Local Season Mediterranean

 

Discover the Mediterranean’s Local Season

Windstar is rewriting the script on Mediterranean vacations with an exciting new winter season that offers even more once-in-a-lifetime experiences, more personal interactions with locals, more space at must-see attractions, and more ports of call. In fact, we’ll be one of the few small ship cruise lines sailing these waters this time of year!

COMFORTABLE WEATHER
There’s a reason the “Mediterranean climate” is so desirable. Fall and winter along Europe’s southern coastlines are famously mild and often sunny. In fact, cities like Málaga, Rome and Athens have temperatures that hover around the 70s.

LOWER AIR FARE
Late fall and winter are some of the cheapest times to fly to Europe. Not only that, but travelers often find better deals on certain activities and attractions, leaving more room for unique experiences, seasonal souvenirs and more.

FESTIVE ATMOSPHERE AND UNIQUE EXPERIENCES
The dark days of winter are anything but as Europe decorates for the holidays. In fact, many of Europe’s legendary winter markets kick off well before winter has officially begun — some as early as the first week of November. Many cities and countries have their own distinct winter celebrations, like the Venice’s Carnevale and Greece’s Epiphany, a January “festival of lights” that closes out the Christmas season.

NEW PORTS AND OVERNIGHT STOPS
Our winter itineraries include unique destinations not available during the summer months, like Naples, Catania, Genoa and more. They also feature overnight stays in cities like Venice and Livorno, the gateway to iconic Florence and Pisa.

To book, call your Travel Advisor or Windstar Cruises for special offers.

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Showing 59 of 59 voyages from this special
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Destination
Departure Port
Ship
Dates
Duration
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Cruise only
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$2,559 per guest
?
All-inclusive
from
$3,252USD per guest

Southern Spain Winter Escapes

Port to port
Barcelona to Málaga
Departure
November 7, 2025
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$2,239 per guest
?
All-inclusive
from
$2,932USD per guest

Masterpieces at Sea: Brushes & Tapas

Port to port
Málaga to Barcelona
Departure
November 14, 2025
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$2,159 per guest
?
All-inclusive
from
$2,852USD per guest

Southern Spain Winter Escapes

Port to port
Barcelona to Málaga
Departure
November 21, 2025
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$3,799 per guest
?
All-inclusive
from
$4,492USD per guest

Southern Spain Winter Escapes

Port to port
Málaga to Barcelona
Departure
December 13, 2025
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$5,999 per guest
?
All-inclusive
from
$7,385USD per guest

Star Collector: Winter in Spain and the Rivieras

Port to port
Málaga to Rome
Departure
December 13, 2025
Duration
14 Days
Ship
Star Legend
?
Cruise only
from
$9,199 per guest
?
All-inclusive
from
$11,377USD per guest

Star Collector: Winter Mediterranean Adventure

Port to port
Málaga to Venice
Departure
December 13, 2025
Duration
22 Days
Ship
Star Legend
?
Cruise only
from
$3,799 per guest
?
All-inclusive
from
$4,492USD per guest

Europe's Winter Riviera

Port to port
Barcelona to Rome
Departure
December 20, 2025
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$6,199 per guest
?
All-inclusive
from
$7,684USD per guest

Star Collector: Winter in Europe's Rivieras & Croatia

Port to port
Barcelona to Venice
Departure
December 20, 2025
Duration
15 Days
Ship
Star Legend
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$4,791USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Rome to Venice
Departure
December 27, 2025
Duration
8 Days
Ship
Star Legend
?
Cruise only
from
$5,899 per guest
?
All-inclusive
from
$7,384USD per guest

Star Collector: Winter in Europe's Rivieras & Croatia

Port to port
Venice to Barcelona
Departure
January 4, 2026
Duration
15 Days
Ship
Star Legend
?
Cruise only
from
$8,799 per guest
?
All-inclusive
from
$11,175USD per guest

Star Collector: Winter Mediterranean Adventure

Port to port
Venice to Barcelona
Departure
January 4, 2026
Duration
24 Days
Ship
Star Legend
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$4,791USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Venice to Rome
Departure
January 4, 2026
Duration
8 Days
Ship
Star Legend
?
Cruise only
from
$2,378 per guest
?
All-inclusive
from
$3,071USD per guest

Europe's Winter Riviera

Port to port
Rome to Barcelona
Departure
January 12, 2026
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$5,599 per guest
?
All-inclusive
from
$7,183USD per guest

Star Collector: Winter in Spain and the Rivieras

Port to port
Rome to Barcelona
Departure
January 12, 2026
Duration
16 Days
Ship
Star Legend
?
Cruise only
from
$6,478 per guest
?
All-inclusive
from
$7,171USD per guest

Winter Riviera & Madrid Cruise Tour

Port to port
Rome to Barcelona
Departure
January 12, 2026
Duration
12 Days
Ship
Star Legend
?
Cruise only
from
$3,599 per guest
?
All-inclusive
from
$4,490USD per guest

Southern Spain Winter Escapes

Port to port
Barcelona to Barcelona
Departure
January 19, 2026
Duration
9 Days
Ship
Star Legend
?
Cruise only
from
$5,599 per guest
?
All-inclusive
from
$7,183USD per guest

Star Collector: Winter in Spain and the Rivieras

Port to port
Barcelona to Rome
Departure
January 19, 2026
Duration
16 Days
Ship
Star Legend
?
Cruise only
from
$8,399 per guest
?
All-inclusive
from
$10,775USD per guest

Star Collector: Winter Mediterranean Adventure

Port to port
Barcelona to Venice
Departure
January 19, 2026
Duration
24 Days
Ship
Star Legend
?
Cruise only
from
$7,499 per guest
?
All-inclusive
from
$8,192USD per guest

Winter Riviera & Madrid Cruise Tour

Port to port
Barcelona to Rome
Departure
January 24, 2026
Duration
11 Days
Ship
Star Legend
?
Cruise only
from
$3,399 per guest
?
All-inclusive
from
$4,092USD per guest

Europe's Winter Riviera

Port to port
Barcelona to Rome
Departure
January 28, 2026
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$5,599 per guest
?
All-inclusive
from
$7,084USD per guest

Star Collector: Winter in Europe's Rivieras & Croatia

Port to port
Barcelona to Venice
Departure
January 28, 2026
Duration
15 Days
Ship
Star Legend
?
Cruise only
from
$3,599 per guest
?
All-inclusive
from
$4,391USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Rome to Venice
Departure
February 4, 2026
Duration
8 Days
Ship
Star Legend
?
Cruise only
from
$5,999 per guest
?
All-inclusive
from
$7,484USD per guest

Star Collector: Winter in Europe's Rivieras & Croatia

Port to port
Venice to Barcelona
Departure
February 12, 2026
Duration
15 Days
Ship
Star Legend
?
Cruise only
from
$8,899 per guest
?
All-inclusive
from
$11,275USD per guest

Star Collector: Winter Mediterranean Adventure

Port to port
Venice to Barcelona
Departure
February 12, 2026
Duration
24 Days
Ship
Star Legend
?
Cruise only
from
$4,199 per guest
?
All-inclusive
from
$4,991USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Venice to Rome
Departure
February 12, 2026
Duration
8 Days
Ship
Star Legend
?
Cruise only
from
$3,399 per guest
?
All-inclusive
from
$4,092USD per guest

Masterpieces at Sea: Europe’s Winter Riviera

Port to port
Rome to Barcelona
Departure
February 20, 2026
Duration
7 Days
Ship
Star Legend
?
Cruise only
from
$5,599 per guest
?
All-inclusive
from
$7,183USD per guest

Star Collector: Winter in Spain and the Rivieras

Port to port
Rome to Barcelona
Departure
February 20, 2026
Duration
16 Days
Ship
Star Legend
?
Cruise only
from
$7,499 per guest
?
All-inclusive
from
$8,192USD per guest

Winter Riviera & Madrid Cruise Tour

Port to port
Rome to Barcelona
Departure
February 20, 2026
Duration
12 Days
Ship
Star Legend
?
Cruise only
from
$7,699 per guest
?
All-inclusive
from
$8,590USD per guest

Madrid & Southern Spain Winter Escapes Cruise Tour

Port to port
Barcelona to Barcelona
Departure
February 23, 2026
Duration
13 Days
Ship
Star Legend
?
Cruise only
from
$3,599 per guest
?
All-inclusive
from
$4,490USD per guest

Southern Spain Winter Escapes

Port to port
Barcelona to Barcelona
Departure
February 27, 2026
Duration
9 Days
Ship
Star Legend
?
Cruise only
from
$3,599 per guest
?
All-inclusive
from
$4,391USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Rome to Venice
Departure
March 15, 2026
Duration
8 Days
Ship
Star Legend
?
Cruise only
from
$6,999 per guest
?
All-inclusive
from
$8,583USD per guest

Star Collector: A Winter Muse in the Mediterranean

Port to port
Venice to Athens, Greece
Departure
March 23, 2026
Duration
16 Days
Ship
Star Legend
?
Cruise only
from
$10,899 per guest
?
All-inclusive
from
$13,275USD per guest

Star Collector: Coastlines of Antiquity: Italy, Croatia, and Greece

Port to port
Venice to Istanbul
Departure
March 23, 2026
Duration
24 Days
Ship
Star Legend
?
Cruise only
from
$4,199 per guest
?
All-inclusive
from
$4,991USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Venice to Rome
Departure
March 23, 2026
Duration
8 Days
Ship
Star Legend
?
Cruise only
from
$15,889 per guest
?
All-inclusive
from
$15,889USD per guest

Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama

Port to port
San Juan to Puerto Caldera
Departure
March 27, 2026
Duration
24 Days
Ship
Star Seeker
?
Cruise only
from
$7,399 per guest
?
All-inclusive
from
$8,983USD per guest

Star Collector: Eastern Mediterranean Jewels

Port to port
Rome to Istanbul
Departure
March 31, 2026
Duration
16 Days
Ship
Star Legend
?
Cruise only
from
$4,299 per guest
?
All-inclusive
from
$5,091USD per guest

Winter in Italy and the Adriatic

Port to port
Rome to Athens, Greece
Departure
March 31, 2026
Duration
8 Days
Ship
Star Legend
Callfor
availability

Madrid & Southern Spain Winter Escapes Cruise Tour

Port to port
Barcelona to Barcelona
Departure
January 2, 2027
Duration
13 Days
Ship
Star Explorer
?
Cruise only
from
$5,499 per guest
?
All-inclusive
from
$6,390USD per guest

Southern Spain Winter Escapes

Port to port
Barcelona to Barcelona
Departure
January 6, 2027
Duration
9 Days
Ship
Star Explorer
?
Cruise only
from
$7,899 per guest
?
All-inclusive
from
$9,483USD per guest

Star Collector: Winter in Spain and the Rivieras

Port to port
Barcelona to Rome
Departure
January 6, 2027
Duration
16 Days
Ship
Star Explorer
?
Cruise only
from
$11,899 per guest
?
All-inclusive
from
$14,275USD per guest

Star Collector: Winter Mediterranean Adventure

Port to port
Barcelona to Venice
Departure
January 6, 2027
Duration
24 Days
Ship
Star Explorer
Callfor
availability

Winter Riviera & Madrid Cruise Tour

Port to port
Barcelona to Rome
Departure
January 11, 2027
Duration
11 Days
Ship
Star Explorer
?
Cruise only
from
$4,399 per guest
?
All-inclusive
from
$5,092USD per guest

Europe's Winter Riviera

Port to port
Barcelona to Rome
Departure
January 15, 2027
Duration
7 Days
Ship
Star Explorer
?
Cruise only
from
$7,499 per guest
?
All-inclusive
from
$8,984USD per guest

Star Collector: Winter in Europe's Rivieras & Croatia

Port to port
Barcelona to Venice
Departure
January 15, 2027
Duration
15 Days
Ship
Star Explorer
?
Cruise only
from
$4,999 per guest
?
All-inclusive
from
$5,791USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Rome to Venice
Departure
January 22, 2027
Duration
8 Days
Ship
Star Explorer
?
Cruise only
from
$7,499 per guest
?
All-inclusive
from
$8,984USD per guest

Star Collector: Winter in Europe's Rivieras & Croatia

Port to port
Venice to Barcelona
Departure
January 30, 2027
Duration
15 Days
Ship
Star Explorer
?
Cruise only
from
$11,899 per guest
?
All-inclusive
from
$14,275USD per guest

Star Collector: Winter Mediterranean Adventure

Port to port
Venice to Barcelona
Departure
January 30, 2027
Duration
24 Days
Ship
Star Explorer
?
Cruise only
from
$4,999 per guest
?
All-inclusive
from
$5,791USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Venice to Rome
Departure
January 30, 2027
Duration
8 Days
Ship
Star Explorer
?
Cruise only
from
$4,399 per guest
?
All-inclusive
from
$5,092USD per guest

Europe's Winter Riviera

Port to port
Rome to Barcelona
Departure
February 7, 2027
Duration
7 Days
Ship
Star Explorer
?
Cruise only
from
$7,899 per guest
?
All-inclusive
from
$9,483USD per guest

Star Collector: Winter in Spain and the Rivieras

Port to port
Rome to Barcelona
Departure
February 7, 2027
Duration
16 Days
Ship
Star Explorer
Callfor
availability

Winter Riviera & Madrid Cruise Tour

Port to port
Rome to Barcelona
Departure
February 7, 2027
Duration
12 Days
Ship
Star Explorer
Callfor
availability

Madrid & Southern Spain Winter Escapes Cruise Tour

Port to port
Barcelona to Barcelona
Departure
February 10, 2027
Duration
13 Days
Ship
Star Explorer
?
Cruise only
from
$5,499 per guest
?
All-inclusive
from
$6,390USD per guest

Southern Spain Winter Escapes

Port to port
Barcelona to Barcelona
Departure
February 14, 2027
Duration
9 Days
Ship
Star Explorer
Callfor
availability

Madrid & Southern Spain Winter Escapes Cruise Tour

Port to port
Barcelona to Barcelona
Departure
February 19, 2027
Duration
13 Days
Ship
Star Explorer
?
Cruise only
from
$5,599 per guest
?
All-inclusive
from
$6,490USD per guest

Southern Spain Winter Escapes

Port to port
Barcelona to Barcelona
Departure
February 23, 2027
Duration
9 Days
Ship
Star Explorer
Callfor
availability

Winter Riviera & Madrid Cruise Tour

Port to port
Barcelona to Rome
Departure
February 28, 2027
Duration
11 Days
Ship
Star Explorer
?
Cruise only
from
$4,699 per guest
?
All-inclusive
from
$5,392USD per guest

Europe's Winter Riviera

Port to port
Barcelona to Rome
Departure
March 4, 2027
Duration
7 Days
Ship
Star Explorer
?
Cruise only
from
$5,499 per guest
?
All-inclusive
from
$6,291USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Venice to Rome
Departure
March 19, 2027
Duration
8 Days
Ship
Star Explorer
?
Cruise only
from
$5,199 per guest
?
All-inclusive
from
$5,199USD per guest

Winter Italy and the Dalmatian Coast

Port to port
Rome to Venice
Departure
March 27, 2027
Duration
8 Days
Ship
Star Explorer