Boats sail roughly April to late October. Within that, the experience changes.
April and early May. The first trips of the year, thin schedules, cold on deck and genuinely worth doing if you dress for it. Fin whales and early humpbacks. This is also when North Atlantic right whales are in Cape Cod Bay in numbers, which affects boats more than it rewards passengers, because nothing may approach within 500 yards of one.
Late May and June. Humpbacks arrive properly. Mothers with calves born that winter in the Caribbean show up, and a calf learning to breach beside its mother is the sight of the season. Fog is the June risk, and it cancels trips.
July and August. Peak: most departures, most passengers, most reliable sightings, warmest deck. Book two or three days ahead in August and take a morning departure, because the sea breeze fills in after lunch and the boat rides better before it does.
September. The connoisseur's month. Whales are still feeding hard, boats are half empty, the light is better and the afternoon chop is less reliable but often absent. If your dates are flexible, come now.
October. Schedules thin out toward the end of the month and the last departures of the year go in a cold wind. Sightings can still be excellent. Check that the operator is still running before you plan around it.
Nothing runs from November to March. The whales are in the Caribbean or off the southeastern United States, and so is the market.