Historic Hotels of America®, an official program of the National Trust for Historic Preservation, is pleased to announce its Top 25 Historic Hotels of America Most Romantic Hotels List. At any time of the year, historic hotels are the perfect place to celebrate special occasions that create lifelong memories and are the ideal location for a romantic proposal. Couples can enjoy quality time together, or celebrate with their friends and families, to mark special milestones, including romantic getaways, engagements, weddings, honeymoons, vow renewals, and more.

The historic hotels selected for The 2024 Top 25 Historic Hotels of America Most Romantic Hotels List all radiate romance, and they offer diverse experiences for their guests, from glamorous city center icons and beachfront Grande Dames to charming mountaintop escapes and pastoral paradises. Regardless, all of these historic hotels offer special romance, wedding, or engagement packages for couples looking to celebrate their love, whether it is an intimate getaway or a celebration with friends and family. For those planning to get engaged, these hotels offer creative planning services to craft the perfect proposal. Planning a special moment in 2024? The 25 destinations described here, and many more historic hotels inducted into Historic Hotels of America, provide beautiful venues and breathtaking views to set the stage for historic love.

Woolverton Inn (1792)
Stockton, New Jersey
Secluded in the farmlands of Stockton, New Jersey, sits the charming and historic Woolverton Inn. The cozy Inn rests high above the Delaware River and is situated on 300 acres of rolling farmland and surrounded by forests. Established in 1792, the Inn is a romantic escape into the pastoral countryside, and allows its guests to unwind, making it a perfect place to propose. The Inn recommends its “Perfect Proposal” package, which includes staging support from an event coordinator and candles, flowers, and Champagne. To preserve its tranquil atmosphere, the Inn has an “only children 12 and up” policy, and there are no televisions in the guestrooms. From proposals to weddings, honeymoons, and milestone anniversaries, guests return year after year to celebrate their relationships. One couple noted in the guestbook, “We now call the Woolverton Inn our place. The entire experience takes us away each time we hide away here and we fall deeper in love with each other...” Woolverton Inn was inducted into Historic Hotels of America in 2023.

Island House Hotel (1852)
Mackinac Island, Michigan
Open May through October, Island House Hotel on Mackinac Island provides guests with the island’s famous historic charm and gorgeous waterfront views. This historic estate has greeted guests from the mainland since 1852, and for over 150 years, couples have said “I will,” “I do,” and “I still do” on its grounds. Guests are encouraged to pop the big question on either the terrace or the porch of the historic Island House Hotel, with a spectacular view of boats gliding into the harbor, or carefree bicyclists wheeling and horse-drawn buggies passing on the street below. The Hotel’s timeless elegance brings lovebirds back to Island House Hotel year after year to celebrate weddings, reunions, anniversaries, and vow renewals, and to pass these traditions on for generations. Couples staying at Island House Hotel enjoy romantic, candlelit dining in the elegant 1852 Grill Room, with entertainment provided by a talented pianist and sunset hues reflecting on the water. The Hotel offers guests private carriage rides for two, picnic lunches, and stargazing by the campfires. One couple interviewed recently by the hotel has visited the Island House Hotel 36 times since 1995 and are celebrating their 50th anniversary there in 2024—bringing their two children, their spouses, and eight grandchildren to experience the island’s enchantment. The Island House Hotel was inducted into Historic Hotels of America in 2005.

Omni La Mansion del Rio (1852)
San Antonio, Texas
Blending Spanish Colonial architecture with European style, the Omni La Mansion del Rio surrounds guests with the romance, grace, and charm of a grand hacienda. Located on the historic River Walk, or Paseo del Rio, along the banks of the San Antonio River, the hotel is a romantic, tranquil getaway. Omni La Mansion del Rio’s courtyard transports guests away from the hustle and bustle of downtown San Antonio into an intimate and romantic garden setting. It is a popular place for couples to get engaged, get married, or celebrate a special anniversary. If you choose to enhance the engagement experience, the concierge can help by including a signature candlelight set-up, with both pillar and votive candles, which truly complement the natural beauty of this elegant outdoor space. The AAA Four Diamond Ostra restaurant is not only known for its romantic and relaxing atmosphere, but also for its unique dining experience. Built on three levels that descend down to San Antonio’s festive River Walk, Ostra offers a romantic atmosphere, featuring graceful palms, flowing waters, and scenic views. Sitting under graceful palms and watching the flow of the river and the people strolling by, diners are carried away to another place and time, making the perfect setting for an intimate celebratory dinner. Omni La Mansion del Rio was inducted into Historic Hotels of America in 2010.

The Inn at Leola Village, Est. 1867 (1867)
Leola, Pennsylvania
Discover The Inn at Leola Village, a pastoral retreat tucked away in the countryside of Lancaster County, Pennsylvania. Once an Amish tobacco farm, the Inn was saved from demolition and transformed into a warm, inviting country getaway. The Inn’s distinctive rooms and suites are located within restored antique barns and farmhouses. The carefully preserved cottages boast original woodwork and reflect its Amish heritage. Each suite is individually decorated with period and reproduction furnishings, creating a haven of comfort and luxury. Accommodation options include rooms with oversized whirlpool tubs and soothing fireplaces, along with fine linens and special amenities. Guests can enjoy the Inn’s fragrant herb and perennial gardens, the full-service wellness Spa, where couples’ massages and specialized services focus on personal relaxation, and the rustic Italian-inspired cuisine available at Osteria Avanti. The Inn at Leola Village, Est. 1867 was inducted into Historic Hotels of America in 2001.

Mohonk Mountain House (1869)
New Paltz, New York
Mohonk Mountain House, designated a National Historic Landmark by the U.S. Secretary of the Interior, is perched above a glacial lake among the Shawangunk Mountains in the Hudson Valley, offering breathtaking and unparalleled views. This historic hotel offers tailored engagement packages to enhance the special occasion, such as a private carriage ride overlooking scenic landscapes, exclusive rooftop dining with a stunning five-state view, or a “Will you marry me?” banner dropped from across the lake. Whether the proposal is made within a cozy Victorian-inspired guestroom by a fireplace, or at an iconic outdoor location like Sky Top Tower, the natural beauty of Mohonk Mountain House’s surroundings enhances the occasion and makes it unforgettable. The destination is also perfect for weddings and vow renewals. One couple visited recently to renew their vows on their 20th wedding anniversary with an intimate ceremony at Sky Top Tower, complete with Champagne and music. Family owned for over 150 years, Mohonk Mountain House was inducted into Historic Hotels of America in 1991.

St. James Hotel MN (1875)
Red Wing, Minnesota
The St. James Hotel MN in Red Wing, Minnesota, is a haven for romance, offering guests Midwestern luxury in an authentic historic setting, surrounded by stunning natural beauty. Step inside and be transported to a bygone era. The hotel’s intricate woodwork, grand staircase, and cozy fireplace sets the scene for an intimate escape. Couples can enjoy breathtaking views of the Mississippi River while taking a romantic stroll along the scenic riverfront or enjoy the views from their guestroom. Located in downtown Red Wing, guests can explore the charming town, attend a performance at the Sheldon Theatre, or take a scenic hike up He Mni Can-Barn Bluff. The Hotel offers several proposal packages for popping the question in the historic library, port wine cellar, or restaurant. Inducted into Historic Hotels of America in 1994, the Italianate-style building is listed in the National Register of Historic Places.

Jekyll Island Club Resort (1887)
Jekyll Island, Georgia
With sweeping Spanish moss and hundred-year-old live oaks, Jekyll Island is one of the most romantic spots in Georgia. Jekyll Island Club Resort, built in the Queen Anne style in 1887, offers guests Southern hospitality in a setting that evokes Victorian romance. The fairytale feel of Jekyll Island Club Resort makes this historic resort a romantic haven, and the perfect place to propose, get married, or enjoy a romantic getaway. For proposals, the Resort recommends staging it at sunset at the top of the turret. The turret is the second tallest structure on Jekyll Island, and the tallest structure in the Jekyll Island Historic District. The manicured grounds of Crane Cottage are appealing to any passerby, but also offer couples the perfect romantic garden to sneak away to on the grounds of Jekyll Island Club Resort. The sunken garden features a lush lawn, a sweeping ivy-covered trellis, a running fountain, and an abundance of flowers. A private candlelit dinner experience can be arranged in advance, and special delivery of the ring can be arranged with the catering team. Whether you want a special toast or an extra sweet dessert moment, the Resort can help arrange a special moment with catering, photography, and privacy in the perfect spot. The Jekyll Island Club Resort was inducted into Historic Hotels of America in 1994.

Wentworth Mansion (1886)
Charleston, South Carolina
The historic Wentworth Mansion is in the heart of historic downtown Charleston, South Carolina, where guests are steps away from some of the most romantic experiences in the South, including the Charleston Battery, Rainbow Row, and private carriage rides for two. The hotel was originally a grand family home, built in 1886. With its Italian crystal chandeliers, hand-carved marble fireplaces, and Tiffany –stained-glass, the Mansion offers guests history, grandeur, and romance. One heartwarming story that encapsulates the romance of Wentworth Mansion involves a couple visiting Charleston for the first time. The hospitality team worked with the guest to orchestrate a sunset proposal on the cupola, overlooking the Holy City. The romantic proposal was enhanced with Champagne, candlelight, roses, and a photographer to capture the unforgettable moment for the couple to look back on for years to come. The dedicated staff at Wentworth Mansion takes pride in curating enchanting and intimate experiences, from arranging carriage rides to organizing candlelit dinners in the hotel’s AAA Four Diamond restaurant, Circa 1886. Intimate and welcoming, Wentworth Mansion was inducted into Historic Hotels of America in 2003.

Union League Club of Chicago (1886)
Chicago, Illinois
A downtown Georgian Revival-style landmark, the historic Union League Club of Chicago is a stately and sophisticated social club and hotel dating back to 1886. Love is always in the air at this historic venue, and its dedicated team of wedding and event professionals pride themselves on the attention to detail and collaboration required to bring each couple’s wedding vision to life. With a host of event spaces from intimate to grand, engagements, elopements, and wedding parties love the warmth and charm that this private club offers their guests, and the overnight accommodations and multiple on-premises dining options ensure an unforgettable experience. One former bride said of the location, “If you want a place that is a cut above the rest, provides more personalized attention than a hotel and really pride themselves on customer service, Union League Club is the place for your wedding day.” The setting for countless private member events and more than 35 weddings per year, members and their guests receive food and beverage service that meets the highest standards of catering, within the impeccable atmosphere for which the Club is known. Whether planning a wedding for 400 guests, 50, or a rendezvous for two, the Union League Club offers a variety of outstanding rooms to meet a member’s needs, all of which are carefully appointed and include pieces from the Club’s extensive art collection. The Union League Club of Chicago was inducted into Historic Hotels of America in 2021.

Casa Monica Resort & Spa (1888)
St. Augustine, Florida
The ambiance of Casa Monica Resort & Spa in St. Augustine, Florida, exquisitely joins together the hotel’s historic roots with a bohemian aesthetic to being open, curious, and adventurous. Guests can discover the Old-World romanticism of St. Augustine on a lover’s getaway to the Casa Monica Resort & Spa, centrally located in one of North America’s most historic cities. While visiting the Casa Monica Resort & Spa, guests can discover curated luxury experiences, including couples’ treatments at the Poseidon Spa, shaded poolside cabanas, and carriage rides through St. Augustine’s charming streets. Guests can slow down and spend time together exploring both local and international art at the Grand Bohemian Gallery. For a unique date night, guests can reserve their spot at the Magic Hideaway—an intimate magic show experience featuring interactive mind-bending illusions and tempting bites and libations from Cordova. The cobblestone streets surrounding the Resort will lead couples to the legendary St. Augustine Historic District, where guests can explore the city’s landmarks, museums, dining, bars, and shopping. Or guests can stroll along the pristine coquina shores of St. Augustine’s beaches. After exploring, guests can dine at the resort’s Cordova coastal chophouse, where guests can reserve a private dining experience in the eclectic and intimate Wine Room—the perfect spot for a surprise proposal. Guests can enjoy luxurious accommodations in the Anastasia Suite, complete with a spiral staircase and stunning views of the Lightner Museum, or the Kessler Suite, a four-story tower penthouse with panoramic views of the Historic District. The Casa Monica Resort & Spa was inducted into Historic Hotels of America in 2001.

The Union Station Nashville Yards (1900)
Nashville, Tennessee
From its origins as a Gilded Age train terminal, where countless couples bid farewell and were reunited, to its new life as a luxury hotel, The Union Station Nashville Yards has always been a top romantic destination in Nashville. For over a century, countless couples have been married at the terminal, and the hotel is eager to welcome guests back for their anniversaries and to help create new memories. The most romantic place to get engaged and to exchange vows at The Union Station Nashville Yards is in front of the Grand Lobby’s historic fireplace. Above the fireplace, the Grand Lobby also features an original curved stained-glass ceiling that has been a beautiful backdrop for hundreds of weddings and engagements – and was recently included in The 2023 Top 25 Historic Hotels of America Most Magnificent Ceilings and Domes List. Guests who book a suite package for their engagement are then invited back to take their engagement photos on property, free of charge. The hotel also offers a romantic honeymoon package for a luxurious stay in one of the hotel’s premium suites, decked out with romantic touches such as rose petals and candles. The package also includes a special welcome dinner at Stationairy, featuring a curated menu by Executive Chef Brian Kersey, and a curated list of recommended romantic spots and activities in Nashville. But ahead of the honeymoon, The Union Station Nashville Yards’ culinary team is delighted to work with guests to create a proposal to remember by delivering the ring during their meal. The Union Station Nashville Yards was listed in the National Register of Historic Places in 1969, and the hotel was inducted into Historic Hotels of America in 2015.

XV Beacon (1903)
Boston, Massachusetts
As guests approach XV Beacon from the cobblestone, gas-lit streets of Boston’s historic Beacon Hill neighborhood, the past becomes tangible with the present. For couples looking for a romantic getaway, luxurious accommodations offer gas fireplaces in each well-appointed guestroom, which the concierge team can decorate with flowers, candles, balloons, and more by request. Couples can enjoy private dining in their guestrooms or enjoy an intimate dinner at the hotel’s exclusive wine cellar. XV Beacon unites the past and present to create an unmatched atmosphere, where tradition feels exciting, making XV Beacon a perfect place to pop the question, whether it is on the exclusive roof deck overlooking the city of Boston atop Beacon Hill, or for a more intimate setting in one of the luxurious guestrooms with a rose petals turndown service, and a bottle of chilled Champagne next to the in-room gas fireplace. Guests of XV Beacon have access to an expert concierge team that will assist in designing the perfect moment and is sure to make any proposal memorable. The historic XV Beacon dates back to 1903 and was inducted into Historic Hotels of America in 2016.

The Plaza (1907)
New York, New York
European elegance meets modern-day grandeur at The Plaza, a New York City landmark. When The Plaza opened its doors in October 1907, it began its iconic history as host to illustrious dignitaries, home to acclaimed architect Frank Lloyd Wright, and the opulent background for the world-famous children’s book, Eloise. The Plaza’s impeccable white-glove service and Beaux-Arts décor, sumptuous guestrooms and architectural details, make this magnificent hotel the ultimate in luxurious destinations for weddings, romantic getaways, and proposals. Couples looking for a grand New York City wedding will find unparalleled opulence and romance at The Plaza. The dedicated staff at The Plaza is committed to working with every couple to make their wedding a one-of-a-kind affair no one will forget. Couples are invited to say “I Do” in either the neo-classical Grand Ballroom or The Terrace Room, both of which have been magnificently restored. Since it opened in 1907, this historic hotel has served as a dramatic and beautiful backdrop for romantic weddings, society balls, charity galas, and other major events. The Plaza was designated a National Historic Landmark by the U.S. Secretary of the Interior in 1986 and was inducted into Historic Hotels of America in 1991.

The Otesaga Hotel (1909)
Cooperstown, New York
Every historic hotel is unique in its offerings, location, and architecture for memorable engagements, but with Otsego Lake as its backdrop, The Otesaga Hotel provides a majestic and enchanting location for an engagement. The resort was recognized as a leader in hospitality and service as a winner of Historic Hotels of America Awards of Excellence in 2023. In addition, sharing the charming village of Cooperstown, New York, with the National Baseball Hall of Fame and Museum makes The Otesaga a unique venue for a baseball-themed engagement. A popular site to pop the question is on the back lawn of the resort, overlooking the lake and surrounded by century-old oak trees. The lake dock, with its quaint stillness and breathtaking views of the lake, is another admired area to get down on one knee. Some couples want to be on the lake, in an old-fashioned boat with the resort as a backdrop, and there are some who prefer to be on a horse-drawn carriage pulling up to the resort’s front portico. The concierge has assisted couples with everything from reserving a special spot at the resort, to arranging a horse-drawn carriage. There are unique ways to make the event a memorable one at The Otesaga, and the hotel welcomes guests’ creativity. For example, if the couple are baseball fans, the resort offers a baseball base for the ring presentation or wraps the ring around a baseball. The Otesaga, very creatively, has also enlisted dogs to deliver the ring. The historic Otesaga opened in 1909 and was inducted into Historic Hotels of America in 1994.

Hotel Boulderado (1909)
Boulder, Colorado
Hotel Boulderado opened in 1909 in Boulder, Colorado in the foothills of the Rocky Mountains, and has helped orchestrate romantic memories for countless guests for over 100 years. For romantics, Hotel Boulderado provides the ambiance of a historic boutique hotel with the comfort of modern amenities. One of the most romantic places inside Hotel Boulderado is the original grand cherrywood cantilevered staircase landing, which overlooks the lobby under a glowing stained-glass canopy ceiling. The staircase landing is a popular spot for guests, as it is the perfect spot for photos, to ask someone for their hand in marriage, and to say “I Do” as their wedding guests watch on from the surrounding mezzanine. Hotel Boulderado offers 10,000 sq. ft. of event space to host all wedding-related events, including ceremonies, receptions, rehearsal dinners, farewell brunches, bridal showers, and more. Hotel Boulderado’s newly remodeled Event Center provides a memorable space for up to 240 guests, while intimate historic rooms are perfect for smaller parties. Guests planning to pop the question at the hotel should tell Hotel Boulderado’s reservation team that an engagement is being planned when booking to see what amenities and upgrades are available at that time. Hotel Boulderado was inducted into Historic Hotels of America in 1996, and it is listed in the National Register of Historic Places.

The Hermitage Hotel (1910)
Nashville, Tennessee
Since 1910, The Hermitage Hotel, a five-star and AAA Five Diamond hotel, has been the premier choice for couples wanting an elegant and memorable Nashville experience. Warm surroundings, exemplary service, careful planning of the finer details, an award-winning culinary team, and beautiful Nashville honeymoon suites are just a few of the five-star ingredients that make the experience at The Hermitage Hotel spectacular. There have been many engagements at this historic hotel over the years, and some of the most sought-after locations are at the top of the staircase leading into the historic lobby, next to a cozy fire, or in front of the holiday tree in December. The Veranda and Mezzanine area are also stunning spaces for engagements. For couples planning an engagement, The Hermitage Hotel can arrange special experiences like custom-designed desserts, photography, and specialty ring placement. For example, when a guest asked his fiancée to marry him in December, the ring was hidden among the ornaments in the Christmas tree and he played a game to help her find the surprise hidden in the tree. She said yes! The hotel has also arranged specialty, private dinners on the Veranda, a historic space designed with sky-painted ceilings and flooded with natural light. The Hermitage Hotel was designated a National Historic Landmark by the U.S. Secretary of the Interior, and was inducted into Historic Hotels of America in 1996.

Chatham Bars Inn (1914)
Chatham, Massachusetts
Plan a seaside getaway to remember at Chatham Bars Inn in Chatham, Massachusetts, where its timeless charm and beauty makes it one of the most romantic spots on Cape Cod to pop the big question. The Inn opened in 1914 and was inducted into Historic Hotels of America in 2020. The Inn’s private beach offers pristine views of Chatham Harbor, seals popping up from the water, and fishing boats passing by—the perfect location for sunrise or sunset proposals. A proposal at sea is another option, and one of the most romantic proposal settings is on an evening sunset cruise with Champagne. As the sun sets and the last sunbeams touch the horizon, the sky lights up in many shades of orange, pink, purple, and blue, creating the perfect romantic atmosphere. If guests want to travel to North Beach Island via a short boat ride, the Chatham Bars Inn team can help facilitate special requests to make the proposal perfect. The Inn’s restaurant, STARS, offers magnificent views overlooking Chatham Harbor, combined with gracious service that anticipates every need, and guests can dine under a high ceiling and charming chandeliers, with soft music and a warm, crackling fireplace. These are just a few ideal locations at Chatham Bars Inn, where romance meets the sea. The Inn does not offer a standard proposal package but handles proposals personally, arranging a unique stay for every couple. The Inn is happy to arrange creative ring deliveries, candlelit dinners on the beach, photographers, music, Champagne, and personalized décor upon special request.

Omni William Penn (1916)
Pittsburgh, Pennsylvania
With a blend of classic elegance and modern sophistication, Omni William Penn has served as Pittsburgh’s premier hotel since 1916. Industrialist Henry Clay Frick envisioned his creation as a showplace that would rival Europe’s most elegant hotels. Today, the hotel features the largest amount of event space of any hotel in the city, including the elegant Grand Ballroom, one of only a few remaining two-tiered ballrooms in the country, which is the most sought-after ballroom to host a wedding in the city. For weddings, engagements, and city center escapes, the Omni William Penn hotel stands as a romantic destination, seamlessly blending history and luxury to create an unforgettable experience. Within its historic walls, this iconic hotel exudes a timeless charm. The luxurious ambiance beckons guests to relax and celebrate, providing an intimate and enchanting atmosphere that sets the stage for romance. One famous couple who are rumored to have been engaged here are comedian Bob Hope and his wife, Dolores. In the golden era of Big Bands, Dolores was a captivating singer in the supper club. While Dolores has confirmed in an interview that the proposal happened elsewhere, Omni William Penn was the backdrop for the early chapters of their well-known Hollywood love story. With its rich history and opulent surroundings, the Omni William Penn hotel is an idyllic choice for couples seeking a romantic retreat in the heart of Pittsburgh. Omni William Penn was inducted into Historic Hotels of America in 2010.

The Vinoy Resort & Golf Club, Autograph Collection (1925)
St. Petersburg, Florida
Known for its pink façade and Mediterranean Revival-style architecture, The Vinoy Resort & Golf Club, Autograph Collection, stands out as a romantic haven along the waterfront of St. Petersburg, Florida, where it has weaved a rich tapestry of history and charm since opening its doors on New Year’s Eve in 1925. Recently, The Vinoy recently underwent a careful renovation and a restoration—with meticulous attention to the Vinoy Grand Ballroom, perfect for weddings and receptions—that captures the magic of Florida’s Golden Age. St. Petersburg, with its cobblestone streets, charming cafes, and vibrant arts scene, adds an extra layer of romance to the Resort’s allure. As guests explore the city’s cultural gems, waterfront parks, and sunset views over Tampa Bay, this ambiance intertwines with the Resort’s historical charm. The Vinoy offers couples endless activities, such as a round of golf or a tennis match, pool day relaxation, and various international dining options. The Vinoy Resort & Golf Club, Autograph Collection, was inducted into Historic Hotels of America in 1991.

La Valencia Hotel (1926)
La Jolla, California
When guests enter La Valencia Hotel, in La Jolla, California, they encounter a special charm found only within these pink walls. From the stunning ocean views to the Mediterranean-style architecture, the Pink Lady of La Jolla is the perfect backdrop for an engagement and anniversary trips. One of the most romantic settings at La Valencia Hotel for a proposal is the ocean view garden space overlooking the Pacific Ocean and pool deck. Surrounded by roses, palms, and pink Mediterranean-style architecture, the garden is a special spot to propose. The garden features the unique 1928 tile portrait of the original “Pink Lady,” an alluring antique piece believed to be the work of tile artist Ernest Batchelder. Another stunning location is the signature restaurant’s ocean view terrace. Guests can reserve Table 625 at the end of the terrace for an elevated view of the sunset. From flower deliveries and rose petal drops to coordinating live music, the Hotel team can assist in making the moment memorable with the help of trusted local vendors. The Hotel offers a specialty Champagne delivery with any room package, and staff can coordinate tossing rose petals in the room for a special celebration. The Hotel can help to orchestrate a proposal, and staff are prepared to accommodate a special candlelit dinner experience. For example, the staff once delivered a “Golden Snitch” that held the ring to a couple that loved the Harry Potter series. La Valencia Hotel has also partnered with local photographers who can be in on the secret and capture the “Yes!” moment. Established in 1926, La Valencia Hotel was inducted into Historic Hotels of America in 1989 and is a Charter Member.

The Fairmont Sonoma Mission Inn & Spa (1927)
Sonoma, California
One of the most romantic proposal venues in California Wine Country is the storied Fairmont Sonoma Mission Inn & Spa. Hundreds of couples have popped the big question at the iconic resort, which opened in 1927. This historic hotel is the ultimate destination for a romantic proposal, with amenities including a geothermal spa, Michelin star-rated dining, easy access to hundreds of world-class wineries, and the resort’s romance-inspired Mission Spa Suites. The Mission Spa Suites are the Inn’s most romantic accommodations, boasting an open floor plan with oversized Jacuzzi soaking tub designed for two, a four-poster king-size bed, and wood burning fireplace. A new package, “Spa Under the Stars,” offers couples a chance to experience the spa’s geothermal waters privately for up to two hours. Guests often choose to propose during private picnics in the vineyards, on hot-air balloon excursions, and during horseback rides. Private candlelit dinners can be arranged in-room and elsewhere at the historic hotel. All of these make wonderful places to pop the question—or to unwind with a partner. One of Wine Country’s most romantic destinations, Fairmont Sonoma Mission Inn & Spa was inducted into Historic Hotels of America in 2014.

The Royal Hawaiian, A Luxury Collection Resort (1927)
Honolulu, Hawaii
Since its opening in 1927, The Royal Hawaiian has been recognized as an icon of luxury and romance. The hotel’s soaring pink turrets have lured couples from around the globe, who come to the resort to discover the expansive beach at sunset, to share intimate moments in lush and legendary gardens, and to immerse themselves in timeless beauty. At the “Pink Palace of the Pacific,” the ideal location for a proposal is at a beachfront table at the hotel’s famous Mai Tai Bar, or on the sandy beach right near the bar; it all depends on how much privacy the couple desires. Just steps from the beach, with a view of Diamond Head and directly facing the shoreline of Waikiki Beach, the hotel provides the perfect place to pop the question. Along the beach or at the Mai Tai Bar while watching the sunset over the Pacific Ocean is the most popular time of day for couples to get engaged. If a couple does not mind an audience, the proposal can be prearranged with the hotel’s food and beverage department, and the nightly entertainer will direct the audience’s attention to the proposal. The Royal Hawaiian, A Luxury Collection Resort was inducted into Historic Hotels of America in 2011.

The Graylyn Estate (1932)
Winston-Salem, North Carolina
The Graylyn Estate in Winston-Salem, North Carolina, is an outstanding historic destination for romantic getaways, and a beautiful location for hosting special occasions. The Manor House, a 20th-century castle set on 55 pristine acres, was inspired by Romanesque Revival-style architecture, and features European ironwork, encouraging guests to feel as if they have entered their own picturesque fairytale. Couples visiting the estate can explore the grounds together, passing gardens, the historic stone gazebo and Koi Pond, and manicured lawns. The serenity and privacy of the Estate provide the perfect backdrop for romantic moments, proposals, and heartfelt conversations. The Graylyn Estate has several romantic locations for intimate and captivating proposals. Staff recommend proposing at sunset on the historic bridge or in front of the Mews Fountain. Another perfect place for a proposal is during a private, candlelit dinner in the hotel’s Persian Card Room. This intimate location is decorated with 18th-century painted wood panels made in Syria and purchased by the Gray family in Istanbul during the 1920s. Couples visiting The Graylyn Estate can truly indulge by booking its Romantic Getaway Package for couples planning a proposal, wedding night, overnight escape, or anniversary celebration. The Graylyn Estate was inducted into Historic Hotels of America in 2016.

The Hotel Hershey® (1933)
Hershey, Pennsylvania
Chocolate lovers can delight at The Hotel Hershey, known for its refined elegance, signature service, and abundant amenities. A one-of-a-kind destination for romance, the Forbes Four Star, AAA Four Diamond historic hotel is situated high atop Hershey, Pennsylvania—known as “The Sweetest Place On Earth.” Here, couples can enjoy cocoa-inspired dishes, decadent desserts, and signature Hershey’s Chocolate martinis during a romantic dinner. Guests can indulge in total luxury at The Spa At The Hotel Hershey with signature chocolate treatments, including a Couples Cocoa Massage. For a romantic meal, Historic Hotels of America recommends dinner at The Circular, The Hotel Hershey’s flagship restaurant. Built by Milton S. Hershey in 1934, this historic restaurant’s unique shape, original stained-glass windows, and spectacular views overlooking the formal gardens create an atmosphere perfect for an intimate meal and cocktails. Two of the most popular places to propose at the hotel are The Fountain Lobby, one of the most breathtaking spaces at The Hotel Hershey, and the formal gardens. For a proposal in the gardens, guests can plan a proposal during golden hour for the perfect lighting, and then celebrate for the rest of the evening. The Hotel Hershey® was inducted into Historic Hotels of America in 1991.

The Highlander Hotel (1967)
Iowa City, Iowa
Romance should be fun, and The Highlander Hotel offers an enjoyable getaway for couples looking to celebrate their love at an exciting and stylish retreat. Located near downtown Iowa City, Iowa, The Highlander Hotel was founded as The Highlander Supper Club in 1967 and has been a local landmark for generations. In the early 2020s, the historic supper club was reimagined as a cozy, trendy, and “hippie chic” hotel, complete with an arcade, pool with adults-only hours, vintage romantic movies, and more. The Penthouse Suite offers couples a soaking tub for two, and guests can request sparkling wine, roses, and a charcuterie board upon arrival. Guests can find the right moment to propose during a game, dinner, or while relaxing in their suite. For larger romantic celebrations, The Highlander Hotel’s Ballroom can comfortably seat up to 200 guests for dinner or hold up to 600 for a cocktail reception. The origins of this romantic historic hotel dates back to the late 1960s, when it opened as a prestigious supper club. Boldly embracing the romance of nostalgia and the best of vintage Midcentury Modern-style aesthetics, The Highlander Hotel was inducted into Historic Hotels of America in 2023.

“Every day is Valentine’s Day at Historic Hotels of America, and we are pleased this winter to spotlight The 2024 Top 25 Historic Hotels of America Most Romantic Hotels List. These romantic historic hotels range from intimate and charming to grand and opulent,” said Lawrence Horwitz, Executive Vice President, Historic Hotels of America and Historic Hotels Worldwide. “Staying at a historic hotel is a wonderful opportunity to create an ever-lasting memory, whether you are visiting for a romantic getaway, proposing, or planning a gathering. Each of these destinations provides the setting, the staff support, and the ambience for the perfect proposal or the perfect wedding.”