Act fast: “Book your photographer as soon as possible so that you can get the person you want for the date you have selected,” says Kelley DeBettencourt. “Especially for Saturdays in September!”

Don’t scrimp: “Photography is probably the most important investment in your wedding day. But while budget plays a huge role in decision making, you should not pick your photographer based on price only,” says Larisa Stinga. This is also valid advice for the photographers, she notes. Rather than accepting every paying client, a photographer needs to ensure a good fit.

Think local: The Island is a particular place with specific travel considerations, says Tim Correira. “You should hire someone who knows what it takes to get there, which is especially important if the boats are cancelled or there’s a possibility of a hurricane. If you are importing a photographer from off-Island, have them arrive a few days in advance.”

Hire a second photographer if you can afford it: “Having a second shooter is a great way to allow your photographer to be in two places at once, and it’s a good idea if you have a larger wedding,” says Stinga. “But the main advantage is that a second shooter allows your main photographer to be more creative, to seek images that they wouldn’t have time to capture.”
Other photographers agree: if both parties are getting ready at the same location or your wedding is less than fifty people, you can probably go without a second shooter, says Correira. Otherwise, it’s worth the additional (moderate) expense.

Spring for the engagement session: An engagement session prior to the wedding is a great way “to learn more about each other, get comfortable and familiar with my style and the flow of the session, and see if they like the images and which ones are their favorite,” says Mila Lowe.

Use your hair and makeup trial to your full benefit: Stinga takes the engagement session/photo trial one step further. “I encourage my brides to use their hair and makeup trial for their engagement session,” she says. “That way they can see what it will look like in the pictures and also feel fabulous.”

Create a shot list – within reason: Photographers want you to be upfront with them about your expectations, but sometimes a general conversation can be more productive than a list of 100 specific shots you want them to capture. “I discourage a lengthy list because then I’m running around trying to orchestrate things and I don’t have a chance to see what’s happening,” says Jocelyn Filley. “The little unpredictable moments of the day are the ones that really tell the story, so I want to make sure I always have time for those.”

Cater your requests to the photographer: Clients sometimes send inspiration photos that would be impossible to replicate on the Vineyard due to vastly different conditions, such as portraits taken in the middle of the desert, says Correira. Instead, it’s more helpful to show examples from your photographer’s own portfolio that he or she can easily recreate, he notes. “My favorite is a bride will make a PDF of photos I’ve taken and say, ‘These are ten photos that you’ve taken recently. We love these.’”

Don’t forget about film: Many photographers have transitioned to digital-only photography, which allows them to shoot more photos at a lower cost. But for lovers of film and its idiosyncrasies, there’s no comparison. “There is so much I love about film. It’s the thing that excites me most about photography,” says Filley. “It keeps me truly present in the moment…and the results are unparalleled.”

Consider the timing for portraits: Every photographer has a favorite time of day to shoot portraits. Lowe prefers “the last hour or two hours before sunset and the first hour or two hours after sunrise, known as ‘the golden hour.’” Stinga says “‘the secret sauce’ to her cinematic-style images is blue light”– a soft, even light that lasts about ten to fifteen minutes after the sun goes down. You probably like your chosen photographer because of the way they work with light. Make sure to discuss with them their ideal time to take portraits and plan accordingly.

Think about backgrounds: Not sure where to take your portraits? Lowe says consider what you like. “Are you beach lovers? Do you prefer to go for a hike and be in the woods? Do you want a classic location that you can tell is Martha’s Vineyard, like a lighthouse?” When in doubt, you can’t go wrong with a location that offers visual diversity. “I like wooded areas that go up near the beach,” says Correira. “A beach that’s just a beach is great, but it’s one note.”

Stick close to your ceremony: While your portrait background is important, you don’t want to spend your whole day in the car. “Every minute is precious. It’s going to fly by,” says Correira. “Engagement photos, that’s the time to drive around, go to the [Gay Head] cliffs, try out different locations,” he says, noting that it’s an hour and a half round trip from Edgartown to Aquinnah.

Don’t forget about crowds: If you’re camera shy, you may want to avoid busy locations and times of day for portraits, says Stinga. “You want to make sure you can have intimacy to open up, to be vulnerable, and to feel relaxed. Some people will not show emotion in public and a crowded place will definitely kill the vibes.”