| ★ |  USS Constitution leads the Parade of Sail | WCVB Channel 5 Boston @wcvb | 17.8K | — | |
| 1 |  Thousands come to see the Tall Ships in Boston Harbor | WCVB Channel 5 Boston @wcvb | 161.8K | — | 92 |
| 7 |  Tartan Army leaves Boston with songs, kilts and lasting memories | WCVB Channel 5 Boston @wcvb | 117.4K | — | 88 |
| 20 |  Tall ships from around the world are visiting Boston | WCVB Channel 5 Boston @wcvb | 114.0K | — | 88 |
| 2 |  Sail Boston 2026 continues with free tours, events | WCVB Channel 5 Boston @wcvb | 42.0K | — | 92 |
| 10 |  Germany's Gorch Fock wins Five Sisters Cup | WCVB Channel 5 Boston @wcvb | 39.2K | — | 88 |
| 15 |  America's tall ship docks in Boston | WCVB Channel 5 Boston @wcvb | 28.6K | — | 88 |
| 16 |  Vespucci's descendants visit ship named for explorer at Sail Boston | WCVB Channel 5 Boston @wcvb | 26.2K | — | 88 |
| 19 |  Multiple boats burned in massive fire at Winthrop yacht club | WCVB Channel 5 Boston @wcvb | 21.2K | — | 88 |
| 5 |  Portuguese tall ship brings hundreds of letters to Mass. students | WCVB Channel 5 Boston @wcvb | 7.5K | — | 89 |
| 6 |  Want to adopt these famous Massachusetts bridges? | WCVB Channel 5 Boston @wcvb | 3.7K | — | 89 |
| 8 |  CityLine: Boston Harbor Now | WCVB Channel 5 Boston @wcvb | 3.4K | — | 88 |
| 3 |  Sailors from around the world march in Boston parade | WCVB Channel 5 Boston @wcvb | 2.9K | — | 91 |
| 4 |  Boston readies for World Cup, Sail Boston with safety plan | WCVB Channel 5 Boston @wcvb | 2.1K | — | 90 |
| 12 |  Different nations represented in Boston's Parade of Sail | WCVB Channel 5 Boston @wcvb | 1.8K | — | 88 |
| 9 |  Peabody's Lafuente Sign and Awning all about being seen | WCVB Channel 5 Boston @wcvb | 1.8K | — | 88 |
| 11 |  CityLine: A waterfront for all | WCVB Channel 5 Boston @wcvb | 1.6K | — | 88 |
| 13 |  Rescuers speak after two brothers, dog saved from sinking sailboat in Essex River | WCVB Channel 5 Boston @wcvb | 1.1K | — | 88 |
| 17 |  Watch: Two men, one dog rescued from sinking boat on the North Shore | WCVB Channel 5 Boston @wcvb | 812 | — | 88 |
| 18 |  New England travelers still stuck in Middle East following US airstrikes | WCVB Channel 5 Boston @wcvb | 351 | — | 88 |
| 14 |  Editorial: May 1, 2026: A fresh start for the Sox? | WCVB Channel 5 Boston @wcvb | 260 | — | 88 |