Outlook Hill proposal

A Unforgettable Governors Island Proposal at Collective Retreats | NYC Proposal Photographer

As a NYC proposal photographer, I’ve captured hundreds (a few thousand) proposals across every corner of the city—but few spots rival the magic of Governors Island at sunset, where there are no crowds and no unobstructed views. For Dhruv’s surprise proposal at Collective Retreats, we planned every detail carefully to make sure this early October moment unfolded flawlessly against one of the most scenic backdrops in New York City.

Planning the Perfect Governors Island Proposal

Governors Island is unlike any other proposal location in NYC—it’s peaceful, scenic, and feels like a world away from the city, even though it’s just an 8-minute ferry ride from Lower Manhattan. Dhruv and I coordinated the timing down to the minute. They’d spend the day on the island at the retreat, and I would arrive to their private cabin just before they’d come back for dinner.

We chose Collective Retreats, the island’s beautiful glamping-style resort, for its private, relaxed setting and incredible views of the Statue of Liberty. After a quick walkthrough earlier in the week, we decided to capture the big moment at Outlook Hill, one of the island’s highest points with a 360° panoramic view of Manhattan, New Jersey, New York Harbor, and Lady Liberty herself.

Why Governors Island is a Hidden Gem for Proposals

For couples looking for something unique yet quintessentially New York, Governors Island offers it all—privacy, skyline views, and a touch of adventure. The ferry ride adds to the excitement, the lighting is incredible near golden hour, and there are endless opportunities for stunning photographs.

Whether you’re planning a sunset proposal at Collective Retreats, a romantic picnic by the harbor, or a panoramic moment atop Outlook Hill, this destination feels like your own private slice of New York City.

Jonathan Heisler Photography is comprised of  Professional New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings. 

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A Perfect NYC Proposal Location: Outlook Hill, Governors Island

Sunset Surprise Proposal on Governors Island’s Outlook Hill with the Manhattan Skyline

Governors Island is one of the city’s hidden gems—just a short ferry ride from Lower Manhattan, yet it feels worlds away. Outlook Hill, the island’s highest point, offers 360-degree views of the harbor, the Statue of Liberty, and of course, the Manhattan skyline. For Sid, it was the ideal setting to propose: romantic, peaceful, and visually stunning.

As a seasoned NYC proposal photographer, I always scout locations in advance and plan around lighting conditions and crowds. For this proposal, the timing was everything. Sid planned a whole day on the island with massages at the spa and a fantastic afternoon adventure ending atop Outlook Hill with the Manhattan skyline behind them.

Why Governors Island is Ideal for NYC Proposals

Unlike many popular proposal spots in NYC, Governors Island offers a calm, crowd-free environment—especially during sunset hours. Its unique mix of natural beauty and sweeping city views makes it perfect for couples looking for a peaceful, scenic proposal experience.

Whether you're planning to propose on Governors Island or another iconic NYC location, having a professional proposal photographer ensures the moment is preserved beautifully and discreetly. From candid emotion to scenic portraits, every element of Sid’s proposal came together flawlessly—and I was honored to be there to document it.

Planning a Governors Island Proposal?

If you're considering popping the question on Governors Island, especially at Outlook Hill, let’s talk! I’ll help you plan the timing, navigate the best light, and capture your once-in-a-lifetime moment against one of the most stunning views in New York City.

Jonathan Heisler Photography is comprised of Professional New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings.

BOOK NOW!