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28 Romantic Date Ideas You Can Take Your S/O On This Fall In Boston

I hope you're ready to make a lasting impression!
28 Romantic Date Ideas You Can Take Your S/O On This Fall In Boston

Boston is a great city full of fantastic things to do and see. So why is it that just when you need something romantic to do, you can't think of anything other than the typical candlelit dinner? We're not knocking the dinner idea or anything, but there are so many other things in the city to choose from. And that's why we did the hard work for you rounding up these 28 romantic date ideas for you to take your other half on this fall in Boston. 

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Take a New England fall foliage sightseeing tour

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If you're bored in Boston, spend a day viewing the spectacular fall foliage around New England's most beautiful countryside destinations. The tours last approximately 9 hours and include stops for photo ops, shopping, and eating.


Rent a waterfront cottage for the night

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Forget renting a cheap hotel room, show your sweetheart that they're worth a little extra investment by renting a waterfront cottage for a night or two. You are definitely going to want to take advantage of this idea before winter rolls around and freezes everything over. Here are a few that look particularly appealing, there's even a yacht!

Fly the skies in a hot air balloon

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Hot air balloon rides aren't something you do often, so make this the year you finally check this off your romantic date-idea bucket list. Plus, imagine the fantastic views of the fall foliage.


Pick pumpkins together then carve them

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It's pumpkin-everything season, and if you can't escape it you must embrace it. Whether you choose to get a pumpkin straight from the patch (recommended) or simply at the local grocery store, you can make picking and carving them into a fun and decently cheap date night.

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Have a couple's spa day

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Nothing is more romantic than a day spent relaxing together, and let's be honest, you both deserve it. Luckily, there are tons of spas around the city to schedule a couple's spa day at. So go ahead, book this one in ASAP - and get the package that includes a bottle of champagne for a little extra kick.

Stroll along the beach

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If you like long walks on the beach then Boston is a great place to be. With several beautiful beaches to choose from, you have plenty of options for a day by the sea. If you really want to make it fancy, pack a homemade lunch and stay to watch the sunset.

Go on an Old Town Trolley Tour

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Sit back and relax while you are chauffeured around the city from destination to destination learning about the city's history.


Take a food tour

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You heard me right, food tours are a thing. And excitingly there are several different food tours to go on, featuring a variety of eateries and themes, so choose the one that best fits your tastes and schedules. These tours totally put an unusual twist on dinner dating.

Game Night at the Knight Moves Cafe

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If you enjoy some friendly competition with your other half, an evening playing board games at the Knight Moves Cafe is definitely warranted. Although I've never counted, some people claim there is easily over 1,000 games to choose from. In addition to the small admission fee, you have the option to bring your own snacks and booze for an extra $5.


Hire a photographer 

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Okay, you aren't just hiring a photographer for nothing, you're hiring a photographer to take some lovely couple's photos! Not only is this romantic, but it will last a lifetime - plus you can upload the photos to your social media and make everyone jealous of your adorable, picturesque relationship.

Spend an evening stargazing

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If you find yourselves bored on a warm clear night, head out to one of Boston's remote locations or the Observatory for an evening of stargazing. After all, there is something oddly romantic about laying under the stars together, and if you're really lucky a shooting star will pass by to wish on.

Take a boat cruise on the water

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Being a coastal town, Boston is full of cruise options. From a dinner cruise on the ocean to a sightseeing cruise on the river, there are tons of companies and choices for couples interested in spending time together sailing the open waters.

Cuddle up by a fireplace

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It doesn't matter if it's yours, a friends, or in a hotel room, sometimes there is nothing better to do on a chilly fall evening than cuddling by a nice, warm, crackling fireplace.

Taste some ciders

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Pumpkin spice may be the domineering drink flavor of the season, but apple cider is the true top dog. You can choose to sample cider at one of the many fall festivals tasting events or any time at one of these three cider houses, Downeast Cider House, Bantam Cider Company, Prospect Cider Works.

Attend a couple's class

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Cooking, crafting, photography, meditating - if there is something that the two of you have been yearning to learn more about together you can bet that there is a class for it and there is no better time to invest in your future than now.

Go for an impromptu ice cream run

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Ice cream is great any time of the year, including in the fall. Keep things exciting with a spontaneous ice cream run; and if you really want it to be interesting, try one of Boston's unusual ice cream parlors, like FoMu.

Painting with a twist

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Paint, drink, and bond over an artsy evening together. Then take your masterpieces home to remember the night forever (even if you drank too much to actually remember). Check out this list of studios for dates and rates!

Get tattooed together

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Relax, you don't have to get matching tattoos, but you can still get some fresh ink together. I mean let's be honest, no one wants to sit around and wait for someone while they're getting tatted, so make it a new-aged date instead. Here is a list of Boston tattoo studios.

Admire the skyline views

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The Boston skyline is one of the most iconic in New England, and rightfully so. No matter if you choose to view it on land or sea - or 52 floors high from this restaurant, it will surely not disappoint.

Enjoy a classical music concert

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If you enjoy having an excuse to dress up... The Boston Symphony Orchestra plays some of the most beautiful and fancy classical music concerts around - some of which are completely free.


Pick out a book for each other

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This is for all those bookworm couples out there. Check out your local library or bookstore and find a book that you'd like your partner to read while they do the same for you. Try to pick something nice, not something like "Dating for Dummies."

Watch a romantic movie at the theater

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Save the horror film for a less-romantic evening. Go to your favorite theater and watch that romance film you've been wanting to see. The best part? Having bae's shoulder to cry on during those tear-jerking love scenes.

Grab some sweets at the candy store

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Sweets have been a symbol of love for a long time. From a dozen fancy chocolate covered strawberries to those kind-of-gross but equally addicting sweetheart candies given out as Valentine's treats, you can get pretty much whatever your heart's desire (pun intended) at any of these deliciously sweet Boston candy stores.

Learn about the city's history together

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As one of the oldest cities in America, you can be certain about one thing: there is plenty of history to be learned about here. While there are many guided tours to choose from if you would like to save a little bit of money you can self-guide yourselves to all of the historical locations. Cheap and effective.

Lock your love in place

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There are a few different bridges throughout Boston that have become the subject of love locking - the art of couples padlocking a section of the bridge's chainlink fence with a custom lock (usually with their initials etched on the surface). One popular area for love locks is the bridge running over the Massachusets Turnpike.

Book a private hot tub at Inman Oasis

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Get hot and bothered in one of Inman Oasis's private hot tubs. Choose between a fiberglass tub with hydraulic jets or an authentic Japanese style wooden tub for a more intimate experience. An hour soak is $70, that's only a measly $35 per person.


Treasure hunt at one of Boston's antique stores

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It's true that you never know what you might find shopping at a secondhand store. From eccentric clothing to rare artifacts worth lots of money, antique store shopping is like modern-day treasure hunting. Here's a list of local antique stores.

Watch the sunrise 

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We already covered watching the sunset during a sunset cruise, but if you are a couple of early birds then the sunrise might be more your style. Rumor has it some of the best places to watch the sunrise is from Revere Beach, Castle Island, and right outside the JFK Library.

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