first steps on an exciting journey

Planning your engagement session in Boston? Whether you're dreaming of city skyline views, charming brownstones, or a scenic waterfront backdrop, a little preparation can go a long way in making your session fun, relaxed, and full of incredible photos. Here are some easy tips to help you make the most of it!

#1 Start with a Vision: What’s the Vibe of Your Boston Engagement Session?

Before we plan locations or outfits, take a few minutes to daydream. What do you want your engagement session to feel like? Do you love bold, vibrant cityscapes or something softer and more romantic?

A great way to get inspired is by checking out engagement photos online. Browse my portfolio of engagement photography here, scroll through Pinterest, or search for "Boston engagement session inspiration." Save the images that speak to you and share them with your photographer—this helps us craft a session that feels authentically you.

#2 ask your photographer for ideas

Your photographer isn’t just there to take pictures, we’re also a great resource when it comes to planning your engagement session! With 20 years of experience, I’ve discovered countless hidden gems and scenic spots all over Boston that make for incredible backdrops. Once you have a general idea of the style and vibe you want, let’s talk! I can suggest unique locations that fit your vision, whether it’s a romantic cityscape, a cozy café, or a spot with personal meaning to you both. I have written another resource article on my favorite Boston Engagement session locations. Please give it a read and see if it sparks any ideas!

#3 select a location meaningful to both of you

Often times I am asked by clients about how to choose a location for their engagement session. Although it can be challenging, I ask the following questions:

Where is the location where you first met?

Where is the location where you had your first date?

Where is a place you like to spend time together?

Is there a spot that you feel compliments your relationship?

More often than not, answering these questions will provide you with the inspiration you need to find the right spot for your engagement session.

#4 Choose the right season

If you're planning an outdoor session, the time of year matters! Spring and fall are the most popular for good reason—the weather is comfortable, and the city is bursting with either fresh greenery or stunning fall colors.

That said, don't rule out summer or winter! A snowy Boston session can be incredibly magical, and summer offers warm golden light and vibrant city energy. No matter the season, we’ll find the perfect backdrop.

#5 consider Scheduling Your Session in the Morning

I would highly recommend scheduling your engagement session in the early morning if possible. This will result in the best light and fewer crowds especially if you want photos in busy spots like the Public Garden or Seaport. The soft morning light is also very flattering, and you won’t have to dodge tourists or rush-hour foot traffic.

Not a morning person? Sunset works too, but keep in mind that popular locations may be much busier.

#6 Research Your Location

Boston has some iconic engagement spots, but many require permits or reservations such as the Boston Public Library or City Hall. Some places also have rules about what you can wear, when you can be there, and whether you can bring props. The last thing you want is a surprise on the day of your session! Make sure to check ahead or chat with your photographer. We can help you navigate the logistics and find the perfect hassle free spot.

#7 make it a date!

The best way to get natural and candid photos? Treat your session like a fun date! Think about things you love doing together. Activities such as grabbing coffee, taking a stroll, or sharing a drink at your favorite bar are excellent ideas! When you’re focused on each other instead of the camera, the moments become real, and that’s what makes the photos so special.

#8 What to wear

Deciding what to wear doesn’t have to be stressful! Here are some simple tips:

• Be comfortable. If you feel good in what you're wearing, it’ll show in the photos. Be sure to also consider the time of year and forecast.
• Stick to solid colors. Bold patterns can be distracting. Solid colors, neutrals, and classic tones work best.
• Coordinate, don’t match. Choose colors that complement each other (all warm tones or all cool tones) rather than wearing identical outfits.
• Put a little thought into it. Take a few minutes to plan so your outfits feel intentional, not last-minute.

#9 Bring a second outfit

A quick outfit change is an easy way to add variety to your photos! If we’re shooting in multiple locations, consider one look that’s casual and fun, and another that’s a bit more elevated and stylish. We’ll plan a quick stop somewhere for you to change, and just like that—you get two totally different vibes in one session!

#10 Schedule your makeup trail for the same day as your engagement session 

If you’re planning to hire a professional hair and makeup artist for your wedding, chances are they offer a trial session before the big day. A great way to make the most of it is to schedule your trial for the same day as your engagement session. This way, you get to see how your makeup looks on camera, make sure you love the artist’s work, and feel extra confident knowing you’ll look amazing in your engagement photos. Additionally, it’s a great test run for the wedding day. It’s a simple way to elevate your session while giving you peace of mind for your wedding day look.

#11 Always have a back up plan

Even the best-laid plans can hit a snag. Unexpected weather, last-minute location closures, or something totally unplanned can easily happen. That’s why having a backup plan is always a good idea!

• Check the forecast the night before and the morning of your session.
• Have a backup date schedule in advance just in case.
• Decide early if you want to reschedule and let your photographer know.

If the weather isn’t ideal but still manageable, we still make it work, think cozy raincoat vibes or a fun umbrella moment! A little flexibility goes a long way in making sure you still get amazing photos.

#12 Be on Time

I know this one sounds obvious, but it’s super important. Many locations require specific time slots and if you’re late, that time is just lost. It can’t be pushed back. Plus, the sun is always moving, and being on time helps us get the best lighting and shots. Plan to arrive at least 15 minutes early, and check the parking situation beforehand so you're not scrambling at the last second.

#13 grab a bite before hand

Here is another very simple but often unknown tip. Approximately an hour before the start of your session I would high recommend that you two have either a decent sized snack or a small meal. This is will give you a decent boost of energy as well as help stabilize your mood. I often find that if the thought of being in front of the camera gives you a bit of anxiety, eating will help with that too.

#14 trust your photographer

I love it when a couple comes to me with a couple of specific ideas about their engagement session because it tells me that they are extremely interested in the idea of awesome portraits and want them to be a successful as possible. One aspect of that to be careful with is being too specifically in love with a certain idea, pose, or anything else. Remember your photographer has been creating portraits for years and if they have a suggestion about how to capture a certain idea, even if it seems counterintuitive, you should listen. They are invested in your happiness and success and you will be thankful you did.

FINAL THOUGHTS

Your engagement session should be fun, stress-free, and totally about you. A little planning goes a long way, and when you’re relaxed and enjoying the experience, the photos will capture that effortlessly. I can’t wait to help you create something amazing! Let’s chat and start planning your perfect Boston engagement session.