Sinatra Smash Cocktail | An Easy Classic

Several years ago, Jerry took me to Vegas for my birthday and I had my first Sinatra Smash Cocktail. Even though it's fruity, it's all grown up!  

How to Make a Sinatra Smash at Home

In this recipe you'll find simple steps on how to create your own vanilla simple syrup and sweet and sour mix.  (Hint: If you're like me and find that sometimes you don't want to mess with all that, keep scrolling for some easy hacks.)  This recipe makes 2 cocktails.

1. Make Vanilla Simple Syrup: in a stainless steel pot, bring 1 cup water to boil.  Add 1 cup sugar and 1 vanilla bean* split down the center. Lower heat and simmer until sugar has dissolved.  Turn off heat and cool.
2. Make Sweet & Sour Mix: Combine ½ cup fresh squeezed lemon juice with ¼ cup vanilla simple syrup.  Mix well and refrigerate until ready to use.
3. Put it all together: In the bottom of a shaker, muddle 6 blackberries and a mint leaf with ⅔ ounce vanilla simple syrup.
4. Fill shaker ½ way with ice and add 2 ½ ounce sweet & sour mix, 1 ½ ounce Creme de Cassis, and 4 ounces Gentleman Jack Whiskey.
5. Shake vigorously.  Strain over 2 glasses of ice.
6. Garnish with blackberries and mint leaves.

*Note: No bean? No problem. Add 1 tablespoon vanilla extract after syrup cools.

Where can you Find a Sinatra Smash?

We went to the Sinatra restaurant at the Encore Hotel & Casino in Vegas where they serve it up.  What a treat! With a base of bourbon (my favorite spirit, next to a a high quality sipping tequila is a close second... Maestro anyone?), it's a deep mellow beverage with a fruity fresh edge.

Why's call a 'Smash?'

When you're making this tasty libation you muddle the blackberries in the cocktail shaker.  You gotta admit Sinatra Smash is waaaay cooler than a Sinatra Muddle!  Besides what a great nod to all of Blue Eyes smash hits.

What to serve up with a Sinatra Smash

Personally, I think this cocktail is best served all by itself before dinner.  If you want to follow it up with the best steak of your life, then check out this quick and easy method for Filet Mignon just like Ruth Chris Steakhouse does it.  You'll love it!

Served simply over ice is always best, but in a cocktail it lends its own unique personality to the beverage.  It's iconic.  Frank himself was very much the same.

Try making some crystal clear ice to go in it!

What is Creme de Cassis?

That is the #1 question I get when laying out this cocktail recipe for someone.  The #2 question is closely related, which is: what is cassis?  In short, cassis is French for the blackcurrant berry.

It's a very sweet berry that's also earthy and tart.  Creme de Cassis is a thick dark liquor that has extracted the intense flavors of this berry beautifully.

In the language of a oenophilia (wine lover) you could describe the flavors of Creme de Cassis with words like: intense berry, licorice, Cuban cigar, and maybe even cherry cough drop.  Granted, taken out of context it does not sound very appealing.  However, added to your Sinatra Smash... invaluable!

Variations on the Sinatra Smash

I don't know about you, but the only time I reach for our Creme de Cassis is when I'm making this cocktail.  If I don't have it, I've used Chambord.  This is not only a lovely substitute but it's excellent over vanilla ice cream!

There have also been days when making vanilla simple syrup is simply too taxing and I can't be bothered.  On those days, I added ½ teaspoon vanilla extract, 1 teaspoon sugar and gave it a few more shakes in the shaker to help the sugar dissolve.

Other Cocktails You Might Enjoy

As side from the Sinatra Smash, my second favorite refreshing adult beverage is a Blood and Sand cocktail.  It's got deep rich smokey notes (from the Scotch) that's balanced nicely with fresh squeezed orange juice, blood oranges if you can find them.

I used blood oranges and black Luxendo cherries in this Black Old Fashion too, hence the name.  This is an excellent whisky drink that's smooth, mellow and slightly sweet.  It's easy to make too!

4.75 from 8 votes

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Sinatra Smash Cocktail

Sinatra Smash Cocktail Recipe - Fell in love with this at the Wynn in Vegas.  Tangy sweet, smooth and fruity with a kick of bourbon. Still a Favorite! | www.lakesidetable.com

Course Drinks

Cuisine American

Keyword beverage, cocktail

Prep Time 10 minutes

Cook Time 5 minutes

Servings 2

Calories 215 kcal

Author Sinatra Restaurant Las Vegas

Ingredients

Sinatra Smash Cocktail

• 8 blackberries fresh
• mint leaves optional
• 2 ½ ounce homemade sweet and sour
• ⅔ ounce vanilla simple syrup
• 1 ½ ounce Creme de Cassis
• 4 ounce Gentleman Jack Whiskey

Vanilla Simple Syrup

• 1 cup sugar
• 1 cup water
• 1 vanilla bean*

Sweet and Sour Mix

• ½ cup lemon juice fresh
• ¼ cup simple syrup

Instructions

Vanilla Simple Syrup

1. Set a pot with 1 cup water and 1 cup sugar to boil, about 5 minutes.  

2. Cut vanilla bean in ½ long wise.  Scrape the seeds from the bean and put it in the pot with the sugar water.

3. Gently simmer the sugar vanilla water until all the sugar has dissolved.  Remove from heat and let cool.

Homemade Sweet and Sour Mix

1. Mix ½ cup lemon juice with ¼ cup vanilla simple syrup.  Keep refrigerated until ready to use.  If you make extra, it will keep 3-4 days.  

Sinatra Smash Cocktail

1. Muddle 6 blackberries and a mint leaf in the bottom a cocktail shaker with the sweet and sour mix. Reserve 2 of the blackberries.
2. Add the rest of the ingredients to the shaker, add ice and shake well.  Strain over ice in 2 glasses.  
3. Garnish with a blackberry and mint leaves.

Recipe Video

Recipe Notes

*Vanilla bean - if you don't have a vanilla bean handy, substitute 2 teaspoons vanilla extract after the simple syrup has cooled.  However, if you do have a vanilla bean, keep the outer husk and bury it in your sugar bag or canister for delicious vanilla sugar.  Yum!

Make a larger batch of simple syrup and sweet and sour mix to have on hand.  They both keep well for almost a week in the refrigerator!

 

Nutrition Facts

Sinatra Smash Cocktail

Amount Per Serving (2 drinks)

Calories 215 Calories from Fat 2

% Daily Value*

Fat 0.2g0%

Saturated Fat 0g0%

Trans Fat 0g

Monounsaturated Fat 0g

Cholesterol 0mg0%

Sodium 42.7mg2%

Potassium 0mg0%

Carbohydrates 18.7g6%

Fiber -22g-92%

Sugar 17.1g19%

Protein 0.4g1%

Vitamin A 0IU0%

Vitamin C 0mg0%

Calcium 0mg0%

Iron 0mg0%

* Percent Daily Values are based on a 2000 calorie diet.