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 & Panamanian Adventure
Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
28 days
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
St. John's
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
Day 9
Basseterre
Day 10
Gustavia
Day 11
St. John's
Day 12
Les Saintes
Day 13
Roseau
Day 14
Mayreau
Day 15
Bridgetown
Day 16
AT SEA
Day 17
Basseterre
Day 18
St. John's
Day 19
Les Saintes
Day 20
Roseau
Day 21
Mayreau
Day 22
Anse Mitan
Day 23
Bridgetown
Day 24
Tobago Cays
Day 25
Pigeon Island
Day 26
Pigeon Island
Day 26
Castries
Day 26
The Pitons
Day 27
Mayreau
Day 28
Bequia
Day 29
Bridgetown
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
Sat
Feb 21
2026
WIND SPIRIT
$11,071
$8,299
Click on the date to view the map and itinerary by date