Florida Keys: Stay in Peaceful Paradise and Walk to the Hottest Party Destination

Last Updated on April 18, 2021 by Marybeth

The Florida Keys:  Yes, “paradise” often comes to mind but not always “peaceful.”  Mixed in with the hottest party destination just down the street? How can all of this even exist in one sentence, much less within the same two blocks? Well, these are The Keys, after all.

As The Keys aren’t exactly famous for their beaches (you knew that, right?) we’re not doing our usual The Beach, The Bar, then The Bungalow. We’re starting with The Bungalow, your peaceful paradise:  Drop Anchor Resort in Islamorada. Once you walk onto its lush, superbly kept gardens and pathways with views past tiki umbrellas and lounge chairs placed to maximize the vistas and your comfort, you know you’re never going to leave. Your blood pressure drops to 90/60, and that hellish workweek you just had is as shady a memory as your freshman statistics final.

Islamorada is blessed with many little pockets of peaceful paradise for a weekend or week long stay. But one that meets all of our Triple B criteria – clean, cozy, cute, and affordable? The list narrows. And this time we ramped up the cute to gorgeous: Drop Anchor Resort.

For the retro-vintage-throwback Florida lover in all of us, Drop Anchor is the answer. At first glance I thought “Wow, SO CUTE and colorful, and the hush that settles over you like that clean sheet Mom gently pulled up when you were sick…  but the name? Drop Anchor? So clunky.”

But then, yes, Drop Anchor! For the end of the day, finally settling in, hustle and effort behind you. Mooring. Drop that anchor – clunk! – and rest those limbs; you deserve it.  Your partner brings you a drink and you two actually talk about things other than the kids, that a-hole at work, or who’s turn it is to go to the grocery store.

If/when you’re able to heave yourself out of that chair, just a tiny toddle down the road (and not that busy Keys highway; a smaller, safe side road) is the hottest party destination: Hog Heaven Sports Bar and Grill.

Hog Heaven’s front view… From this you’d never imagine the view out back…

“The hottest party destination in almost 100 miles” is how they describe themselves. Had I read that before planning this getaway, I may have been frightened away. Shaking our booties until 4 a.m. hasn’t been on our radar for quite awhile (or ever, to be honest.) Chilling by the water with a cold glass and warm appetizer, mellifluous acoustic guitar floating over and under the air* as the sun sinks down is more like it.

Here’s the thing that is so surprising:  I usually do SO MUCH RESEARCH before a trip, hours and hours (happily; I compare it to scarfing down brownies, or running 20 miles – neither of which I do, but that same feeling they describe) (well, maybe sometimes the brownies…) that I should have seen the Hog Heaven description, plus their much more us-friendly “by day… a relaxed sports bar with some of the freshest seafood in town” and “a happy hour that can’t be beat.” Also “the perfect place to unwind or recharge, whatever the case may be.” So I would have known that Hog Heaven wouldn’t be frighteningly hip or noisy and we wouldn’t have been the oldest people in the room. I read none of this and only was so stoked because our hotel was within walking distance of a waterfront bar! Sometimes ignorance, and just the knowledge of easy walking proximity, is bliss.

Hog Heaven’s other face, the view out back. Their own private beach!

Onto the facts, starting with

THE BUNGALOW

Drop Anchor Resort and Marina

84959 Overseas Highway

Islamorada, FL

305-664-4863

• VIBE:  Did we mention the most relaxing place we’ve ever experienced? Paired with Caribbean colors and 1950’s architecture that make you smile.
• WALK:  The Bar – Hog Heaven – is a block or so away, as is Island Grill, another idyllic waterfront eatery.
• DECOR:  Fun and bright exteriors with a calm and luxurious feeling interior.
• SLEEP:  Our room was tiny – we were forewarned, and I loved its jewel-box feel – and the ultra cozy bed with perfect sheets (have I already told you I’m annoyingly picky about sheets?) was tucked into its own alcove.
• EXTRAS:  Pool towels available, some rooms come with full kitchens, living and dining areas. There are various outdoor seating areas, hammocks, grills, and of course the swimming pool overlooking the ocean. Dockage for your boat.
• RATES:  Off season rooms start around $178, which, for The Keys, is within our Triple B budget. Not far from here is a well known bungalow-style hotel that may have been the site for a recent favorite Netflix drama, with rates starting around $400 and reaching up toward $2500 a night… what? Wow.
• WE LOVE:  Besides the walkable neighborhood feeling? Our portable blood pressure machine reading while staying here.

Our little deck and the view from our jewel-box of a room, #14B

THE BAR

Hog Heaven Sports Bar and Grill

85361 Overseas Highway

Islamorada, FL

305-664-9669

Back view again, grainy but oh well, CH needs a new phone…

• VIBE:  Laid back sports bar with fresh seafood during the day, hottest party destination at night, staying open until 4 a.m. (I’m wincing:  10 p.m. is my bedtime.) We can’t, obviously, account for the party vibe into the early morning hours, but how welcoming and chill and beautiful it is late afternoon and young evening? Way better than our photos can convey.
• ARRIVE:  Walk from The Bungalow – Drop Anchor – if you can, but there is a sizeable parking lot out front, and access from the ocean with your boat, as well.
• SIT:  Inside (but why?) and outside, under cover, or out there on their own private beach.
• SIP: Happy hour ever day from 4 to 7 p.m.  Try the Hog-o-rita, the Piggy Punch,  the Hair of the Hog, 6 different tequilas, Florida craft beers – the list goes on. Not as many wine choices, but they offer a higher priced and a lower priced choice for each category.
• NOSH:  Their vast menu makes it hard to choose, but how about some staff favorites such as the Crab and Shrimp Chimichanga, Lobster Mac, Pork Belly Sandwich, Surf ‘n Turf Burger. Wings, BBQ ribs, Caprese Pasta, sliders, crab cakes, Bruiser Burger… see what we mean? Or bring your catch of the day, they’ll cook it for you.
• LISTEN: Live music and/or a DJ every night.
• WE LOVE:  How funky and biker they look out front, and then you walk out back….

And just about a thousand more pictures of Drop Anchor, because it is that photogenic:

Our sweet room is on the left, but you can rent the entire cottage as well

Those chairs are calling. To borrow from an old Mary Chapin Carpenter song, “You can feel as well as see how peace can hover.”

Can’t you?

(*Borrowed these lyrics, as well, thank you Mary Chapin Carpenter!)

Islamorada is almost exactly midway between Miami and Key West – 80 miles from each – and happens to be our very favorite Florida Keys town.