Coastal Portland Maine Engagement Session on a Sailboat

A Coastal Portland Maine Engagement Session

Tom and Alexandra celebrated their engagement with a dreamy sunset sail in Portland, Maine, beautifully photographed by Ellen Sargent Photography. The New England coast has always held a special place in their hearts after years of traveling together as nurses, and the water was the perfect setting to capture their love story.

How Tom and Alexandra Met

The couple first met while working as nurses in their hometown emergency room in Pennsylvania. After over a year of working together, Tom finally asked Alexandra out. What she thought was a casual group hangout turned out to be their first date—and even though she accidentally stood him up for their second date by oversleeping, their bond only grew stronger.

Together, they decided to pursue travel nursing, living and working in Massachusetts, Vermont, Maine, Washington, California, and Alaska. Their shared adventures across the country ultimately made New England feel like home.

A Surprise Sailboat Proposal

Tom planned an unforgettable proposal during a summer trip celebrating Alexandra’s birthday. After surprising her with a lobster-catching boat trip and skydiving, Tom organized a surprise sailing trip for their families around Nantucket.

While Alexandra and her mother sat laughing on the side of the sailboat as waves splashed them, Tom got down on one knee and proposed. Alexandra, who always thought Tom would never be able to surprise her, was completely shocked and overjoyed.

Why They Chose Portland for Their Engagement Photos

Since they got engaged on a sailboat, a sunset sail in Portland felt like the perfect way to celebrate their engagement session. They discovered Nautilus Sailing and spent the evening dressed up for the occasion, enjoying the stunning views of the Maine coast before heading to Four Street for a romantic dinner.

Looking Ahead to Married Life

Tom and Alexandra tied the knot on September 1, 2024, at Willowdale Estate in Topsfield, Massachusetts. Their wedding was a celebration filled with meaningful details, farm-to-table food, live music, and plenty of dancing—complete with a first dance they had practiced for months.

Photographer: Ellen Sargent Photography

Plan Your Own Portland, Maine Engagement Session

A Portland, Maine engagement session offers a mix of coastal charm, nautical beauty, and romantic New England vibes. Whether you choose a sunset sail like Tom and Alexandra or stroll through the city’s cobblestone streets, there are endless ways to make your session feel authentic to your story.

For more inspiration for Maine weddings and engagements, visit Evergreen Weddings Magazine to buy the latest issue!

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