1620 Winery & Bar is right on the water in Plymouth with outdoor seating and an outdoor fire pit.
CabbyShack has delicious, fresh seafood with a fun, laid-back atmosphere. This is a great spot to grab a drink and some authentic seafood.
Indian Pond Country Club is private, so Pinehills is a great spot to go golf for the day. This is Jon's recommendation (of course) and has golfed there multiple times and highly recommends it!
Plymouth Bay Winery offers yummy wine and wine jelly tasting. Highly recommend!