5 Cocktails to Try this Holiday Season

Elevate your festive celebrations with a delightful sip of the season!

The older and, hopefully, wiser I get, the less interested I am in complicated things. Give me the classics! They’ve held up for a reason. That extends to shoes, suiting, outerwear, watches, and yes, my cocktail preferences. 

With the end-of-year holidays in full swing, here’s some holiday cheer with a few cocktails to make the season merry and bright.

The Old Tom Martini

Every time I get back to my hometown of Detroit, usually around the holidays, I make a point to try out at least one new restaurant. The city has come so far in the last 15 years, and I love to see what’s new and exciting downtown.

A few years ago, my wife and I stopped in on a typically frigid Michigan night. As usual, we sat in the bar area close to the kitchen. 

It’s fascinating to watch a truly marvelous kitchen team in the middle of a bustling dinner service. It may look chaotic, but it’s a carefully choreographed dance of metal, fire, sound, and scent. 

The steak that night was excellent, yes, but what really stood out for me was the cocktail I had. I took a look through the standard offerings, but nothing really appealed to me. So, I asked the bartender to surprise me. 

A few minutes later, something in a traditional martini glass showed up. Intrigued, I took a sip. What was that? 

It was slightly oaked, a little sweet, with a bright orange finish. 

On my way out, I went over to the bartender, shook his hand, and asked what he’d made. It was a riff on a classic martini with a cask-aged Old Tom Gin from Valentine Distilling. I’ve tried to recreate that here. 


  • 2.5 oz Old Tom Gin (I use Liberator from Valentine)
  • 1 cap full Dry French Vermouth (Noilly Prat is excellent)
  • 2 drops Orange bitters
  • Orange peel for garnish


Fill a mixing glass with plenty of quality ice-ideally, from water run through a charcoal filter. I’ve taken to using one big ice club, as it melts more slowly. 

Add a capful, or about half an ounce, of vermouth to the mixing glass. I hold the glass in my hand and move it around to coat the ice, but you can use a bar spoon just as well. 

Add 2.5 oz of Old Tom Gin and stir, with the bar spoon, for 20 seconds. 

Add two drops of orange bitters into the glass and stir for another 10 seconds. 

Strain into a classic martini glass or cocktail coupe. 

Add a thin slice of orange peel to garnish. 

The Winter Negroni

I’m not quite sure why, but the Negroni has been the unofficial drink of the #menswear crowd. 

Maybe it’s because it’s really easy to make. Maybe it’s because of the signature red of the Campari photographs well.

Or, perhaps it’s because any variety of three ingredients can dramatically change the character of the same drink it that much easier to argue, trivially, over the correct proportion of said ingredients. Indeed, entire books have been written on the subject. 

I make mine up in batches and keep it in the fridge. It’s a little nod to my late grandfather, who kept a stash of his ‘medicine (a dry V/O Manhattan)’ in a large cough syrup bottle in the fridge so he could have a half pour every afternoon. 

He lived to 101, so I suppose he did something right.

For me, the sweet vermouth dictates what kind of Negroni I’m making. In summer, I’ll go for something lighter in body and, indeed, a little sweeter. In winter, though, I look for darker, richer, and spicier varietals of this fortified wine. 


  • 1 oz London Dry Gin
  • 1 oz sweet vermouth
  • 1 oz Campari
  • 1 orange slice
  • Old Fashioned Glass


Stick an old-fashioned glass in your freezer for 15-20 minutes prior to serving. 

As for serving, there’s nothing wrong with eyeballing the ingredients into the glass over ice and stirring with the orange slice. I’ve definitely done it. 

But, most of the time, I prefer to measure. So, I’ll start with the gin, and layer the vermouth and Campari on top. 

As for gin, it does have to be London dry. I’m not especially particular about brands here, though I’ve found Tanqueray works well for my palate and the flavors I enjoy.

If I can find a rare sale, I’ll spring for a bottle of Monkey 47, a gin from Germany’s Black Forest. 

As for vermouth, I prefer the character and taste of Punt e Mes (or ‘Point and a Half’) for my winter Negronis. It’s more herbal and spiced than traditional sweet vermouths. 

On the part of Campari, some guys are willing to put up big bucks for a bottle of vintage stuff. I don’t particularly care to, though. 


The Slightly Shaken Perfect Manhattan

Most people stir their Manhattans. My wife’s great-grandmother apparently did. 

My grandfather just mixed his up and stuck it in the fridge. 

For me, unless I’ve got ingredients already chilled, stirring just dilutes the flavor of the drink I’m making. 

So, I prefer to give a brief shake before service. And, I find the ‘classic’ 2:1 ratio of whiskey to sweet vermouth a little too sweet for my liking, so I’ve got a twist. 


  • 2oz rye whiskey 
  • 0.5oz dry vermouth
  • 0.5oz sweet vermouth
  • 2 drops Angostura bitters
  • Luxardo cherry, if you can find them


This one is pretty simple to make. I pour all the ingredients into the shaker glass. I use a Boston shaker, but a more traditional one would be just fine, too. 

Give everything a shake for about 10 seconds. 

Pour into a cocktail coupe or traditional martini glass, and add the cherry. 

It’ll be a little cloudy at first, but clears up and ends up at the perfect sipping temperature in three or four minutes. 

The Old Fashioned

As I mentioned at the outset, the older I get, the less interested I am in sweet cocktails. Alcohol has a ton of natural sugars in it anyway. 

Close-up of a person squeezing an orange peel into an Old Fashioned.
Photo By LAVA /

So, an Old Fashioned is a little challenging for me, But, I know people love them, so here we go. 


  • 2.5 ounces rye whiskey (I like Whistle Pig’s Piggyback or Knob Creek)
  • 3 dashes of Angostura bitters
  • 1 bar spoon simple syrup
  • One large, round ice cube made with filtered water
  • Thin strip flamed of orange and Luxardo cherry to garnish


Combine whiskey and bitters in a mixing glass over a few ice cubes. 

Pour out the bar spoon and, using that spoon, stir for 15 seconds or so. It gets the drink cold, but no need to dilute it. 

Strain over the ice cube and give a few more stirs. 

Garnish with the flamed orange and Luxardo cherry. 


The “No-Groni” 

My wife and I used to enjoy a Negroni on Friday afternoons after work as a great way to kick off the weekend. But, when we found out we were expecting our second child, that wasn’t an option for her. 

I went out and tried a few ‘No-Gronis’ on her behalf, with limited success. They were flat and far too herbal. So, I created my own. 

The secret ingredient here is Chinotto, an Italian soda with flavors of rhubarb, cinnamon, and orange blossom, not unlike my favorite Punt e Mes vermouth. 

The sweet comes from Cheerwine, a cherry-flavored soda from Salisbury, North Carolina. And, the splash of soda balances things out. 

Apologies in advance, as I neglected to get a photo!


  • 1.5oz Chinotto soda
  • 1.5oz Cheerwine soda
  • 1.5oz soda water
  • Orange slide to garnish
  • Optional rosemary spring or juniper berries


This is kind of a layered drink, and I do prefer doing it in this order. I pour the Chinotto, then the Cheerwine, then top with soda water. 

Because there’s no alcohol in this, I treat it as more of a long drink and use a Collins glass. 

You can garnish with a thin orange slice and rosemary spring. 

If you’d like the flavor of gin without the alcohol, try gently muddling a few juniper berries at the bottom of the glass before adding your ice. 

Happy Holidays!

As always, I hope you enjoy with friends and family this holiday season

Please remember to drink in moderation!


Questions? Comments? Leave them below!

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