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Sailing and sail racing are central activities at SYC. Many of the members own sailboats and participate in the various activates and regattas. The dockage facilities provide a gathering place for the dedicated sailors. A group of "Old Salts" can often be found discussing sailing tactics or helping one another work on boats. Most of the fleet of sailboats are used regularly and any SYC members interested in crewing are encouraged to participate.
Boat Name |
Owner |
Make/Model |
Year |
Length |
| Ariel | Bob Hock, Lois Strong, Tom Benner | C&C | 1985 | 27 |
| Bobsy | John Alden | Sabre 36 Mark I | 1987 | 36 |
| Sea U There | Ward White | Island Packet | 1982 | 26 |
| Cradle Song | Peter Kramer | Pearson | . | 35 |
| Island Time | Guy Mariande | Beneteau O352 | 1999 | 35 |
| Misty | John Jacobs | Gulfstar | 1983 | 36 |
| Playmate | Dan Kelly | Hunter | 1974 | 30 |
| Rhapsody | Ed Velen | C&C Mark 1 | 1971 | 37 |
| Sailaway | Phil Cornett | Pearson | 1978 | 30 |
| Valhalla | Don Dietrich | C&C 29-2 | . | 29 |
| Breaking Wind | Patricia McGinnis | Beneteau First 35s5 | 1993 | 35 |
| Frankly Speaking | Frank Spalla | Pearson 34 CB | 1984 | 34 |
| Incommunicado | Dave Smith | Hunter 28.5 | 1988 | 28 |
| Twilight | Mac Smith | LaFitte 44 | 1982 | 44 |
| Spindrift | Dave Westerheide | Catalina 36 | 1989 | 36 |
| Windfall | Mike Woods | Herreshoff Cat Ketch |
Sailing into Ponce Inlet after a Spice Cup race.
