A frosty glass, a slice of pineapple perched on the rim, and a little umbrella swaying gently. A moment that truly encapsulates the beginning of your holiday is when a bartender expertly sets down your Piña Colada at the bar, topped with creamy coconut, smooth rum, and the promise of sun-soaked days ahead.

However, the holiday cocktail represents more than just a signal to unwind; it serves as a definitive symbol of location. Be it an Aperol spritz enjoyed while people-watching in a sunny square, an Irish coffee savored on a chilly evening in Cork, a dry Martini indulged in at a posh London hotel bar, or a frosty daiquiri that refreshes you on a sweltering afternoon in Havana – the world’s iconic cocktails are deeply intertwined with the essence of our beloved destinations.

As the latest champion is announced at the World’s 50 Best Bars awards in Madrid (this year it’s Handshake Speakeasy in Mexico City, for those curious), let’s celebrate the significant role played by the humble holiday cocktail by exploring the quirky, fascinating, and sometimes outrageous history of 30 cocktails that have truly made their mark.

1. Manhattan: New York City, USA

2. Singapore sling: Singapore

3. Pisco sour: Lima, Peru

4. Daiquiri: Santiago De Cuba, Cuba

5. Caipirinha: São Paulo, Brazil

6. Espresso martini: London, UK

7. Mai tai: California, USA

8. Old fashioned: Kentucky, USA

9. Vesper martini: London, UK

10. Bloody Mary: Paris, France

11. Cosmopolitan: Florida, USA

12. Irish coffee: County Clare, Ireland

13. Grasshopper: New Orleans, USA

14. Margarita: Tequila, Mexico

15. Negroni sbagliato: Milan, Italy

16. Negroni: Florence, Italy

17. Sazerac: New Orleans, USA

18. Hanky panky: London, UK

19. Mojito: Havana, Cuba

20. Mint julep: The Deep South, USA

21. Bellini: Venice, Italy

22. Penicillin: New York, USA

23.Aperol spritz: Veneto Region, Italy

24. Painkiller: British Virgin Islands

25. French 75: Paris, France

26. Whisky highball: Japan

27. Piña colada: Puerto Rico

28. Vieux carre: New Orleans, USA

29. Ferroviario: Buenos Aires, Argentina

30. Jungle bird: Kuala Lumpur, Malaysia

American whiskey, vermouth

The exact origins of the Manhattan cocktail are often debated; one popular story suggests it was crafted in the 1870s at the Manhattan Club in New York for a banquet that was hosted by Churchill’s mother. Regardless of its true beginnings, the Manhattan has cemented its place as one of the most iconic dark-spirit cocktails in the world.

The Manhattan Club officially closed its doors in 1979, but the bar at 60th-floor Manhatta in NYC’s Financial District acts as a remarkable alternative, offering breathtaking views of lower Manhattan (manhattarestaurant.com; $23/£17.60).

The Beekman offers double rooms starting at £648.

Discover more cocktail ideas in our expert guide to the best bars in New York.

The ingredients include gin, Benedictine, cherry liqueur, dry curaçao, grenadine, pineapple and lime juice, along with bitters.

This vibrant, pinkish drink was crafted around 1915 by Ngiam Tong Boon, a bartender at the Long Bar in the original Raffles Hotel. Its creation aimed to deceive critics at a time when women were discouraged from openly enjoying traditional alcoholic drinks in public.

The Long Bar at Raffles is famous for selling around 1,200 Singapore Slings each day, which certainly indicates they have a successful formula (raffles.com; £23).

Raffles Singapore offers rooms starting from £884.

The ingredients include Pisco, lime juice, egg whites, sugar syrup, and aromatic bitters.

Both Peru and Chile assert that they are the rightful home of the Pisco Sour. However, this iconic cocktail – a variation of the traditional whiskey sour – was created by American bartender Victor Vaughen Morris in Peru back in 1904, prompted by local celebrations that led to a whiskey shortage.

Country Club Lima Hotel’s English Bar is widely regarded as the place to find the finest Pisco Sour in Lima.

Country Club Lima Hotel offers accommodations starting at £237.

Ingredients include rum, lime juice, and sugar.

The Daiquiri, another cocktail shrouded in debate regarding its origins, is generally believed to be named after an iron mine located near Santiago de Cuba, with its creation dating back to the late 1800s. However, it wasn’t until the 1940s, during a time of rationing that limited the availability of whiskey and vodka, that the cocktail – alongside rum – truly gained popularity.

The historic Floridita in Havana is known as the birthplace of the frozen daiquiri, where Ernest Hemingway devised his stronger version, the Papa Doble, priced at $6.25/£4.80.

The luxurious Gran Hotel Manzana Kempinski La Habana offers accommodations starting from £295.

Cachaça, sugar, lime

In the 19th century, farmers in the vicinity of São Paulo pioneered a mixture of the readily available sugarcane and galeguinho, a fruit reminiscent of lemons, along with Cachaça, Brazil’s most popular distilled beverage. This concoction not only served as a treatment during the Spanish flu pandemic but continues to be a favored home remedy for colds.

Bar Veloso in São Paulo is famous for its Caipirinhas and flavorful coxinhas (Brazilian chicken croquettes) priced at £2.75.

Hotel Emiliano offers double rooms starting at £458.

The drink features vodka, coffee liqueur, espresso, and sugar.

Originating in London, this cocktail began as the “Vodka Espresso,” served short over ice, topped with the iconic three-coffee bean garnish. It was invented by British mixologist Dick Bradsell at the Soho Brasserie in 1983, inspired by a supermodel’s request for a beverage that would “wake me up and f – – k me up.”

Although the Soho Brasserie has closed its doors, you can still spot the old sign from the venue and enjoy a wonderful rendition of this modern classic at the nearby Bar Swift for £14.

The charming Kettner’s offers doubles starting from £285.

Explore the best places for a drink in London with our comprehensive guide to the best bars and pubs in the city.

This delightful drink combines rums, dry curacao, orgeat syrup, lime juice, and sugar syrup.

This classic Tiki cocktail rose to fame thanks to the now-iconic Polynesian-themed Trader Vic’s restaurants during the Tiki bar craze of the 1940s and 50s. An appearance in Elvis’s 1961 film, Blue Hawaii, only added to its popularity. Today, it remains a favorite among those who enjoy strong and sweet beverages.

While many of Trader Vic’s famed locations (such as the one at London’s Hilton Park Lane) have since closed, Athens’s Tiki sanctuary Baba Au Rum is known for serving what many consider to be Europe’s best Mai Tai. They craft this drink using the original recipes from Trader Vic and feature an award-winning selection of spirits. Guests can enjoy it under the watchful eye of Mr. Presley himself—at least in poster form—for €11/£9.20.

The NEW Hotel in Athens offers rooms starting from £186.

The drink is made with American whiskey, sugar, and Angostura bitters.

Various claims surround the origins of this cocktail, but the most prominent story attributes its creation to a bartender at the Pendennis, a gentlemen’s club in Louisville, Kentucky. According to legend, he crafted the drink in the 1890s at the request of Colonel James E. Pepper, a distinguished bourbon distiller from Kentucky, who later took the recipe to New York. Of course, the truth of this tale can vary depending on whom you ask.

One of the finest versions can be found at Death & Co in New York City, a renowned cocktail establishment that has published two books dedicated to the art of classic cocktails, justifying its price of $17/£13.

If you’re looking to indulge, The Mercer offers doubles starting at £815.

The ingredients include gin, vodka, and Kina Lillet.

The iconic drink associated with 007 makes an appearance in Ian Fleming’s inaugural Bond novel, Casino Royale, where the famous line “shaken, not stirred” originates. This signature cocktail was reportedly inspired by Fleming’s visits to Dukes Bar located in London.

Dukes Bar continues to serve the Vesper but offers a more intense, unshaken variant that is chilled to near-freezing temperatures and served without any dilution. It’s definitely not for the timid, priced at £25.

Dukes London provides accommodations starting from £414.

The cocktail is composed of vodka, tomato juice, lemon juice, Tabasco, salt, and pepper.

A well-known gathering spot from the 1920s for adventurous American expats (who introduced canned tomato juice) and Russians escaping revolution (who brought vodka), it is no surprise that Harry’s New York Bar in Paris became the birthplace of this iconic brunch cocktail.

Visit the original location at Harry’s New York Bar (€14/£11.70).

Ritz Paris offers accommodations starting from £1,720.

Explore more of the finest beverages in Paris with our expert guide to the city’s best cafes and bars.

Citron vodka, cranberry juice, triple sec, lime juice

The Cosmo boasts an intriguing history, featuring a rise to fame during the 1970s among the gay communities in Massachusetts and the trendy singles bars of San Francisco. Its comeback in the late 90s was largely influenced by endorsements from celebrities like Madonna and the iconic character Carrie Bradshaw from Sex and the City. However, it was Cheryl Cook, a bartender at the now-closed Strand Restaurant in Miami’s South Beach, who elegantly served it in a Martini glass—catering to the desire of patrons who wanted to be seen with that classy drink. For that reason, we credit her with its rise to prominence.

The Strand may no longer be around, but you can still channel your inner star by visiting Miami’s Carbone ($22/£17).

Alternatively, the Setai in Miami Beach offers accommodations starting from £688.

Irish whiskey, coffee, sugar, cream

While variations of this delightful beverage were enjoyed in Central European coffee houses as early as the mid-1800s, it was in 1943 that the drink truly captured hearts. A chef at Foynes Air Base, the flying boat terminal near what is now Shannon Airport, started integrating whiskey into coffee for cold and weary travelers, and it quickly gained popularity.

By the 1950s, Irish coffee had cemented its place in American culture, particularly in New York. Today, The Dead Rabbit is celebrated for crafting arguably the finest version of this drink, priced at $16.

If you’re looking for a place to stay, 33 Hotel New York City in Seaport offers accommodations starting from £428.

Crème de menthe, crème de cacao

This striking green dessert beverage originates from the Creole culture of New Orleans, with its official creation credited to Philip Guichet, the proprietor of Tujague’s restaurant in the French Quarter, back in 1918. By the 1960s, it had garnered popularity throughout the American South and has since become a nostalgic classic served in establishments globally.

Tujague’s continues to stand as a beloved landmark in New Orleans, with the Grasshopper cocktail being its most popular offering ($12/£9.20).

The Windsor Court also offers luxurious accommodations starting from £378.

Tequila, triple sec, lime juice, sugar

The story behind the world’s most famed tequila cocktail is somewhat elusive. Some accounts indicate that the creation can be attributed to Carlos “Danny” Herrera, who was asked to craft a tequila drink for Marjorie King, a star of the Ziegfeld Follies who had an allergy to most other spirits, at his establishment, Rancho La Gloria, located near Tequila, in 1938.

This iconic drink has undergone numerous transformations, but if you’re looking for something unique, consider trying the Margarita al Pastor at a bar in Mexico City called Licorería Limantour. This special cocktail features a blend of tequila, triple sec, lime, and an intriguing “taco mix” composed of pineapple, coriander, and chilies, priced at £5.

If you’re planning a visit, Hotel Geneve in Mexico City offers double rooms starting at £93.

Campari, vermouth, Prosecco

The slightly humorous name of this drink, which means “mistake,” pays tribute to its origin story. In 1972, bartender Mirko Stochetto at Bar Basso was preparing a Negroni but accidentally reached for a bottle of Prosecco instead of gin. The outcome was a lighter, longer, and more refreshing beverage that quickly gained popularity among patrons. Initially served in a whimsically oversized wine glass, you can still order it that way today.

Currently managed by his son, Maurizio, Bar Basso continues to serve this delightful mistake for €10/£8.40.

Château Montfort offers doubles starting from £451.

Explore more of the finest bars in Milan by checking out our expert guide to the best nightlife in the city.

Gin, Campari, vermouth

Considered one of the most iconic cocktails, this Italian classic is believed to have originated at Florence’s Caffè Casoni in 1919. The story goes that Count Camillo Negroni requested bartender Fosco Scarselli to replace the soda in his Americano with gin, resulting in a stronger and shorter drink.

Over the years, Caffè Casoni has transformed into Caffè Giacosa, where the Negroni is celebrated with almost reverent admiration (0039 055 202 1617; €15/£12.50).

The hotel La Gemma offers double rooms starting from £628.

If you’re looking for more inspiration for your visit to Florence, check out our expert guide to the best bars and nightlife.

Ingredients include American whiskey or cognac, absinthe, sugar, and Peychaud’s bitters.

This cocktail, known as the official drink of New Orleans and often regarded as America’s oldest cocktail, was originally crafted with cognac. It was supposedly created by pharmacist Antoine Amédée Peychaud in the mid-1800s. However, the cognac was replaced with whiskey after the phylloxera epidemic of the 1880s wiped out grapevines, leading to the birth of a true classic.

The Sazerac Bar at the Roosevelt Hotel has been significant in New Orleans’ drinking culture, being the first establishment in the city to welcome women when a group of them took a stand at the bar in 1949 ($22/£17).

The Roosevelt Hotel offers accommodations starting at £388.

Ingredients: Gin, vermouth, Fernet Branca

This creation is attributed to Ada Coleman, who was the head bartender at the Savoy’s American Bar back in 1903, making her mark in an overwhelmingly male-dominated field. She crafted the cocktail for Sir Charles Hawtrey, a regular patron and a known cocktail enthusiast. After enjoying the drink, Hawtrey famously remarked, “By Jove! That is the real hanky-panky,” thus giving her drink its memorable name.

The American Bar is still the finest spot to enjoy Ada’s celebrated cocktail (£20).

The Savoy offers doubles starting from £900.

Ingredients include rum, lime juice, mint, sugar, and soda.

Some believe that we owe this delightful drink to none other than Sir Francis Drake, or at least to its 16th-century brandy-based predecessor, the “El Draque”. Lime juice was recognized as an effective remedy for scurvy and dysentery, and it seems that the addition of alcohol enhanced its popularity among his crew. With all its components native to Cuba, this drink has become a key cultural symbol of the island.

La Bodeguita del Medio, a favorite haunt of Hemingway, is located in Havana and is widely recognized as the official birthplace of the Mojito (0053 7 8671374; £4).

Hotel Nacional de Cuba offers double rooms starting at £102.

Bourbon, sugar, mint

This mix of mint and bourbon, once thought to have medicinal properties in the Middle East—its name deriving from the Persian word “gulab”, meaning flower water—originated in the American South. It was typically served in punch bowls at social events throughout the 18th century. However, it wasn’t until the 1930s, when it became the official drink of the Kentucky Derby, that it was presented in its now-iconic metal tumbler filled with crushed ice.

Tied to the tradition of the Kentucky Derby, Louisville’s Brown Hotel is well-known for serving this refreshing drink ($14/£11).

Rooms at the Brown Hotel start at £174.

Prosecco, peach puree

This delightful concoction was created in the 1940s by Giuseppe Cipriani at Harry’s Bar in Venice. The cocktail’s name was inspired by the distinctive pink color of the peach puree, which evoked the work of 15th-century Venetian painter Giovanni Bellini (though which artwork it resembles remains a mystery).

Harry’s Bar remains a timeless favorite in Venice. While the drink has gained global popularity, it is best enjoyed here (€22/£19).

At Baglioni Hotel Luna, rooms start from £801 for a double.

Explore the finest bars in Venice in our guide to Venice nightlife.

Ingredients include blended Scotch, lemon juice, honey ginger syrup, and a single malt float.

Originating from Sam Ross at Milk & Honey in New York during the speakeasy revival of the mid-2000s, this cocktail remains one of the few drinks introduced after the turn of the millennium that continues to appear on bar menus across the globe.

The original location of Milk & Honey is now home to the renowned Attaboy bar, co-owned by Sam Ross, where the Penicillin cocktail remains a favorite among patrons, priced at $20/£15.30.

For accommodations, citizenM New York Bowery offers rooms starting from £121.

Aperol, Prosecco, soda

The iconic spritz that won over the globe (its name is synonymous with a vibrant orange hue) is not merely a modern-day concoction. The Aperol brand was established by brothers Luigi and Silvio Barbieri back in 1919. However, it wasn’t until the 1950s that the authentic spritz recipe came to life – crafted as a light, pre-dinner beverage – which quickly became a sensation. Jump ahead to the marketing boom of the 2000s, and this delightfully easy-to-enjoy bubbly and bittersweet drink solidified its status in the cocktail elite, becoming a staple on sun-drenched patios worldwide.

In Venice, the renowned Terrazza Aperol offers the beloved spritz throughout the day (€7/£6).

Hotel Villa Franceschi features stays starting from £246.

Rum, coconut cream, orange, and pineapple juice

The Soggy Dollar Bar, established by George and Marie Myrick on Jost Van Dyke island in 1970, has become a beloved Caribbean landmark. In its early days, visitors had to wade through the water to reach the bar, giving rise to its unique name. Perhaps its most notable contribution to cocktail culture is the creation of the ultimate desert-island drink, which is rumored to be named after a local bush rather than the effects of its ample rum content.

The Soggy Dollar is still operating and now accepts card payments, ensuring that your cash remains secure ($9/£6.90).

The Hideout offers accommodations starting at £650 for a two-night stay.

Ingredients include gin, lemon juice, sugar, and Champagne.

Originating in 1915 at Harry’s New York Bar in Paris, the sophisticated French 75, also known as Soixante Quinze, derives its name from the French 75mm field gun. You may wonder about the link; the answer lies in their shared potency.

Harry’s New York Bar is undoubtedly the best venue in Paris—and indeed the entire globe—to savor this cocktail (€16/£13).

For those looking for accommodation, Hôtel Fauchon offers rooms starting from £449.

Japanese whisky and soda

Although Japan did not create the whisky soda, the demand for affordable and easy-to-make drinks after the Second World War, along with the influence of whisky giant Suntory, led to bars offering highballs on tap and stores selling them in cans. This drink has since become an integral part of Japanese drinking culture.

You can find high-quality canned highballs at nearly every convenience store in Japan. For a unique experience, visit one of Star Bar’s four branches and enjoy their exquisite “Ninja Ice” variation (starbar.jp; £12).

The Tokyo EDITION offers stays starting from £840 for doubles.

Ingredients include rum, coconut cream, and fresh pineapple.

While tales of an 18th-century pirate concocting the Piña Colada to inspire his crew are enticing, the true origins of the drink are credited to bartender Ramón “Monchito” Marrero. In 1954, he aimed to craft a cocktail that truly reflected the essence of Puerto Rico during his tenure at the Beachcomber Bar in the Caribe Hilton Hotel.

Although the hotel still stands, the bar has since vanished. For a taste of the Piña Colada, make your way to San Juan’s Barrachina, which also lays claim to this iconic cocktail ($9/£6.90).

You can find accommodations at the Caribe Hilton, with rates starting from £290.

The ingredients include rye whiskey, cognac, benedictine, sweet vermouth, Angostura bitters, and Peychaud’s bitters.

In 1937, Walter Bergeron, the head bartender at the Carousel Bar located in Hotel Monteleone, crafted a drink that serves as a heartfelt homage to its surroundings. The drink’s name, which translates to “old square,” pays respect to the iconic French Quarter. Each ingredient reflects the diverse cultural tapestry of the area, featuring cognac and Benedictine to honor the French, rye whiskey representing the Americans, sweet vermouth for the Italians, and bitters that pay tribute to the Caribbean heritage.

The Carousel Bar and Lounge continues to serve this robust cocktail from New Orleans at a price of $21/£16.

At Hotel Monteleone, accommodations start at £321 for double rooms.

Fernet, vermouth, soda

A long-standing element of Argentinian drinking traditions, largely due to the popularity of fernet (a complex and aromatic bitter liqueur from Italy), this traditional cocktail can be found in a variety of venues, from casual all-day cantinas to upscale bars.

Throughout Argentina, this refreshing mix is readily available, but it’s at Buenos Aires’ Tres Monos where you’ll discover a particularly delightful version that features strawberry, rosemary, and thyme for only $8/£6.

For accommodations, Mine Hotel offers rates starting from £119.

The drink consists of rum, Campari, pineapple juice, lime juice, and sugar syrup.

The Jungle Bird cocktail, conceived in the 1970s by Jeffrey Ong, who worked as a manager at the Aviary Bar in Kuala Lumpur Hilton, was inspired by the vibrant tropical birds that adorned the hotel’s poolside.

The Aviary Bar remains popular today, with its signature Jungle Bird cocktail still delivering a delightful experience at £12.

You can stay at Hilton Kuala Lumpur with room rates starting from £325.

Broaden your horizons with award-winning British journalism. Try The Telegraph free for 3 months with unlimited access to our award-winning website, exclusive app, money-saving offers and more.