I take it that you want to find something right around Boston/South shore to do? Do you have any idea of what you want to do? Fine dinning, long weekend on the Cape, night in the city? What are some of her favorite things to do? I am pretty familiar with the area so if you can give me an idea of what she likes or possibly something you may have in mind I may be able to help.
Hey there! I live in the South Shore too (Quincy)! There's a beautiful park in Weymouth off of Bridge St. that overlooks the ocean, and there's this spot that faces the skyline of Boston - very pretty. There's also Nantasket Beach, where there's a ton of restaurants on the beach that could be quite romantic. Also, the public gardens/Boston Common are GOEGEOUS, especially at night. You could always take her to a nice restaurant or to a show in the theatre district, and walk right over to the common and propose there. The North End is also magical at night because they put up all those white string lights all over the place. As you can see, I like the outdoor settings a lot, but there's also some great indoor places if it's cold out, like the observatory at BU or something like that. Hope it goes well! Definitely write a post after it's done!
Haven't been there in years even though it's my "home" territory. IMO, there are so many great places -- a walk along the beach in Duxbury, the Pru Tower in Boston, Edaville Railroad if its still there, Plymouth Plantation, The Boston Commons as previously mentioned, the North End, a ferry ride from Weymouth to the City, it all depends on what seems the perfect setting for you. I live in Colorado and my husband has a commercial hot air ballooning company -- he has lots of people propose in the balloon so that's a great idea, too if there is someone in the area that does that. Good luck.
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