Find Your Cruise Vacation

Roundtrip

10-Night Caribbean Cruise

$3,999

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Nov 27, 2024

Ports:

Departs Nov 27, 2024 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$3,999

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Dec 07, 2024 View Other Dates

Ports:

Departs Dec 07, 2024 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,599

Roundtrip

14-Night Caribbean Cruise

$4,799

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Dec 07, 2024 View Other Dates

Ports:

Departs Dec 07, 2024 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$4,799

Roundtrip

7-Night Caribbean Cruise

$2,293

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Dec 14, 2024

Ports:

Departs Dec 14, 2024 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,293

Roundtrip

14-Night Caribbean Cruise

$4,999

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Dec 14, 2024 View Other Dates

Ports:

Departs Dec 14, 2024 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$4,999

Roundtrip

14-Night Caribbean Cruise

$5,699

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jan 18, 2025 View Other Dates

Ports:

Departs Jan 18, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$5,699

Roundtrip

7-Night Caribbean Cruise

$4,049

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 01, 2025 View Other Dates

Ports:

Departs Feb 01, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$4,049

Roundtrip

7-Night Caribbean Cruise

$3,299

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 15, 2025 View Other Dates

Ports:

Departs Feb 15, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$3,299

15-Night Repositioning Cruise

$2,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 22, 2025

Ports:

Bridgetown → Lisbon

Departs Feb 22, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,399

9-Night Mediterranean Cruise

$4,299

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Apr 06, 2025

Ports:

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

Departs Apr 06, 2025 from Lisbon, Portugal

Up to 2 deals including an Avoya Exclusive

From

$4,299

7-Night Mediterranean Cruise

$3,199

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Apr 23, 2025 View Other Dates

Ports:

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

Departs Apr 23, 2025 from Rome (Civitavecchia), Italy

Up to 2 deals including an Avoya Exclusive

From

$3,199

Roundtrip

7-Night Mediterranean Cruise

$7,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

May 21, 2025 View Other Dates

Ports:

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

Departs May 21, 2025 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$7,399

Roundtrip

7-Night Mediterranean Cruise

$7,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

May 28, 2025 View Other Dates

Ports:

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

Departs May 28, 2025 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$7,399

Roundtrip

7-Night Mediterranean Cruise

$4,999

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jun 14, 2025

Ports:

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

Departs Jun 14, 2025 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$4,999

Roundtrip

7-Night Mediterranean Cruise

$5,299

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jun 21, 2025 View Other Dates

Ports:

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

Departs Jun 21, 2025 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,299

Roundtrip

7-Night Mediterranean Cruise

$5,699

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Oct 04, 2025 View Other Dates

Ports:

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

Departs Oct 04, 2025 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,699

10-Night Mediterranean Cruise

$4,199

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Oct 25, 2025

Ports:

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

Departs Oct 25, 2025 from Barcelona, Spain

Up to 2 deals including an Avoya Exclusive

From

$4,199

14-Night Repositioning Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Nov 04, 2025

Ports:

Lisbon → Bridgetown

Departs Nov 04, 2025 from Lisbon, Portugal

Up to 2 deals including an Avoya Exclusive

From

$2,599

7-Night Panama Canal Cruise

$2,999

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Dec 13, 2025

Ports:

Colon → San Blas Island → Cartagena → Santa Maria → Oranjestad

Departs Dec 13, 2025 from Colon, Panama

Up to 2 deals including an Avoya Exclusive

From

$2,999

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 28, 2026

Ports:

Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

From

$2,499

Roundtrip

7-Night Caribbean Cruise

$2,699

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 07, 2026

Ports:

Departs Mar 07, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,699

22-Night Repositioning Cruise

$4,099

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 21, 2026

Ports:

Departs Mar 21, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$4,099

Roundtrip

7-Night Mediterranean Cruise

$5,199

Windstar Cruises – Wind Spirit

98 Reviews

Date:

May 07, 2026 View Other Dates

Ports:

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

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

Up to 2 deals including an Avoya Exclusive

From

$5,199

Roundtrip

7-Night Mediterranean Cruise

$5,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jun 04, 2026 View Other Dates

Ports:

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

Departs Jun 04, 2026 from Piraeus (Athens), Greece

Up to 2 deals including an Avoya Exclusive

From

$5,399

Roundtrip

7-Night Mediterranean Cruise

$4,999

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jun 11, 2026 View Other Dates

Ports:

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

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

Up to 2 deals including an Avoya Exclusive

From

$4,999