Trip to Anywhere

10 Picturesque Historic Hotels


Every place has its story, but none more so than sites that date back to eras long past. With these meticulously restored historic hotels, you’ll find yourself following the footsteps of royalty, millionaires, revolutionaries, luminaries, and more, all while basking in modern-day luxury.

The Milestone Hotel



Ambassadors and barons once called this home, making a stay here a milestone of achievement for sure.

It was 1689 when Foot Onslow, a Commissioner of Excise under William III, built Kensington House on this site, but it wasn't until 1830 that the property's story started getting colorful. That was when the house became a private asylum, only to be replaced by a second mansion by the same name, courtesy of the notorious company promoter, "Baron" Albert Grand, the founder of London's famous Leicester Square. Called the "White Elephant," this building stood until the 1880s, after which it was replaced with the two houses that mark the Milestone today.

The first to be completed was No. 1 Kensington Court, where the first Baron Redesdale—the diplomat, author, and grandfather of the scandalous, notorious Mitford sisters—made his home. That was back in 1883, but hot on his heels was another noteworthy resident: Count Peter Grigorevich, the Russian Ambassador to London. It wasn't until 1922 that the two houses were joined together to become a hotel, but an unfortunate fire damaged them both in 1986. Thankfully, it fell under the patronage of the esteemed Red Carnation Hotel Collection in 1998, which has restored it to the glory of its past and updated it with all the luxuries of the future.

Goldeneye Resort



James Bond may be fictional, but his “birthplace” sure isn’t.

We're not talking about the place the 007 character was born in the novels but rather where the Bond was dreamt up. His nascent city is still open to speculation by fans of the books and movies, but there's no question about the fact that his life began in Jamaica, when Ian Fleming built his dream house, GoldenEye, in Oracabessa (Golden Head) Bay.

Having been stationed in Jamaica during WWII to investigate U–boat activities, he fell in love with the island and purchased property there after the war. He started writing his novels in 1952, putting down 2,000 words per day until Casino Royale was completed, and didn't stop until all 13 were finished. All were written right in his bedroom in GoldenEye.

He's not the only writer to have found his muse here, though. Chris Blackwell, the founder of Island Records, bought the property after Fleming's passing, and it was while Sting was staying there that The Police wrote "Every Breath You Take." Today, it's part of the Island Outpost's collection of laid–back yet sophisticated hotels and villas in Jamaica.

Moana Surfrider, a Westin Resort & Spa



Go with the FLOW at the hotel named “First Lady of Waikiki.”

There's nothing quite like having a story already before its history even starts, which is the case with this regal property. When it opened on March 11, 1901 as Waikiki's first hotel, its first guests was a group of 114 Shriners, an appendant body to the Freemasonry. Hosted by the local Aloha Temple Shriners, this gathering was certainly one way to kick off the grand opening of W.C. Peacock's newest venture, which commanded a hefty $1.50 per night cost.

Ownership changed hands only a few years later when hotelier Alexander Young purchased it in 1905, but he was only able to enjoy it for five years before he passed. His estate managed its operations until the 1932 purchase by the Matson Steamship Company, Hawaii's predominant passenger carrier. This made total sense; by 1918, Hawaii was welcoming 8,000 visitors per year, and this grande dame hotel doubled in size to accommodate its popularity. However, its guest demographic changed a bit in the 40s, when the property showed its commitment to defense by housing servicemen and defense–related personnel as well as guests. After victory, the hotel grew in size again with another expansion project, followed by yet one more by Kenji Osano when he purchased the adjacent property. But what was old was made new again in 1983, when a $50 million, 20–month restoration based on original plans from 1915 was revealed. Since then, another $30 million has gone into enhancements, making it a perfect blend of old Waikiki glamour and modern amenities and luxury.

Ballynahinch Castle Hotel



Ever wish you could outrun your problems? The Martins of Galway may have done exactly that.

In the vast and wild Connemara Burren seems as good of a place as any to hide out, especially if you have 196,000 acres in which to do it. According to written anecdotes, it seems that the Ballynahinch estate was used by the Martins not only as a sporting retreat, as was the fashion in the late 1700s, but also to get off the radar of their creditors.

Before the Martins had the run of the land, it was part of the domain of the O'Flaherty Clan. Although the castle as it stands today was only built around the end of the 18th century, the first castle on the estate was erected in the 1580s…by a pirate queen who married into that family. Grace O'Malley was her name, and she became the formidable chieftain of her clan after her father's passing. Notable owners after her included Richard "Humanity Dick" Martin, the founder of the Society for the Prevention of Cruelty to Animals, and High Highness the Maharaja Jam Sahib of Nawanagar, or Ranjitsinhji "Ranji," Prince of Cricketers. It was he who erected the fishing piers and huts along the river and landscaped the gardens and woods guests can enjoy today when they stay at this luxury country house hotel that is now owned by Ireland's tourist board.

The Roosevelt Hotel New Orleans, a Waldorf Astoria Hotel



In a city where music has always reigned, staying here is like sleeping on hallowed ground.

New Orleans is known for a whole lot of things, from its chart–topping cuisine to notorious holiday celebrations. But what ties it all together is that it's a destination that marches to the beat of its own drummer, creating a rhythm of joy that's easy to just fall into. And what better place to embrace the music than the Roosevelt Hotel, first known as the Grunewald Hall performing arts center?

Although it was relaunched as the Grunewald Hotel in 1893 and expanded as the same in 1907, its musical history continued long after. It became one of the hottest entertainment spots in the Crescent City with the opening of The Cave, a basement grotto filled with rock formations, nymphs, and gnomes—and one of the country's first nightclubs, rousing with the sound of Dixieland jazz.

Although this famous venue gave way to The Blue Room and the Sazerac Bar after it became The Roosevelt, the richness of its trappings and music heritage continued on. Louis Armstrong, Ray Charles, and other modern legends have performed here, and future musical geniuses will find themselves pampered in grand style after a $145 million restoration.

CastaDiva Resort & Spa



Who knew you could find such peace in a place once filled with drama queens and kings?

Opera divas, couture designers, painters, sculptors, poets, playwrights, artists…name the creative genre, and odds are, a guest or owner held that occupation. First built in the early 19th century, the founder was an "eccentric, libertine by nature" Parisian dressmaker named Madame Ribier, who "made a fortune dressing the ladies of high society and 'possibly undressing their husbands'" in Villa Roccabruna, the heart of the resort. The second owner was Giuditta Pasta, a legendary opera singer, who bought the villa in 1827 and renamed it Villa Roda. It was during this time that her engineer uncle refurbished the main home alongside a painter and a sculptor in the design of Teatro alla Scala in Milan, and two guesthouses were built.

During this time, this property was a hotbed of creative activity. Anna Bolena was written here in 1830 by guest Gaetano Doninzetti; Vincenzo Bellini, soprano and composter Isabella Colbran, artist Maria Luisa Hadfield Cosway, composer Gioacchino Rossini, and many more all visited here and found added inspiration.

It wasn't until 1906 that Roda was renamed Villa Roccabruna after a total rebuild in the Liberty style under the ownership of the Wild family. Known as cotton magnates from Switzerland by way of Turin, they were the last to live on the estate before half a century of empty halls. In 2000, the Italian Hotel Residence Club took it over, making it possible for you to find your muse here as well.

The Buccaneer



With a past like this, the only thing this pirate will run away with is your imagination

Dashing and romantic in setting and attributes, it makes sense that this hotel's name takes after a term for a swashbuckling pirate. Its origins date back as far as that part of history; it was 1653 when Charles Martel, a Knight of Malta, raised up the French manor home that remains on this historic site where indigo and tobacco ended up being grown. However, sugar became the primary crop when Governor von Prock built a home of his own on the estate and turned the original manor into a sugar factory and mill. It was in this reincarnation that Alexander Hamilton spent time as a child, whose pitter–patter footsteps you can quite literally walk in should you stay in the Hamilton Wing.

In The Buccaneer's next life as Estate Shoys, it became a cotton plantation. Next, it was a cattle farm for the Heyliger Company and for its current owners, the Armstrongs, who purchased the property in 1922. It wasn't until 1947 that the family opened 11 guestrooms to the public, making it the first hotel on St. Croix to be built, owned, and operated by a local family. Since then, this member of Historic Hotels of America has grown within its 340 acres, with three beaches, a full golf course, eight tennis courts, and more. It's also entranced many more, so much so that it set the scene for ABC's "The Bachelor" in 2013.

Sofitel Amsterdam The Grand



Nice enough for nuns, naughty enough for princes, fancy enough for kings, and just right for you.

Grand and legendary are two parts of its name this historic hotel lives up to, but that's not why it's twice as memorable. This property isn't just a former convent—it's two: St. Cecily's on the northern bounds and St. Katherine's to the south. Two charming courtyards, linked by a central element, harken back to those days, along with a tiny tower on the north rooftop that was built in the same style as the former.

Although the property's 1411 origins may have been spiritual, it gave way to secular life in 1578, when it was transformed into a hotel for "Princes and Gentlemen of Standing," and fittingly renamed Princenhof, or Court of Princes. During this time, the Princes of Orange William the Silence, Prince Maurits, and Prince Frederik Hendrik at one point called its halls home. In 1632, so did Maria de Medici, Queen of France, whose stay was seen as formal recognition of the newly established Dutch Republic, despite the fact that the mission to reconcile her with her son, Louis XIII, during her visit failed.

Shortly after that, the Admiralty of Amsterdam took over the entire complex and erected the glorious Admiralty Building in 1662, a setting so stunning that it was chosen to become the Amsterdam City Hall for 180 years, after Napoleon's brother Louis, King of Holland, declared it so. In 1992, it became possible for visitors to retrace the steps of nuns, princes, queens, kings, and emperors as guests of what is now a premier hotel.

Ashford Castle



Everyone that visits Ireland raves about the Guinness. But how about staying at the home of The Guinness?

That's right—this property provides an opportunity to walk the same halls as the founder of the famous brewery, Sir Benjamin Lee Guinness, who became one of the wealthiest men in Ireland. But this lakefront castle's history goes even farther back than that 1852 change in hands. It actually dates all the way to 1228, when it was founded by the Anglo–Norman de Burgo family following their defeat of the native O'Connors of Connaught, and served as their stronghold for over 350 years.

However, when Guinness purchased the property, he extended the estate to 26,000 acres, which his son did even more justice by developing the woodlands and restoring the buildings to greater glory. It wasn't until 1939 that Ashford Castle was open to the public, when Noel Huggard established it as a first–class hotel—a category it remains in today, thanks to Red Carnation Hotels' efforts. Since they took it over in 2013, it's been voted Best Resort & Inn in Great Britain and Ireland by Travel + Leisure readers during the World's Best Awards 2016.

Hotel El Convento



The New World this may be, but this is the oldest member of Historic Hotels of America.

Three hundred and seventy years is time enough to have multiple lifetimes' worth of adventures, and the Hotel El Convento has certainly had plenty of those. Ground for its construction was broken in 1646 by order of King Phillip IV of Spain, who had decreed that it would be the site of a Carmelite convent for those sisters who chose to devote their lives to the Roman Catholic church. It wasn't until July of 1651, though, that it was finally inaugurated as the Monastery of Our Lady Carmen of San Jose. Set across the street from San Juan Cathedral, the oldest cathedral in the Western Hemisphere, it was an ideally located home for these nuns until 1903—252 years.

Half a century went by where the property was in turn a retail store, dance hall, and a rooming flophouse devoid of even running water or electricity. However, Robert Frederic Woolworth, heir to the Woolworth fortune, saw its promise and began Operation Bootstrap in 1959 to restore the building. El Convento Hotel opened in 1962 to great applause.

Today, as Hotel El Convento, it's even more a property to put your hands together for. Recent renovations and upscale amenities have made it a modern experience in a historical space, and the answer to vacationers' prayers.

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