Everything to know about vacationing in the middle Keys

In April (of 2018), we (by we, I mean the dogs, too!) ventured over 7 hours and 300 miles from O-town to Marathon in the Florida Keys. This time nearly 6 months post-hurricane Irma. A bit skeptical when we had made our reservations earlier in the year (as we had kept up with forums, YouTube videos, and updates from others who had visited the Keys since October) – we weren’t sure what to expect vacationing in the middle Keys!

But the moment we passed that blue bridge in Key Largo, the real feelings had settled in, and we knew the Florida Keys had never left. Not to worry – the Keys is fine, folks!

[Related Read: The best of Key Largo from a Florida native]

Honestly, we were amazed by the quick transformation in 6 months time – the difference was being able to see clear views of the Gulf and the Atlantic on both sides (as much of the mangroves and foliage had been cleared out from the storm).

Oh, who am I kidding? Let’s get to the good stuff. What’s open, and what’s not? What still exists, and what doesn’t? What is there to do, and what did we do with our time?

And with having 10 days, that’s a lot to fill our plate with!

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How to vacation in the middle Keys – Marathon, Florida

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I’ll say this – thus far, we didn’t find anything that “doesn’t exist” anymore. There were many parts of the state parks in and around Marathon that remained “closed off” due to construction or re-construction, and there were a few beaches that remain closed due to severe damage (but, it looks as if they’ll be coming back eventually).

But fishing charters, snorkeling and diving excursions were still a go! A couple of bars and restaurants had tarps over their roofs, but that didn’t stop them from serving, and it didn’t stop us from going there. Boaters still huddled together at the sandbars on Saturday afternoons, and people crowded the bridges for fishing morning, day and night. Life is still good, and going strong in the Florida Keys!

[See the video highlights of our trip to the Florida Keys post hurricane Irma]

Where did we stay?

The last two years, we’ve been staying in Marathon – smack dab in the middle of the Florida Keys. It’s a nice, happy medium between Key Largo and Key West. All amenities are a short driving distance, and there’s so much to do within an hour north and south.

There are a few hotels in Marathon, but it’s more convenient for us to stay in a duplex when staying over a week (especially when our adventure contains two pups). The owners of the duplex (who live next door to the rental) we have stayed at the last two years are awesome, and offer a deal you just simply can’t pass up when staying a week with two dogs. And honestly, you can’t say no to a place that’s right on the canal (perfect for those with a boat).

What did we do?

So like the nerds me and my husband are, we go into each trip with a motive. Majority, how are we looking to spend most of our time in Marathon? Having brought our two dogs and the Hobie kayaks, we knew this would be our outdoorsy, play-by-ear, try new things and check off our definite to-dos (if we were able) at the top of our list ‘kind of trip’.

Bridge fishing

We morning and night fished a few bridges north of Marathon, near Grassy Key and Long Key. Most of what we caught were small, except for a nice Hog fish, and we even witnessed schools of Tarpon hanging out and rolling under the bridge as well. Nonetheless, the bridges are a great place for a walk or pictures at sunrise and sunset!

Stargazing

The hubs had bought me a telescope for our 2nd wedding anniversary, so of course we had to bring that with us on this trip. Seeing as the Keys is much darker, and you can see way more stars than from home – we took the opportunity to do some stargazing in Big Pine Key. The reserve has some designated hiking areas for visitors, so we picked one of those spots for late night stargazing.

Even if you don’t have a telescope, and you want to see one beautiful sight, I highly recommend making a point to do this! And we have found Big Pine Key is the best place to at night.

Key deer spotting

We’re a little obsessed with the Key Deer thing – I mean, they’re a cute, smaller breed of deer that roam the island of Big Pine Key. So many times, especially at night, we will take a cruise through Big Pine Key just in search of Key Deer.

This trip, we were in the midst of a wildfire that erupted in Big Pine, which took days to contain. Because of this, Key Deer were out in the open, sometimes in herds, more often and during the day. I was even approached by one in the parking lot of a Winn Dixie. As you can imagine – I am still awe-struck about it today!

Kayaking

Obviously, since we hauled the yaks with us in the first place. Our intentions were more so to do exploring that we didn’t necessarily do last time. And mainly just to test the waters post Irma – we weren’t sure what to expect. Pleasantly surprised, the water was clearer than our trip last year! We were able to see perfectly in 4-5 feet of water on both sides.

Kayaking through the mangrove tunnel in Curry Hammock State Park is always a highlight (our next task is figuring out where there are more!), and our little man seemed to enjoy adventures out on the kayak as well.

Follow us kayaking the mangrove tunnel in our highlights video.

Snorkeling

The hubs did more research on this ahead of time, and our fingers were crossed in hopes to be able to snorkel Indian Key (which was only a mile or so out). I’m not one for “deep water” snorkeling, so knowing this was more of island reef snorkeling we were hoping for good weather, calm seas and clear water!

By far, this was the best snorkeling spot yet to date! From varieties of fish I’d never known, to some of the biggest conchs I’ve seen in my life. Not only can you explore and get to know the history of Indian Key, but nearly the entire north side is coral reef for snorkeling, while the south side is incredibly shallow (perfect for paddle boarding and getting a glimpse of crabs, small fish, conchs and small sharks!).

We even attempted fishing by doing an entire lap around the island, and managed to catch a few decent sized snapper fairly easy. But if you go to Indian Key, come for the snorkeling.

Watch our highlights video to see more in depth of our Indian Key snorkeling adventures.

Fishing

We carried over our usual spots from the last time we visited Marathon, but we also wanted to try a few other places on the Gulf side (No Name Key area and the Gulf side of Curry Hammock State Park), as well as in and around Indian Key. The Tarpon were rolling like crazy during this trip (you could literally find schools of them everywhere), but we were not equipped for hooking them this time around.

Hiking

Part of our love for coming to the Keys is not only for the outdoors, but enjoying it as much as our pups! We found a few more great places to hike in the State Parks. All the parks remain open, though portions or areas of beach were still closed off for construction.

Check out the coolest State Park hiking spots we encountered in our highlights video.

State Parks/Beaches

Bahia Honda (Big Pine Key)

A sight for sore eyes, for sure! We come here mainly for this view, and unfortunately this time around we did not get to snorkel or kayak the beach of Bahia Honda since it was closed for reconstruction from the hurricane. No matter, the Bay side beach was still open, and you can still walk the bridge to get the perfect Instagram photo!

Windley Key (Islamorada)

Formed of Key Largo limestone and fossilized coral, this State Park was once a railroad and quarry for the production of Keystone. There are many various trails to hike in this state park, and areas to explore that still contain parts of the quarry walls and machinery used in the early 1990s.

Indian Key (Islamorada)

Just south of Islamorada, Indian Key is just a short distance off the Atlantic. This tiny island has so much history, yet it’s popular for kayakers, paddle boarders and boaters for it’s snorkeling, fishing and exploring. Rentals and put in is available at Robbie’s – it’s that easy!

Check out our snorkeling highlights at Indian Key!

Curry Hammock State Park (Marathon)

By far our favorite State Park for kayaking and hiking. The trail head is actually off-site, just down the road, but the State Park entrance is where you can find kayak rentals and the put in to kayak the mangrove tunnel. This is the hot spot for kite surfers, and the park offers a small beach area that remained open post Irma.

Long Key State Park (Long Key)

Long Key suffered what seemed the most destruction – as much of the beach area was closed off to the public. But the trails remained open, and foliage had been cleared out by the storm for some epic views of the water.

Sombrero Beach

A drastic change since last year (although, I would say it is more beautiful and efficient now) since there is no longer the grassy “park area” behind the – what used to be – sand dunes. It is now all just sandy beach, which in turn makes the park feel more open and bigger. Park pavilions and on-site showers and bathrooms still remain, though the small boat dock is no more.

This is the largest public beach in the middle keys that is also dog-friendly! We enjoyed coming here with and without the dogs to relax and wade in the water as we watched boats go in and out of the channel.

Anne’s Beach

What was once a unique public dog beach with coves and small hiking trails, Anne’s beach was closed off and suffered severely from the storm. Hopefully, in time, this park will find itself once again and reopen to the public!

The Eats

Herbie’s Bar & Chowder House

Don’t let outside appearances fool you! This little hole in the wall is known for their 24 daily craft style beers on tap. We bopped over to Herbie’s on a late afternoon after Sombrero Beach, starting with an Iguana Bait Kolsch and a Spearfish Amber. I had the shrimp po’ boy and my husband had a buffalo-style Mahi sandwich. Get the basket of their seasoned fries – I’m telling you what – you won’t be disappointed. And obviously, we had the Key Lime Pie for dessert, as well as my first time trying mead – the Key Lime Pie mead as a dessert drink!

Sweet Savannah’s

Ice cream and cupcakes, anyone?! How about both? We came here twice on our 10-day trip (we could have more, but you know, #lifechoices). Get the Sweet Savannah Sundae – comes with your choice of a fresh daily made cupcake (I had their sweet and salty cupcake), two scoops of your choice of ice cream, your choice of toppings, nuts, whip cream and a cherry.

Yeah, tell me about it.

There are several sundae combos to choose from, like Mint Mania (which my husband had), along with obviously ice cream, shakes, coffee drinks, cookies and their Key Lime Pie (which was good, but had better elsewhere).

Key’s Fisheries

Unfortunately, we were only told about this place late in the game by our neighbor who lived next door to our rental. While there’s also a huge billboard for this place, strutting their Lobster Reuben (that I had been eyeing our entire trip) – for some reason we weren’t struck on going until it was told by word of mouth. So we went.

Might easily be the best low-key place to eat in the middle keys. And that’s saying something. Maybe it was the Lobster Reuben I had – but it was that good, ya’ll. My husband had their chicken sandwich special, and though it may not look like much on the outside – you get a killer view while enjoying your meal. It’s a self serve kind of place, so don’t be alarmed and taken back by surprise. Diners sit at picnic tables or in the upstairs bar, but they call your name over speakerphone when your food is ready to be “picked up”.

After having lunch, we went upstairs to their second story raw bar and were able to try our very first stone crab claw! Needless to say, I love seafood, but I’m not keen on anything “raw”. But so worth the experience, and a cold drink with a great view!

Curly’s Coffee

Good. Iced. Coffee. Period. You’ll miss this place by a mile passing it. It’s a teeny, tiny 8×8 square shack – literally. But it’s the Starbucks of Marathon, I tell you. It even has a drive-thru, if you can believe it. I would have stopped by here every morning for coffee, but it’s rather pricey, and this gal needs more coffee for the price!

Lazy Days (Marathon)

A beautiful sunset dinner on the water. More on the upscale side price-wise – yet, you’re in the Keys, so not really. Be sure to have their Moscow mule – it was really good! My husband was really into their “banana bread” rolls they served – alas, we took them with our to-go leftovers. We each had one of their daily specials – the ribeye and a Greek-style hog fish special, which were great.

The Florida Boy

We had passed this restaurant about 10x in our last two trips, and decided to make a point to stop. We sat at the outdoor covered patio near the bar. There was nothing really spectacular about this place, but I had to try the Lobster Mac and cheese on the menu. It was good, although nothing to brag about.

Marathon Bagel Company

This little gem is literally hidden in the Bealls Outlet shopping center just minutes from our rental. It’s a tiny, quaint breakfast shop with bagel sandwiches and coffee. A great, quick stop for a hearty breakfast without the hefty price! The bacon, egg and cheese bagel sandwich (probably their most standard sandwich) was great! Unlimited refills on coffee when dining in, so of course I was one happy camper.

Island Fish Co.

We went to Island Fish Co. for dinner on our last trip to Marathon, but primarily this place is on our “must list” for its deep fried key lime pie. So, essentially that’s exactly what we went back for. That, their conch ceviche as an appetizer as well as their flour-less chocolate cake. You read me right.

Hear me out now – if you get both, be prepared to take some to-go. The chocolate cake is richer than rich, and the deep fried key lime pie easily feeds three. And we only had an appetizer before that.

S.S. Shipwreck

Go for the buffalo chicken sandwich – hands down.  We must have dined in and ordered these sandwiches to-go about 4-5 times this trip (same as last trip, as well) – they’re that good. So when you’re passing through Grassy Key to Marathon, stop in.

Wooden Spoon

Again, try not to judge a book by it’s cover. A definite hole in the wall for sure, but hey – it’s breakfast. Nothing fancy here. It’s a crazy, busy, chaotic kitchen most mornings at the wooden spoon, but the servers are so friendly it’s hard to pass. The half order of biscuits and gravy were more than enough for one person (trust me), and any of their classic “your way” grand-slam style specials are delicious.

Stout’s

Another little breakfast joint not far from our rental – a little slower pace, and cute quaint style on the inside. The pancakes here are to die for – they’re the fluffiest, cake-like pancakes I’ve ever had (and they’re huge!). Our favorites thus far are the chocolate chip and strawberry pancakes, though their biscuits and gravy are really good, too.

No Name Pub

You can find No Name Pub in Big Pine Key (you might get lost getting there, but don’t fret – there are signs to help you!), since Big Pine connects to No Name Key. This tiny building has more than meets the eye – once you step inside! We have this tradition when we go – get the key lime pie first (the best key lime pie, so far, in all of the Keys in our opinion) and then stay for one of their pizza selections and a craft beer. Honestly, you can’t go wrong by checking this one off your list – make sure you add a dollar to their collection before you leave!

Key West

We made a day trip down to Key West to check out the sites! Honestly, it was like Key West was left untouched by Irma, since in our eyes remained unchanged. And since we had very limited time here, we decided to stop by some of our favorites as well as try something new.

If you’re visiting KW and Duval Street for the day, our advice is to park by the Fire Station (which is basically directly in the center of Duval Street’s hustle and bustle).

Smathers Beach

One of two public sandy beaches on Key West – these are obvious must-sees! Luckily, this long strip of beach still exists and is still beautiful to enjoy if you’re staying in or visiting the lower Keys. Just across the street there are several hotels and condo rentals that overlook this beach (a perfect, quiet area if you’re looking to stay away from the hustle and bustle).

Flying Monkeys

Sure, while we could go to Fat Tuesdays for the same exact thing – we like the underrated-ness of Flying Monkeys frozen cocktails. Plus, it was where we had our post dinner rehearsal outing the night before our wedding. Of course that has some sentimental value!

The Waterfront Brewery

Not exactly a hop, skip and a jump from Duval (since this beaut is located on Key West’s marina), but once you make it there you’ll never want to leave. The marina is lined with shops, restaurants and of course – boats, boats, and more boats. We were really excited to try this new brewery, and were impressed with the flavors and the price of our flight! The Key Lime beer was the all around favorite of choice.

The Commodores Boathouse

Come for happy hour (drinks and half off apps)! And luckily we did, because the Boathouse was overflowing by the time we received our check. But if you come early enough for happy hour, the appetizers are half off and drinks are cheap! We shared several different appetizers (which were more than enough as a meal for each of us) – the conch fritters, filet kabobs, and grouper bites.

Kermit’s

If you’re in Key West, do yourself a favor and be sure to stop by Kermit’s for chocolate-covered key lime pie ON A STICK. Seriously, enough said. 

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