My New Favorite Boston Spots

Day trips need not be far or pricey or take a lot of time. Sometimes you don’t have a full day, sometimes you are sick of driving, and sometimes you just want to get the most out of the time and money you have. One of the reasons we bought the condo that we did was because of its proximity to some beautiful areas of Boston.

South Boston beach

Over the years, walking around South Boston’s Castle Island has been our most favorite activity, year round, but of course especially in summer. We are both water signs, and being near the ocean brings out a calm in us like nothing else. So, through job stresses, condo association nightmares (I have STORIES, my friends!), and in happy times, we have made our way around what is known as the Sugar Bowl, a beautiful loop that juts out into the bay.

Castle Island

From our walk, you can see the harbor islands, and stop for an ice cream or fried clams at Sully’s, a South Boston landmark that, because of government funding, is able to keep its food very affordable for everyone. This makes Castle Island the perfect place for anyone; you don’t need to be rich to get away down here.

Sullivan's Castle Island

Once we get to Castle Island, we never want to go inside again. Last Saturday, when the sun was shining bright and it was *hot* for the first time, we decided that after our walk, a picnic was in order. After such an enjoyable visit to the JFK Presidential Library recently, I suggested that we head there for its views and uplifting sense of calm. And there I discovered my new favorite place for picnics.


It reminded me of this, one of my favorite JFK quotes:

“We are tied to the ocean. And when we go back to the sea, whether it is to sail or to watch – we are going back from whence we came.”

JFK Presidential Library

Brilliant blue skies are almost hard to distinguish from the water, and a large expanse of stones provides the perfect place to soak up some sun. The wide, flat stairs were toasty warm, providing the perfect place for a rest after lunch.

JFK Presidential Library

We could have easily stayed there for hours. After such a long winter, I wanted to get a sunburn. That’s bad, isn’t it? Embarrassed smile

JFK Presidential Library

We will be returning for picnics outside the JFK Library all summer long. I can’t think of a better place to enjoy a quiet meal and some of the best views Boston has to offer.

If you had to pick one favorite spot, what would it be?

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Tags: beaches in MA, Boston, Castle Island, day trip, South Boston

  1. Michelle’s avatar

    I’ve never been to Castle Island and I really want to go this summer. Maybe I’ll convince Bret to go one weekend!


    1. traveleatlove’s avatar

      We could also always meet at the JFK red line stop and go for a long walk down there one of these nice days!


    2. Emily @ A Cambridge Story’s avatar

      I’ve been to Castle Island once, years ago. It’s definitely a slice of urban heaven. I tend to go to Fresh Pond in Cambridge a lot – or Middlesex Fells or Blue Hills – when I need a quick escape.


    3. Melissa’s avatar

      I’ve never been to Castle Island either! Perhaps this is the year.


    4. Charlene’s avatar

      My husband and I are originally the ‘burbs but moved away to Philly for college, then to NY/NJ for work. We’ve only recently returned to Boston (after quitting our jobs to travel for 6 months!) so we’re thrilled to finally be living in the city itself! I’ve never spent much time in Boston proper (despite having grown up less than 10 miles away) so I don’t have a favorite spot yet. I’ll be sure to check out Castle Island – it looks wonderful!


    5. Daisy’s avatar

      I would love to do a long walk around Castle Island. Its been on my to do in Boston list for years. I have so many favorite spots. Close to me are Christopher Columbus Park and the views at Long Wharf and surrounding wharfs.


      1. traveleatlove’s avatar

        I think we need to pick a warm Sunday for a Castle Island walk and dbar brunch!


      2. ashleigh’s avatar

        I love castle island! I’m actually thinking of making the trek over there this weekend. I wish I lived closer!


      3. Heather’s avatar

        I’ve never been to Castle Island but heard lots about it!

        My favorite spot is in Boothbay Harbor, Maine – right on the water eating a lobster. Heaven.


      4. Bianca @ Confessions of a Chocoholic’s avatar

        Even though I went to UMass Boston, I’ve actually never been to Castle Island – eep! But that will change soon!

        My favorite picnic spot is the Memorial Drive side of the Charles River in Harvard Square :)


      5. Megan’s avatar

        Hmm… I love places like that. I always bug Jeff to drive over to Jamaica Pond or Fresh Pond so we can stroll around with Gunner. I like being anywhere near water and away from all the city noises.


      6. MelissaNibbles’s avatar

        I’ve never been to Castle Island. I should make point to get out there this summer.


      7. Elizabeth’s avatar

        Both castle island and the jfk library have been on my list forever. The photos are absolutely gorgeous. Definitely needs to happen this spring


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