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Ultimate Frank Sinatra Travel Guide

Frank Sinatra has been one of the unsung heroes of travel marketing for 70 years, along with Ernest Hemingway and Elizabeth Taylor. If they patronised your establishment, then it would be forever sprinkled with showbiz stardust.


The 20th century’s undisputed King of Cool, Sinatra’s music became the soundtrack of post-World War II America. His explosive private life, which included passionate affairs with the world’s most beautiful women, dubious connections to the Mafia and friendships with Humphry Bogart, JFK and Sammy Davis Jr., dominated Hollywood gossip columns for decades.

The Rat Pack in Las Vegas
The Rat Pack - Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop

Sinatra and his Rat Pack immortalised Las Vegas in song and on film; he sung about New York and Chicago being his kind of towns and his movies took fans all over the world, from New York to Hawaii, Miami to Myanmar.



If you’re looking for a holiday or night out with a hint of retro cool, ask yourself, “where would Frank Sinatra go?”


From Frank Sinatra’s favourite bars in New York, to the best Sinatra experiences in Las Vegas (the city he helped create), discover his favourite hotels, restaurants, holiday destinations and Sinatra-related things to do in this Ultimate Frank Sinatra Travel guide.


Atlantic City

Sinatra and the Rat Pack performed often in Atlantic City, which is no surprise given its close associations to organised crime, gambling and the Miss America Pageant. When Sinatra was being questioned by the FBI about his ties to the mob, a 2-week long party he hosted at The Claridge, on South Indiana Avenue, was frequently cited as evidence, as the party was allegedly attended by mob boss Sam Giancana.


In the 1980s, Sinatra performed at Bally’s which now incorporates some of the old Claridge building.


Cairo

In September 1979, Sinatra stayed at the opulent Mena House Hotel in Cairo, where he performed a charity concert in the shadow of the Pyramids. The New York Times described the gala event as “a bunch of beautiful people created their own island of conspicuous opulence in a sea of Egyptian poverty...”


Frank Sinatra concert at Cairo Pyramids
Sinatra performing at the Pyramids of Giza in Cairo, Egypt

Chicago

“Chicago is my kind of town,” sang Frank, and with good reason. He started his career performing at the city's glamourous Empire Room at the Palmer House Hotel.


Sinatra’s favourite bars were the Green Mill - part of The Joker Is Wild (1957) was filmed here – and the Twin Anchors. His favourite restaurant was Gene & Georgetti, an Italian steakhouse founded in 1941.


Later in his career, his hotel of choice whenever he was in town was the Drake Oakbrook Hotel.


Dominican Republic

Altos de Chavón is a place like no other—a replica 16th century Mediterranean village in the heart of the Dominican countryside. Meticulously designed by Dominican architect, Jose Antonio Caro, and Italian master designer and cinematographer, Roberto Coppa. The amphitheatre was opened by Sinatra in 1982 with a concert televised live by HBO.

France

It is well known that Sinatra hated fancy restaurants, preferring ma and pop style diners and little Italian steakhouses, but he made an exception for Tour d’Argent restaurant in Paris. He enjoyed several romantic dates with Ava Gardner at this one Michelin-star historic gem in the 1950s. In her later years, Gardner was known to visit by herself and reminisce with the waiting staff about the times she spent here with Frank.


In 1958, at the absolute pinnacle of his fame, Grace Kelly invited Sinatra to perform at a fundraiser at the Sporting Club in Monaco, to raise money for the United Nations Refugee Fund. He was introduced by Noel Coward as one of the greatest artists of all time, and played with the Quincy Jones Orchestra (the first time they had played together) in front of stars like Cary Grant, Natalie Wood, and Douglas Fairbanks Jnr.

Every year, Sinatra would visit his old friend Grace Kelly in the South of France for her annual Red Cross Ball. When he was in town, he stayed at the Hotel de Paris in Monaco.


They would often eat at The Pirate restaurant, a favourite of Aristotle Onassis, located on the beach at Saint-Jean-Cap-Ferrat and boasting large outdoor barbecue pits blazing, and men dressed as pirates with no shirts on cooking on the grills. The restaurant owner was a bona fide local legend who turned service into a kind of billionaire’s theatre, encouraging guests to break everything when they had finished. Gleaming Ferrari's, Rolls Royce's and Alfa Romeo's were parked outside every night during the height of its popularity in the 1970’s and 80’s. Check out this hedonistic (and hilariously judgemental New York Times restaurant review from 1972).


Havana

Ava and Frank spent part of their honeymoon in Havana (along with Miami), staying at the infamous Hotel Nacional, witness to endless celeb trysts, political scandals and excessive alcohol abuse during its uninterrupted reign as Cuba’s top hotel. The lovebirds stayed in a 3rd floor suite, enjoying a blissful few days exploring the city, drinking mojitos and visiting the red-light district of La Playita by night.

Frank Sinatra in Havana Cuba
A youthful Sinatra at Sloppy Joes in Havana, Cuba with the Fischetti Brothers

Hawaii

Sinatra visited Hawaii many times, for holidays, performances and shooting movies. From Here to Eternity (1954), in which he won the best supporting actor Oscar, was filmed in Hawaii, as was None but the Brave (1965). In 1964, while filming the latter, Sinatra had a near death experience as he was struck by a freak wave at Wailua Bay.


The Royal Hawaiian Hotel is a grand dame pink palace that has been attracting discerning travellers since the 1920s, including Mr Sinatra. He was also known to stay at the elegant Kahala Hotel.


Kenya

Mount Kenya Safari Club in Nanyuki, Kenya, has been a magnet for royalty, millionaires, and stars since its opening in 1959. Owned by actor William Holden, the club hosted Ernest Hemingway, Clark Gable, the Ratpack and Steve McQueen amongst many other illustrious stars. The Trophy Lounge is filled with starry images of past guests, including Charlie Chaplin, John Wayne, Grace Kelly, Ava Gardner and Marlon Brando.


Las Vegas

Sinatra’s legendary Vegas career started out at The Sands, which was, rather tragically, blown up in 1995 to make way for a convention centre car park. He later enjoyed residencies at Caesars Palace and The Golden Nugget.

You can pay tribute to the Chairman of the Board and his Rat Pack at the Wynn Hotel’s Sinatra restaurant, or by indulging in a steak at the classic Vegas hangout, The Golden Steer Steakhouse. Piero’s restaurant opened in 1982 and became a firm favourite with the Rat Pack in their twilight years. Scenes from Martin Scorsese’s Las Vegas gangster epic Casino were filmed here.


Check out the Rat Pack is Back tribute show at the Tuscany Suites & Casino for a taste of that old Rat Pack magic.


Los Angeles

Food

Everyone who is anyone in Hollywood, since its very beginning, has eaten at Musso and Frank. Sinatra was no different.


Patsy D’Amore’s Villa Capri was his favourite restaurant in LA. They had a genuine New York wood-fired pizza oven and Sinatra regularly used them to cater at his legendary parties, according to his former valet George Jacobs. You can still get a taste of Frank’s favourite dish, the Steak Sinatra, which is served by the grandson of Patsy D’Amore’s original sous chef at Johnny Costa’s Ristorante in Palm Springs.

Frank Sinatra and Lauren Bacall Matteos Restaurant, Los Angeles, 1957
Sinatra and chic as ever Lauren Bacall at Matteo's in Los Angeles

Matteo’s was another favourite, owned by his old friend Matty “Matteo” Jordan from Hoboken, as was La Dolce Vita in Beverly Hills, where guests can request the singer's personal booth.


Drink

Frank was a regular at the Formosa, and was often seen drinking his troubles away here during his explosive marriage to Ava Gardner.


Hotels

The Beverly Hills Hotel has a Frank Sinatra Suite, inspired by the mid-century design that he loved, all simplicity and geometric patterns. He and the Rat Pack spent many drunken nights at the hotel’s legendary Polo Lounge.


During his early years in LA, Sinatra lived at the Sunset Tower Hotel alongside other celebrities including John Wayne and Howard Hughes.


Things to do

Visit the ‘Sinatra: An American Icon’ exhibition at the Grammy Museum, and check out some serious Sinatra memorabilia, including his iconic black fedora.

Frank Sinatra's black fedora hat, Grammy Museum, Los Angeles
Sinatra's black fedora can be seen at the Frank Sinatra exhibition at the Grammy Museum in Los Angeles

Get a selfie with Frank’s star on the Hollywood Walk of Fame, which can be found at 1600 Vine Street.


Check out the iconic Capitol Records, where Sinatra recorded most of his music, in Studio A. The building isn’t open to the public but tours are occasionally available.


Stop by Sy Devore, the famed ‘tailor to the stars,’ whose clientele included Bing Crosby, Spencer Tracy, John Wayne, Rock Hudson, Richard Burton, and Nat King Cole. Devore even outfitted Presidents John F. Kennedy and Lyndon Johnson and later kitted out George Clooney and Brad Pitt in Ocean’s 11. If you want a suit like Sinatra, ask for your lapels to be exactly 2 1/4” wide.


Miami

Miami, and the iconic Fontainebleau Hotel, featured prominently in Sinatra’s life. The Ratpack performed here on a regular basis, he shot three movies here (A Hole in the Head, Tony Rome, and Lady in Cement), and it’s where Frank allegedly first met crime boss Sam Giancana in 1958 (at least, that’s what he told the FBI). He also stayed here that same year with short-lived flame Lauren Bacall.

Frank Sinatra at the Fountainebleau Hotel, Miami
Sinatra in the bar of the Fountainebleau Hotel with owners Bernice and Ben Novack - photo courtesy of the estate of Bernice and Ben Novak

The Fontainebleau was the location of Frank’s fateful introduction between good time girl Judith Campbell and Giancana, which became big news when it was revealed that Campbell was Giancana’s lover at the same time that she was having an affair with John F Kennedy. In files released after his death, the FBI reported that Miami Police department received a bomb threat in early 1966 aimed at Sinatra during one of his performances at the hotel, which threatened that some one would throw a hand grenade at him while he performed on stage.


Art Deco gem the Cardozo Hotel featured in A Hole in the Head (1959).


New York

“New York New York, it’s a wonderful town!” So sang Francis Albert Sinatra in the 1949 musical On the Town. He was born in Hoboken, across the water from Manhattan, and maintained a close connection to the city throughout his life.

Food

In his old Hoboken neighbourhood, you’ll find Leo’s Grandezvous, established in 1936, and one of Sinatra’s preferred places to eat in New York. At nearby Dom’s Bakery, you can still pick-up Sinatra’s favourite loaf. Dom was known to ship his bread to California for Frank, Dean Martin and Lucille Ball to enjoy a slice of his mouth-watering bread. Frank was also partial to the bread at Parisi bakery in Little Italy; he was known to have it flown over to his estate in Palm Springs.


Frank Sinatra’s two favourite restaurants in New York were Jilly’s and Patsy’s. Sinatra ate and drank at Jilly’s at least 3 or 4 nights a week whenever he was in town. Jilly’s specialized in Cantonese food. Regulars thought Howie, the chef, made the best barbecued pork in the city. Jilly’s closed in the 1980’s and was re-opened as Russian Samovar. The interior is still much the same, and they even have the same wooden bar that Frank propped up all those years ago. There are also regular jazz and piano nights that often include Sinatra’s music, to accompany your caviar.

Jilly's Restaurant New York original menu
Sinatra's favourite restaurant Jilly's, New York, original menu

Italian restaurant Patsy’s, has been in the same family since the 1940s and still plays host to Sinatra's relatives whenever they are in town. It was a home from home for Sinatra, he was very friendly with the family and was known to help in the kitchen and answer the phones when they were busy. His favourite dishes were Clams Posillipo, Chicken Picatta and Veal Cutlets. His favourite dessert was Pasticiotto, a lemon pie he would have with extra ice-cream. Anything he did not finish; he’d take home for breakfast the next day.


Drink

Happily, many of Frank’s favourite watering holes are in NYC are still open in some form or another today; former speakeasy the 21 Club, P.J. Clarke’s on Third Avenue (virtually unchanged since it opened in 1884 – Sinatra’s table was table 20, marked today with a photo of Old Blue Eyes), and the historic Beekman Tower, a spot he'd visit after his shows, often putting on impromptu performances for fellow drinkers. Harlem Jazz bar Birdland was also a favourite and was also popular with Frank’s ex-wife Ava Gardner and alleged ex-lovers Marilyn Monroe and Marlene Dietrich.

Image courtesy of New York Post

What was Frank Sinatra’s favourite drink? When he was not drinking his famous Jack Daniels over ice, he was known to drank Bolla Soave wine, known for its melon-and-orange-zest flavours, as well as its ability to improve with age.


Hotels

Sinatra stayed in Cole Porter’s favourite suite at the Waldorf Astoria. In 1947, his FBI file reports that he had an engagement with a prostitute in room 5H at 2.30am…


Things to do

Hoboken Museum has created a self-guided walking tour of Frank’s old neighbourhood, including the houses he once lived in and the church where he was baptized and where he married his first wife Nancy.


Sinatra Saturdays at The Carnegie Club offers a Sinatra tribute act in its stylish Cocktail and Cigar Lounge.


At Point Pleasant Beach in New Jersey, you’ll find the Sinatra House, owned by a former Sony executive who was a huge Sinatra fan. His tunes blast from speakers across the Boardwalk.


Palm Springs

When Frank hit the big time, he chose the desert city of Palm Springs to put down roots. He commissioned renowned architect E. Stewart Williams to design his modernist his home Twin Pines, complete with grand-piano-shaped pool. Stays cost from $2,500 per night.


Twin Palms Frank Sinatra House exterior, Palm Springs
The piani-shaped pool at Sinatra's Twin Palms House in Palm Springs

The Palm Springs Historical Society offers a Sinatra walking tour every Friday morning.


When not partying at Sinatra’s pad (which witnessed A LOT of fights, according to ex-wife Ava Gardner) Sinatra and his friends could often be found hanging out at the Riviera Palm Springs hotel, which has since morphed into the Margaritaville Resort.


Melvyn’s Restaurant at the Ingleside Inn was one of the top places to dine in Palm Springs. Sinatra held his pre-wedding lunch here in 1976.


Johnny Costa’s Ristorante has been a favourite with locals for years. Sinatra’s favourite dishes were – the Steak Sinatra and Linguine Clams – which are still on the menu. Sinatra loved Johnny’s cooking; he was the former sous chef at the legendary Villa Capri in Los Angeles, owned by Frank’s good friend Patsy D’Amore.


If you don't have plans to go to Palm Springs anytime soon, have a go at making Steak Sinatra at home:


Spain

Hotel Pez Espada in Torremolinos Spain was the hotel that set off the hotel explosion on the Costa del Sol in the mid-1960s. Sinatra got into a fight in the hotel bar and had to pay a fine.

In April 1956, outdoor shooting started for Sinatra's movie "The Pride and The Passion" (starring Cary Grant alongside FS) in a spot called El Hoyo de Pinares outside Madrid. Sinatra arrived in on set on April 17 1956, and for the weeks of shooting, took residence in Madrid at The Castellana Hilton, which is now the Intercontinental Hotel. He stayed here a few times with Ava Gardner too, before she moved to the city. Check out the Ava Gardner Travel Guide for more Spain-set Hollywood gossip.


The still stylish Chicote Cocktail Bar was one of Gardner’s favourite drinking places in Madrid and she brought Sinatra here several times. The bar earned a place in Ernest Hemingway’s short story, The Denunciation.


Frank Sinatra and Ava Gardner in Tossa Del Mar
Frank and Ava Gardner during filming of Pandora and the Flying Dutchman (1951) with Tossa Del Mar Bay in the background

Sinatra came to visit Ava on the set of the exquisite Pandora and the Flying Dutchman (1951) in Tossa Del Mar and they stayed together at Hotel Diana, which is still a delightfully romantic boutique hotel by the beach.


UK

Sinatra performed on stage in London many times throughout his career, including at the iconic London Palladium with wife Ava Gardner watching from the front row. His hotel of choice in the English capital was The Savoy.


He often lunched with Roger Moore at the exclusive London club Annabel’s; on one such occasion the two men took out Sinatra’s new wife, Mia Farrow, and she revealed that her and Frank had been watching The Saint in bed at The Savoy Hotel.


Resources

Sinatra: The Life - Anthony Summers and Robbyn Swan

Frank Sinatra FBI Report – Internet Archive

Mr S: My Life with Frank Sinatra – George Jacobs

Frank Sinatra and popular culture: essays on an American icon

Patsy's Cookbook - Salvatore Scognamillo

When the Chairman Took the Thrown in Monte Carlo – U Discover Music

Frank Sinatra’s Favourite Haunts – Esquire Magazine

Ava Gardner - Lee Server

Baby I Don’t Care: Biography of Robert Mitchum by Lee Server

The Dark Heart of Hollywood – Douglas Thompson

My Word is My Bond – Roger Moore

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