The Elizabeth Islands are a chain of four main islands and numerous smaller islands, extending about fifteen miles southwest from Woods Hole to Cuttyhunk. Shore lines range from small beautiful beaches to rugged bluffs. Their relative inaccessibility and the fact that they are still controlled by the descendants of the original land grant family protect them from a lot of mainland traffic. There are a few hundred year round residences on Cuttyhunk and a few summer homes on the other islands.
The wind factor is unpredictable but can be minimized by leaving early in the morning. Listen to NOAA radio and do not go out if winds are above 5 to 10 knots. Do not launch or land on an east facing beach if winds are out of the east. If you are returning the next day, it will be early afternoon when you get back to Woods Hole. Try and catch the tides right but if that is not possible, there are a couple beach sites outside Woods Hole Harbor which I will describe later.
The current factor is predictable but complicated. You are going to have to spend time studying Eldridge's tide chart and current tables. You should always try to time your leaving and returning to Woods Hole at slack tide. Eldridge has a tide chart for Woods Hole. Pick a slack high tide early in the morning. I recommend slack high because, strange as it seems, the tidal current ebbs to the west (Cuttyhunk) and floods to the east (Woods Hole). You therefore ride the ebb at least part way to Cuttyhunk. Now turn to the tidal current flip charts for Buzzards Bay and Vineyard Sound in Eldridge. This will give the current velocities and direction with arrows hour by hour for your whole trip. You need to bring this with you. I could write an entire article on these charts. One slight complication is that the current charts are based on the tide change at Pollock Rip, but that is only one half hour earlier than Woods Hole. So just factor the current a half hour after what the current chart shows.
As I have said, there are several ways to start your trip. The simplest and the best is the following: you check NOAA and it is going to be 5-10 knots out of the west, shifting to the southeast in the evening. Good for a launch at the public boat ramp in Woods Hole and a trip down Vineyard Sound, where we will start out in the lee of the wind and mostly have a following current. I recommend the public boat ramp because it is relatively easy to find, has the best location right across from Hadley Harbor (one of my most favorite places) and close to the ferry to Martha’s Vineyard. That is important because you cannot leave a car at Woods Hole overnight. You have to leave your boat at the ramp, drive back to the public parking for the ferry, take the shuttle bus back to the ferry dock and walk back to the ramp. Allow at least 45 minutes for this. Just to the north of the ramp (about 100 yards) is a small beach owned by the Oceanographic Institute, outside the harbor on the northeast side of Penzance Point. Make a mental note of this. If, on the return to Woods Hole from Buzzards Bay, you miss the tide, you may go out and around Penzance Point, avoid the "hole" and land on that beach. Meanwhile, back at the ramp, we shove off at or slightly before slack high tide. This is important, because from the ramp you will be going straight across into Hadley Harbor. Once in the harbor, follow the channel to the left between Nonamesset Island, Goats Neck, and Naushon Island and then under a small causeway bridge into Vineyard Sound. You have about one and a half hours from slack tide at Woods Hole before the current is running too strong against you under that bridge.