Boston Engagement Photographer | Back Bay, the Seaport & Crane Beach

I am a Boston engagement photographer with a studio in the Seaport, and I photograph engagement sessions the way I photograph weddings: editorial, a little cinematic, and built around places that mean something to you. Below are four real sessions from this year, from a foggy Back Bay morning that ended in a Dorchester pub to a windy afternoon on Crane Beach, plus the locations, timing and planning advice I give every couple.

Quick facts

• Studio · 374 Congress St, Suite 305, Boston, MA 02210 (Seaport)
• Best months · late April through early June, and late September through October
• Magnolias on Commonwealth Ave · late April into early May
• Public Garden · no permit needed for a small handheld session
• Boston Public Library · formal shoots need a BPL events reservation, weekdays 8 to 9am
• Crane Beach · no portrait permit needed on the beach; Castle Hill on the Crane Estate needs a $300 Trustees permit
• Session length · about two hours, two locations
• Contact · 617.652.6799 · info@perlaimages.com

Real sessionsBest locationsPlanningFAQ

Real Boston engagement sessions

Meg and Nick · Back Bay and McGonagle’s, Dorchester

Fog so low the Prudential disappeared, a reflecting pool, long stone colonnades, then a short drive south to McGonagle’s, an Irish pub in Dorchester with green leather booths and a Guinness mural outside. See Meg and Nick’s Back Bay engagement photos.

Jimmy and Gabi · Krasi, Commonwealth Ave and a rooftop

They met at Krasi, a Greek restaurant in the Back Bay, so we started there in May, walked the magnolias on Commonwealth Avenue and finished on a rooftop at sunset. Later I photographed their wedding at Raffles Boston. See the full Jimmy and Gabi engagement gallery.

Evan and Juliana · Fan Pier and the Seaport

A spring session a short walk from my studio: the Fan Pier boardwalk, the garden path with the towers over the hedges, the harbor lawn, and golden hour backlight on the Harborwalk. See Evan and Juliana’s Seaport engagement photos.

Maeve and Michael · Crane Beach, Ipswich

About fifty minutes north of Boston, Crane Beach is dunes, grass and miles of pale sand, and on an overcast, windy afternoon it is as good as any beach in New England. Maeve and Michael brought a printed photo book to flip through in the dunes, and they were later married at the Red Barn at Outlook Farm in Maine. See Maeve and Michael’s Crane Beach engagement photos.

Brenna and Ben · Castle Hill on the Crane Estate, Ipswich

Up the hill from Crane Beach, Castle Hill is a 1920s Great House, formal garden rooms full of stone columns and roses, and a pergola looking out over the water. Brenna and Ben’s session was photographed under our Trustees portrait permit. See Brenna and Ben’s Crane Estate engagement photos and the Castle Hill permit rules.

The best places for engagement photos in Boston

The best Boston engagement photo locations are Back Bay and Commonwealth Avenue, the Seaport and Fan Pier, the Public Garden, Beacon Hill, the Boston Public Library, the North End, a rooftop at sunset, a restaurant or pub that is yours, and Crane Beach just north of the city.

Back Bay and Commonwealth Avenue

Brownstones, iron railings, magnolias in late April and May, and the Commonwealth Avenue mall running down the middle. The most classic Boston look there is. Back Bay engagement photos.

The Seaport and Fan Pier

Boardwalk over the harbor, the Financial District skyline across the water, a garden path and a big lawn, all within a few minutes’ walk. Seaport engagement photos.

The Public Garden

The lagoon bridge, willows and flower beds. Boston Parks does not require a permit for a small engagement session with handheld cameras.

Beacon Hill

Gas lamps, brick sidewalks, Acorn Street and quiet residential lanes. Go early, because Acorn Street draws a crowd by mid morning.

Boston Public Library, Copley Square

The courtyard and reading rooms are some of the most beautiful interiors in the city. Formal shoots need a reservation through the BPL events office and happen before opening, usually a weekday between 8 and 9am. See my Boston Public Library wedding photographer guide.

The North End and the waterfront

Narrow streets, bakeries, and the wharves toward the harbor. Great for a walking, eating, real-life session.

A rooftop at sunset

Jimmy and Gabi finished on top of a parking garage across the city. Rooftops give you the skyline with nobody in the way, and a garage is often the easiest one to get onto.

A restaurant or pub that is yours

Krasi, where Jimmy and Gabi met. McGonagle’s in Dorchester for Meg and Nick. Starting somewhere that matters is the fastest way to real photos. Ask the owner ahead of time and go before service.

Crane Beach and the North Shore

Dunes and open sand about fifty minutes north. Crane Beach and Castle Hill are owned by The Trustees. Portrait sessions on the beach do not need a permit; sessions at Castle Hill on the Crane Estate do, at $300 per 90 minute slot for Trustees members. See Crane Beach engagement photos and Crane Estate engagement photos at Castle Hill.

Back Bay, the Seaport or the beach?

• Back Bay · classic Boston. Brownstones, magnolias, stone and towers. Best in spring and fall, morning or late afternoon.
• The Seaport · modern Boston. Harbor, boardwalk and skyline. Best in the last two hours before sunset.
• A pub, restaurant or rooftop · your Boston. Warm light, real moments, and the photos you will frame.
• Crane Beach · a day out of the city. Dunes and open sand. Best on a soft, overcast day.

Most couples pick one classic and one personal. If you cannot decide, pick the place you would go on a Saturday anyway.

Why do an engagement session at all?

Because it is the rehearsal nobody tells you about. By the end of a session you know how I work, how I will ask you to move, and that you do not need to know what to do with your hands. On the wedding day that saves real time during portraits, and you look like yourselves in them. You also leave with photos for save the dates, your wedding website and the guest book, and with a gallery of the two of you that has nothing to do with a dress or a timeline.

Planning your Boston engagement session

When to book

Late April through early June and late September through October are the most requested weeks in Boston, with magnolias in the spring and gold trees in the fall. If you want your photos for save the dates, plan the session four to six months before the wedding.

Time of day

The last two hours before sunset give you warm light and a glowing skyline. Early morning gives you empty streets and soft, even light. Overcast and even foggy days are good days in this city, as Meg and Nick’s session shows. Rain is the only thing we reschedule for.

Two locations, one session

Every session on this page covered two or three spots: a classic look and something personal. Streets and a pub. A pier and a lawn. A restaurant and a rooftop. Plan on about two hours for two locations.

What to wear

Simple solids photograph best against Boston’s brick, stone and water: white, cream, black, navy, camel and denim. Bring a second outfit if we are changing locations, comfortable shoes for walking, and a layer for the wind on the water.

Permits

Public sidewalks, the Commonwealth Avenue mall and a small session in the Public Garden do not need one. The Boston Public Library, Castle Hill on the Crane Estate and any private business do. I will tell you what your locations need when we plan.

Plan your engagement session

Planning the wedding too? See how I work as a Boston wedding photographer, my guide to the best Boston wedding venues, or, if you want to keep it small, Boston elopements and Boston City Hall weddings.

Boston engagement photographer FAQ

How much does a Boston engagement photographer cost?

Engagement sessions are included in most of my full day wedding collections, and standalone sessions are available. See pricing or start your inquiry and I will send details for the date and locations you have in mind.

Where are the best places for engagement photos in Boston?

Back Bay and the Commonwealth Avenue mall, the Seaport and Fan Pier, the Public Garden, Beacon Hill, the Boston Public Library in Copley Square, the North End and a rooftop at sunset. Just outside the city, Crane Beach in Ipswich is the favorite beach location.

Do you need a permit for engagement photos in Boston?

Not for public sidewalks, the Commonwealth Avenue mall or a small handheld session in the Public Garden. The Boston Public Library requires a reservation for formal shoots, Castle Hill on the Crane Estate requires a Trustees photography permit (Crane Beach itself does not), and restaurants and shops need the owner’s permission.

When is the best time of year for engagement photos in Boston?

Late April through early June for magnolias and green trees, and late September through October for fall color. Overcast days work beautifully in the city.

How long does an engagement session take?

Plan on about two hours for two locations. Every session on this page covered two or three spots.

Where is your studio?

The Perla Images studio is at 374 Congress Street, Suite 305, in Boston’s Seaport, a short walk from Fan Pier Park.

Do you photograph engagement sessions outside Boston?

Yes. Crane Beach and the North Shore, Cape Cod, Newport and Nantucket are all regular locations.

Can you photograph a surprise proposal in Boston?

Yes. The Fan Pier boardwalk, the Public Garden bridge and Commonwealth Avenue in magnolia season are the most popular spots. We plan the timing and where I will wait out of sight together.

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