Many boaters think of Greenwich as being somewhat unwelcoming to outsiders (dare we say “snobby”?), but in recent years the town has made an effort to change that reputation. Boaters looking to sample the shoreside attractions—Greenwich, of course, is a well-known shopper’s mecca packed with trendy, famous-name stores and boutiques—should start at the Grass Island Marina. Grass Island is 1 of 4 town-run marinas, but the only one that offers transient dockage. There is no charge to tie up during the day, and an overnight charge based on vessel size. Best of all, the dock puts you within easy walking distance of downtown. The Grass Island dock can accommodate 2 or 3 boats of moderate size on a first-come, first served basis, and fills up quickly during summer.
Another option is to anchor in one of the many coves surrounding the nearby islands. If you have a dinghy, the harbormaster will do his best to accommodate you with tie-up space along the Grass Island dock; however, there is no launch service or official dinghy rack.
There’s another nice spot to anchor on the northwest side of Great Captain Island, overlooking the Belle Haven Country Club—just mind the channel and mind the charts, especially Cormorant Reef and the smaller rocks. A lot of people run aground here each year.
Great Captain Island is a popular picnic and swimming spot among local boaters. One can dinghy ashore and enjoy the beach or wander the island. There are restrooms and picnic facilities ashore.
There’s a second small anchorage east of Calf Island, which us managed by the Calf Island Conservancy and offers hiking trails, wildlife observation stations, and even camping (with permits). It is a popular spot among local kayakers and small-boaters.
The charts list another mooring area on the Hyannis River inside Cos Cob Harbor, but the water’s pretty skinny here and the moorings crowded. Anyone looking for a peaceful afternoon on that side of town should head all the way east to Greenwich Cove and follow the buoys through the mooring area to the northeast side of Greenwich Island.