The Best Wedding Planners in the U.S., Canada, and Overseas

The Best Wedding Planners in the U.S., Canada, and Overseas


Alicia Caldecott’s A Day in May Event Planning & Design, founded in 2007, creates weddings along the shores of the Great Lakes and destinations worldwide. From a flower-filled yacht for an eloping couple to a cherry-themed wedding at a private residence on the coast of Michigan (think rustic crates filled with cherries and berries, stationery with sweet cherry illustrations, and small bowls of cherries as place settings), A Day in May brings serious charm to each event.

Alison and Bryan: Based in Detroit, Michigan, and Los Angeles, California

Photo: Courtesy of Alison and Bryan

Based in Detroit and L.A., and traveling wherever their clients take them, Alison and Bryan are a husband-and-wife team with more than 175 weddings under their belts. For the great-great-grandson of Henry Ford, they created a giant suspended floral installation to mimic the flowers that grow wild in Sperlonga, a favorite spot for the couple. For a bride from Mexico and a groom from France, they produced an event in a castle in Brittany, France, accommodating three different cultures and languages in the process. But their signature is blending these globally inspired details with the laid-back vibe of the West Coast and the charm and comfort of the Midwest.

Estera Events: Based in Chicago, Illinois

Offering services from month of coordination to entire wedding weekend coordination, one of Estera Events’ favorite challenges is transforming private homes into custom wedding venues. In Chicago alone, the team has converted the Art Institute of Chicago into a romantic alfresco wedding, created a rustic-inspired wedding at the Chicago Cultural Center, and designed a whimsical golden-themed wedding at the Museum of Contemporary Art Chicago.

Lola Event Productions: Based in Chicago, Illinois

wedding venues

Photo: Courtesy of Cristina G Photography



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Kevin Harson

I am an editor for VanityFair Fashion, focusing on business and entrepreneurship. I love uncovering emerging trends and crafting stories that inspire and inform readers about innovative ventures and industry insights.

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