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Wind Surf
Windstar Cruises
Wind Surf Sailing Dates and Sailing Calendar
For more information, prices, and detailed day-by-day Wind Surf itineraries, please click one of the Wind Surf sailing dates below.
Sail Date |
Itinerary Name and Ports |
Duration |
Save to Favorites |
Priced From(per person) |
|---|---|---|---|---|
|
Sep 2, 2026
(Wednesday) |
8 Night Classic Italy and Dalmatian Coast Cruise
From Civitavecchia (Rome), Italy to Venice, Italy Ports: Civitavecchia (Rome), Sorrento, Giardini Naxos, Kotor, Dubrovnik, Split, Rovinj, Venice |
8 Nights
|
  Add to Favorites |
$9,848
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Sep 10, 2026
(Thursday) |
9 Night Adriatic Icons and Venetian Treasures Cruise
From Venice, Italy to Venice, Italy Ports: Venice, Rovinj, Zadar, Hvar, Dubrovnik, Kotor, Piran, Venice
Special Promotions
|
9 Nights
|
Add to Favorites |
$4,749
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Sep 19, 2026
(Saturday) |
8 Night Classic Italy and Dalmatian Coast Cruise
From Venice, Italy to Civitavecchia (Rome), Italy Ports: Venice, Rovinj, Split, Kotor, Dubrovnik, Giardini Naxos, Sorrento, Civitavecchia (Rome)
Special Promotions
|
8 Nights
|
Add to Favorites |
$9,848
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Sep 19, 2026
(Saturday) |
18 Night Star Collector Culture and Charms of Italy and Croatia Cruise
From Venice, Italy to Civitavecchia (Rome), Italy Ports: Venice, Rovinj, Split, Kotor, Dubrovnik, Giardini Naxos, Sorrento, Civitavecchia (Rome), Siracusa, Gozo, Valletta, Porto Empedocle, Trapani, Lipari, Sorrento, Amalfi, Civitavecchia (Rome) |
18 Nights
|
Add to Favorites |
$17,006
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Sep 27, 2026
(Sunday) |
10 Night Sicilian Splendors Cruise
From Civitavecchia (Rome), Italy to Civitavecchia (Rome), Italy Ports: Civitavecchia (Rome), Siracusa, Gozo, Valletta, Porto Empedocle, Trapani, Lipari, Sorrento, Amalfi, Civitavecchia (Rome)
Special Promotions
|
10 Nights
|
Add to Favorites |
$5,033
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Sep 27, 2026
(Sunday) |
18 Night Star Collector Italian Charms and Croatian Coastlines Cruise
From Civitavecchia (Rome), Italy to Venice, Italy Ports: Civitavecchia (Rome), Siracusa, Gozo, Valletta, Porto Empedocle, Trapani, Lipari, Sorrento, Amalfi, Civitavecchia (Rome), Sorrento, Giardini Naxos, Kotor, Dubrovnik, Trogir, Rovinj, Venice |
18 Nights
|
Add to Favorites |
$15,662
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Oct 7, 2026
(Wednesday) |
8 Night James Beard Foundation and Wine Cruise Classic Italy and Dalmatian Coast Cruise
From Civitavecchia (Rome), Italy to Venice, Italy Ports: Civitavecchia (Rome), Sorrento, Giardini Naxos, Kotor, Dubrovnik, Trogir, Rovinj, Venice
Special Promotions
|
8 Nights
|
Add to Favorites |
$9,848
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Oct 15, 2026
(Thursday) |
10 Night Classic Italy and Dalmatian Coast Cruise
From Venice, Italy to Civitavecchia (Rome), Italy Ports: Venice, Rovinj, Split, Dubrovnik, Kotor, Giardini Naxos, Sorrento, Civitavecchia (Rome)
Special Promotions
|
10 Nights
|
Add to Favorites |
$5,200
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Oct 15, 2026
(Thursday) |
15 Night Star Collector Italian Trio Cruise
From Venice, Italy to Barcelona, Spain Ports: Venice, Rovinj, Split, Dubrovnik, Kotor, Giardini Naxos, Sorrento, Civitavecchia (Rome), Portofino, Monte Carlo, Sanary Sur Mer, Palamos, Barcelona |
15 Nights
|
Add to Favorites |
$8,703
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Oct 15, 2026
(Thursday) |
23 Night Star Collector Riviera Rhapsody Cruise
From Venice, Italy to Lisbon, Portugal Ports: Venice, Rovinj, Split, Dubrovnik, Kotor, Giardini Naxos, Sorrento, Civitavecchia (Rome), Portofino, Monte Carlo, Sanary Sur Mer, Palamos, Barcelona, Palma de Mallorca, Cartagena, Almeria, Malaga, Gibraltar, Cadiz (Seville), Lisbon |
23 Nights
|
Add to Favorites |
$9,644
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Oct 25, 2026
(Sunday) |
5 Night Quick Getaways Yachtsmans Harbors of the Rivieras Cruise
From Civitavecchia (Rome), Italy to Barcelona, Spain Ports: Civitavecchia (Rome), Portofino, Monte Carlo, Sanary Sur Mer, Palamos, Barcelona
Special Promotions
|
5 Nights
|
Add to Favorites |
$1,896
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Oct 25, 2026
(Sunday) |
13 Night Star Collector Enchantment of the Western Mediterranean Cruise
From Civitavecchia (Rome), Italy to Lisbon, Portugal Ports: Civitavecchia (Rome), Portofino, Monte Carlo, Sanary Sur Mer, Palamos, Barcelona, Palma de Mallorca, Cartagena, Almeria, Malaga, Gibraltar, Cadiz (Seville), Lisbon |
13 Nights
|
Add to Favorites |
$5,446
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Oct 30, 2026
(Friday) |
8 Night Spanish Symphony Cruise
From Barcelona, Spain to Lisbon, Portugal Ports: Barcelona, Palma de Mallorca, Cartagena, Almeria, Malaga, Gibraltar, Cadiz (Seville), Lisbon
Special Promotions
|
8 Nights
|
Add to Favorites |
$2,877
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Dec 5, 2026
(Saturday) |
14 Night Ocean Crossing Cruise
From Lisbon, Portugal to Philipsburg (St. Maarten), Netherlands Antilles Ports: Lisbon, St John's, Philipsburg (St. Maarten) |
14 Nights
|
Add to Favorites |
Call
For Price Inside (double occupancy) Learn More |
|
Dec 19, 2026
(Saturday) |
7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise
From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles Ports: Philipsburg (St. Maarten), Gustavia St. Barts, Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Philipsburg (St. Maarten) |
7 Nights
|
Add to Favorites |
$2,798
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Dec 19, 2026
(Saturday) |
14 Night Star Collector Caribbean Explorations Cruise
From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles Ports: Philipsburg (St. Maarten), Gustavia St. Barts, Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Philipsburg (St. Maarten), Gustavia St. Barts, Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Philipsburg (St. Maarten) |
14 Nights
|
Add to Favorites |
$6,000
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Dec 26, 2026
(Saturday) |
7 Night Classic Caribbean Cruise
From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles Ports: Philipsburg (St. Maarten), Gustavia St. Barts, Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Philipsburg (St. Maarten) |
7 Nights
|
Add to Favorites |
$3,167
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Dec 26, 2026
(Saturday) |
14 Night Star Collector Caribbean Explorations Cruise
From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles Ports: Philipsburg (St. Maarten), Gustavia St. Barts, Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten) |
14 Nights
|
Add to Favorites |
$6,000
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Jan 2, 2027
(Saturday) |
7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise
From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)
Special Promotions
|
7 Nights
|
Add to Favorites |
$2,798
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Jan 2, 2027
(Saturday) |
14 Night Star Collector Caribbean Explorations Cruise
From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Charlestown, Iles des Saintes, Mayreau, Roseau, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Special Promotions
|
14 Nights
|
Add to Favorites |
$6,000
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
