5 from 6 votes

The pineapple daiquiri is a creamy, boozy beverage is perfect for a hot summer day and loaded with pineapple flavor (and rum, of course)! Try a tequila sunrise or salty dog cocktail next.

Pineapple cooler summer cocktail with lime, strawberry and a maraschino cherry on a napkin

Guys, it's summer. I know that the calendar says it's not until Thursday the 21st, but Massachusetts has never been one to… oh, I don't know, pay attention in the least to where seasons actually fall.

It was 85° yesterday, and today it's going to be the same, and if it started snowing tomorrow, there's no part of me that would be surprised at this point.

Speaking of yesterday's weather, I ran around like a bunny in it! Okay, maybe not so much like a bunny because I had a path I had to follow and some semblance of direction in life.

It was the Spectacle Island 5K which is a beautiful Boston Harbor Island and it's becoming an annual tradition for Bill and I to participate. Last year I just photographed him because it was his first race ever (!), and this year I ran with him.

He's faster than I am, so finished well before me and grabbed a few shots when I was crossing the finish line:

Leslie Haasch running the Spectacle Island 5K

What I've learned, is that evidently I am a descendant of hover cat and my feet never actually touch the ground. So why do my feet hurt so much?!

My uterus has been a real moody jackass for the last week, so the fact that I was able to run this at all was a small miracle for me. AND I finished 58 seconds shy of my personal best.

I have no idea how that is possible, because if you look at a picture of Spectacle Island, you'll notice that it's a bunch of hills. And I hate hills. And my uterus also hates hills.

Bill and Leslie after the Spectacle Island 5K

So to honor my completion of the race and the unofficial start of summer here in the Bay State, today's recipe is bright and sunshine-y – much like my lemon poppyseed dressing recipe (which p.s.: you guys have fallen in love with it and it makes my heart sing).

These pineapple coolers are also full of booze, which is important for a good summer cocktail. Say what you will about alcohol and dehydration in summer heat, but… well, okay, yeah, that's a real thing.

So don't go nuts and chug six of these, but sip and enjoy while you sit on your porch, basking in the sun. Like a lizard. If lizards drank booze.

There's no rule that says you have to garnish this with anything. Not a damn thing, if you don't want to. But I'm all about adding fruit to my drinks because 1) that gives it more color and makes me feel fancy, and 2) it's food, and I like food.

You know those crazyass milkshakes that they “garnish” them with something like a strip of bacon, a donut, and an entire ice cream sandwich?

That's using the term garnish extremely loosely. So I don't (usually) go that crazy with it, but I do love me some maraschino cherries. I'd eat an entire container of those in one sitting if ~~I didn't need them for recipes~~ it were socially acceptable.

You can even add a straw if you want to be fancy schmancy. Or if you just like to drink out of straws.

Either way.

Pineapple cooler summer cocktail with lime, strawberry and a maraschino cherry with a straw

A few tips for making pineapple coolers

Try a piece of the pineapple before you blend it to see how sweet it is. That'll give you a good idea of how much sweetener, if any, you'll want to add during the blending process.
Speaking of pineapple, save a chunk or two if you want to use them as garnish (like, for real garnish, not ridiculous milkshake garnish). I promptly forgot when I was shooting this recipe and I will regret it until the day I die.
Use a good blender. I probably should have started with this one. Our blender is… not great, so we end up with a thicker and more toothsome drink when we make it. I'm actually totally good with that because I enjoy it that way, but if you have the Vitamix blender of my dreams you can get it smooth and creamy.

Aside from advising you to make these immediately, I really don't have much else to say about them.

So… just… go do that, okay?

Pineapple cooler summer cocktail with lime, strawberry and a maraschino cherry

Pineapple not your thing?

Well then why are you here?! Just kidding – thanks for sticking around. But if pineapple's not your favorite, here are some other options for your summer indulgence:

A Strawberry Rhubarb Sangria that's prettier than most beautiful humans
This festive Red White and Blue Moscato Sangria
Or one of the other drinks I have on here! Tequila Sunrise, Salty Dog, Watermelon Margaritas, Blood Orange Sangria, Raspberry Rosé Sangria and French 75 Cocktail are all winners!

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