Small Ship Select Sailings

 

There are certain sailings that daring travelers dare not miss. Sailings that go above and beyond, with enhanced itineraries so deliberately designed and carefully constructed that they stand out as the best of the best. These are those sailings. No detail or opportunity is overlooked. You’ll explore the most unique UNESCO Heritage sites, enjoy the most unusual regional delicacies, and discover the most story-worthy cultural insights. These are unforgettable voyages for all those who feel they’ve “been there and done that,” designed by the Windstar destination experts who have themselves, “been there and done that,” in every corner of the world, on every sea. Designed for the savvy traveler, these Select Sailings are Windstar’s must-do voyages to must-see destinations.

WINDSTAR'S SELECT SAILINGS
SPECIAL AVAILABLE Adriatic Archipelagos & Greek Goddesses

Adriatic Archipelagos & Greek Goddesses

Port to port
Athens, Greece to Venice
Duration
9 Days
All-Inclusive From?
$3,760
Cruise Only From?
$2,869
SPECIAL AVAILABLE Around Iceland

Around Iceland

Port to port
Reykjavik to Reykjavik
Duration
7 Days
All-Inclusive From?
$3,982
Cruise Only From?
$3,289

Around Iceland: A Total Solar Eclipse

Port to port
Reykjavik to Reykjavik
Duration
7 Days
Call for
Availability
SPECIAL AVAILABLE Beach Fun & Sun: A Remote Caribbean Getaway

Beach Fun & Sun: A Remote Caribbean Getaway

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
6 Days
All-Inclusive From?
$3,092
Cruise Only From?
$2,399
SPECIAL AVAILABLE Classic Italy & Dalmatian Coast

Classic Italy & Dalmatian Coast

Port to port
Venice to Rome
Duration
8 Days
All-Inclusive From?
$4,070
Cruise Only From?
$3,278
SPECIAL AVAILABLE Costa Rica & Panama Canal

Costa Rica & Panama Canal

Port to port
Colón to Puerto Caldera
Duration
7 Days
All-Inclusive From?
$3,092
Cruise Only From?
$2,399
SPECIAL AVAILABLE Dreams of Tahiti

Dreams of Tahiti

Port to port
Papeete to Papeete
Duration
7 Days
All-Inclusive From?
$3,592
Cruise Only From?
$2,899
SPECIAL AVAILABLE Panama Canal, Cartagena, San Blas Islands & More

Panama Canal, Cartagena, San Blas Islands & More

Port to port
Balboa, Panama City to Oranjestad
Duration
6 Days
All-Inclusive From?
$2,199
Cruise Only From?
$2,199
SPECIAL AVAILABLE Tahiti & the Tuamotu Islands

Tahiti & the Tuamotu Islands

Port to port
Papeete to Papeete
Duration
11 Days
All-Inclusive From?
$4,597
Cruise Only From?
$3,508
SPECIAL AVAILABLE Treasures of the Greek Isles

Treasures of the Greek Isles

Port to port
Athens, Greece to Athens, Greece
Duration
7 Days
All-Inclusive From?
$4,071
Cruise Only From?
$3,378
SPECIAL AVAILABLE Wine Cruise: Yachtsman’s Harbors of the Rivieras

Wine Cruise: Yachtsman’s Harbors of the Rivieras

Port to port
Rome to Barcelona
Duration
7 Days
All-Inclusive From?
$3,071
Cruise Only From?
$2,378
SPECIAL AVAILABLE Yachtsman's Harbors of the Rivieras

Yachtsman's Harbors of the Rivieras

Port to port
Rome to Barcelona
Duration
7 Days
All-Inclusive From?
$2,772
Cruise Only From?
$2,079
SPECIAL AVAILABLE James Beard Foundation & Wine Cruise: Adriatic Archipelagos & Greek Goddesses

James Beard Foundation & Wine Cruise: Adriatic Archipelagos & Greek Goddesses

Port to port
Venice to Athens, Greece
Duration
9 Days
All-Inclusive From?
$6,290
Cruise Only From?
$5,399
SPECIAL AVAILABLE Winter Italy and the Dalmatian Coast

Winter Italy and the Dalmatian Coast

Port to port
Venice to Rome
Duration
8 Days
All-Inclusive From?
$3,791
Cruise Only From?
$2,999
SPECIAL AVAILABLE Canary Island Idyll

Canary Island Idyll

Port to port
Santa Cruz de Tenerife to Santa Cruz de Tenerife
Duration
10 Days
All-Inclusive From?
$4,489
Cruise Only From?
$3,499
SPECIAL AVAILABLE Europe's Winter Riviera

Europe's Winter Riviera

Port to port
Rome to Barcelona
Duration
7 Days
All-Inclusive From?
$3,492
Cruise Only From?
$2,799
SPECIAL AVAILABLE Spanish Symphony

Spanish Symphony

Port to port
Barcelona to Lisbon
Duration
8 Days
All-Inclusive From?
$4,291
Cruise Only From?
$3,499
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
6 days
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
Falmouth Harbour
Day 3
Road Bay
Day 4
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 4
Soper's Hole
Day 5
Soper's Hole
Day 6
Jost Van Dyke, Great Harbour
Day 7
Gustavia
Day 8
Philipsburg, St. Maarten
ALL DATES &
FARES
Holiday Sailings
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with unlimited select beer, wine, and cocktails, Wi-Fi, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun
Dec 14
2025
WIND SURF
$3,092
$2,399
Sun
Dec 28
2025
WIND SURF
$3,592
$2,899
Sun
Jan 4
2026
WIND SURF
$3,292
$2,599
Sat
Jan 24
2026
WIND SPIRIT
$3,392
$2,699
Sat
Jan 31
2026
WIND SPIRIT
$3,192
$2,499
Sat
Feb 14
2026
WIND SPIRIT
$3,292
$2,599
Sat
Feb 21
2026
WIND SPIRIT
$3,292
$2,599
Sat
Mar 7
2026
WIND SURF
Call For Availability
Sat
Mar 14
2026
WIND SURF
Call For Availability
Sat
Mar 28
2026
WIND SURF
$3,092
$2,399
Click on the date to view the map and itinerary by date