Chapter I | "An Entirely Different Climate" The Trials of Sailing at Fishers, 1614-1900 | 3 |
| Early Storms | 5 |
| Shipwrecks at Fishers | 6 |
| "Some Small Bunches of Rocks" | 8 |
| The First Yachts | 11 |
| The Ubiquitous Catboat | 14 |
| The First Fishers Island Yacht Club | 16 |
| "An Ideal Summer Resort" | 18 |
| The First Yachtsman: George Bartlett | 20 |
| Sailing to Fishers Island in the 1890s | 22 |
Chapter II | "It Was a Getaway" Fishers Becomes a Sailing Center, 1900-1938 | 25 |
| The Fergusons and Their Boats | 26 |
| A Catboat Class for Hay Harbor | 28 |
| The Fishers Island One Design | 30 |
| Cupid Takes a Back Seat | 34 |
| "A Whole Summer Lay Ahead" | 34 |
| Too Many Wrecks to Name | 36 |
| The Second Yacht Club Is Founded, for Keeps | 38 |
| Changing Harbors | 40 |
| A Fleet of Schooners | 43 |
| Barlovento | 46 |
| The Commuters | 49 |
| "Simple Facilities for Yachtsmen" | 53 |
| Individualists | 54 |
| The Fishers Island Sound 31 | 56 |
| The Herreshoff 23 | 58 |
| The Bullseyes Have Arrived | 60 |
| The Luders 16 | 63 |
| "I Loved the Racing" | 65 |
| Squalls and Other Troubles | 67 |
| "A Boy's Eye View of West Harbor" | 68 |
Chapter III | "There Will Be Yachting" The Challenges of Storm, War, and Revival, 1938-1970 | 71 |
| The Quincy Adams 17 | 74 |
| The Rhodes 27 | 79 |
| His Favorite Place | 81 |
| The War Comes | 82 |
| A Difficult Postwar Revival | 83 |
| The Brown Navy | 85 |
| From the Yard to the Race Course | 86 |
| The New Commuters | 88 |
| A Declaration of Independence | 92 |
| Captain Pete | 94 |
| Barlovento II | 96 |
| Reyn du Pont | 98 |
| Jack Whiticar | 100 |
| The Captains | 100 |
| Ed Hedge | 102 |
| The Launch Boys | 103 |
| Off Soundings and the Parsons Trophy | 104 |
Chapter IV | "The Energy Within the Club" New Generations Sail into a New Century, 1970-2003 | 107 |
| Eliot Porter | 108 |
| Bullseye Travels | 110 |
| 'Round Island Race | 112 |
| Burgees and Uniforms | 113 |
| Peter Sanger | 114 |
| The Joys of the Cruising Life | 115 |
| Escaping the Doldrums | 117 |
| FIST | 120 |
| Hooked! | 121 |
| The International One Design | 123 |
| "This Is a Team Sport" | 126 |
| Storms and Wrecks | 127 |
| Expansion into the New Century | 129 |
Appendix 1 | Officers of Fishers Island Yacht Club | 133 |
Appendix 2 | Fishers Teams at Championships | 134 |
Appendix 3 | Fishers Boats and Classes | 136 |
| Acknowledgments and Sources | 148 |
| Index | 152 |