A Romantic Annapolis Helicopter Proposal at Whitehall

Annapolis Proposals, Behind the Scenes


Scott called in early August to discuss the idea of a helicopter proposal at Whitehall!  He wanted to take his girlfriend on a helicopter ride tour of Annapolis, and needed a place to land that was close by and would provide him the perfect setting to propose.

Needless to say, I loved the idea!  A helicopter proposal is such a natural extension of Whitehall’s offerings as a premiere waterfront wedding venue. With such a huge waterfront lawn, you could land 20 helicopters!


Behind the Scenes

After several phone calls with Scott and Sentimental Fools Planning, he settled on a plan and enlisted some amazing vendors to help execute it – keeping Tiffany in the dark about all of it! He said they usually don’t plan anything when they travel, so keeping this whole adventure spontaneous was key to not arousing her suspicions!

Seth from Monumental Helicopters came by to scout the location, and agreed that the lawn was the ideal place to land. We discussed the possibilities of a groom making an entrance on a helicopter for their wedding or an exit after a ceremony! So many possibilities with 135 acres and 1 ½ miles of shoreline – Whitehall certainly has the space for it!

The Sentimental Fools did all the planning, WhiteGlove Rentals had the perfect “props” for the occasion, photography was provided by 1783 Photography, video captured by Donna J Daughters, and plants were by B Willow.


The Proposal

Scott and Tiffany arrived at Whitehall on September 22 (one week later than originally planned, thanks to Hurricane Florence!), under the premise was that they were participating in a photo shoot for Monumental Helicopter and Whitehall to promote both of our businesses. The helicopter arrived, and they went on their 15 minute tour of Annapolis by air, returning to Whitehall.

As Scott and Tiffany walked up to the mansion, the photographers were snapping and filming away to capture each moment.  When they reached the front porch, the doors opened, and the scene was set!

Scott reached for the ring (which he had Fed-Ex’d to me the week before so he wouldn’t have to have it in the big box in his pocket!), got down on one knee and proposed!!


She said yes!


After lots of hugs, kisses, and many photographs, the happy couple went onto the porch to enjoy the sunset views, some chocolate covered strawberries and sparkling cider.

Scott had arranged for family and friends to provide YouTube congratulations. They laughed and cried with all of their well-wishers and left Whitehall to have a lovely dinner and spend the weekend in Annapolis.

We hope they return to have their wedding at Whitehall next year! Wouldn’t that be the perfect circle! And to land in the helicopter before the ceremony! Wow!

Planning a helicopter proposal of your own?  We’d love to help!  Click here to contact us.

Photo of Whitehall

Couple walking towards Whitehall Mansion

The proposal location

Thanks so much to all these lovely vendors!

Venue: Whitehall

Helicopter: Monumental Helicopters

Planning: The Sentimental Fools

Photography: 1783 Photography

Video/Photography: Donna J. Daughters

Rentals: White Glove Rentals

Plant Rentals: B.Willow

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