| Sirocco | 47 | 2006 | Heesen Yachts |
| Sirma III | 34.75 | 1990 | Palmer Johnson Yachts |
| Sirius of Man | 30.48 | 2002 | Sunseeker |
| Sirius | 30.95 | 2004 | Custom Line |
| Sirenuse | 32.26 | 2022 | Monte Carlo Yachts |
| Sirena | 34.14 | 2024 | Benetti SpA |
| Siren | 73.5 | 2008 | Nobiskrug |
| Sirea | 35.05 | 2004 | Horizon Yachts |
| Siran | 67.01 | 1992 | Feadship |
| Sirahmy | 43 | 1981 | Benetti SpA |
| Sir' Reel | 28.42 | 2017 | Viking Yachts |
| Sir Winston Churchill | 41.07 | 1966 | Dunston Shipyard |
| Sir Robert Baden Powell | 42 | 1957 | Edgar André |
| Sintra | 32.6 | 1959 | Abeking & Rasmussen |
| Singular | 30.91 | 2013 | Azimut Yachts |
| Sindonemo | 30.48 | 2000 | Yachting Developments |
| Sincerity | 29 | 1928 | Baglietto S.p.A. |
| Sinbad | 38.4 | 2002 | Delta Marine |
| Simply Splendid | 28.06 | 2016 | Sunseeker |
| Simplicity | 34.1 | 2012 | Westport Yachts |
| Simplicity | 43.3 | 2024 | Gulf Craft |
| Sima | 29.5 | 1983 | Cantiere Navale St. Margherita Ligure |
| Sima | 39.6 | 2007 | CRN |
| SimSim I | 37.95 | 2017 | Sanlorenzo |
| Sily | 49.8 | 2013 | Heesen Yachts |
| Silvia | 29.1 | 2018 | Azimut Yachts |
| Silvertip | 33.8 | 2002 | Yachting Developments |
| Silvermoon | 28.5 | 2021 | Riva S.p.A. |
| Silverlining | 31.6 | 2011 | Phithak Shipyard and Services |
| Silverado | 36.82 | 1974 | Willard Boat Works |
| SilverCat | 35.9 | 2025 | Silver Yachts |
| Silver Wind | 43.63 | 2014 | ISA Yachts |
| Silver Wave II | 35 | 2000 | Chantiers Naval de Biot |
| Silver Wave | 45.72 | 2009 | Palmer Johnson Yachts |
| Silver Star I | 55.2 | 2023 | Admiral |
| Silver Spray | 33.4 | 1916 | Scheepswerf Piet Smit |
| Silver Spirit II | 29.57 | 1990 | Azimut Yachts |
| Silver Shalis | 53.3 | 2010 | Delta Marine |
| Silver Seas | 32.61 | 1998 | Burger Boat Company |
| Silver Moon | 34.55 | 2010 | Kulach Yachts |
| Silver Mama | 28 | 2008 | AB Yachts |
| Silver Lining | 50 | 2016 | Christensen Shipyards, LLC. |
| Silver Fox | 28.02 | 2002 | Crescent Custom Yachts |
| Silver Fast | 77 | 2015 | Silver Yachts |
| Silver Dream | 43.8 | 2001 | Warren Yachts |
| Silver Cloud | 36 | 2008 | |
| Silver Angel | 64.5 | 2009 | Benetti SpA |
| Silolona | 49.68 | 2004 | Konjo Boat Builders of Ara |
| Silky | 28.05 | 2010 | Sea Force IX, Inc. |
| Silhouette | 28.04 | 2020 | Ferretti Yachts |
