
Let’s be honest. Do we really need a reason to book a trip? A three-day weekend? Sure. A birthday? Absolutely. An anniversary? Why not? But sometimes the best excuse is one that’s delightfully ridiculous.
Case in point. National Rum Day on August 16.
Is it a real holiday? Not exactly. But, is it a perfectly acceptable reason to escape to somewhere with palm trees, ocean breezes, and a cocktail in hand? One hundred percent.
Rum has been part of tropical vacations for generations, with every island and coastal destination putting its own spin on the spirit. Some cocktails have become so iconic that they’re forever linked to the places where they were born. If there were ever a time to plan a getaway around a drink menu, National Rum Day just might be it.
Here are four resorts where the cocktail isn’t just something you order. It’s part of the destination’s story.
Sip a Mai Tai Where Hawaii Does It Best

Sheraton Kauai Coconut Beach Resort. Kauai, Hawaii
The Mai Tai is practically synonymous with Hawaii, and there’s no better place to enjoy one than overlooking the ocean on Kauai’s beautiful Royal Coconut Coast.
At Sheraton Kauai Coconut Beach Resort, every Mai Tai gets an authentic island upgrade thanks to locally distilled Koloa Rum, made right on Kauai. The cocktail itself has quite a history. Created in the 1940s by legendary bartender Victor “Trader Vic” Bergeron, its name comes from the Tahitian expression meaning “out of this world,” after a guest took that unforgettable first sip.

That description still fits.
Whether you’re watching hula dancers during the resort’s Luau Ka Hikina, floating in the zero-edge infinity pool, or settling in around the fire pits as the sun disappears into the Pacific, a Mai Tai somehow makes every moment feel even more like vacation.
- Order yours when you get to Sheraton Kauai Coconut Beach Resort
Raise a Glass to the Original Piña Colada

Caribe Hilton. San Juan, Puerto Rico
Some hotels have signature cocktails. Caribe Hilton has the signature cocktail.
This legendary beachfront resort is where the original Piña Colada was created in 1954 after bartender Ramón “Monchito” Marrero spent months perfecting a drink that captured the spirit of Puerto Rico. His winning recipe blended Don Q Gold Rum, Coco López coconut cream, heavy cream, and pineapple juice into what would eventually become Puerto Rico’s national drink.
One fun piece of trivia? The very first Piña Coladas were shaken by hand because blenders weren’t yet part of the equation.

Today, you can order the original while relaxing beside the oceanfront infinity pool or from the swim-up bar, where every sip tastes like a tropical vacation. Even better, Puerto Rico is just a short flight from many U.S. cities, and U.S. travelers don’t even need a passport.
- When’s the last time you had a REAL Pina Colada? Don’t put it off any longer and book your stay at the Caribe Hilton
Cool Off with Puerto Rico’s Frozen Holiday Favorite

Hyatt Regency Grand Reserve Puerto Rico
Most people think of coquito as a Christmas tradition, but this resort proves it’s just as delicious in the middle of summer.
Set on its own private peninsula near El Yunque National Forest, Hyatt Regency Grand Reserve Puerto Rico has given the island’s beloved holiday drink a frozen makeover that’s made for pool days.
If you’ve never tried coquito, imagine Puerto Rico’s answer to eggnog, only with plenty of Caribbean personality. Coconut cream, condensed milk, evaporated milk, warming spices, vanilla, and rum come together in a rich, creamy cocktail that has been passed down through Puerto Rican families for generations. Every family has its own recipe that’s guarded almost as carefully as grandma’s holiday cookies.
The resort transforms that comforting classic into a frozen cocktail that’s somewhere between a milkshake and a beachside treat. It’s creamy, refreshing, and proof that some holiday traditions deserve to be enjoyed all year long.
- I’ve been to Puerto Rico in the summer and I can say that it’s beautiful any time of year. As long as you have that coquito in hand at the Hyatt Regency Grand Reserve Puerto Rico
Order the Drink That Was Born in the Florida Keys

Three Waters Resort & Marina, Islamorada Resort Collection. Islamorada, Florida
The Rum Runner isn’t just a Florida Keys favorite. It was actually invented here.
At what is now Three Waters Resort & Marina, bartender “Tiki John” found himself with an assortment of leftover bottles before a new liquor delivery arrived in the 1970s. Instead of letting them go to waste, he mixed light and dark rum with banana liqueur, blackberry flavors, and fruit juices. The accidental creation became one of the Keys’ most famous cocktails.
Named after the daring rum smugglers who once raced through these waters during Prohibition, the Rum Runner is equal parts history lesson and happy hour.

Today, you can enjoy one at the resort’s famous open-air Tiki Bar while listening to live music and watching boats drift into the marina. Or take your cocktail aboard the Rum Runner Water Taxi as the Florida Keys put on one of their spectacular sunset shows. Either way, it’s hard to imagine a better place to celebrate National Rum Day.
- For those of us in Florida, it’s time to hop in the car and drive down. For everyone else, the airport is calling, and so is Three Waters Resort & Marina
Cheers to Celebrating the Little Things
One of my favorite things about travel is that it doesn’t always have to revolve around a milestone. Sometimes the best trips happen simply because you decided to celebrate something unexpected.
OK, so maybe National Rum Day isn’t a “holiday” you’ll find on your work calendar (if it is, can we trade jobs?), but that’s part of its charm. It’s one more reminder that life gives us plenty of opportunities to say “why not?” Whether that’s a weekend in the Florida Keys, a few days in Puerto Rico, or an island escape to Kauai, sometimes all it takes is one great cocktail to inspire the next adventure.
And if that adventure happens to include a Mai Tai, a Piña Colada, a frozen Coquito, or the original Rum Runner? I’d call that a reason to raise a glass.
