Description: Pleasure Bay is a completely enclosed tidal pond, approximately 3/4 of a mile in diameter. It is best in SW- S- SE, O.K. in NE, NW is very gusty. It has protected flat-water sailing. The wind is usually somewhat up and down. Summertime launching restrictions may be in place until 6:00 on good days. Being ringed by streetlights is an advantage for sailing late in the day.

Driving directions:
From the south - Take exit 15 off 93 S. Follow signs for Columbia Rd, S. Boston or Castle Island. Follow the shore all the way to Pleasure Bay. There’s a monument and small lot to the south of the bay. Many sailors park there, although you can park anywhere around the bay. You can also launch into Boston Harbor from the lot.
From the west - take Rt. 90 E to South Boston, exit 25 to Summer St. Go across the channel and take your 4th left on East Broadway. That brings you out to Pleasure Bay. To the right is the south parking lot, or park anywhere around the bay and rig on the grass.

Link to Google map