Every March, we escape to Florida — a sun-soaked ritual of beer, beaches, and bonding with family. Orlando is a non-negotiable stop (because Disney Springs is genuinely a blast), but the real adventure starts when we pack up the car and head for the coast. If you’re like us — a couple in your late 20s traveling with fun-loving in-laws in their 50s — you’re looking for that sweet spot: somewhere not overrun by 21-year-old spring breakers but not so sleepy it feels like a retirement brochure.

You want somewhere chill, with a dash of divey chaos when the mood strikes. Bonus points for walkable beach bars, live music, and coastal charm. After a bit of trial and error (Indian Rocks Beach, we liked you, but the vibes were… a little too chill), we’ve got some solid contenders for your next Gulf Coast escape — all drivable from Orlando.

1. Dunedin & Honeymoon Island – Quirky, Laid-Back, and Super Walkable

📍 Approx. 2 hours from Orlando

Dunedin is that under-the-radar beach town you didn’t know you needed. Think charming waterfront streets, colorful cottages, and a downtown filled with craft breweries, live music bars, and plenty of dives to crawl through. It’s got a distinctly local vibe — not flashy, not touristy, just fun.

Why you’ll love it:

• Tons of bars and breweries within walking distance (shoutout to Dunedin Brewery)

• Chill, slightly quirky crowd — not too young, not too old

• Easy access to Honeymoon Island for beach time and nature trails

Vibe: Funky, local, lively-but-laid-back

2. Pass-a-Grille – Old Florida Meets Beach Bar Magic

📍 Approx. 2 hours from Orlando

Pass-a-Grille is technically part of St. Pete Beach but feels like a world away. This small strip of paradise has just enough happening to keep things interesting — waterfront bars, live music, and some divey gems — but without the chaos of Clearwater or the spring break surge of Daytona.

Why you’ll love it:

• The Hurricane Seafood Restaurant rooftop bar for sunset views

• A quaint, low-rise town with walkable streets and classic beach bar vibes

• Quiet beaches, but you can still let loose at nearby St. Pete Beach if the mood hits.

Vibe: Chill days, rowdy-ish nights, salt-soaked sunsets

3. Mexico Beach & Cape San Blas – Remote and Gorgeous

📍 3.5–4 hours from Orlando — a bit of a stretch but worth a detour

If you’re up for a longer drive or a stop on your way north, Mexico Beach and Cape San Blas deliver that sugar-white sand and clear emerald water dream — but without the commercial chaos of Destin or Panama City. There’s a rustic charm here, plus the sunsets are unbeatable.

Why you’ll love it:

• Small-town feel, uncrowded beaches

• Ideal if you’re looking to completely unplug

• A few low-key bars, but they not a nightlife destination

Vibe: Bring your cooler, stay a few nights, reset your soul

4. Cocoa Beach – Dive Bars and Laid-Back Surfers

📍 Approx. 1 hour from Orlando (East Coast bonus pick)

While not on the Gulf, Cocoa Beach deserves a mention for its dive bar density and laid-back energy. It’s close, unpretentious, and full of surfers, beach bums, and the occasional rocket launch.

Why you’ll love it:

• Bars like Coconuts on the Beach or the iconic Sandbar Sports Grill

• A bit gritty, but in the best way

• Great day trip if you want beach and beers fast

Vibe: Flip-flops, $3 beers, good music, no judgment

5. Anna Maria Island – Chill Sophistication

📍 About 2.5 hours from Orlando

For a more scenic and slightly upscale vibe (but still casual), Anna Maria Island hits all the marks. The beaches are pristine, and there are enough good bars and restaurants to keep things fresh. You can find divey beach bars, but also nice dinners by the water.

Why you’ll love it:

• Laid-back but not boring

• Quiet beaches, vibrant sunsets, a decent mix of ages

• No high-rises, no chains, all charm

Vibe: Sophisticated beach bum

Final Thoughts: Your Unicorn Exists

If you’re craving a “relax one night, party the next” kind of trip that works for both dive bar lovers and your chill in-laws, places like Dunedin, Pass-a-Grille, and even Cocoa Beach might be your unicorn. They’ve got that rare mix of walkability, good drinks, and good energy — without sacrificing the sand or soul.

Pro Tip: If you’re planning for March, check for spring break schedules and local events. Even mellow towns can get wild at the wrong time. Or go midweek to dodge the crowds.

Until then, keep the sunscreen close and the beer closer. Cheers to your next coastal escape!