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Best Places to Propose in Boston

Places to Propose
best places to propose in Boston, MA

Boston is one of the country’s most beautiful and historic cities. It has a little something for everyone, including colonial architecture, green spaces, cultural destinations, and world-class food. If you’re ready to propose, you’re likely to find whatever experience you’re looking for in Boston.

Where to Propose in Boston

Above the City

Love is in the air! Sweep your loved one off their feet (literally) with a helicopter ride around New England and the Boston area! With an aviation company such as Boston Helicopters, embark on tours of the city of Boston, the seacoast, or a combination of the two settings. And for even more romance, take a tour of the Boston skyline as the sun sets, and twilight hits the sky.

Our adventurous couple, Ravi & Swetha, took a life changing ride around the city they where they met, and are ready for the new and exciting journey of marriage with their custom rose gold engagement ring!

Over a Delicious Meal


Located in Boston’s historic North End neighborhood, Mamma Maria is in good company with shops, other wonderful restaurants, and trendy boutiques. From the warm bread served at the table to classic Italian desserts like panna cotta, you’ll have a meal to remember at this charming old-world restaurant. Enjoy a traditional Italian dinner of pasta or rabbit with a bottle of Chianti. Once your bride-to-be is contentedly full, make her night even better by presenting her with a diamond engagement ring.

At a romantic Boston landmark


Who would guess that the top of the Prudential Tower contained a beauty like Skywalk Observatory? Fifty floors up, the Skywalk Observatory offers breathtaking views of Boston. You’ll get a 360-degree bird’s eye view of major landmarks that include Fenway Park, Harvard University, and Boston Harbor. Take the audio tour to learn about the history of the city and all it has to offer. Then, as you look out on the Boston skyline with your sweetie, give her the only thing that can compete with the view: a sparkling diamond engagement ring!

The Boston Harbor Hotel at Rowes Wharf not only has a rich history, but it has also received several awards, including the distinction of being one of the “World’s Best Places to Stay” on the Condé Nast Traveler Gold List. Boston Harbor is a hub of activity — you’ll have your choice of dining options, public art, and transportation by boat to a variety of destinations. At night, the grand arch at the entrance of the hotel lights up and makes a perfect setting for your proposal.

In a Beautiful Outdoor Setting


Boston Public Garden is one of the most idyllic settings in the city. You’ll find everything you’re looking for in a beautiful backdrop: flowers and trees, horses and ducklings, and families enjoying picnics and lemonade. It’s right out of a painting. Take your lady out pedaling on a Swan Boat and breathe in the fresh air together before you propose. Once you’re back on land, you may want to skip your way through the garden and announce your engagement to passersby!

Or follow the example of real-life couple Chase and Sarah and go right next door to Boston Common, an iconic destination and the oldest city park in the country.


Chase took advantage of Sarah’s work trip to Boston to plan the perfect romantic proposal. He worked with Paparazzi Proposals and the management at Prezza Restaurant to surprise Sarah and capture her reaction on camera. Chase proposed to Sarah on the walking bridge in Boston Common, and of course she said “yes”! The couple hopped into a horse-drawn carriage, and Sarah happily announced their engagement to every person who passed by.



The carriage took Chase and Sarah to Prezza, where a special table was waiting for them. It was decorated with black-and-white photos of them and a custom table tent reading “RESERVED for the Newly Engaged Couple,” with their names and the date. To wrap up a wonderful evening, the couple returned to their hotel room to find a bouquet of a dozen red roses waiting for them.

Proposal pictures and story sponsored by Paparazzi Proposals

When booking, enter code mytriorings$100 to receive $25 off the standard proposal photography package and $75 off a photo voucher for prints.

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Additional photos: Flickr/boblinsdell; Flickr/jeffgunn

Modern Couple's Guide To Proposing
My Trio Rings

As the Modern Jeweler for the Modern Couple, MyTrioRings.com brings couples authentic & affordably priced diamond bridal jewelry. The My Trio Rings Blog focuses on Wedding Trends, Jewelry Buying Tips and ways to save on celebrating the timeless tradition of marriage!

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