Updated Daily at 6:00 AM • November 13, 2026 100 Verified Sailings Fares From $1,100 / person

Star Legend Cruise Deals & Special Offers (Windstar)

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Showing 45 Curated Cruise Deals
#2 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)
#3 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
#4 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
#6 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
#7 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
#8 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
#9 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
#10 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
#12 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
#17 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
#18 Deal

Star Collector: Iberian Charm, Italian Elegance & Riviera Nights (15 Nights)

Offer #1673664
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (05-Nov-2027)
Returns: Lisbon (20-Nov-2027)
Inside —
Oceanview $4,704
Balcony $7,779
Suite $12,054
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#19 Deal

San Juan & The Virgin Islands (7 Nights)

Offer #1705921
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (20-Dec-2027)
Returns: San Juan (27-Dec-2027)
Inside —
Oceanview $2,443
Balcony $3,458
Suite $5,558
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
#20 Deal

Star Collector: Sicilian & Riviera Splendors (17 Nights)

Offer #1719596
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (21-Oct-2028)
Returns: Barcelona (07-Nov-2028)
Inside —
Oceanview $5,497
Balcony $9,322
Suite $13,487
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1719596)
#21 Deal

Ocean Crossing (14 Nights)

Offer #1705919
Star Legend - Windstar
Cruise Line: Windstar
Departs: Cadiz (06-Dec-2027)
Returns: San Juan (20-Dec-2027)
Inside —
Oceanview $4,730
Balcony $11,100
Suite $15,300
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#22 Deal

Windward Ways & Tobago Cays (8 Nights)

Offer #1637769
Star Legend - Windstar
Cruise Line: Windstar
Departs: Bridgetown (04-Dec-2026)
Returns: Oranjestad (12-Dec-2026)
Port fees ($353) verified
Inside —
Oceanview $2,740
Balcony $3,900
Suite $5,513
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#23 Deal

Star Collector: Italian Charms & Croatian Coastlines (18 Nights)

Offer #1719612
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (21-Jul-2028)
Returns: Venice (08-Aug-2028)
Inside —
Oceanview $5,910
Balcony $9,870
Suite $14,100
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1719612)
#24 Deal

Jewels Of The Windward Islands (7 Nights)

Offer #1637767
Star Legend - Windstar
Cruise Line: Windstar
Departs: Bridgetown (27-Nov-2026)
Returns: Bridgetown (04-Dec-2026)
Port fees ($311) verified
Inside —
Oceanview $2,419
Balcony $3,399
Suite $4,869
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#25 Deal

Star Collector: Iberian Charm, Italian Elegance & Riviera Nights (15 Nights)

Offer #1673660
Star Legend - Windstar
Cruise Line: Windstar
Departs: Lisbon (17-Mar-2027)
Returns: Rome (Civitavecchia) (01-Apr-2027)
Inside —
Oceanview $5,004
Balcony $8,679
Suite $12,392
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#26 Deal

San Juan & The Virgin Islands (7 Nights)

Offer #1706096
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (14-Feb-2028)
Returns: San Juan (21-Feb-2028)
Inside —
Oceanview $2,443
Balcony $3,458
Suite $5,558
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Valentine's Day Sailing
#27 Deal

Star Collector: Latin America Explorer (16 Nights)

Offer #1637745
Star Legend - Windstar
Cruise Line: Windstar
Region: Panama Canal
Departs: Oranjestad (12-Dec-2026)
Returns: Puntarenas (28-Dec-2026)
Port fees ($493) verified
Inside —
Oceanview $5,628
Balcony $7,788
Suite $12,629
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Christmas Holiday Sailing
#28 Deal

Star Collector: Iberian Charm, Italian Elegance & Riviera Nights (15 Nights)

Offer #1719599
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (31-Oct-2028)
Returns: Lisbon (15-Nov-2028)
Inside —
Oceanview $5,079
Balcony $9,354
Suite $14,272
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1719599)
#29 Deal

Naturally Costa Rica (7 Nights)

Offer #1637750
Star Legend - Windstar
Cruise Line: Windstar
Region: Panama Canal
Departs: Puntarenas (09-Feb-2027)
Returns: Balboa (16-Feb-2027)
Port fees ($321) verified
Inside —
Oceanview $2,582
Balcony $3,562
Suite $4,822
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
  • Valentine's Day Sailing
#30 Deal

Star Collector: Songs Of Sicily & Southern Italy Via The Corinth Canal (20 Nights)

Offer #1664466
Star Legend - Windstar
Cruise Line: Windstar
Region: Europe
Departs: Rome (Civitavecchia) (11-Aug-2027)
Returns: Athens (31-Aug-2027)
Inside —
Oceanview $6,861
Balcony $11,661
Suite $17,361
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#33 Deal

Star Collector: Windward Islands & Spanish New World (16 Nights)

Offer #1637770
Star Legend - Windstar
Cruise Line: Windstar
Departs: Bridgetown (04-Dec-2026)
Returns: Balboa (20-Dec-2026)
Port fees ($941) verified
Inside —
Oceanview $5,742
Balcony $7,262
Suite $11,545
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#37 Deal

Sicilian Splendors (10 Nights)

Offer #1719589
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (22-May-2028)
Returns: Rome (Civitavecchia) (01-Jun-2028)
Inside —
Oceanview $3,633
Balcony $6,233
Suite $9,583
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Onboard Credit
  • Memorial Day Sailing
#38 Deal

Sicilian Splendors (9 Nights)

Offer #1664433
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (11-Aug-2027)
Returns: Rome (Civitavecchia) (20-Aug-2027)
Inside —
Oceanview $3,270
Balcony $5,745
Suite $8,760
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#39 Deal

Europe's Winter Riviera (7 Nights)

Offer #1664443
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (05-Nov-2027)
Returns: Barcelona (12-Nov-2027)
Inside —
Oceanview $2,544
Balcony $3,524
Suite $5,869
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#40 Deal

Windward Islands Surf & Sunsets (7 Nights)

Offer #1705922
Star Legend - Windstar
Cruise Line: Windstar
Departs: San Juan (27-Dec-2027)
Returns: San Juan (03-Jan-2028)
Inside —
Oceanview $2,656
Balcony $4,301
Suite $6,401
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
#41 Deal

Quick Getaways: La Dolce Vita In Italy & France (3 Nights)

Offer #1664426
Star Legend - Windstar
Cruise Line: Windstar
Departs: Rome (Civitavecchia) (29-May-2027)
Returns: Rome (Civitavecchia) (01-Jun-2027)
Inside —
Oceanview $1,100
Balcony $1,670
Suite $2,871
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Memorial Day Sailing
#42 Deal

Naturally Costa Rica (8 Nights)

Offer #1637758
Star Legend - Windstar
Cruise Line: Windstar
Region: Panama Canal
Departs: Balboa (20-Dec-2026)
Returns: Puntarenas (28-Dec-2026)
Port fees ($319) verified
Inside —
Oceanview $2,942
Balcony $4,062
Suite $6,483
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Christmas Holiday Sailing

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At-a-Glance Fare Comparison: Top 10 Sailings

Voyage Ship & Departure Inside Balcony Online Booking
Knot Your Average Crossing (15N) Star Legend • 02-Mar-2027 — $4,671 Select Cabin »
Star Collector: Caribbean Charms To Iberian Shores (21N) Star Legend • 21-Feb-2028 — $7,106 Select Cabin »
Panama Canal, Cartagena, San Blas Islands & More (8N) Star Legend • 12-Dec-2026 — $2,201 Select Cabin »
Star Collector: Captivating Caribbean (15N) Star Legend • 27-Nov-2026 — $4,349 Select Cabin »
Ocean Crossing (14N) Star Legend • 28-Feb-2028 — $4,100 Select Cabin »
Star Collector: Spanish Shores Transatlantic Crossing (23N) Star Legend • 02-Mar-2027 — $9,711 Select Cabin »
Star Collector: Atlantic Crossing To The Virgin Islands (21N) Star Legend • 06-Dec-2027 — $11,758 Select Cabin »
Star Collector: Lovely Leewards (14N) Star Legend • 07-Feb-2028 — $5,694 Select Cabin »
Star Collector: Lovely Leewards (14N) Star Legend • 31-Jan-2028 — $5,694 Select Cabin »
Star Collector: Lovely Leewards (14N) Star Legend • 20-Dec-2027 — $6,744 Select Cabin »
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