| Award |
Cruiser of the Year |
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Horizon Award for Cruising |
| Description |
Conveyed annually for the greatest frequency and quality of participation in scheduled cruising activities during the term of the watch.
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Conveyed annually to an individual new to TSS for the greatest frequency and quality of participation in scheduled cruising activities during the term of the watch.
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| 2024 |
Tom & Lesa Dailey, Panacea |
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| 2023 |
Ed Boudreaux & Shannon Arthur, Lagniappe
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Jim & Terry Alley, Danny Boy |
| 2019 |
Ed Boudreaux & Shannon Arthur, Lagniappe |
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Tom & Lesa Dailey, Panacea |
| 2018 |
Len Berkstresser, Wildfire |
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Ed Boudreaux & Shannon Arthur, Lagniappe |
| 2017 |
Don & Trina Swartz, Endeavor |
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Tom Conaty, Karen Ann |
| 2016 |
Greg & Iola Herschell, Gypsea |
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Mike & Jeanine Rendas, Finesse |
| 2015 |
Diane & Chris Eggert, Gato Go |
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Lyda Brown, Gasconade |
| 2014 |
Robert & Kathy Huxtable, Sailbrooke |
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Diane & Chris Eggert, Gato Go |
| 2013 |
Steve & Kathy Hodge, Endeavor |
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Becky & Sally Deyanger |
| 2012 |
Andy Tucker, Synchronicity |
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Steve & Melissa Nickolson, Camelot |
| 2011 |
Greg & Iola Herschell, Panacea |
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Rick & Diane Parish, Sea Breeze |
| 2010 |
Bill & Elaine Cullen, Triumph |
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Don & Trina Swartz |