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: Grand Caribbean Adventure
Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
55 days
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
Falmouth Harbour
Day 3
Road Bay
Day 4
Soper's Hole
Day 4
Jost Van Dyke, Great Harbour
Day 5
Jost Van Dyke, Great Harbour
Day 6
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 7
Gustavia
Day 8
Philipsburg, St. Maarten
Day 9
Basseterre
Day 10
Gustavia
Day 11
St. John's
Day 12
Les Saintes
Day 13
Mayreau
Day 14
Kingstown
Day 15
Bridgetown
Day 16
Anse Mitan
Day 17
Castries
Day 17
Pigeon Island
Day 18
Pigeon Island
Day 19
Bequia
Day 20
Mayreau
Day 21
St. George's
Day 22
Bridgetown
Day 23
Man-O-War Bay
Day 24
Mayreau
Day 25
Soufriere
Day 26
AT SEA
Day 27
Kralendijk
Day 28
Willemstad
Day 29
Oranjestad
Day 30
AT SEA
Day 31
Santa Marta
Day 32
Cartagena
Day 33
AT SEA
Day 34
Bocas del Toro
Day 35
AT SEA
Day 36
Colón
Day 37
Colón
Day 38
Bocas del Toro
Day 39
Isla San Andres
Day 40
AT SEA
Day 41
AT SEA
Day 42
Roatan
Day 43
Belize City
Day 44
Costa Maya
Day 45
Cozumel
Day 46
AT SEA
Day 47
Grand Cayman
Day 48
Cayman Brac
Day 49
Ocho Rios, Jamaica
Day 50
AT SEA
Day 51
Santo Domingo
Day 52
La Romana
Day 53
AT SEA
Day 54
Jost Van Dyke, Great Harbour
Day 55
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 56
Philipsburg, St. Maarten
ALL DATES &
FARES
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
Jan 4
2026
WIND SURF
$24,744
$19,299
Click on the date to view the map and itinerary by date