Dreaming of a picture-perfect proposal? Most of us do, but like a lot of major life events, it’s all in the planning. If you don’t want to spontaneously pop the question at a less-than-perfect moment, there are plenty of locations all around the city that are sure to stand out in your mind and memories forever. We proudly present five of the best places to propose in Boston.

1. Fan Pier Park

What’s your point of view? Some of us believe we’ll have our whole lives to enjoy intimacy. For the proposal, focus on wow factor. That’s easy to arrange with the breathtaking waterfront views available at Fan Pier.

To make a day of it, start out at Rowe’s Wharf, where you and your soon-to-be betrothed can hop on a few bikes and make the most of the Boston Harborwalk. It’s a scenic ride to Fan Pier, with museums and fascinating architecture to enjoy along the way.

Once you’ve arrived, hit up Babbo Pizzeria e Enoteca on Fan Pier Boulevard for some of the most popular wood-fired pizza Boston has to offer. Cap it off with some of their famous gelato, and head back out just in time for the sun to go down and the city lights to come up.

Alternatively, start your evening out at Committee, one of the city’s hottest spots serving Mediterranean fare. Have a few of their clever cocktails on the patio before making your way closer to the water’s edge. There, a stroll along the cobblestone path sets the tone leading up to the big moment.

No matter how you spend your time before the big question, Fan Pier provides some of the best nighttime views of Downtown. Better yet, it’s one of the best spots in all of Boston to take photographs. This makes it an ideal proposal spot for those who want a stunning, momentous snap of the occasion.

2. Christopher Columbus Park

Like Fan Pier, Christopher Columbus Park features plenty of waterfront views. Still, there is perhaps more versatility in proposal planning when you include the park, especially depending on the season.

For instance, a spring or early summer proposal begs for a setting in full bloom. Pack a picnic lunch, or grab some carry out from one of the many delicious nearby eateries. Walk it off with a pleasant, easygoing wander through the Rose Kennedy Rose Garden. There are many varieties of gorgeous and fragrant perennials to behold.

From there, make your way out to the fountain in the middle of the park, where you can pop the question amongst the park’s many shade-providing trees.

If a more celebratory social gathering is in order, consider a fall or winter proposal in the park. Late November brings the Annual Trellis Lighting Ceremony, where soft blue lights drape the trellis and the hot chocolate flows. This location is well known as one of the most romantic places in the city, in addition to being one of the five best places to propose in Boston. Don’t be surprised if someone nearby drops a knee as well.

For lovers who want a fresh start, consider the heralding in the new year with a crisp, brilliantly lit proposal. Christopher Columbus Park is an excellent place to catch the Harbor’s New Year’s fireworks display.

3. Boston Public Garden

For a park-like setting with a little more fanfare, try Boston Public Garden. It’s a great place to end up after visiting one of the nearby cafes or restaurants. Prize-winning flowers and famous sculptures adorn the 24-acre botanical space.

Make your move as you gaze down at the lagoon from the historic trellis bridge or traverse the lagoon itself in a swan boat. Either way, your ears might be privy to some mood music courtesy of one of the Garden’s many visiting performers, known as buskers.

If temps are low, start out with some ice skating at nearby Boston Common. Grab a hot drink and stroll through the Garden to peacefully admire the city lights. It’s significantly less crowded during the colder months.

If all goes according to plan, there’s good news. In addition to being one of the best places to propose in Boston, the Public Garden hosts weddings. Imagine yourself saying “I do!” beneath the tendrils of great weeping willow trees, with one of those infamous swan boats floating by in the background.

4. Acorn Street, Beacon Hill

We could describe Acorn Street as charming, old-fashioned, and romantic. Yet it also has a reputation for being one of the most photographed locations in the city. If you’re looking for an intimate moment, is a photo mecca really one of the best places to propose in Boston? As it turns out, perhaps.

Cobblestones characteristic of old Boston pave the private little street, which is narrow and lined by row houses. It extends for a mere block between West Cedar and Willow. The real headline here is that this historic little picturesque gem is located in Beacon Hill. Therefore, there are a wealth of date options to explore before finding yourself on this storied pathway.

History and architecture buffs will enjoy Beacon Hill’s famous walking tour, which takes visitors through many historical areas, including Louisburg Square. Outdoorsy types can start the date at Charles Hill Esplanade for some kayaking, where they might afterward happen upon a pop-up brewery.

Charles Street is also a great boutique shopping destination, where you can buy a few nice things for your honey before presenting the ring. The restaurants are well-represented as well. Go elegant Italian at Toscano, or try a romantic French bistro like The Hungry I. The latter is a mere 0.1 miles from your proposal destination, Acorn Street.

Imagine Acorn Street in the fall just before sunset, with fallen foliage and shades of ochre and rust. Pop the question in the autumnal glow on this quiet street; you won’t need a photograph to remember it forever, but you should take one anyway.

5. Comm Ave (Commonwealth Avenue)

If you’re unsure as to which avenue to go with your proposal, just go Commonwealth Avenue. Historical areas, gardens, malls, and more make it a prime destination for couples who want to experience Boston and hit a major milestone along the way.

For starters, book a room at Comm Ave’s No. 284 – A Boston Guest House. An extraordinary take on a hotel, it offers luxurious rooms ensconced in a brick building in the Back Bay neighborhood. Their list of services and amenities is rich and varied, offering guests everything from photographic services and chauffeured limousines, to dentist appointments and theater tickets. It is a singularly excellent place from which to start a weekend getaway.

No. 284 is close to Copley Square, where you can visit the Boston Public Library and a whole host of architectural landmarks. The hotel is also a few skips away from a lot of fine dining, from Deuxave, serving Modern French, to Casa Romero, rated the best Mexican restaurant in New England.

The Back Bay neighborhood also features so many shops and cafes that there truly is something for everyone. Finally, it’s not far from Fenway Park, should you be sports fanatics looking to catch a game.

All told, Comm Ave is a great jump off point for a Choose Your Own Adventure-style proposal. With the best of the city within arm’s reach, it is inarguably one of the best places to propose in Boston.

In Conclusion – Best Places to Propose in Boston

Ready to lock it down in Beantown? The rundown on five spots today should have you on the right path. To summarize:

• Fan Pier – The picture-perfect moment you’re looking for. Even if you’ve lived in the Boston area all your life, capturing a proposal in front of the iconic city skyline is something many couples dream of.

• Christopher Columbus Park – A rosy picnic proposal near the fountain, or a wintertime celebration under trellis lights or fireworks? Either way, there are chances for a very one-on-one encounter that isn’t devoid of that extra something special.

• Boston Public Garden – A proposal spot and a wedding venue all in one. Take your future spouse on a famous swan boat, or on a stroll through stunning botanicals after having a day to remember at one of many surrounding attractions.

• Acorn Street – A proposal straight out of the movies. Amble down this historic cobblestone street, basking in the glow of your love. This neighborhood is the perfect place to make what they think is the average coffee date a night to remember forever.

• Commonwealth Avenue – A luxury stay in a prime location will springboard you into a whirlwind of activity – museums, restaurants, shopping, sporting events. Or just order room service and take a stroll through a historic neighborhood. A great option for those who want to have a long weekend together.

Finding the right spot can take a lot of pressure off of a proposal. Hopefully, your jitters have melted away with the realization that all will go well when you choose one of the best places to propose in Boston.