Graycliff Hotel, Nassau, Bahamas

Located downtown in the heart of old Nassau and just minutes from the Bahamas’ pristine white sand beaches is Graycliff Hotel, an elegant colonial mansion surrounded by tropical gardens. Originally built in 1740 by famed pirate Captain John Howard Graysmith and later owned by Polly Leach, a close companion of Al Capone, Graycliff has a long history of being a sophisticated gathering spot for the rich and famous.

The five-star Graycliff Restaurant is home to Mariah Carey’s “favorite table in Nassau” – the one in the wine cellar’s private dining room, the same room where Beyonce and Jay-Z are rumored to have gotten engaged. Additional visiting celebrities include Nicholas Cage, The Beatles, Jackie Onassis, Michael Jordan, Paul Newman, Bill Clinton, and Billy Joel, who once topped off dinner with an hour and a half piano set in the dining room.
(Photo credit: Nassau & Paradise Island Promotion Board

Jefferson Hotel, Richmond, Virginia

The Jefferson Hotel opened in 1895 and some of its first guests were there for the wedding of socialite Irene Langhorne, including Irene’s sister who became “Lady Astor.” Margaret Mitchell, author of Gone with the Wind, stayed at the hotel when she was writing the novel, and it is said that the staircase in Scarlett O’Hara’s mansion was inspired by The Jefferson’s grand staircase.  

At least 13 presidents have stayed at the hotel as well as Hollywood icons like Charlie Chaplin and Frank Sinatra. 

The Royal Hawaiian, Honolulu, Hawaii

Since its opening in 1927, The Royal Hawaiian— known as the “Pink Palace of the Pacific”—has been synonymous with luxury, elegance, and glamour. Its timeless Spanish-Moorish architecture, coral-pink façade, and unparalleled beachfront location make it a magnet for Hollywood stars and filmmakers.
 
The hotel’s Spanish-Moorish design, grand arched breezeways, and lush tropical gardens evoke the opulence of a bygone era, making it feel like a film set straight out of Hollywood’s golden age. It’s played a starring role in numerous films and TV shows, from classics like The Black Camel (1931) to modern productions such as Punch-Drunk Love (2002) and the Hawaii Five-0 reboot (2016–2019). Hollywood icons like Marilyn Monroe, Frank Sinatra, and Shirley Temple have stayed at the hotel.

Regina Isabella Resort, Ischia, Italy

Opened in 1956 by publisher and film producer, Angelo Rizzoli, the 128-room 5-star Regina Isabella Resort combines Italian chic with traditional and updated mid-century classic styles, with acres of shiny, decorative tile floors that are the hallmark of the region.

Now privately owned and operated by the Carriero family, the hotel’s debut came at the height of the “Dolce Vita” era. The Regina Isabella has welcomed Hollywood and world glitterati from the day of its opening – from Clark Gable, Charlie Chaplin, Maria Callas and Ava Gardner, to the vacationing Elizabeth Taylor and Richard Burton during the filming of “Cleopatra,” to the cast of “The Talented Mr. Ripley” (filmed on Ischia).

Palmer House, Chicago, Illinois

Louis Comfort Tiffany masterpieces, and a breathtaking ceiling fresco by French painter Louis Pierre Rigal – are lovingly preserved in the Palmer House decor. Hard to imagine that it was the first hotel to 
incorporate the light bulb, the telephone, and the vertical steam lift (elevator) into its design.

Now part of the Historic Hotels of America, by the turn of the 20th century, the Palmer House had become Chicago’s liveliest social center, hosting a long list of prominent figures—including those ranging from U.S. presidents to Charles Dickens to Oscar Wilde. In 1933, the Empire Dining Room of Palmer House was converted into an entertainment epicenter and supper club. It hosted legendary entertainers, including Frank Sinatra, Judy Garland, Ella Fitzgerald, Harry Belafonte, Louis Armstrong, and Liberace.

The Drake, Chicago, Illinois

Listed in the National Register of Historic Places., The Drake Hotel opened on New Year’s Eve, 1920, with a Renaissance-era Italian design.

Throughout the ‘Roaring 20’s’, The Drake became high society’s first choice in opulence with The Fountain Court (now the Palm Court) hosting Chicago’s social elite for daily tea.

Many U.S. presidents have spent the night in the six-room Presidential Suite, and Winston Churchill, Amelia Earhart, Eleanor Roosevelt, Walt Disney, Frank Sinatra, Dean Martin, Charles Lindbergh, Pope John Paul II, and Princess Diana have all called the Drake home for a night or two. 

The Drake has also had several movies filmed under its roof, including The Blues Brothers, Risky Business, and My Best Friend’s Wedding.

Photo credit: Stephanie D’Adamo

Westin Poinsett, Greenville, South Carolina

For one hundred years, the Mansion House Hotel stood on South Main Street in Greenville, South Carolina. In 1924, the hotel was demolished to make room for the construction of the Poinsett Hotel. When it opened on June 20, 1925, it was one of the most beautifully furnished hotels in the country.

In June 2000, after a series of ups and downs, the Poinsett Hotel celebrated the 75th anniversary of its original grand opening with an exhibit of historic memorabilia in City Hall and a reception in the Gold Ballroom of the hotel.

Until early 1990, the Poinsett Hotel was considered one of the eleven most endangered historical sites in South Carolina. Today it is where celebrities like George Clooney and Renee Zellweger stay when they visit the city and feels like you are stepping back in time when you enter the lobby.

Hotel del Coronado, Coronado, California

The Hotel del Coronado seaside resort – with its elegant red cupolas and towers – opened in 1888. Its founders dreamed of creating a seaside resort that would be “the talk of the Western world” and it has, perhaps beyond their wildest dreams.

In 1958, the hit sensation Some Like It Hot (1959) was filmed at Hotel del Coronado. The film showcased the talents of Marilyn Monroe, Tony Curtis, and Jack Lemmon, while also highlighting the hotel’s assets: a spectacular sun-drenched silhouette of Victorian architecture, the perfect backdrop for the film’s 1929 setting.

The hotel was designated a National Historic Landmark District by the U.S. Secretary of the Interior in 1977, and was inducted into Historic Hotels of America in 2018.

The Hollywood Roosevelt, Los Angeles, California

As one of the most historic hotels in Los Angeles, The Hollywood Roosevelt has seen decades of famous faces. In 1929, the hotel was the location of the very first awards ceremony of the Academy of Motion Picture Arts and Sciences (the Oscars). The ceremony was hosted by Douglas Fairbanks and attended by the who’s who of Golden Age Hollywood.

Today, the hotel still buzzes with industry executives and talent, and is a popular destination for locals and tourists. The movie Catch Me If You Can (2002) produced by Steven Spielberg and starring Tom Hanks and Leonardo DiCaprio was filmed at the htoel, and guest can learn about and access those locations.

The Hollywood Roosevelt is a part of the Historic Hotels of America collection.

Hotel Carmichael, Carmel, Indiana

Hotel Carmichael, a Marriott Autograph Collection hotel, is a beautiful picture of old Hollywood and the classic American Songbook, featuring a beautiful grand staircase and chandeliers in the entryway, portraits of musicians, checkered floors, and a cabaret on its lower level. Guests can also stop by Adagio, Carmichael’s lobby lounge, which hosts a state-of-the-art Steinway and Son’s grand piano, playing a slower tempo genre as the name suggests.

Vinoy Resort & Golf Club, St. Petersburg, Florida

Celebrating its centennial in 2025, The Vinoy is a classic downtown St. Petersburg landmark standing as a pillar of the community and a beacon for travelers since its New Year’s Eve opening in 1925.

Known for its signature pink facade, Mediterranean Revival style and old-Florida hospitality, went through a renovation and rebrand in 2023. The new, sophisticated aesthetic reflects The Vinoy’s timeless glamour and tips its hat to a longstanding legacy.

If walls could talk, The Vinoy’s would have endless stories to share thanks to a rich history that includes hosting U.S. presidents, celebrities and athletes, and even serving as military housing in the 1940s.

Photo credit: The Vinoy Resort & Golf Club, Autograph Collection

Bottleworks Hotel, Indianapolis, Indiana

For a stay that feels like a step into a time machine, The Bottleworks Hotel is a perfect contender. The hotel, which was once part of the largest Coca-Cola bottling plant in the world in the mid-1900s, has since been transformed into a luxury hotel while never neglecting its roots. The hotel’s exterior is still original to the property, and its art-deco style is still prevalent through its terrazzo floors, classic wooden fixtures, and Hollywood-esc decor.

Hotel Legends, Biloxi, Mississippi

Inspired by Hollywood’s Golden Age, the sapphire-colored hotel is rooted in the rich history that Biloxi is known for. The hotel is filled with Hollywood nostalgia and the era’s glitz and glamour is on full display, from elegant chandeliers to midcentury furniture and more.