The city sprawls out below; its lights blooming like hothouse flowers amid the constant beat of the DJ. There’s a whir of excitement as conversations unravel, secrets are whispered, and deals are made over drinks. Somehow the air feels different up here, poised as we are at the intersection between metropolis and stars.
This is the rooftop life. From the vantage point of a sky-high lounge, it feels like an endless summer with the stresses of daily life just a bit further away.
Grab your shades by day and your favorite puros and journey with us from swanky New York terraces to tropical Bali oases, as we take happy hour and cool-view nights to new heights. You have our permission to wear your sunglasses at night as well–as in Cory Hart’s 1983 hit “I Wear My Sunglasses at Night.”
MILAN – Ceresio 7
If old-school American cocktails mixed with Italian flair seem like they might be your thing, head to Ceresio 7 on the fourth floor of a historic 1930s-era building in the Garibaldi district. From the moment you step out onto the open-air terrace, it’ll be obvious that the space was designed with Milan’s fashion-forward in mind.
Dsquared2, the designer duo behind the concept partnered up with the architectural firm Storage to create the one of a kind space, which features two pools, a retro-sleek bar, a restaurant, and a dedicated cigar lounge, all overlooking the glammest of Italian cities. Order up an aperitivo. We recommend “Different Habits”–a killer combo of Macallan 12-year-old whisky, rooibos tea, IPA and honey reduction, and Oloroso sherry, and retreat to the dedicated cigar lounge for a puff in Milanese style.
Dress code: Fashion week chic meets pool party. Anything from Dsquared’s latest collection. ceresio7.com
MUMBAI – AER at Four Seasons
There’s no place quite like India when it comes to stimulating the senses. Escape the clamor and humidity in the city below and head up to the 34th floor of the Four Seasons hotel in Mumbai’s commercial hub. AER guests have their choice of sea views or city sparkle depending on which direction they turn. Sure, it’s got all the ingredients for a great rooftop terrace–incredible views, a DJ pumping beats into the night air, cocktails a plenty. But AER goes one step further with an impressive array of whiskeys and cigars. Choose from Single-Malt, Blended Scotch, Irish, American, or Asian whisky or pick your poison from the cocktail and mocktail list. More of a beer dude? No problem. Order three beer buckets and get one free, while tucking into the cigar menu, which features Cohiba Robustos, Montecristo No. 1-5, Romeo y Julieta Churchills, Petit Julieta and a selection of Partagas. All good reasons for why AER is the only bar in India to make Asia’s Top 50 Bars list.
Dress Code: Smart casual – light luxury. fourseasons.com/mumbai
LONDON – Boisdale of Canary Wharf
While this isn’t the highest spot in London, it’s certainly a favorite terrace for cigar lovers. The vibe is Scottish highlands meets British library luxe. There are three Boisdales throughout the city, but their Canary Wharf location is a stand-out for its glamorous polished wood bar and extensive selection of some of the world’s finest brown liqueurs. The bar also has a walk-in humidor, a cigar library where guests can sample the wares before making a purchase, an oyster and caviar bar and regular live music acts. Check out the collection of vintage Cubans in the library and then head to the heated cigar terrace, where you can wrap yourself in a tartan blanket, throw down some Scotch and take in the bonnie surroundings.
*If you’ve got your heart set on a higher terrace, head to Skylight at Tobacco Dock, where you can challenge your friends to shuffleboard or croquet tournaments, watch sporting events, and even ice skate in the winter months. Smoking is allowed in the outside spaces but expect more cigarette smokers than lovers of the leaf.
Dress Code: On the smarter side. This is London’s business district, so expect to see suits peeping out from underneath those plaid blankets. boisedale.co.uk
BALI – Rock Bar at the Ayana Resort & Spa
Bali’s iconic Rock Bar redefines the rooftop genre. Balanced 45 feet above the Indian Ocean atop natural rocks, the bar has some serious wow-cred. Turn in a 360-degree circle and all you’ll see are breaking waves, sunlit cliffs and party-goers reveling in the out-of-this-world vibe. Part prehistoric perch, part minimalist masterpiece–the architecture, created by Japanese architect Yashuhiro Koichi from SPIN Design Studio, highlights the bar, which in itself is a work of beauty. It’s crafted with thousands of layers of recycled glass canes. There are designated smoking and non-smoking areas, but no cigars sold on site. If you have a few days on the island, you can also check out more cigar dedicated places such as Ku De Ta in Seminyak and the Viceroy Bar in Ubud.
Dress Code: Bali has a reputation for being extra chill, but the Rock Bar is more about the swank and swagger than your average beach bar. Their website specifically requests that guests don’t ruin the landscape by wearing tank tops, board-shorts or alcohol-branded attire. ayana.com
CUBA – Havana Hotel Nacional de Cuba
It would be remiss, to write an article about rooftop bars and cigars without saving a slot for Havana. The rooftop terrace on the top of the historic Hotel Nacional de Cuba, offers both stunning views of the Malecón seawall and premium Cuban cigars. Its glory might be fading a bit around the edges, with its crumbling 1930s facade and bathrooms that are a bit south of vintage-cool; but is there anywhere else in the world that has a bar named Churchill’s, not because it adds cache to the branding but because Winston Churchill actually, really truly, stayed there? (Along with some other cool cats throughout history, such as Jean Paul Sartre and Francis Ford Coppola.) Pick up your sticks at the Habanos lounge downstairs and then head to the sky deck for a Cuban ron añejo and a date with history.
Dress Code: Tip your fedora and unbutton a few buttons on your shirt, and you’ll look the part. hotelnacionaldecuba.com
Charleston, South Carolina – Pavilion Bar
Forgo some of America’s most famous rooftop locations like Los Angeles and Miami for a bit of Southern charm. Charleston’s historic mansions, cobblestone streets and world-class food scene has already made the town a vacation bijou, but the combo of old-world elegance and beachy cool is also the perfect background for some rooftop lounging with a drink and a smoke. The sophisticated Pavilion Bar at the Market Pavilion Hotel maxes out on Charleston chic. It features the city’s only rooftop cascading pool with views of the historic downtown, fresh seafood and a classic boozy rum punch amongst other libations. Ask the staff where you can cut and smoke your stogie—cigars are only allowed in the Western back portion of the terrace.
Dress Code: If you stay in the hotel, you can spend the day lounging in the pool, but don’t expect to belly up to the bar in the evening in flip-flops and a towel. After 5pm the terrace turns up the class and your clothing should too–no tank tops, sportswear, or cut-off shorts are allowed. Go for a breezy linen shirt and crisp chinos and you’ll fit right in. marketpavillion.com
These are just a few examples of the many rooftops around the world that offer vertigo-inducing views, well-crafted cocktails and a unique experience for both cigar connoisseurs and for those seeking to relax in style. As of the writing of this article, all the bars on this list are cigar-friendly, but smoking laws change as fast as a guillotine cutter gets the job done. It’s always wise to check with the wait staff before you light up.