Windstar's Holiday Sailings

 

A Windstar Holiday is Beyond the Ordinary

A Windstar cruise is always a special occasion, but join us at Thanksgiving, Christmas, Hanukkah, or New Year’s and you’ll find us at our festive best. We decorate the ship as befits the season, from gingerbread villages to a flameless menorah, and toast the season with eggnog, themed cocktails, and champagne. Plus, you’ll find all your favorite holiday menu items like roast turkey, prime rib, and pumpkin pie, sometimes with the kind of unique twist you’d expect from the official cruise line of the James Beard Foundation. (Christmas pudding soufflé, anyone?) When you’re not playing holiday trivia or watching holiday movies, you can join our New Year’s Eve deck party or the chef’s Christmas High Tea. And to top it all off, attend a Windstar Crew Show that puts Santa’s magic bag of tricks to shame.
 
 
Stress-Free Holidays
Make this the year that your family enjoys a care-free holiday season, free from all the cooking, cleaning, and entertaining. With our relaxed and casual style, you don’t even have to dress up, and everywhere on the ship will be decorated so the magic of the season truly shines.
 
On-Board Family
We’ll spoil you with our crew who will make this a holiday you’ll remember and strive to make it a part of your yearly tradition. They’ll share their traditions with your family as well.
 
Something in Your Stocking
On Christmas sailings, anticipate special welcome treats in your suite or stateroom, like Christmas cookies and candy canes, mandarin oranges, roasted peanuts and chocolate candies.
 
Windstar Traditions
We have a few holiday traditions of our own we like to share, like the Captain reading The Night Before Christmas, the crew leading a sing-along of Christmas carols, and a guest-led Hanukkah menorah lighting. On New Year’s Eve, get your camera ready for a seafaring tradition as our oldest crew member rings out the previous year, and the youngest rings in the new one.
 
Festive Feasts
We’ll serve all your holiday favorites with classic trimmings, along with decadent options like butter-poached lobster tail. We make sure that vegetarians don’t miss out on the fun either, with delicious creations like Roasted Pumpkin Squash Soup and Beetroot, Broccoli & Goat Cheese Tart.
 
Christmas High Tea
A true holiday highlight is Windstar’s Christmas High Tea, featuring Christmas Cake and Stollen. Served in Compass Rose, the Lounge, or even on open deck if weather allows, this elegant affair is often accompanied by a local band.
 
Crew Talent Show
Cheer on your favorite crew members as they display a wide range of talents beyond their uncanny ability to read your mind and deliver top-notch service. From the cultural to the kitschy, they’ll keep you entertained in an evening full of warmth and good humor.
 
Warm Your Feet by the Beach
While everyone else might be shivering in the snow, you’ll spend your days frolicking on the beach, sunning yourself on the teak decks, or hiking in the cloud forests. With voyages to the Caribbean, Costa Rica & the Panama Canal, Tahiti, and more, you won’t have to worry about shoveling your driveway or packing your puffer jacket.

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Showing 58 of 58 voyages from this special
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San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Departure
November 23, 2025
Duration
7 Days
Ship
Star Pride
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$4,099 per guest
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All-inclusive
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$5,485USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
November 23, 2025
Duration
14 Days
Ship
Star Pride
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Cruise only
from
$7,199 per guest
?
All-inclusive
from
$7,793USD per guest

Final Rose & Overwater Bungalows + Air Package from LAX

Port to port
Moorea to Papeete
Departure
November 24, 2025
Duration
11 Days
Ship
Star Breeze
?
Cruise only
from
$7,899 per guest
?
All-inclusive
from
$8,592USD per guest

Golden Days in Bora Bora Air + Overwater Villa Package from LAX

Port to port
Papeete to Papeete
Departure
November 24, 2025
Duration
11 Days
Ship
Star Breeze
?
Cruise only
from
$5,299 per guest
?
All-inclusive
from
$5,992USD per guest

Dreams of Tahiti Air + Hotel Package from LAX

Port to port
Papeete to Papeete
Departure
November 25, 2025
Duration
10 Days
Ship
Star Breeze
?
Cruise only
from
$7,399 per guest
?
All-inclusive
from
$8,092USD per guest

Golden Days in Bora Bora Air + Overwater Villa Package from SEA

Port to port
Papeete to Papeete
Departure
November 26, 2025
Duration
12 Days
Ship
Star Breeze
?
Cruise only
from
$2,899 per guest
?
All-inclusive
from
$3,592USD per guest

Dreams of Tahiti

Port to port
Papeete to Papeete
Departure
November 27, 2025
Duration
7 Days
Ship
Star Breeze
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$6,392USD per guest

Overwater Bungalow & Tahitian Paradises Cruise Tour

Port to port
Papeete to Papeete
Departure
November 27, 2025
Duration
10 Days
Ship
Star Breeze
?
Cruise only
from
$2,399 per guest
?
All-inclusive
from
$3,092USD per guest

Beach Fun & Sun: A Remote Caribbean Getaway

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Departure
December 14, 2025
Duration
6 Days
Ship
Wind Surf
?
Cruise only
from
$4,499 per guest
?
All-inclusive
from
$5,885USD per guest

Star Collector: Caribbean Explorations

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Departure
December 14, 2025
Duration
14 Days
Ship
Wind Surf
?
Cruise only
from
$6,899 per guest
?
All-inclusive
from
$7,988USD per guest

Tahiti & the Tuamotu Islands Air + Hotel Package from LAX

Port to port
Papeete to Papeete
Departure
December 16, 2025
Duration
14 Days
Ship
Star Breeze
?
Cruise only
from
$7,299 per guest
?
All-inclusive
from
$7,992USD per guest

Winter Riviera & Madrid Cruise Tour

Port to port
Barcelona to Rome
Departure
December 16, 2025
Duration
11 Days
Ship
Star Legend
?
Cruise only
from
$4,499 per guest
?
All-inclusive
from
$5,588USD per guest

Tahiti & the Tuamotu Islands

Port to port
Papeete to Papeete
Departure
December 18, 2025
Duration
11 Days
Ship
Star Breeze
?
Cruise only
from
$2,899 per guest
?
All-inclusive
from
$3,691USD per guest

An ABC Christmas

Port to port
Oranjestad to Bridgetown
Departure
December 20, 2025
Duration
8 Days
Ship
Wind Spirit
?
Cruise only
from
$3,599 per guest
?
All-inclusive
from
$4,589USD per guest

Canary Island Idyll

Port to port
Santa Cruz de Tenerife to Santa Cruz de Tenerife
Departure
December 20, 2025
Duration
10 Days
Ship
Wind Star
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,992USD per guest

Costa Rica & Panama Canal

Port to port
Puerto Caldera to Colón
Departure
December 20, 2025
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$3,199 per guest
?
All-inclusive
from
$3,892USD 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
$5,299 per guest
?
All-inclusive
from
$6,784USD 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
$2,899 per guest
?
All-inclusive
from
$3,592USD per guest

Classic Caribbean

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Departure
December 21, 2025
Duration
7 Days
Ship
Wind Surf
?
Cruise only
from
$4,899 per guest
?
All-inclusive
from
$6,285USD per guest

Star Collector: Caribbean Explorations

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Departure
December 21, 2025
Duration
14 Days
Ship
Wind Surf
?
Cruise only
from
$7,099 per guest
?
All-inclusive
from
$8,089USD per guest

Tahiti & the Tuamotu Islands Air + Hotel Package from LAX

Port to port
Papeete to Papeete
Departure
December 27, 2025
Duration
13 Days
Ship
Star Breeze
?
Cruise only
from
$3,399 per guest
?
All-inclusive
from
$4,191USD 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
$2,899 per guest
?
All-inclusive
from
$3,592USD per guest

Beach Fun & Sun: A Remote Caribbean Getaway

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Departure
December 28, 2025
Duration
6 Days
Ship
Wind Surf
?
Cruise only
from
$5,099 per guest
?
All-inclusive
from
$6,683USD per guest

Star Seeker Maiden Voyage

Port to port
Málaga to Miami
Departure
December 28, 2025
Duration
16 Days
Ship
Star Seeker
?
Cruise only
from
$3,099 per guest
?
All-inclusive
from
$3,792USD per guest

Windward Island Delights

Port to port
Bridgetown to Bridgetown
Departure
December 28, 2025
Duration
7 Days
Ship
Wind Spirit
?
Cruise only
from
$4,699 per guest
?
All-inclusive
from
$5,689USD per guest

Tahiti & the Tuamotu Islands

Port to port
Papeete to Papeete
Departure
December 29, 2025
Duration
10 Days
Ship
Star Breeze
?
Cruise only
from
$3,799 per guest
?
All-inclusive
from
$4,789USD per guest

Canary Island Idyll

Port to port
Santa Cruz de Tenerife to Santa Cruz de Tenerife
Departure
December 30, 2025
Duration
10 Days
Ship
Wind Star
?
Cruise only
from
$8,899 per guest
?
All-inclusive
from
$8,899USD per guest

Legendary Temples: Chiang Mai & Angkor Wat Cruise Tour

Port to port
Klong Toei (Bangkok), Thailand to Phuket, Thailand
Departure
November 21, 2026
Duration
19 Days
Ship
Star Seeker
?
Cruise only
from
$7,299 per guest
?
All-inclusive
from
$7,299USD per guest

Thailand & The Steps Of Angkor Wat Cruise Tour

Port to port
Klong Toei (Bangkok), Thailand to Phuket, Thailand
Departure
November 21, 2026
Duration
15 Days
Ship
Star Seeker
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
November 22, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
November 22, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$5,999 per guest
?
All-inclusive
from
$7,682USD per guest

Star Collector: Twice the Tahiti

Port to port
Papeete to Papeete
Departure
November 23, 2026
Duration
17 Days
Ship
Star Breeze
?
Cruise only
from
$4,499 per guest
?
All-inclusive
from
$5,489USD per guest

Tahiti & the Tuamotu Islands

Port to port
Papeete to Papeete
Departure
November 23, 2026
Duration
10 Days
Ship
Star Breeze
?
Cruise only
from
$3,499 per guest
?
All-inclusive
from
$3,499USD per guest

Colombian & Southern Caribbean Coastlines

Port to port
Bridgetown to Colón
Departure
November 24, 2026
Duration
11 Days
Ship
Wind Star
?
Cruise only
from
$5,399 per guest
?
All-inclusive
from
$5,399USD per guest

Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal

Port to port
Bridgetown to Puerto Caldera
Departure
November 24, 2026
Duration
18 Days
Ship
Wind Star
?
Cruise only
from
$5,199 per guest
?
All-inclusive
from
$5,199USD per guest

Tantalizing Thailand & Sparkling Singapore

Port to port
Klong Toei (Bangkok), Thailand to Phuket, Thailand
Departure
November 25, 2026
Duration
11 Days
Ship
Star Seeker
?
Cruise only
from
$6,799 per guest
?
All-inclusive
from
$6,799USD per guest

Treasures Of Thailand & Chiang Mai Cruise Tour

Port to port
Klong Toei (Bangkok), Thailand to Phuket, Thailand
Departure
November 25, 2026
Duration
15 Days
Ship
Star Seeker
?
Cruise only
from
$2,999 per guest
?
All-inclusive
from
$3,692USD per guest

Dreams of Tahiti

Port to port
Papeete to Papeete
Departure
December 3, 2026
Duration
7 Days
Ship
Star Breeze
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Colón to Puerto Caldera
Departure
December 5, 2026
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Colón to Puerto Caldera
Departure
December 5, 2026
Duration
10 Days
Ship
Wind Star
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
December 6, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
December 6, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$7,299 per guest
?
All-inclusive
from
$7,893USD per guest

Final Rose & Overwater Bungalows + Air Package from LAX

Port to port
Moorea to Papeete
Departure
December 7, 2026
Duration
11 Days
Ship
Star Breeze
?
Cruise only
from
$7,899 per guest
?
All-inclusive
from
$8,592USD per guest

Golden Days in Bora Bora Air + Overwater Villa Package from LAX

Port to port
Papeete to Papeete
Departure
December 7, 2026
Duration
11 Days
Ship
Star Breeze
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Colón to Puerto Caldera
Departure
December 19, 2026
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Colón to Puerto Caldera
Departure
December 19, 2026
Duration
10 Days
Ship
Wind Star
?
Cruise only
from
$4,299 per guest
?
All-inclusive
from
$4,299USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
December 20, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,699 per guest
?
All-inclusive
from
$2,699USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
December 20, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Puerto Caldera to Colón
Departure
December 22, 2026
Duration
11 Days
Ship
Wind Star
?
Cruise only
from
$5,899 per guest
?
All-inclusive
from
$5,899USD per guest

Cambodia, Vietnam & the Heart of Hanoi Cruise Tour

Port to port
Halong Bay (Hanoi) to Klong Toei (Bangkok), Thailand
Departure
December 24, 2026
Duration
13 Days
Ship
Star Seeker
?
Cruise only
from
$7,999 per guest
?
All-inclusive
from
$7,999USD per guest

Legendary Hanoi & Angkor Wat Cruise Tour

Port to port
Halong Bay (Hanoi) to Klong Toei (Bangkok), Thailand
Departure
December 24, 2026
Duration
18 Days
Ship
Star Seeker
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Puerto Caldera to Colón
Departure
December 26, 2026
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$6,699 per guest
?
All-inclusive
from
$6,699USD per guest

Ancient Wonders Of Vietnam & Angkor Wat Cruise Tour

Port to port
Halong Bay (Hanoi) to Klong Toei (Bangkok), Thailand
Departure
December 27, 2026
Duration
15 Days
Ship
Star Seeker
?
Cruise only
from
$2,699 per guest
?
All-inclusive
from
$2,699USD per guest

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Departure
December 27, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$7,599 per guest
?
All-inclusive
from
$7,599USD per guest

Star Collector: Captivating Vietnam & Thailand

Port to port
Halong Bay (Hanoi) to Phuket, Thailand
Departure
December 27, 2026
Duration
21 Days
Ship
Star Seeker
?
Cruise only
from
$4,099 per guest
?
All-inclusive
from
$4,099USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
December 27, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$4,599 per guest
?
All-inclusive
from
$4,599USD per guest

Vietnam & Cambodia Revealed

Port to port
Halong Bay (Hanoi) to Klong Toei (Bangkok), Thailand
Departure
December 27, 2026
Duration
10 Days
Ship
Star Seeker
?
Cruise only
from
$4,499 per guest
?
All-inclusive
from
$5,489USD per guest

Tahiti & the Tuamotu Islands

Port to port
Papeete to Papeete
Departure
December 28, 2026
Duration
10 Days
Ship
Star Breeze