Small Ship Grand Adventures

 
Multiple destinations. Multiple months. Private-yacht style.

Multiple destinations. Multiple months. Private-yacht style.

From the 17th to 19th centuries, it was a rite of passage for young aristocrats to embark on a Grand Tour. This extended journey to the world’s great cities was a way to breathe life into their classical education, broadening their horizons and gifting them with knowledge and understanding that would enrich their own lives and their society.
 
Windstar's Grand Adventures offer homage to those extended journeys with meticulously curated voyages spanning multiple destinations over multiple months, each one highlighting a region unique in its cultural and natural heritage. Visit places both on and off the beaten track, checking must-sees off your bucket list and discovering secret places that few travelers ever see. Take the time to get to know people who still live much as their ancestors did. Taste fine wines and cuisines perfected over generations. Admire works of art from Roman aqueducts to tie-dyed sarongs. And spend relaxing days on deserted islands, in Japanese gardens, or cruising stunning fjords and canals. It’s the kind of education and perspective you can only get from travel. And it’s the kind of travel you can only get from a private yacht-style cruise on Windstar.

Windstar Knows the Way to A Grand Adventure
Windstar's Grand Adventures offer homage to those extended journeys with meticulously curated voyages spanning multiple destinations over multiple months, each one highlighting a region unique in its cultural and natural heritage. Visit places both on and off the beaten track, checking must-sees off your bucket list and discovering secret places that few travelers ever see. It’s the kind of education and perspective you can only get from travel. And it’s the kind of travel you can only get from a private yacht-style cruise on Windstar.
One Unforgettable Journey
One Unforgettable Journey
From the 17th to 19th centuries, it was a rite of passage for young aristocrats to embark on a Grand Tour. This extended journey to the world’s great cities was a way to breathe life into their classical education, broadening their horizons and gifting them with knowledge and understanding that would enrich their own lives and their society. These are Windstar's version of the Grand Tour.
WINDSTAR VOYAGES TO GRAND ADVENTURES

Star Collector: 2026 Grand Europe Adventure

Port to port
Stockholm to Athens, Greece
Duration
80 Days
All-Inclusive From?
$48,119
Cruise Only From?
$40,199
SPECIAL AVAILABLE Star Collector: Grand Caribbean & Americas Explorer

Star Collector: Grand Caribbean & Americas Explorer

Port to port
San Juan to Juneau
Duration
49 Days
All-Inclusive From?
$25,210
Cruise Only From?
$20,359
SPECIAL AVAILABLE Star Collector: Grand Caribbean & Panamanian Adventure

Star Collector: Grand Caribbean & Panamanian Adventure

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
28 Days
All-Inclusive From?
$11,071
Cruise Only From?
$8,299
SPECIAL AVAILABLE Star Collector: Grand Caribbean Adventure

Star Collector: Grand Caribbean Adventure

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
55 Days
All-Inclusive From?
$24,744
Cruise Only From?
$19,299
Star Collector: 2026 Grand Europe Adventure
Port to port
Stockholm to Athens, Greece
Duration
80 days
Day
Port
Day 1
Stockholm
Day 2
Tallinn
Day 3
Helsinki
Day 4
Helsinki
Day 5
VENTSPILS, Latvia
Day 6
Gdansk
Day 7
Bornholm
Day 8
Copenhagen
Day 9
AT SEA
Day 10
Haugesund
Day 11
Alesund
Day 12
ANDALSNES, Norway
Day 13
TRONDHEIM, Norway
Day 14
FROYA / SISTRANDA LIGGEKA, Norway
Day 15
Olden
Day 16
Bergen
Day 17
AT SEA
Day 18
Leith (Edinburgh), United Kingdom
Day 19
AT SEA
Day 20
Invergordon, United Kingdom
Day 21
Kirkwall, United Kingdom
Day 22
Portree, United Kingdom
Day 23
Oban
Day 24
Portrush, United Kingdom
Day 25
Isle of Man
Day 26
Dun Laoghaire (Dublin), Ireland
Day 27
Belfast, United Kingdom
Day 28
Londonderry
Day 29
Killybegs
Day 30
Galway
Day 30
SCENIC CRUISING CLIFFS OF MOHER
Day 31
Dingle, Ireland
Day 32
Ringaskidd (Cork)
Day 33
Waterford
Day 34
Isles of Scilly, United Kingdom
Day 35
Rouen
Day 36
Rouen
Day 37
Rouen
Day 38
Honfleur
Day 39
St-Malo
Day 40
Guernsey, Guernsey
Day 41
Lorient
Day 42
Bordeaux
Day 43
Bordeaux
Day 44
Bordeaux
Day 45
Bordeaux
Day 46
Bilbao
Day 47
Bilbao
Day 48
Gijon
Day 49
Vigo
Day 50
Leixoes (Porto), Portugal
Day 51
Lisbon
Day 52
Lisbon
Day 53
Seville
Day 54
Seville
Day 55
Tangier
Day 56
Málaga
Day 57
Cartagena
Day 58
Valencia
Day 59
Barcelona
Day 60
Palamos
Day 61
Sanary-sur-Mer
Day 62
Monte Carlo
Day 63
Cannes
Day 64
Portofino
Day 65
Portoferraio
Day 66
Porto Ercole
Day 67
Rome
Day 68
Sorrento
Day 69
Messina (Taormina)
Day 70
AT SEA
Day 71
Gythion
Day 72
Monemvasia
Day 73
Athens, Greece
Day 74
Kusadasi
Day 75
AT SEA
Day 76
Kavala, Greece
Day 77
Thessaloniki, Greece
Day 78
Thessaloniki, Greece
Day 79
Volos, Greece
Day 80
Skopelos, Greece
Day 81
Athens, Greece
ALL DATES &
FARES
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
Wed
Jul 15
2026
STAR LEGEND
$48,119
$40,199
Click on the date to view the map and itinerary by date