Updated Daily at 6:00 AM • November 13, 2026 100 Verified Sailings Fares From $898 / person

Wind Surf Cruise Deals & Special Offers (Windstar)

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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
#2 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
#3 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
#4 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)
#5 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)
#6 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
#7 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
#8 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)
#9 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
#10 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)
#11 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
#12 Deal

Star Collector: Caribbean Explorations (15 Nights)

Offer #1707597
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (19-Dec-2027)
Returns: St Maarten (Philipsburg) (03-Jan-2028)
Inside —
Oceanview $4,620
Balcony —
Suite $6,045
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Christmas Holiday Sailing
  • New Year's Eve Sailing
#13 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707642
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (30-Jan-2028)
Returns: St Maarten (Philipsburg) (13-Feb-2028)
Inside —
Oceanview $3,970
Balcony —
Suite $5,300
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1707642)
#14 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707605
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (16-Jan-2028)
Returns: St Maarten (Philipsburg) (30-Jan-2028)
Inside —
Oceanview $3,970
Balcony —
Suite $5,300
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#15 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707646
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (13-Feb-2028)
Returns: St Maarten (Philipsburg) (27-Feb-2028)
Inside —
Oceanview $4,250
Balcony —
Suite $5,650
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
#16 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707644
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (06-Feb-2028)
Returns: St Maarten (Philipsburg) (20-Feb-2028)
Inside —
Oceanview $4,320
Balcony —
Suite $5,790
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
#17 Deal

Star Collector: Caribbean Explorations (15 Nights)

Offer #1707595
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (12-Dec-2027)
Returns: St Maarten (Philipsburg) (27-Dec-2027)
Inside —
Oceanview $4,845
Balcony —
Suite $6,270
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
#18 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707640
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (20-Feb-2028)
Returns: St Maarten (Philipsburg) (05-Mar-2028)
Inside —
Oceanview $4,180
Balcony —
Suite $5,510
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#19 Deal

Star Collector: Caribbean Explorations (13 Nights)

Offer #1707601
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (03-Jan-2028)
Returns: St Maarten (Philipsburg) (16-Jan-2028)
Inside —
Oceanview $3,955
Balcony —
Suite $5,320
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Onboard Credit
#20 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707594
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (05-Dec-2027)
Returns: St Maarten (Philipsburg) (19-Dec-2027)
Inside —
Oceanview $4,460
Balcony —
Suite $5,790
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#21 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707645
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (05-Mar-2028)
Returns: St Maarten (Philipsburg) (19-Mar-2028)
Inside —
Oceanview $4,320
Balcony —
Suite $5,650
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1707645)
#22 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707643
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (27-Feb-2028)
Returns: St Maarten (Philipsburg) (12-Mar-2028)
Inside —
Oceanview $4,320
Balcony —
Suite $5,720
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#23 Deal

Star Collector: Caribbean Explorations (15 Nights)

Offer #1707591
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (20-Nov-2027)
Returns: St Maarten (Philipsburg) (05-Dec-2027)
Inside —
Oceanview $4,845
Balcony —
Suite $6,420
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • Thanksgiving Sailing
#24 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707603
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (09-Jan-2028)
Returns: St Maarten (Philipsburg) (23-Jan-2028)
Inside —
Oceanview $4,530
Balcony —
Suite $5,650
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#25 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1707593
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (28-Nov-2027)
Returns: St Maarten (Philipsburg) (12-Dec-2027)
Inside —
Oceanview $4,530
Balcony —
Suite $6,000
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#26 Deal

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

Offer #1707610
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (30-Jan-2028)
Returns: St Maarten (Philipsburg) (06-Feb-2028)
Inside —
Oceanview $2,273
Balcony —
Suite $3,113
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#27 Deal

Star Collector: Riches Of The Rivieras, Romans, And Greeks (14 Nights)

Offer #1664875
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: Athens (14-Oct-2027)
Returns: Barcelona (28-Oct-2027)
Inside —
Oceanview $4,617
Balcony —
Suite $6,227
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#28 Deal

Classic Caribbean (7 Nights)

Offer #1707634
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (27-Dec-2027)
Returns: St Maarten (Philipsburg) (03-Jan-2028)
Inside —
Oceanview $2,432
Balcony —
Suite $3,272
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
  • New Year's Eve Sailing
#29 Deal

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

Offer #1707647
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (13-Feb-2028)
Returns: St Maarten (Philipsburg) (20-Feb-2028)
Inside —
Oceanview $2,448
Balcony —
Suite $3,288
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
#30 Deal

Classic Caribbean (7 Nights)

Offer #1707636
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (23-Jan-2028)
Returns: St Maarten (Philipsburg) (30-Jan-2028)
Inside —
Oceanview $2,362
Balcony —
Suite $3,202
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#31 Deal

Classic Caribbean (7 Nights)

Offer #1690761
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (28-Nov-2027)
Returns: St Maarten (Philipsburg) (05-Dec-2027)
Inside —
Oceanview $2,572
Balcony —
Suite $3,412
Signature Perks Onboard Credit Free Drinks Shore Excursions
Special Offers & Amenities Available on This Sailing:
  • A Hosted Sailing
  • Private Car & Guide or $400 Per Couple Shipboard Credit
  • Reduced Deposit
#34 Deal

Yachtsman's Harbors Of The Rivieras (8 Nights)

Offer #1664850
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: Tarragona (19-Apr-2027)
Returns: Rome (Civitavecchia) (27-Apr-2027)
Inside —
Oceanview $3,003
Balcony —
Suite $4,083
Signature Perks Onboard Credit Free Drinks Shore Excursions
Special Offers & Amenities Available on This Sailing:
  • A Hosted Sailing
  • Private Car & Guide or $400 Per Couple Shipboard Credit
  • Reduced Deposit
#35 Deal

Classic Caribbean (7 Nights)

Offer #1707638
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (20-Feb-2028)
Returns: St Maarten (Philipsburg) (27-Feb-2028)
Inside —
Oceanview $2,432
Balcony —
Suite $3,272
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1707638)
#36 Deal

Classic Caribbean (7 Nights)

Offer #1707635
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (09-Jan-2028)
Returns: St Maarten (Philipsburg) (16-Jan-2028)
Inside —
Oceanview $2,432
Balcony —
Suite $3,272
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#37 Deal

Wine Cruise: Enchanting Greece & The Amalfi Coast (7 Nights)

Offer #1707555
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Region: Europe
Departs: Rome (Civitavecchia) (27-Apr-2027)
Returns: Athens (04-May-2027)
Inside —
Oceanview $2,545
Balcony —
Suite $3,490
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#38 Deal

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

Offer #1707606
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (16-Jan-2028)
Returns: St Maarten (Philipsburg) (23-Jan-2028)
Inside —
Oceanview $2,448
Balcony —
Suite $3,288
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
#39 Deal

Beach Fun & Sun: A Remote Caribbean Getaway (8 Nights)

Offer #1707592
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (20-Nov-2027)
Returns: St Maarten (Philipsburg) (28-Nov-2027)
Inside —
Oceanview $3,028
Balcony —
Suite $3,988
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
  • Thanksgiving Sailing
#40 Deal

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

Offer #1664816
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (19-Dec-2026)
Returns: St Maarten (Philipsburg) (26-Dec-2026)
Port fees ($280) verified
Inside —
Oceanview $2,658
Balcony —
Suite $3,498
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
#41 Deal

Beach Fun & Sun: A Remote Caribbean Getaway (6 Nights)

Offer #1707602
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (03-Jan-2028)
Returns: St Maarten (Philipsburg) (09-Jan-2028)
Inside —
Oceanview $2,108
Balcony —
Suite $2,828
Signature Perks Onboard Credit Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Onboard Credit
#42 Deal

Star Collector: Enchantment Of The Western Med (16 Nights)

Offer #1664849
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: Lisbon (11-Apr-2027)
Returns: Rome (Civitavecchia) (27-Apr-2027)
Inside —
Oceanview $5,747
Balcony —
Suite $7,667
Signature Perks Free Drinks Reduced Deposit Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Reduced Deposit
#43 Deal

James Beard Foundation: Enchanting Greece & The Amalfi Coast (7 Nights)

Offer #1664876
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: Athens (14-Oct-2027)
Returns: Rome (Civitavecchia) (21-Oct-2027)
Inside —
Oceanview $2,615
Balcony —
Suite $3,560
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#44 Deal

Star Collector: Caribbean Explorations (14 Nights)

Offer #1665111
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (30-Jan-2027)
Returns: St Maarten (Philipsburg) (13-Feb-2027)
Port fees ($578) verified
Inside —
Oceanview $5,230
Balcony —
Suite $6,770
Signature Perks Onboard Credit Free Drinks Reduced Deposit
Special Offers & Amenities Available on This Sailing:
  • $300 per Couple Shipboard Credit
  • Reduced Deposit
#45 Deal

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

Offer #1707648
Wind Surf - Windstar
Cruise Line: Windstar
Ship: Wind Surf
Departs: St Maarten (Philipsburg) (12-Mar-2028)
Returns: St Maarten (Philipsburg) (19-Mar-2028)
Inside —
Oceanview $2,518
Balcony —
Suite $3,358
Signature Perks Free Drinks Land + Sea Cruisetour
Special Offers & Amenities Available on This Sailing:
  • Signature Exclusive Sailing Perks Available (Offer #1707648)

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