Widely regarded as the most prestigious event in the tennis calendar, Wimbledon (SW19) is the oldest of the sport’s Grand Slam tournaments, first in 1877. It is laden with tradition, from spectators feasting on deliciously indulgent strawberries and cream to the classic “almost entirely white” playing attire contrasting with the hallowed, lush green lawns.

Wimbledon is the only Grand Slam played on grass courts (again influenced by tradition), as the grass is the traditional playing surface in tennis. This is why the sport was initially known as “lawn tennis.” The tournament is played over two weeks and attracts 39,000 spectators daily, including royalty and celebrities in the Royal Box. Fitted with 74 dark green Lloyd Loom wicker chairs, the Royal Box offers elevated comfort and some of the best views of its famous Centre Court.

History beckons in the gentlemen’s singles of the 2023 tournament, with defending champion Novak Djokovic aiming to win his eighth Wimbledon crown. Glory would bring him level with all-time leader Roger Federer.

On the women’s side, Kazakhstani player Elena Rybakina will aim to defend her title. The draw will be noticeable for the absence of 23-time Grand Slam champion Serena Williams, who retired from tennis following the September 2022 US Open. It will be the first Wimbledon since 2004 not to feature the American legend (excluding 2020, which was canceled due to the coronavirus pandemic).

Whether you are a diehard tennis fan or only tune in for  SW19, you can’t beat watching the action with a drink in one hand and a quality cigar in the other. It’s a tournament where dreams are fulfilled and shattered as every player goes “In Pursuit of Greatness.”

The ladies play in a best-of-three-set format, with matches lasting 60-90 minutes. The men battle it out over five sets, with games averaging around the two to two-and-a-half-hour mark. While you try to keep up with captivating back-and-forth rallies, we’ve served up five cigar suggestions that will keep you occupied for the matches.

Country of Origin: Dominican Republic

Wrapper: Ecuador Habano

Binder: Nicaragua

Filler: Nicaragua

Length: 7

Ring: 48

Strength: Medium-Full

Smoke time: 120 minutes

Given the tennis hysteria that Wimbledon sparks across Britain during the summer, starting with a smoke inspired by their revered war-time Prime Minister seems fitting. The Davidoff Winston Churchill The Late Hour (Churchill) is cloaked in a beautiful dark chocolate Ecuadorian wrapper, reflecting the dark of night when Sir Winston Churchill was at his most creative. It has an oily texture that looks and feels sophisticated and boasts over an hour of smoking time.

This ace smoke is even more unique because it’s filled with Nicaraguan Condega Visus tobacco aged for six months in the finest Scotch single malt whisky casts.

It retains the scotch elements, beginning with a lovely spicy flavor that lingers on the tongue before developing into creamy wood notes, with hints of toffee, maple, and subtle vanilla.

Country of Origin: Nicaragua

Wrapper: Ecuador Habano

Binder: Nicaragua

Filler: Nicaragua

Length: 6.12

Ring: 52

Strength: Medium

Smoke time: 80 minutes

A cigar with a champion’s look, the Tatuaje Tattoo Bonito was the first in a series from the famed Tatuaje brand to create an affordable smoke with a more premium smoking experience. Rolled in an extra-dark and silky Ecuadorian Habano Maduro wrapper, it has a red band with gold trim and delightful hay and sweet cocoa aromas.

Once lit, the Bonito returns a trademark blast of pepper you’d expect from a Tatuaje cigar, along with cocoa, earth, leather, and a touch of sweetness.

Country of Origin: Nicaragua

Wrapper: Medium

Binder: Ecuador Connecticut Shade

Filler: Sumatra

Length: 6

Ring: 52

Strength: Medium 

Smoke time: 100 minutes

Undercrown Shade is the first release blended by Drew Estate Master Blender Willy Herrera not to fall under the Herrera Estelí umbrella. This smooth and creamy Connecticut blend comes dressed in a brilliant blonde-hued wrapper and is ideal for settling into a lazy hour or two watching SW19.

The silky smooth body maintains its character down to the nub, while the light flavor profile of nuts, sweet, creamy coffee, warm honey, and toast paints the palate with unerring consistency. The Gran Toro will give you 100 minutes of smoking time.

Country of Origin: Nicaragua

Wrapper: Nicaragua

Binder: Nicaragua

Filler: Nicaragua

Length: 5

Ring: 50

Strength: Full

Smoke time: 60 minutes

Boasting a very modest price tag and a rich, full-flavored profile, the JR Esteli Reserva Gordo is well worth making a racket over for all the right reasons. Pick up the Robusto for a 90-minute smoke (the perfect amount for a single match.)

This well-constructed Nicaraguan puro is covered with a gorgeous deep brown wrapper and has a divine earthy and nutty core. Brimming with rich espresso, leather, and the signature sweet hit of Nicaraguan tobacco, it’s a contender at any stogie grand slam.

Country of Origin: Nicaragua

Wrapper: Ecuador Connecticut

Binder: Nicaragua

Filler: Nicaragua

Length: 6.50

Ring: 52

Strength: Mellow – Medium

Smoke time: 85 minutes

Perfect for everyday puffing, particularly when lapping up the sun-drenched magic and occasional rain delays of Wimbledon, the Oliva Connecticut Reserve Torpedo is an enjoyable mellow offering from Oliva. Its light tan wrapper from the famous Connecticut Valley has a silky texture, with pleasant aromas of cinnamon, caramel, and straw purring from the foot. You’ll get around 65 minutes of smoking time with the beautifully shaped Torpedo.

Its elegant presentation is akin to the most graceful stroke in the game (a one-handed backhand) with a clean, white band ornately splashed in gold and brown. This sprightly and toasty Connecticut smoke has a cedary core with nuances of caramel, cocoa, nuts, and understated coffee grounds.

On a warm afternoon of captivating tennis, pair your Oliva Connecticut Reserve Torpedo with a cold beer or a classic Wimbledon concoction of Pimm’s and lemonade.