Historic Hotels of America Announces 2026 Top 25 Hotels for Romantic Proposals
HOSPITALITY
Casa Monica Resort & Spa (1888) St. Augustine, Florida. Credit: Casa Monica Resort & Spa and Historic Hotels of America.
Proposals have become more elaborate and thoughtfully planned in recent years, with couples seeking locations that feel meaningful and memorable. Historic Hotels of America, the official program of the National Trust for Historic Preservation, has released its 2026 Top 25 Historic Hotels for a Romantic Proposal list.
The list highlights properties that offer more than scenic beauty. These hotels combine architectural significance, rich histories, and a sense of place that adds depth to one of life's most important moments. In 2026, couples are increasingly drawn to settings with authentic character and a story to tell.
The "Legacy Backdrop" Advantage
To be considered for the list, a hotel must meet rigorous criteria: it must be at least 50 years old and designated as a National Historic Landmark or listed in the National Register of Historic Places. This requirement ensures that the proposal takes place in a setting of "historic authenticity," where a couple's personal history becomes woven into the building's own timeline.
Key highlights from the 2026 list include:
InterContinental New York Barclay (1926): For the "Cinematic NYC" moment, the Harold S. Vanderbilt Penthouse offers private views of the Chrysler Building, perfect for a golden hour reveal.
Boar's Head Resort (1834): In Charlottesville, the "Winter Wander Trail of Lights" provides a "Tunnel of Lights" specifically designed for guests to pause and capture the big moment.
Island House Hotel (1852): On Mackinac Island, the iconic front porch offers an unhurried atmosphere where the only sounds are the gentle clip-clop of passing horses.
Beyond the View
What sets these properties apart in 2026 is their ability to Operationalize the Surprise. At the Woolverton Inn (1792) in New Jersey, the team specializes in "staging" locations across its pastoral farmland, coordinating everything from ring deliveries on breakfast trays to candlelit setups in a restored stone barn.
Similarly, The Oaks Waterfront Hotel (1800s) in Maryland offers a private sunset cruise aboard a 40-foot Hinckley yacht, Overcomer, providing an "Old-World" sense of luxury and privacy that standard modern resorts cannot replicate.
When History Becomes Part of the Experience
In luxury hospitality, the most distinctive properties aren't necessarily those with the latest amenities, they're the ones with enduring stories and a sense of permanence. Historic Hotels of America's proposal list reflects this shift by highlighting venues where couples can connect to something larger than the moment itself.
For the travel and hospitality industry, the value proposition is clear: authentic history creates emotional resonance that new construction struggles to replicate. These hotels don't just offer beautiful settings, they offer continuity. Couples who get engaged at a historic property often return for anniversaries, creating a relationship with the place that spans decades.
This kind of loyalty is rare in an industry shaped by fleeting trends and viral destinations. Properties with genuine heritage can anchor themselves in guests' lives in ways that transcend a single visit. When a hotel becomes part of a couple's story, marking proposals, anniversaries, and milestones over the years, it builds a connection that's difficult for competitors to disrupt. Brands that cultivate this long-term relationship, rather than chasing novelty, position themselves as irreplaceable parts of their guests' most important memories.