| 1. |  SimGamerTV | Sailwind Episode Six - Brig Maiden Voyage Part One | 13,310 | |
| 2. | SimGamerTV | Navigator's Guide to Sailwind - Using the Chrono Compass | 12,501 | |
| 3. | SimGamerTV | Sailwind Episode Four - Sanbuq Maiden Voyage | 9,355 | |
| 4. | Grillmastah | Surviving In This Open Sea Delivery ~ Sailwind | 7,035 | |
| 5. | SimGamerTV | Sailwind - Customizing the Dhow | 6,972 | |
| 6. | SimGamerTV | Navigators Guide to Sailwind - Using the Sun Compass | 6,512 | Guide |
| 7. | SimGamerTV | Navigators Guide to Sailwind - Using the Quadrant | 6,402 | Guide |
| 8. | SimGamerTV | Sailwind: Episode One - Dhow Maiden Voyage | 6,044 | |
| 9. | Dalton Reutlinger | Sailwind | Hard Start | Economy Update | Let's Play | 001 | 5,987 | |
| 10. | SimGamerTV | Sailwind Episode Five - Junk Maiden Voyage | 5,967 | |
| 11. | SimGamerTV | Sailwind Episode Three - Cog Maiden Voyage | 5,433 | |
| 12. | SimGamerTV | Sailwind - Customizing the Cog | 5,272 | |
| 13. | SimGamerTV | Sailwind Episode Seven - Brig Maiden Voyage Part Two | 4,462 | |
| 14. | PolarBear70 | Sailwind Episode 1 "The Journey Begins in Neverdin" | 4,102 | |
| 15. | Consider | Sailing Across the Sea But I Don't Know How to Sail | Sailwind | 3,664 | Guide |
| 16. | SimGamerTV | Sailwind Episode Two - Kakam Maiden Voyage | 3,041 | |
| 17. | SimGamerTV | Sailwind - Customizing the Kakham | 3,027 | |
| 18. | Dalton Reutlinger | Sea of Thieves Alternative? | Check Out "Sailwind"! | 1,610 | |
| 19. | SimGamerTV | Sailwind | Episode Nineteen - Destination Fire Fish Lagoon | 1,557 | Show |
| 20. | SimGamerTV | Sailwind Patch Notes v0.16 | 1,262 | |
| 21. | Dalton Reutlinger | Running the Cricut! | Sailwind | 1,246 | |
| 22. | Dalton Reutlinger | Sailwind Had An Update! | 1,026 | Vlog |
| 23. | SimGamerTV | Sailwind | Epsiode One - A Fresh Start | 1,009 | |
| 24. | SimGamerTV | Sailwind Ship Ranking Bloopers #Short | 952 | |
| 25. | SimGamerTV | Sailwind Patch Notes v0.17 | 930 | |
| 26. | SimGamerTV | Sailwind | Episode Twelve - Sanbuq Customizations | 884 | |
| 27. | SimGamerTV | Sailwind Navigation - Piloting | 874 | |
| 28. | SimGamerTV | Sailwind | Episode Thirteen - Departing for Happy Bay | 785 | |
| 29. | Dalton Reutlinger | Tale of the Shadow | Sailwind | 724 | |
| 30. | SimGamerTV | Sailwind 0.18 Patch Notes in Less than One Minute! | 720 | |
| 31. | SimGamerTV | Sailwind | Episode Nine - Sanbuq Open Seas | 720 | |
| 32. | SimGamerTV | Sailwind | Episode Twenty - Finding Fire Fish Town | 704 | |
| 33. | SimGamerTV | Sailwind | Episode Twenty-One - Kicia Bay Shipyard | 702 | Show |
| 34. | Dalton Reutlinger | Let's Play - Sailwind | Episode 31 | Brig Maiden Voyage | 695 | |
| 35. | SimGamerTV | Sailwind | Episode Eleven - Dragon Cliffs Arrival | 684 | Show |
| 36. | MKX | A Guide Through Your First Mission in SailWind | 667 | Guide |
| 37. | SimGamerTV | Sailwind | Episode Eight - Sanbuq Departing for Dragon Cliffs | 586 | |
| 38. | SimGamerTV | Sailwind 0.19.x Patch Notes in Less than One Minute! | 576 | |
| 39. | Dalton Reutlinger | Sailwind Tutorial | Starting in Al' Ankh | 575 | |
| 40. | SimGamerTV | Sailwind | Episode Seven - Sanbuq Maiden Voyage | 573 | |
| 41. | SimGamerTV | Sailwind | Episode Eighteen - Aestrin Ahead | 565 | Show |
| 42. | SimGamerTV | Sailwind | Episode Five - The Shipyard | 553 | Show |
| 43. | SimGamerTV | Sailwind | Episode Fourteen - Navigating to Happy Bay | 513 | Show |
| 44. | SimGamerTV | Sailwind | Episode Fifteen - Happy Bay Arrival | 505 | Show |
| 45. | SimGamerTV | Sailwind | Episode Ten - Half Way to Dragon Cliffs | 492 | |
| 46. | SimGamerTV | Sailwind | Episode Sixteen - Departing Happy Bay | 465 | Show |
| 47. | Dalton Reutlinger | Trading | Sailwind | 007 | 452 | |
| 48. | SimGamerTV | Sailwind | Episode Four - Big Earnings | 446 | |
| 49. | SimGamerTV | Sailwind | Epsiode Two - Second Mission | 428 | |
| 50. | Dalton Reutlinger | WE'RE GOIN' HOME!!! | Let's Play | Sailwind | Episode 30 | 426 | Show |
| 51. | SimGamerTV | Sailwind | Episode Six - Custom Dhow Maiden Voyage | 403 | |
| 52. | SimGamerTV | Sailwind | Episode Three - Commodity Trades | 385 | |
| 53. | SimGamerTV | Sailwind | Episode Seventeen - Mount Malefic First Sighting | 382 | Show |
| 54. | Dalton Reutlinger | Let's Play Sailwind | Episode 025 | Ocean Crossing to Al`Ankh | 363 | |
| 55. | MKX | Fresh Start 4 Months Later | Sailwind lets play | Episode 1 | EP 1 | 317 | Let's Play |
| 56. | Dalton Reutlinger | Double Voyage | Let's Play Sailwind | Episode 002 | 280 | Let's Play |
| 57. | Dalton Reutlinger | Let's Play Sailwind | Episode 028 | Al`Ankh Academy | 269 | |
| 58. | Dalton Reutlinger | Let's Play Sailwind | Episode 24 | Prepping for Al`Ankh | 258 | |
| 59. | Old Man Gamer | Following Seas | Sailwind | Freeplay | 234 | |
| 60. | Robert Dodd | Bob Plays Sailwind #1 | 222 | Let's Play |
| 61. | Phrosperatus | Sailwind - Brig - Fort Aestrin to Happy Bay - Beta 0.25.b1 with mods #12 | 192 | |
| 62. | Dalton Reutlinger | Sailwind Livestream | Ft. Aestrin to Happy Bay | Pt 2 | 187 | |
| 63. | Dalton Reutlinger | Sailwind Livestream | Ft. Aestrin to Happy Bay | 184 | |
| 64. | KDoolz | Quality of Life Updates! Yay Mods! | TCG Simulator | 182 | |
| 65. | Dalton Reutlinger | Let's Play Sailwind | Gaff Sail | Episode 005 | 168 | |
| 66. | Phrosperatus | Sailwind - Brig - Maiden Voyage - Fort Aestrin to Happy Bay #9 | 152 | |
| 67. | Phrosperatus | Sailwind - Aestrin - Cog with 2 x 15 yd lateen sails - Episode # 6 | 152 | |
| 68. | Dalton Reutlinger | Sailing Into Some Rough Seas! | Let's Play Sailwind | Episode 004 | 144 | Let's Play |
| 69. | Dalton Reutlinger | Sailwind Livestream | Learning The Trade System | Also House Chores | 131 | |
| 70. | Dalton Reutlinger | Sailwind Livestream | The Search For Eastwind | 128 | |
| 71. | MKX | Late Delivery But It's Fine | Gold Rock City - Al' Ankh Academy | Sailwind | EP 2 | 122 | |
| 72. | Phrosperatus | Sailwind - Update 0.23 - Fresh Easy Start - Episode # 1 | 120 | |
| 73. | Dalton Reutlinger | Sailwind Starter Guide | Starting in Aestrin. | 120 | Guide |
| 74. | DactylRexasaur | 10 Hours of... Sailwind! │ Dactyl Longplays #sailwind | 111 | |
| 75. | Foredoomer Longplays | Sailwind Part 3 Full Game - Longplay Walkthrough No Commentary | 93 | Walkthrough |
| 76. | Psybeak | Psybeak | First stream! - Sailwind pt.1 | 91 | |
| 77. | MKX | Journey To The Infamous Al' Ankh Academy | Sailwind lets play | Episode 2 | EP 2 | 86 | Let's Play |
| 78. | MKX | Our First Voyage | Neverdin - Gold Rock City | Sailwind | EP 1 | 78 | |
| 79. | Phrosperatus | Sailwind - Aestrin - Cog - Modified Sails - Episode # 5 | 77 | |
| 80. | MKX | Sailing Downwind To Albacore Town | Sailwind lets play | Episode 3 | EP 3 | 76 | Let's Play |
| 81. | Phrosperatus | Sailwind - Update 0.23 - Fresh Easy Start - Episode # 2 | 71 | |
| 82. | MKX | Cross Map Haul | Al' Ankh Academy - Albacore Town | Sailwind | EP 3 | 67 | |
| 83. | Phrosperatus | Sailwind - AlAnkh - Dhow - Episode # 7 | 67 | |
| 84. | Dalton Reutlinger | To There Again | Let's Play Sailwind | Episode 005 | 67 | Show |
| 85. | Phrosperatus | Sailwind - Dhow - Trading in Al'Ankh region, between Gold Rock City and and Alchemist's Island #3 | 61 | |
| 86. | Phrosperatus | Sailwind - Kakam - Dragon Cliffs to Crab Beach - Emerald Archipelago - Episode # 12 | 53 | |
| 87. | Phrosperatus | Sailwind - Junk - Dragon Cliffs to Fire Fish Town - Emerald Archipelago to Fire Fish Lagoon #10 | 51 | |
| 88. | Phrosperatus | Sailwind - Brig - Happy Bay to Fort Aestrin #11 | 50 | |
| 89. | Phrosperatus | Sailwind - Sanbuq - Midway from Dragon Cliff to Happy Bay, then to Fort Aestrin. #8 | 43 | |
| 90. | Robert Dodd | Bob Plays Sailwind #2 | 43 | Let's Play |
| 91. | Phrosperatus | Sailwind - Kakam - Crab Beach to Dragon Cliffs - Emerald Archipelago - Episode # 11 | 38 | |
| 92. | Phrosperatus | Sailwind - Kakam - Emerald Archipelago - Medium Start - Episode # 10 | 36 | |
| 93. | Phrosperatus | Sailwind - Kakam - Emerald Archipelago - Crab Beach to Sanctuary - Episode # 9 | 35 | |
| 94. | ItIs_Echo | A Restful Day on the Open Sea | Sailwind | 02 | 30 | |
| 95. | Phrosperatus | Sailwind - Dhow - Trading in Al'Ankh region, between Gold Rock City and Albacore Town #4 | 30 | |
| 96. | Phrosperatus | Sailwind - Kakam - Emerald Archipelago - Dragon Cliffs to Crab Beach - Episode # 8 | 29 | |
| 97. | Phrosperatus | Sailwind - Trading in Al'Ankh region with the Sanbuq #6 | 23 | |
| 98. | Endo Plays Everything | I got lost I beached the boat And then I had real issues Sailwind | 21 | |
| 99. | ItIs_Echo | Storms All Around | Sailwind | 01 | 18 | |
| 100. | ItIs_Echo | A Relaxing Day on the Water | Sailwind | 00 | 17 | |
