This is nothing fancy but a nice place to walk or ride bikes. It is right across from Logal Airport, so if you like to watch the planes and boats, it is a great spot. There is a 3 mile walking path around Pleasure Bay. There is one little place to eat, but they have good hot dogs, burger, fried... More

The loop is short. The path is clear. The breeze is fair. This is the soul of Southie and a pilgrimage is required on Sunday to be part of it. More

For a wonderful 1/2 day trip, take the ferry out to this historic landmark. The ride out is fun. Great views of the harbor, beautiful parkland around the fort. If you've got kids, this is where they will want to take a break from the city. More

I enjoy so many things about Castle Island. The sugar bowl walkway where you walk right out into Boston Harbor. I love the diversity of people young, old, families, all cultures seem to be able to enjoy this place. And then there's Sullivan's. They have thse hot dogs that I think taste so delicious just because it's Castle Island. There's... More

This is one of the best places in the city to run. You can head down along the beaches on the boardwalk and back up and around the island. Perfect on a sunny day. More

Castle Island is a great place to take a walk, get a bite to eat and enjoy the Boston Harbor. There is not a great deal to do here other than go for a walk, fly a kite, have a picnic or enjoy the view of the Harbor. You can also grab some great food at Sullivan's. The food is... More

A must see when in Boston. I live near here and go for walks along the water all the time. Great for bike riding, roller blading and taking the dogs More

Castle Island is a historical military fortification-come-park sticking out into Boston Harbor from South Boston, endlessly popular with young families and couples walking dogs, as well as crusty locals fishing off the pier and a few canoodling teens. Not that easy to get to (parking can be a challenge), but really lovely on a sunny, breezy day. More

There's nothing in my opinion in Boston as relaxing as grabbing a burger and fries at Sullivan's and sitting on the grass near the back of the castle and watching the planes land at Logan, sailboats going by and people fishing from the pier. I've been here dozens of times over the past many years and it never gets old.... More