SOUTH BOSTON – Castle Island

Castle Island’s 22 seaside acres offer something for everyone. For history buffs, the land houses Fort Independence, which was built between 1834 and 1851. You can’t go in or on top of the fort, but you can walk around it and get up close. Castle Island also has a beach and a large playground. The peninsula (it’s no longer an island–it was connected to the mainland in 1928) offers views of Boston Harbor and the boats and is also the perfect spot to watch planes take off and land from Logan Airport. The grassy areas near the water are ideal for flying a kite, and you can ride bike or scooters around the trails here. Finally, no visit to Castle Island is complete without a visit to Sullivan’s for some fried seafood. This restaurant has been a Boston landmark (with good reason–the food is delicious!) since 1951 (thanks Wikipedia and DCR for the info!).

We consider ourselves so lucky to have such beautiful beaches, waterfront views, access to nature, and interesting history in one beautiful URBAN spot. Boston is the best!


2010 Day Blvd.

Boston, MA 02127


Trail Map

Drive down William J. Day Blvd. until you get to a large parking lot. You’ll see Sullivan’s restaurant in front of you. We walked the Castle Island Loop. If you want more exercise, you can easily add the Pleasure Bay Loop as well. We stopped for a bit to fly kites on the grassy area near the water. Then we finished up with a trip to Sullivan’s!

Given Castle Island is IN BOSTON and traffic in and around our beautiful city is perpetually gawd-awful, it’s important to time this trip right. We went on a weekday during the summer, so we timed it to arrive there at 10:30AM. We only hit minimal traffic on the way in (from E. Milton Square to the Savin Hill exit was where it backed up). When we left around 1:30/2pm, we were successful at threading the Boston traffic needle, and it was smooth sailing back to the South Shore.

P.I.N.T. Score

Rated on a scale of 1 (difficult/not good) to 5 (easy/awesome!)

P – Parking & Access – 4 (The parking lot is huge, but it fills up quickly. Parking is free–an extreme rarity in Boston!)

I – Interest Level – 4 (The views of Boston Harbor and the boats, the airplanes taking off from Logan, the playground, the ability to fly kites, and the delicious food from Sullivan’s made this interesting to our kids (and us!) for many reasons.)

N – Navigation – 5 (You can’t get lost on the Castle Island Loop–just follow the path around the fort. )

T – Terrain – 5 (Wheelchair and stroller accessible.)

The P.I.N.T. Score represents our opinions of this trail.  It reflects our experience, perception, and physical health.  Therefore, the scores are not intended to be expert advice, nor will they be accurate for everyone: we cannot judge what may or may not be appropriate for each individual’s different abilities.  Consult a physician or medical expert before attempting any new physical activity. Hiking contains inherent hazards, so hike at your own risk.  You should always make your own decisions about what level of physical activity is appropriate for you and your family. Weather and other factors may affect trail conditions. Remember, trail conditions may change suddenly and drastically at any time.


  1. Fort Independence

2. The kite-flying area

3. Ocean Views

4. Sullivan’s Restaurant

You can’t visit Castle Island without eating at Sullivan’s. It’s sacreligious! We ordered online–the food was ready for pick up right outside the building in less than 10 minutes. Easy!! There is no seating at Sully’s–just find a shady spot on the grass or the surrounding benches and picnic tables.

Sorry–no photos! We ate the food too quickly! But watch the video for a glimpse of what we ate! 😉

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