Departs Oct 17, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$3,399

14-Night Mediterranean Cruise

$5,099

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 17, 2026

Ports:

Departs Oct 17, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,099

8-Night Mediterranean Cruise

$4,299

Windstar Cruises – Star Legend

85 Reviews

Date:

Oct 19, 2026 View Other Dates

Ports:

Istanbul → Myrina → Mykonos → Kusadasi → Bodrum → Santorini → Delphi → Corinth Canal → Piraeus (Athens)

Departs Oct 19, 2026 from Istanbul, Turkey

From

$4,299

7-Night Mediterranean Cruise

$3,199

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 24, 2026 View Other Dates

Ports:

Rome (Civitavecchia) → Portoferraio → Bastia → Calvi → Mahon → Mallorca → Barcelona

Departs Oct 24, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$3,199

17-Night Mediterranean Cruise

$5,799

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 24, 2026 View Other Dates

Ports:

Departs Oct 24, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$5,799

5-Night Mediterranean Cruise

$2,599

Windstar Cruises – Wind Surf

145 Reviews

Date:

Oct 25, 2026

Ports:

Rome (Civitavecchia) → Portofino → Monte Carlo → Sanary Sur Mer → Palamos → Barcelona

Departs Oct 25, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$2,599

13-Night Mediterranean Cruise

$4,999

Windstar Cruises – Wind Surf

145 Reviews

Date:

Oct 25, 2026

Ports:

Departs Oct 25, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$4,999

8-Night Mediterranean Cruise

$3,999

Windstar Cruises – Wind Surf

145 Reviews

Date:

Oct 30, 2026 View Other Dates

Ports:

Barcelona → Mallorca → Cartagena → Almeria → Malaga → Gibraltar → Cadiz → Lisbon

Departs Oct 30, 2026 from Barcelona, Spain

Up to 2 deals including an Avoya Exclusive

From

$3,999

10-Night Mediterranean Cruise

$3,999

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Oct 30, 2026 View Other Dates

Ports:

Barcelona → Tarragona → Mallorca → Valencia → Cartagena → Malaga → Tangier → Lisbon

Departs Oct 30, 2026 from Barcelona, Spain

Up to 2 deals including an Avoya Exclusive

From

$3,999

10-Night Mediterranean Cruise

$3,999

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 31, 2026 View Other Dates

Ports:

Barcelona → Tarragona → Mallorca → Valencia → Cartagena → Malaga → Tangier → Lisbon

Departs Oct 31, 2026 from Barcelona, Spain

Up to 2 deals including an Avoya Exclusive

From

$3,999