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SEAPORT
Ahhh, the Seaport District. Boston's newest, hoppingest, poppingest area. Personally, I have a love-hate relationship with the Seaport. It's nice, for sure. Lots of cool spots, BEAUTIFUL views. All that I love. But I hate that I didn't buy anything down here 20 years ago when it was a dump! Yeah, I'm still bitter. And, seeing that units are selling around $2,000/sf (minimum) that hate ain't going away any time soon:( But, I digress. There is a lot of fun to be had down here when you're visiting. First off, very walkable. Nice and flat and...no cobblestone! Speaking of walking, I mentioned the Harborwalk under the Waterfront section. I'll mention it again because along the Seaport is easily my favorite section. It's called "Fan Pier". Basically, start at the Barking Crab and walk along the harbor til the old World Trade Center (soon to be named, Commonwealth Pier). Absolutely GAWJIS back there. Along the way you'll see all sorts of little goodies. Different parks and pavilions, artwork, fire pits, cornhole stations, open beer gardens, and of course, stunning views. The big boys of the Seaport are the ICA (Institute of Contemporary Art) FREE on Thursdays after 5PM, FYI. The BCEC (Boston Convention and Exhibition Center) and, at least during the summer months, Harbor Lights. Ok, ok, now it's called, Leader Bank Pavilion (yuck) but it is a fantastic place to take in a summer show. I often say, doesn't even matter if you like who's playing. Bring some earplugs and just enjoy the atmosphere! The Harpoon Brewery is a not-so-hidden gem. It's down at the end of the Seaport so a little, out of way BUT totally worth it. Great tours, decent food and usually some different, seasonal fun going on in their parking lot (i.e. pickle ball courts, etc.) Also for my stand-up comedy fans, check out, Laugh Boston. It's located inside the Westin, next to the BCEC. Can pretty much guarantee laughs Thursday - Saturday nights with some Tuesdays & Sundays thrown in there.
South Boston


Hmmm, let's see, how to simply describe or define South Boston? Nope, sorry, can't do it. Too big and diverse. First off, in case you're wondering, not ALL of South Boston is "Southie". At least, not to us. Or more importantly, anyone from, Southie. Back in the day, getting that wrong could get ya hurt! South Boston is pretty big, where Southie is just a little part on the inside. And back in the 70's and 80's THIS was Whitey Bulger's playground. Essentially from the Broadway T Station to Castle Island. It's changed a lot recently and definitely ain't what she used to be. Which is both good and bad. Mostly gone are the hardware stores, butcher shops, and neighborhood taverns. Now it's coffee shops, wine bars, and yoga studios. This is, however, where you will still find the L Street Tavern. Made famous in Good Will Hunting. How do you like them apples? If you can, absolutely make your way down to Castle Island. The best part is, it's no longer an island! So you don't need a special boat ride to get there. Once there, you can go take a look or get a FREE tour at Fort Independence. It's one of the oldest continuously fortified sites in British North America. The island is surrounded by beautiful walking paths that provide views of Boston Harbor, Logan Airport, and the city skyline. There’s a small beach area, picnic spots, and a playground, making it great for families. The area is clean, safe, and generally has a welcoming, laid-back vibe. Also in Southie, for my history nerds, is Dorchester Heights. This is where George Washington set up shop in early 1776 obtaining the high ground of Boston. This position would eventually force the British out of Boston for the last time on March 17th, 1776. If you go, you will be rewarded with a great view of the harbor! On to the rest of South Boston. First, I would be remiss if I did not mention Harriet Tubman Square. There's a wonderful statue of this incredible human. I mention this not just because of that fact but statue is a part of the often, overlooked, Women's Heritage Trail. It's actually many trails, divided by neighborhood. Taken directly from the site I linked to: Founded in 1989, the Boston Women’s Heritage Trail celebrates the past accomplishments of remarkable women in Boston, claiming their rightful place in our City’s history. Through education, reflection, and an interactive city-wide monument, we activate the powerful female side of Boston’s history. I couldn't have said it better myself. So, I didn't. Now the really big show in South Boston has to be the JFK Library. If you're even remotely a fan of 35, go! Exhibits, replica rooms, multimedia experiences, it's got it all. Easy to get to using the Redline of the subway system. Definitely plan to stay at least a few hours!
Crafty Eats: So the Seaport also suffers from "Chain Syndrome" (Welcome to Boston). However, I do like Lolita's on Summer St. Now, I haven't been in forever, but a very cool, hip, little joint is Lucky's Lounge, also on Summer Street. I'll get back there and update, ASAP! Lastly, at least for drinks, but food also, the rooftop bar at the Envoy hotel on Congress Street. Heck, stay there if you can but at least get up there for a beverage:)
Crafty's Eats: While at Castle Island you MUST eat at Sully's. Not only a Boston institution serving hot dogs, lobster rolls and ice cream since 1951 BUT, it's like the only place down there so....ya kinda have to:) Start or end your trip to Castle Island at a local & personal favorite, Amrheins (80 W Broadway) Good for dinner and a drink, great for breakfast! Tell Nicole and/or Jamie that Crafty sent ya! Lastly, if you're in the area (near the Harriet Tubman statue) you have to go to Charlie's. Serving food at 429 Columbus Ave. since 1927! Read their About page here. Amazing!
These pages are designed in hopes to give you a general lay of the land. I try to stay away from talking about the bigger attractions and focus more on the "lesser known" things and the "FREE STUFF". I hope you find it useful. -Crafty




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