Windstar Cruises to Mediterranean | Mediterranean Cruises

14-Night Mediterranean Cruise

$6,999

Windstar Cruises – Star Legend

85 Reviews

Date:

Sep 19, 2026

Ports:

Departs Sep 19, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$6,999

18-Night Mediterranean Cruise

$7,099

Windstar Cruises – Wind Surf

145 Reviews

Date:

Sep 19, 2026

Ports:

Departs Sep 19, 2026 from Venice, Italy

Up to 2 deals including an Avoya Exclusive

From

$7,099

Roundtrip

10-Night Mediterranean Cruise + Tour

$7,399

Windstar Cruises – Wind Star

89 Reviews

Date:

Sep 23, 2026 View Other Dates

Ports:

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

Departs Sep 23, 2026 from Piraeus (Athens), Greece

From

$7,399

Roundtrip

7-Night Mediterranean Cruise

$5,299

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Sep 24, 2026 View Other Dates

Ports:

Piraeus (Athens) → Ermoupoli → Kusadasi → Pythagoreio → Naxos → Folegandros → Milos → Piraeus (Athens)

Departs Sep 24, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,299

Roundtrip

14-Night Mediterranean Cruise

$8,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Sep 24, 2026 View Other Dates

Ports:

Departs Sep 24, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$8,399

Roundtrip

8-Night Mediterranean Cruise

$5,499

Windstar Cruises – Star Legend

85 Reviews

Date:

Sep 25, 2026 View Other Dates

Ports:

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

Departs Sep 25, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,499

Roundtrip

7-Night Mediterranean Cruise

$5,499

Windstar Cruises – Wind Star

89 Reviews

Date:

Sep 26, 2026 View Other Dates

Ports:

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

Departs Sep 26, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,499

Roundtrip

10-Night Mediterranean Cruise

$4,399

Windstar Cruises – Wind Surf

145 Reviews

Date:

Sep 27, 2026 View Other Dates

Ports:

Departs Sep 27, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$4,399

18-Night Mediterranean Cruise

$6,899

Windstar Cruises – Wind Surf

145 Reviews

Date:

Sep 27, 2026

Ports:

Departs Sep 27, 2026 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$6,899

Roundtrip

10-Night Mediterranean Cruise + Tour

$7,199

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Sep 28, 2026 View Other Dates

Ports:

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

Departs Sep 28, 2026 from Piraeus (Athens), Greece

From

$7,199

Roundtrip

10-Night Mediterranean Cruise + Tour

$7,199

Windstar Cruises – Wind Star

89 Reviews

Date:

Sep 30, 2026 View Other Dates

Ports:

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

Departs Sep 30, 2026 from Piraeus (Athens), Greece

From

$7,199

Roundtrip

7-Night Mediterranean Cruise

$5,299

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Oct 01, 2026 View Other Dates

Ports:

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

Departs Oct 01, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,299

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

10-Night Mediterranean Cruise + Tour

$7,199

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 07, 2026 View Other Dates

Ports:

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

Departs Oct 07, 2026 from Piraeus (Athens), Greece

From

$7,199

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

11-Night Mediterranean Cruise

$5,899

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

From

$5,899

11-Night Mediterranean Cruise

$6,199

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

From

$6,199

10-Night Mediterranean Cruise + Tour

$5,299

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Oct 12, 2026 View Other Dates

Ports:

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

Departs Oct 12, 2026 from Piraeus (Athens), Greece

From

$5,299

10-Night Mediterranean Cruise + Tour

$5,299

Windstar Cruises – Wind Star

89 Reviews

Date:

Oct 14, 2026 View Other Dates

Ports:

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

Departs Oct 14, 2026 from Piraeus (Athens), Greece

From

$5,299

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