Sleep Like a King, Drink Like a Legend: 7 Stays Every Gentleman Must Book

There is a distinct difference between a hotel that merely gives you a place to lay your head and an institution that actively improves your life while you’re under its roof.

The world is full of perfectly fine five-star properties with thread counts higher than a diploma and threadbare personalities to match. But the following seven hotels are different. They are architectural icons, historic playgrounds, and living masterclasses in how hospitality was meant to be conducted.

If you’re looking to upgrade your bucket list—or give your affiliate travel booking links a workout on high-ticket reservations — here are seven legendary properties every gentleman should experience at least once.

1. Raffles Hotel — Singapore

The Vibe: Old-world tropical grandeur where history was literally made at the bar.

First opened in 1887 by the Armenian Sarkies Brothers, Raffles is the undisputed grand dame of Far East hospitality. Joseph Conrad, Ernest Hemingway, and Rudyard Kipling all logged time here, giving the hotel an unmatched literary legacy.

Despite a comprehensive restoration that brought state-of-the-art modern comforts to every suite, the property retains its signature colonial architecture, teak verandas, and white-gloved butler service. A stop at the Long Bar to sip a Singapore Sling—and toss peanut shells onto the floorboards, a legal exception to Singapore’s strict anti-littering laws—is non-negotiable.

• The Standout Feature: 100% suite accommodations with dedicated 24-hour butler service.

• Pro Tip: Request a suite on the Palm Garden Wing for maximum privacy and quiet evening drinks on the verandah.

2.The Savoy — London

The Ritual: Ordering a timeless classic at the American Bar, one of the world’s most essential cocktail rooms since the 1890s.

The Savoy understands performance. Sitting on the Strand, overlooking the Thames, it has long been associated with theatre, politics, cocktails, and the old machinery of London glamour. Winston Churchill, Frank Sinatra, and Marilyn Monroe all frequented these halls, giving the property a legendary status in British hospitality. Despite modern updates throughout its Art Deco and Edwardian suites, the hotel retains its crisp British heritage, impeccably tailored staff, and signature discreet service. This is where a gentleman should sit properly, enjoy an impeccably balanced drink, and remember that London always rewards those who know how to behave in a room.

• The Standout Feature: The world-famous American Bar and stunning Edwardian and Art Deco suites directly overlooking the River Thames.

• Pro Tip: Request a high-floor Thames River View Suite to take in the skyline without any street noise from the Strand below.

3. Ritz Paris — Paris

The Ritual: Ordering a custom cocktail at Bar Hemingway, surrounded by classic leather armchairs and decades of literary history.

Situated on the iconic Place Vendôme, The Ritz Paris is the ultimate symbol of French elegance and timeless luxury. Coco Chanel called it home for over thirty years, F. Scott Fitzgerald frequented its halls, and Ernest Hemingway famously "liberated" its bar at the end of World War II. Following a grand multi-million-dollar restoration, the property seamlessly blends historic grandeur—gilded mirrors, plush velvet, and private garden courtyards—with ultra-modern comfort. It remains the absolute gold standard for how a gentleman ought to experience the City of Light.

• The Standout Feature: Unrivalled historic prestige on Place Vendôme, complete with the legendary Bar Hemingway and the world’s first Ritz-designed spa.

• Pro Tip: Head down to Bar Hemingway right when it opens at 5:00 PM to secure one of the few prized seats without an extended wait.

Editor’s Travel Note: The Lobby Test

If you’re stepping into spaces of this calibre, your gear needs to match the architecture. Flimsy plastic sunglasses and generic accessories won't cut it when you're ordering a cocktail from a master bartender. Before you book your next flight, elevate your travel uniform with a pair of premium, uniquely grained frames from our [New Arrivals Collection]—engineered to look sharp from a morning round on the course to a sunset drink on the patio.

4. The Beverly Hills Hotel — Los Angeles, USA

The Vibe: Old-Hollywood royalty nestled inside twelve acres of tropical palms.

Known affectionately as "The Pink Palace," The Beverly Hills Hotel existed before the city itself was built around it. For over a century, its signature banana-leaf wallpaper, striped sun loungers, and secluded garden bungalows have served as the unofficial boardroom for film studio executives, rock stars, and jet-setters.

Bungalow 5 was Howard Hughes’ home for years; Bungalow 1A was tailored for Frank Sinatra. Ordering a McCarthy Salad at the Polo Lounge while eavesdropping on movie deals isn't a cliché here—it’s simply the standard lunch schedule.

• The Standout Feature: Historic private bungalows offering total seclusion right off Sunset Boulevard.

• Pro Tip: Reserve a poolside cabana early in the morning to lock in prime real estate at the iconic pool.

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5. The Gritti Palace — Venice

The Ritual: Sipping a classic Negroni on the Riva Pisani Gritti terrace while watching gondolas navigate the Grand Canal.

Originally built in 1475 as the residence of the Doge of Venice, The Gritti Palace is an unmatched masterclass in Venetian Gothic architecture and royal hospitality. Set directly along the Grand Canal opposite the Santa Maria della Salute church, this historic palazzo has hosted everyone from Ernest Hemingway and Peggy Guggenheim to world leaders and cinema icons. Following an extensive restoration, the palace preserves its precious antique furniture, hand-blown Murano glass chandeliers, and exquisite Rubelli silks while providing state-of-the-art modern comforts. It offers an intimate, highly refined sanctuary in the heart of Venice.

• The Standout Feature: An unbeatable prime position on the Grand Canal featuring private boat dock access and panoramic water views.

• Pro Tip: Reserve a table on the Canal Terrace at sunset for aperitivo to experience the lights reflecting off the Grand Canal at its quietest and most breathtaking.

6. Aman Tokyo — Tokyo

The Vibe: High-altitude zen sanctuary soaring above the chaos of Otemachi.

Occupying the top six floors of the Otemachi Tower, Aman Tokyo redefined what a modern urban hotel could be. Designed by Kerry Hill, the sanctuary draws inspiration from traditional Japanese residential architecture—utilizing basalt stone, Shoji screens, and camphor wood to create a vast, light-filled haven high above the city skyline.

After a day navigating Tokyo’s dense neighborhoods, returning to Aman’s soaring 30-meter-high lobby feels like entering a cathedral of calm. The deep granite furo soaking tubs in every room offer floor-to-ceiling views of the Imperial Palace Gardens and Mount Fuji on clear mornings.

• The Standout Feature: The breathtaking 84-foot indoor pool overlooking the Tokyo skyline.

• Pro Tip: Spend an evening at the hotel's 8-seat omakase counter, Musashi by Aman, for some of the best sushi in the city.

7. Badrutt’s Palace — St. Moritz

The Ritual: Drinking a vintage scotch by the grand open fireplace in Le Grand Hall, surrounded by alpine luxury and high-society history.

Perched high in the Swiss Alps overlooking Lake St. Moritz, Badrutt’s Palace is the birthplace of alpine winter tourism and the absolute apex of mountain glamour. Opened in 1896 by Johannes Badrutt, this fairy-tale fortress has long served as the winter playground for royalty, Hollywood icons, and international tycoons. Alfred Hitchcock was a frequent guest, famously drawing inspiration for The Birds right on the property. Despite its icy mountain backdrop, the palace exudes warmth with its lavish timber paneling, grand gothic arches, and white-gloved service. It remains the ultimate winter sanctuary for the discerning gentleman.

• The Standout Feature: Legendary alpine views over Lake St. Moritz coupled with an infinity pool carved directly into the mountain rock.

• Pro Tip: Book a Lake View Junior Suite on an upper floor during the winter season to watch snow polo matches directly on the frozen lake from your private balcony.

Disclaimer: Gentlemen's Digest only recommends properties we believe deliver exceptional experiences.

Disclaimer: Room service at 3:00 AM in any of these establishments may result in a checkout bill that resembles a modest used car invoice. Enjoy responsibly.