Where To Stay

4 Easy Memorial Day Weekend Getaways from Miami

The unofficial start to summer is just around the corner with Memorial Day Weekend May 27-30. Of course, for Miamians, it’s just another weekend of perfect beach weather and it also coincides with the annual Urban Beach Weekend. If you’re looking for an excuse to get out of town, here are four different getaways that are easy to pull off from Miami.

Key West – See What’s New

It’s a great time to hop in the car and head south to Key West for a laidback Memorial Day Weekend that can be equal parts party and relaxation. If you haven’t been to the Southernmost Point in awhile, there are a handful of new spots to check out.

Make dinner plans at the new Thirsty Mermaid raw bar and restaurant, the latest from the team behind Blackfin Bistro (think of them as the Pubbelly Boys of Key West). Helmed by chef/owner Thomas Quartararo, his wife Kristen Onderdonk and executive chef Ryan Shapiro, they’re putting out some of the freshest and most ambitious dishes on the island.

The long awaited Waterfront Brewery (pictured at top) opened its doors inside a massive space overlooking the historic seaport. Swing in for a flight of beers brewed onsite, including the Crazy Lady Honey Blonde Ale, Extraterrestrial Experimental Beer made with peanut butter and the just released TruMan Double IPA in honor of President Harry S. Truman who once summered in Key West.

There’s also a newly opened outpost of Books & Books, co-founded by legendary YA author and Key West resident Judy Blume, inside The Studios of Key West on Eaton Street. You won’t be at a loss for a good beach or boat read over the holiday weekend.

The drive to Key West is three and a half hours. Check out our day trip to the Florida Keys guide for stops along the way.


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Fort Pierce – Relax

Head north for a chilled out beach getaway to Fort Pierce punctuated by tiki bars and casual, inexpensive restaurants. Spend a day at Fort Pierce Inlet State Park where you can relax on the wide shoreline beach with darker, hard packed sand and a deeper blue-green ocean. There might even be waves for surfing. Hike through their hardwood hammock nature trail where you can look for marsh rabbits, gopher tortoises, butterflies and migratory birds beneath the dense canopy.

Grab lunch at nearby Sharky’s, a no frills, diner-like eatery popular amongst local surfers serving specialties like the blackened grouper Reuben.

In the evening, swing by the Original Tiki Bar & Restaurant for live music, drinks and dinner on the water.

For something a little unusual, consider a pit stop at Al’s Red Barn Grill (pictured above) to pick up freshly squeezed orange and lemon juice or a case of farm fresh Valencia oranges. There’s an “agri” playground for the little ones and a window to order burgers or tacos for lunch at the farm.

It’s a two-hour drive to Fort Pierce. Check out a few other stops along the way with our day trip to Vero Beach guide


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Orlando – Geek Out

The southeast’s largest comics, sci-fi, horror, anime and gaming event is descending on Orlando’s Orange County Convention Center this Memorial Day Weekend May 26-29. MegaCon Orlando is every fan boy and fan girl’s dream with over 1,000 exhibits headlined by top celebs from every genre. Notable attendees include John Cusack, William Shatner, Kevin Smith, Christopher Lloyd, Adam West and Marvel comic book legend Stan Lee (pictured above). Expect the typical panel discussions, Q & As, workshops and seminars with plenty of cos-play, but there’s also a chance for nerds to find true love with Sci-Fi Speed Dating Friday through Sunday. Star Wars fans will delight in an onslaught of events by 501st Legion including an army of Stormtroopers.

It’s a three and a half hour drive to Orlando or a one-hour flight.  


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Anguilla – Go Lux

If you’d truly like to fly the coop for Memorial Day Weekend, consider an escape to idyllic Anguilla and one of its lavish resorts. Unblemished by a cruise ship port, it’s one of the most serene islands in the Caribbean (and a celeb magnet) accessible by ferry from St. Martin/St. Maarten after a three-hour flight from Miami. It’s all about unwinding in luxurious infinity pools carved into craggy cliffs with mind-bending views of the dazzling ocean below.

Anguilla’s original luxury resort Malliouhana reopened at the end of 2014 as a 55-room boutique hotel under the Auberge Resort umbrella. No detail is overlooked in the eclectic design that features waterfall infinity pools and an organic cliffside restaurant by Michelin-rated chef Jeremy Bearman.

For a sharp-angled, modernist approach, Viceroy Anguilla is a sublime, sprawling campus featuring a private beach and three pools overlooking Meads and Barnes Bay.

For those in search of the privacy of a condo with the services of a boutique resort, Ce Blue, with its eight five-bedroom private villas teetering over the lush green hills of Crocus Bay, is the answer.

While in Anguilla, don’t skip a chance to hear reggae icon Bankie Banx at his Dune Preserve beach bar (pictured above) where he performs live weekly or the ooey-gooey lobster quesadillas from Hungry’s Food Van. A day trip to the pink sand beaches of Sandy Island is also a must.

Shayne Benowitz is Miami.com’s travel editor. Follow her on Twitter @ShayneBenowitz.