We list this first because we've learned that it's the most important factor to prevent turning your cruise into stressful work.
When we first started cruising flotilla style, we spent many evenings planning our cruises in the sure and certain knowledge that to count the cruise a success, we had to depart CYC on a certain day and be in certain ports on subsequent certain days so that we'd arrive back at CYC on yet another certain day, even if a particular day's destination was upcurrent and upwind in the rain. We've learned not to do this and, with the few notable exceptions covered later, to go with the flow instead.
Each evening, check the next day's forecast and choose a destination that will provide good sailing based on the predicted wind and currents. If you're eastbound riding the prevailing southwesterly, go for a long run, especially if you will have the current behind you most of the day. If westbound, leave at a time that will take advantage of the westbound current. Then if the wind is moderate, sail until the current goes foul; if there's no wind, motor until you get tired of the noise; if it's a howler, raining, or foggy, stay put and go shopping or do the laundry.
Spending an extra day on Block Island or in Mystic is a viable alternative to pounding through a frontal passage. Basically, the only points in time you do need to be at a certain place at a certain time are transits of such places as the East River, the Cape Cod Canal, and the Elizabeth Island "holes." We'll go into detail about these later. Consider even leaving a day of slack for your departure and arrival to allow for bad weather.
Finally, if you get tired, STOP, even if it means anchoring to take a snooze. Next to alcohol, fatigue is the biggest contributor to boating accidents.