Jaimie & Ari at Winslow Estate

When it comes to waterfront wedding venues on Cape Cod, we try not to play favorites. But with a Mediterranean-style estate set on a private spit of land that juts out into Pleasant Bay, it isn’t hard to understand why the Winslow Estate is a perennial favorite among our couples.

We also make every effort not to pick a favorite season but, rain or shine, fall weddings on Cape Cod are simply spectacular. Jaimie and Ari’s September wedding took place on one such rainy day, which somehow managed to add to the glamour of the sophisticated wedding the brides had planned.

With 17 rooms, including nine bedrooms, Winslow Estate is a great option for couples planning a destination wedding on Cape Cod. The brides were able to enjoy an entire weekend at the historic home celebrating with their closest friends.

After getting ready in separate wings of mansion – no peeking! – the brides came together for a dramatic first look, after which they sat for a regal portrait with their wedding party.

With raindrops plinking on the enormous white tent overhead, Ari and Jaimie exchanged their vows as friends and family looked on.

The ceremony included lots of love and lots of laughs.

Minutes after becoming missus and missus, Jaimie and Ari celebrated the big moment as their guests gave them a rousing round of applause. Then came a little private time to catch their breath and capture the moment with photographer Carly Edmonds of Elarie Photography.

As dusk turned into evening, the brides made their way back into the tent for heartfelt speeches and an elegant dinner. The hearty laughs and tears of joy captured in the photos make it clear that the speeches were absolutely spot on.

As dinner was nearing its completion, dancing commenced, and it didn’t take long for the rhythm section and horns of the band Soho to get everyone up on the dance floor.