Updated Daily at 6:00 AM • November 13, 2026 1,535 Verified Sailings Fares From $898 / person

Windstar Cruise Deals, Perks & Specials

Explore verified Windstar stateroom deals, onboard credits, drink & Wi-Fi packages, and Signature Travel Network amenities.

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Showing 45 Curated Cruise Deals
#1 Deal

Beach Fun & Sun: A Remote Caribbean Getaway (7 Nights)

Offer #1664820
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (02-Jan-2027)
Returns: St Maarten (Philipsburg) (09-Jan-2027)
Port fees ($284) verified
Inside —
Oceanview $898
Balcony —
Suite $1,402
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#4 Deal

Star Collector: Tropical Horizons To Historic Amsterdam (23 Nights)

Offer #1706118
Star Pride - Windstar
Cruise Line: Windstar
Region: N/A
Departs: San Juan (27-Mar-2028)
Returns: Amsterdam (19-Apr-2028)
Inside —
Oceanview $4,211
Balcony $8,581
Suite $14,101
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1706118)
#5 Deal

Ocean Crossing (15 Nights)

Offer #1707627
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (19-Mar-2028)
Returns: Lisbon (03-Apr-2028)
Inside —
Oceanview $2,580
Balcony —
Suite $4,380
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#6 Deal

Ocean Crossing (15 Nights)

Offer #1707626
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Region: Europe
Departs: Lisbon (05-Nov-2027)
Returns: St Maarten (Philipsburg) (20-Nov-2027)
Inside —
Oceanview $2,580
Balcony —
Suite $4,380
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#7 Deal

Ocean Crossing (14 Nights)

Offer #1719840
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Region: Europe
Departs: Lisbon (05-Nov-2028)
Returns: St Maarten (Philipsburg) (19-Nov-2028)
Inside —
Oceanview $2,420
Balcony —
Suite $4,100
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1719840)
#9 Deal

Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing (22 Nights)

Offer #1707622
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (12-Mar-2028)
Returns: Lisbon (03-Apr-2028)
Inside —
Oceanview $4,168
Balcony —
Suite $6,368
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1707622)
#10 Deal

Tahiti & The Tuamotu Islands (11 Nights)

Offer #1663216
Star Breeze - Windstar
Cruise Line: Windstar
Departs: Papeete (18-Feb-2027)
Returns: Papeete (01-Mar-2027)
Inside —
Oceanview $2,549
Balcony $3,907
Suite $9,183
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • A Hosted Sailing
  • $400 per Couple Shipboard Credit (2027)
  • Reduced Deposit
#11 Deal

Star Collector: Caribbean Charms To Iberian Shores (21 Nights)

Offer #1705886
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (21-Feb-2028)
Returns: Lisbon (13-Mar-2028)
Inside —
Oceanview $4,271
Balcony $7,106
Suite $12,461
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1705886)
#12 Deal

Ocean Crossing (15 Nights)

Offer #1664847
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (27-Mar-2027)
Returns: Lisbon (11-Apr-2027)
Inside —
Oceanview $3,105
Balcony —
Suite $4,905
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#13 Deal

Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing (23 Nights)

Offer #1707590
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Region: Europe
Departs: Lisbon (05-Nov-2027)
Returns: St Maarten (Philipsburg) (28-Nov-2027)
Inside —
Oceanview $4,813
Balcony —
Suite $7,228
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Thanksgiving Sailing
#14 Deal

Panama Canal, Cartagena, San Blas Islands & More (8 Nights)

Offer #1637772
Star Legend - Windstar
Cruise Line: Windstar
Region: Panama Canal
Departs: Oranjestad (12-Dec-2026)
Returns: Balboa (20-Dec-2026)
Port fees ($174) verified
Inside —
Oceanview $1,661
Balcony $2,201
Suite $6,806
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#15 Deal

Star Collector: Captivating Caribbean (15 Nights)

Offer #1637768
Star Legend - Windstar
Cruise Line: Windstar
Departs: Bridgetown (27-Nov-2026)
Returns: Oranjestad (12-Dec-2026)
Port fees ($660) verified
Inside —
Oceanview $3,422
Balcony $4,349
Suite $9,478
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#17 Deal

Ocean Crossing (11 Nights)

Offer #1706442
Star Seeker - Windstar
Cruise Line: Windstar
Region: Alaska
Departs: Tokyo (25-May-2029)
Returns: Seward (05-Jun-2029)
Inside —
Oceanview $2,619
Balcony $4,227
Suite $6,627
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Onboard Credit
  • Memorial Day Sailing
#18 Deal

Ocean Crossing (11 Nights)

Offer #1706298
Star Seeker - Windstar
Cruise Line: Windstar
Region: Alaska
Departs: Tokyo (20-May-2027)
Returns: Seward (31-May-2027)
Inside —
Oceanview $2,880
Balcony $3,760
Suite $7,665
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
  • Memorial Day Sailing
#19 Deal

Tantalizing Tuamotu Islands & Beautiful Bora Bora (7 Nights)

Offer #1663205
Star Breeze - Windstar
Cruise Line: Windstar
Departs: Papeete (14-Jan-2027)
Returns: Papeete (21-Jan-2027)
Inside —
Oceanview $1,744
Balcony $2,381
Suite $4,881
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#20 Deal

Dreams Of Tahiti (7 Nights)

Offer #1596129
Star Breeze - Windstar
Cruise Line: Windstar
Departs: Papeete (10-Dec-2026)
Returns: Papeete (17-Dec-2026)
Port fees ($426) verified
Inside —
Oceanview $1,744
Balcony $2,608
Suite $4,776
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#21 Deal

San Juan & The Virgin Islands (7 Nights)

Offer #1618219
Star Pride - Windstar
Cruise Line: Windstar
Departs: San Juan (10-Jan-2027)
Returns: San Juan (17-Jan-2027)
Port fees ($356) verified
Inside —
Oceanview $1,679
Balcony $2,624
Suite $4,889
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1618219)
#22 Deal

Star Collector: Spanish Shores Transatlantic Crossing (23 Nights)

Offer #1705883
Star Legend - Windstar
Cruise Line: Windstar
Departs: Bridgetown (02-Mar-2027)
Returns: Barcelona (25-Mar-2027)
Inside —
Oceanview $5,571
Balcony $9,711
Suite $16,744
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#24 Deal

Star Collector: Atlantic Crossing To The Virgin Islands (21 Nights)

Offer #1705885
Star Legend - Windstar
Cruise Line: Windstar
Region: N/A
Departs: Cadiz (06-Dec-2027)
Returns: San Juan (27-Dec-2027)
Inside —
Oceanview $5,878
Balcony $11,758
Suite $16,798
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
  • Christmas Holiday Sailing
#25 Deal

Star Collector: Spanish Shores Transatlantic Crossing (23 Nights)

Offer #1719851
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (19-Mar-2028)
Returns: Barcelona (11-Apr-2028)
Inside —
Oceanview $5,689
Balcony —
Suite $8,104
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1719851)
#26 Deal

Ocean Crossing (21 Nights)

Offer #1665283
Wind Star - Windstar
Cruise Line: Windstar
Ship: Wind Star
Departs: Puntarenas (08-Feb-2027)
Returns: Papeete (01-Mar-2027)
Port fees ($313) verified
Inside —
Oceanview $5,496
Balcony —
Suite $12,565
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Valentine's Day Sailing
#27 Deal

Star Collector: Atlantic Interludes & Iberian Indulgences (23 Nights)

Offer #1707558
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (27-Mar-2027)
Returns: Tarragona (19-Apr-2027)
Inside —
Oceanview $5,804
Balcony —
Suite $8,449
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#28 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1706094
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (07-Feb-2028)
Returns: San Juan (21-Feb-2028)
Inside —
Oceanview $4,014
Balcony $5,694
Suite $9,054
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1706094)
  • Valentine's Day Sailing
#29 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1705871
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (31-Jan-2028)
Returns: San Juan (14-Feb-2028)
Inside —
Oceanview $4,014
Balcony $5,694
Suite $9,054
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1705871)
  • Valentine's Day Sailing
#30 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1705920
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (20-Dec-2027)
Returns: San Juan (03-Jan-2028)
Inside —
Oceanview $4,434
Balcony $6,744
Suite $10,314
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
  • Christmas Holiday Sailing
  • New Year's Eve Sailing
#31 Deal

Star Collector: Winter In Spain And The Rivieras (16 Nights)

Offer #1664162
Star Explorer - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (10-Nov-2027)
Returns: Barcelona (26-Nov-2027)
Inside —
Oceanview $4,948
Balcony $6,628
Suite $10,868
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
  • Thanksgiving Sailing
#33 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1706095
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (14-Feb-2028)
Returns: San Juan (28-Feb-2028)
Inside —
Oceanview $4,154
Balcony $6,254
Suite $9,614
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1706095)
  • Valentine's Day Sailing
#34 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707607
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (23-Jan-2028)
Returns: St Maarten (Philipsburg) (06-Feb-2028)
Inside —
Oceanview $3,830
Balcony —
Suite $5,160
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1707607)
#35 Deal

Star Collector: Caribbean Islands & Colombian Coast Discovery (14 Nights)

Offer #1706112
Star Pride - Windstar
Cruise Line: Windstar
Departs: San Juan (22-Nov-2027)
Returns: Colon (06-Dec-2027)
Inside —
Oceanview $4,197
Balcony $6,087
Suite $8,817
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Thanksgiving Sailing
#36 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1690877
Star Pride - Windstar
Cruise Line: Windstar
Departs: San Juan (20-Mar-2028)
Returns: San Juan (03-Apr-2028)
Inside —
Oceanview $4,014
Balcony $5,624
Suite $8,984
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1690877)
#37 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1690881
Star Pride - Windstar
Cruise Line: Windstar
Departs: San Juan (13-Mar-2028)
Returns: San Juan (27-Mar-2028)
Inside —
Oceanview $4,014
Balcony $5,624
Suite $8,984
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1690881)
#42 Deal

Star Collector: Caribbean Explorations (13 Nights)

Offer #1707599
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (27-Dec-2027)
Returns: St Maarten (Philipsburg) (09-Jan-2028)
Inside —
Oceanview $3,760
Balcony —
Suite $4,995
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • New Year's Eve Sailing
#43 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1690876
Star Pride - Windstar
Cruise Line: Windstar
Departs: San Juan (15-Nov-2027)
Returns: San Juan (29-Nov-2027)
Inside —
Oceanview $4,224
Balcony $6,604
Suite $10,174
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Thanksgiving Sailing
#44 Deal

Tahiti & The Tuamotu Islands (10 Nights)

Offer #1664035
Star Breeze - Windstar
Cruise Line: Windstar
Departs: Papeete (20-May-2027)
Returns: Papeete (30-May-2027)
Inside —
Oceanview $3,167
Balcony $4,435
Suite $10,166
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • A Hosted Sailing
  • $400 per Couple Shipboard Credit (2027)
  • Reduced Deposit
#45 Deal

Star Collector: Lovely Leewards (14 Nights)

Offer #1705923
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (27-Dec-2027)
Returns: San Juan (10-Jan-2028)
Inside —
Oceanview $4,434
Balcony $6,744
Suite $10,314
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
  • New Year's Eve Sailing

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Beach Fun & Sun: A Remote Caribbean Getaway (7N) Wind Surf • 02-Jan-2027 — — Select Cabin »
Ocean Crossing (16N) Star Pride • 30-Mar-2027 — $5,000 Select Cabin »
Ocean Crossing (16N) Star Pride • 03-Apr-2028 — $7,160 Select Cabin »
Star Collector: Tropical Horizons To Historic Amsterdam (23N) Star Pride • 27-Mar-2028 — $8,581 Select Cabin »
Ocean Crossing (15N) Wind Surf • 19-Mar-2028 — — Select Cabin »
Ocean Crossing (15N) Wind Surf • 05-Nov-2027 — — Select Cabin »
Ocean Crossing (14N) Wind Surf • 05-Nov-2028 — — Select Cabin »
Knot Your Average Crossing (15N) Star Legend • 02-Mar-2027 — $4,671 Select Cabin »
Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing (22N) Wind Surf • 12-Mar-2028 — — Select Cabin »
Tahiti & The Tuamotu Islands (11N) Star Breeze • 18-Feb-2027 — $3,907 Select Cabin »
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