Southie not only has some great bars/restaurants to visit, but it’s a great place to spend some time outdoors taking in the views of the harbor and Boston’s beautiful skyline. My itinerary will include a few bars, some great food and enjoying the outdoors.
Morning: L Street Diner
Afternoon: Sullivan’s and Castle Island
Evening: Shenannigans
Late Night: L Street Tavern
Morning: L Street Diner
One of my favorite places to go when I visit family in South Boston is the L Street Diner for breakfast. And it’s not because we get the best table in the joint when we visit (my Aunt is a regular), but the food always hits the spot. You can’t go wrong with some eggs bene and a towering plate of bacon to start your day off right.
Once you are done with breakfast you may need a little exercise to keep you from retreating home and into an afternoon food coma, so just a short walk away is Sidewalk Café (“South Boston’s #1 Café”) where I think is one of the best places for iced coffee. So grab yourself an iced and get ready because this itinerary is not over.
South Boston has various outdoor areas to enjoy if the weather permits. Telegraph Hill, the Harborwalk and one of my favorite Boston landmarks, Castle Island.
Which leads into my recommendation for the afternoon…
Afternoon: Sullivan’s and Castle Island
Once you have reenergized and afternoon hits, lunch at Sullivan’s and a walk around Castle Island’s “Sugar Bowl” is a great way to spend the afternoon. Growing up I used to go to Castle Island for field trips with school and summer camp. Bagged lunches, tag around the playground and watching airplanes practically land on top of you is where it is at. The menu at Sullivan’s is simple, however they do manage to throw in a lobster roll and fish sandwich, because it is Boston after all.
There are a few fun events that take place in the Castle Island area. One of which is the infamous, New Years Day Polar Plunge, where people from all over run into the freezing water, either to raise money for charity or because they are purely nuts. It’s a fun tradition that always brings a big crowd to L Street Beach every January 1st. Some of the costumes you see are pretty entertaining. I can’t say I have ever made “the plunge,” but I definitely support the cause.
Castle Island has always been one of my favorite places in Boston. It’s the type of place that is fun to visit year round; however, once “Sullys” opens its doors for the season, that’s truly the best time to visit. My family has a personal attachment to Castle Island because of all the time we spent there growing up, especially my grandparents. When they passed, we donated a bench to Castle Island in their memory. So if you happen to see “the bench,” along your visit, take a seat and relax.
Once you are done taking in the sights of Castle Island and the harbor, you may need to head home for a nap to keep up with the remainder of the itinerary… or at least for an outfit change.
Evening: Shenannigans
Shenannigans is a nice, casual place to grab dinner and drinks. Conveniently located close to the Broadway train station for those that are not even going to attempt to find parking in Southie. The menu offers traditional American fare with some favorites such as the Shepherd’s Pie and no Irish bar would complete without Bangers, Mash and Beans on the menu. For those that enjoy live music, Shananigans hosts live reggae bands on Friday nights. If this is not your cup of tea, hop up to The Playwright or Stats (as mentioned in James’ blog post) two other great bars that are fun to visit.
Now it’s off to another Southie gem for some drinks to round out the day….
Late Night: L Street Tavern
The L Street Tavern is a quaint, neighborhood bar that tends to have a group of regulars. They are harmless, I swear, just don’t look at them funny. The L Street Tavern made Southie “famous” when Ben Affleck and Matt Damon filmed, Good Will Hunting, there in the early 90s and won many awards. It may have been the movie to spark interest for others to film in Boston.
L Street Tavern has plenty of memorabilia around the bar to commemorate the success of the movie. I can remember the film crew hogging L Street from East Broadway to the Beach as we tried to visit my Aunt on East 6th and maneuvering the lovely one- ways that fill Southie.
After some drinks to toast the night, you may be ready to head home. Don’t forget to come back to Southie and experience Castle Island when “Spring” finally shows itself.
I hope you enjoyed!
Diana – I enjoy spending as much time outside as possible even if that means finding a bar with a roof deck. I am always up for a challenge, whether it’s hiking a mountain, bowling or singing karaoke in front of complete strangers, I will do it. As long as the day involves a glass of wine, family or friends and a good laugh at the end of it, it’s alright in my book.