How to Propose in Boston

Featured Boston Proposal Tips
  • Choose a special location to pop the question in Boston
  • Practice getting down on one knee beforehand
  • Think about what you will say
  • Make reservations so you have a reason to dress up
  • Hire a proposal photographer to plan and capture the moment

Since 2013, Flytographer has captured thousands of surprise proposal photos all around the globe. Explore romantic proposal ideas and tips from real couples, including their top proposal ideas and tips, and the best ways and the best places to propose in Boston. Explore our customers’ heartwarming Boston proposal stories below.

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Alexandria & Kelsey's Proposal Story in Boston

How did you meet?

Tinder

What is your love story?

I knew Kelsey was the one before we were even out of the “talking phase.” We clicked, and I knew I had found something that was missing from every other relationship before her.

What made you choose this proposal destination?

I used to live in Boston and spent a lot of time in the Commons/Gardens, going through typical 20-something struggles, and it seemed so fitting to enter the best chapter of my life in the same place where I had wondered if I’d ever find something like this.

Best tip for proposing in Boston

Don’t plan it on Marathon Monday when the Sox are going for the division title unless you’re good dealing with lots of people around no matter where you go!

Proposed in Boston in October

Photo Shoot Location: Custom Route

Meghan in Boston for Flytographer


Michael's Proposal Story in Boston

What is your love story?

I like to say we meet via social networking tools (aka Bumble). It was the road well traveled for both of us however when we met there was almost an instant connection. It wasn't long before I felt like this relationship was different - and the rest they say is history!

What made you choose this proposal destination?

We love Castle Island and both live in South Boston / spent a lot of time running or walking out together to the area. It's a beautiful setting and a place where we have spent a lot of time together.

What is your proposal story?

She was shocked! It was a long concocted story about a surprise photo shoot for her one year old nephews first time in Boston - they changed their flights (she and her family are originally from Cleveland) the week of to fly in with the rest of their family (immediately after I proposed). That set off a series of panic in me as the plan had to quickly change - so I went with that the company wouldn't refund my money and therefore the surprise was ruined and had to eat the money. I suggested we just make a 'good situation out of a bad one' and take pictures ourselves Friday morning anyway. After a significant amount of pushback from Kelsey she agreed to take pictures reluctantly and off we went to Castle Island Friday AM. Once we started everything was a breeze and she was shocked when I actually proposed!!!! It was and still feels amazing.

Proposed in Boston in October

Photo Shoot Location: Custom Route

Eva in Boston for Flytographer


Jesse's Proposal Story in Boston

What made you choose this proposal destination?

Boston has always been a special place for us. It’s been a second home. The city holds so many places for memories old and new.

What is your proposal story?

The planning was perfectly corrdinated with our Flytographer photographer and a local proposal decorator. I would propose by the bridge in Boston Public Garden and stumble upon the picnic alongside the shore. However, the rains came in, and cold weather began to flex. I had to change the location of the picnic on the fly to the only refuge in Boston Common, under the Parkman Bandstand. With coordinating between our photographer and decorator, everything went off without a hitch. My fiancé was none the wiser to how close things could’ve unraveled. I brought my soon to be fiancé down to the gardens under the guise of seeing an autumn garden show. When we arrived, of course, there was no show. She thought it was because of the rain. She felt that I was going to be disappointed, and came over to me, only to find me on my knee, which I began to tell her of how we got to where we were, in the day and in our life. After a joyous proposal and embrace, we met our photographer (who was already snapping up pictures from the start) and we got pictures along the gardens until we stumbled upon the picnic surprise. The rain had put not one damper on the day and I cannot be more appreciative for the everyone involved to make this moment special for us.

Proposed in Boston in October

Photo Shoot Location: Custom Route

Olivia in Boston for Flytographer


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