NYC Sunset Boat Cruise

A swoon-worthy proposal story

Propose aboard as the two of you cruise into the sunset.

The scene is set: the two of you are lounging on the deck of the Holly Ann, sipping on a crisp glass of Chenin Blanc as she cruises through Long Island Sound.

As the sun sinks toward the horizon, you seize the moment and get down on one knee. Your partner gasps with surprise before flinging their arms around you with a ‘yes!’

Our crew pops the champagne so you can toast to the future, while the captain sets course for the dockside restaurant where your friends and family are waiting to celebrate with you.

So let's make it count.

Your spouse will tell the story of how you proposed for years to come.

engagement at sea

Our Long Island boat charter is the perfect place for an engagement that’s both intimate and unforgettable. 

Aboard the Holly Ann, we’ll take care of the little details, from keeping the Dom Perignon on ice to playing your song right before the big moment. 

We can arrange:
  • A local photographer or videographer to capture the heightened emotions during and after your proposal
  • Fresh, seasonal flowers to set the mood
  • Gourmet food, prepared by a Hamptons caterer—think charcuterie boards, chocolate-dipped strawberries, or crudité platters
  • Your playlist of choice, from departure to docking
  • Dinner reservations at an water-view restaurant, whether you want to celebrate just the two of you, or gather your friends and family to raise a glass to your new chapter
  • Whatever you want to drink, from the fixings for your favorite cocktail to a nice bottle of rosé—not to mention champagne

A one-of-a-kind

Ready to set sail on the Holly Ann for an intimate proposal they’ll never forget?

INQUIRE ABOUT AN ENGAGEMENT CRUISE