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Your Guide to Key West

Since 1998, I’ve been to the Florida Keys on average, about once per year. It’s a place I connect with on multiple levels. I have roots in Fells Point and since my toddler days and earliest memories of my grandfather holding my hand and walking me down Shakespeare Street to the docks beside The City Pier where the tugboats rested, I’ve always loved the water. For me, Key West is what you get if you throw the foot of Broadway into the Caribbean.

If you too are a fan of both, you know what I mean.

No trip to the Florida Keys is complete without driving through them, particularly if it’s your first visit. Flights into Fort Lauderdale or Miami are priced reasonably. Some prefer to hop on a puddle jumper into Key West but for me, the drive “down” is like a huge welcoming mat that gradually brings you into a Key West state of mind. Coming home is a different story. When the unfortunate hour arrives and your visit is officially over, the puddle jumper back to Lauderdale/Miami is recommended. But by all means, enjoy the drive on your way there and make a few strategic stops along the way.

Here are a few recommendations:

Gilbert’s in Key Largo (Mile Marker 108.5)
Loralei’s in Islamorada (Mile Marker 82)
Morada Bay in Islamorada (Mile Marker 81.6)
No Name Pub in Big Pine Key (Mile Marker 30.2)
Mangrove Mama’s (Mile Marker 20)

Key West

Driving Directions to Key West

There are just 3 things you need to know when driving to the Florida Keys:

1. Get on the Florida Turnpike and follow the signs to Key West.
2. Rent a convertible
3. Turn the convertible in within 24 hours. You won’t need it afterwards.

Did I say rent a convertible?


At first, the drive doesn’t seem like any big deal (even less of a big deal if you head to the Keys straight from Lauderdale). Before long you are on the Florida Turnpike. About 45 minutes into your drive you will hit Florida City. Shortly thereafter “the tunnel” begins, just as you approach Key Largo.

Soon you’ll notice water to both sides of your convertible. At first, it’s a bit swampy but gradually, you begin to see more of the ocean bays to your left and the Gulf to your right. The drive just continues to get more beautiful along the way as you venture deeper into “the tunnel”. It’s as if you can feel your body begin to unwind. Vacation is calling…

Be sure to get to the 7 Mile Bridge during daylight hours (Mile Marker 47). Words will never to that drive justice. It’s a vibe you need to live and breathe. But the 3 1/2 hours from Miami are well worth it, especially if equipped with sunscreen, a little cooler (stop at Tom Thumb’s and get a cheap styrofoam cooler), great tunes, A/C cranking and the wind through your hair.

A great place to stop for a cool dip is Bahia Honda State Park (below at Mile Marker 36)

Bahia Honda

As mentioned earlier, once in Key West, dead-head your convertible at the Key West Airport.

Turn. It. In.

You won’t need the car during your stay. Save your money and rent a bicycle. Get those cheap old ones – the cruiser bikes. We usually pay about $10-12 per day per bike and rent the bikes from a place on Truman Ave just off Duval. Not only are bikes cheaper, they are more convenient. You don’t have to worry about drinking and driving or parking. It’s a no brainer and if you can’t handle the bicycle after pit stops along Duval, cab rides are cheap. Rickshaws are available too, but more costly.

Don’t be tempted to rent a scooter. It’s more expensive, more dangerous, other knuckleheads are driving them during their Duval Crawl and there are still parking issues. Plus, you really don’t get to places any faster. Trust me, I know these things…

[Related Article: Cool Sailing on the Bay]


It’s best to stay near Duval Street, the true heartbeat of the 2-mile by 4-mile island. Now there are certain places that are very nice down near Mallory Square and there are many bed and breakfasts that are also very nice, depending on your budget. If you are going to do Key West right, you won’t be in your room much at all. So, get a place that is nice, clean and convenient but won’t break the bank.

Try Home Away or my girl Susie Rodnon. She’s a local and will work hard for you to find a place that is priced fairly to fit your needs. I’ve leaned on Susie for help for the last 6 years or so and she always delivers!


Things To Do

1. Do a sunset/snorkel cruise…well worth it! Try either Sunny Days or Sebago. The trip to Dry Tortugas is an all-day event but breathtakingly beautiful and well worth it particularly if you are staying for 4 or more days. If you’d rather keep your excursion to 4 hours, then try one of the snorkeling trips to the coral reef. Or if you don’t want to snorkel at all, there are plenty of sunset booze cruises available. Usually $50 will get you some decent munchies, the cruise, a band on board and of course those cold libations.

2. If you like jet skis, there is a place down at the Gulf end of Duval near Mallory Square just behind the Ocean Key Resort. (Side Note: I’ve stayed here a couple of times and it’s a great spot). It’s the ultimate jet ski tour. You go out for 90 minutes and do a complete lap around the island. It’s about $100 but well worth it. The guided tour is a blast and you’ll learn more about the island.

Key West Jet Ski

3. The Hemingway Home tour on Whitehead Street is worthy and I’m not much on such tours. My attention span is that of a child’s but I did enjoy this tour. Hemingway was an interesting guy to say the least. He was a big fan of the Original Sloppy Joe’s which is now Captain Tony’s. The tour is a nice thing to do if it’s overcast or if you want to get out of the sun for a bit. It takes about an hour.

4. Sunsets at Mallory Square are fun…lots of Vaudeville-like acts there…there are a few tiki bars (the one adjacent to Ocean Key is great) in the area with live music, all of which take advantage of the gorgeous sunsets.

5. Once when I took the kids to the Keys, we did a tour of the dolphin playground…they swim up next to the boat…that was very cool… Check Sunny Days or Sebago. For those who think Key West isn’t for kids, I’m here to tell you that it can be if you want it to be and mine can’t wait to go back. But if they are under 15-ish…keep them out of the bars, even if it’s just for lunch. I made that mistake when my daughter was around 10 and the guy up on stage at Sloppy Joe’s was dropping F-bombs like a sailor. My daughter looked at me and said, “Dad, I don’t think this place is appropriate for children.” Let’s just say it wasn’t one of my finer parental moments.

Places to Eat, Drink & be Merry

1. Irish Kevin’s Bar….is a riot…acoustic guitar players that mix in some off-color humor…and sing-a-longs…very fun place. I learned not to take the young-ins there (see above).

Irish Kevin's

2. Hog’s Breath (it’s better than no breath at all): Always home to fun-loving and talented bands.

3. Schooner Wharf Bar – Key “A Last Little Piece of Old Key West”…during the day….go and get a grouper sandwich…it rocks and the entertainment is usually Michael McCloud….he’s very, very mellow which is great in the sunshine while having a cocktail…he’s also very funny….in an extremely dry sort of way. This is the ultimate in laid back Key West. If you are looking for energy, bring your own.

4. SLOPPY JOE’S BAR…a Key West institution that might put you in an institution of your own. And then of course there’s the “Original” Sloppy Joe’s, now known as Captain Tony’s Saloon.

5. Other places on Duval we’ve enjoyed: Rick’s Bar, Durty Harry’s, The Smokin’ Tuna, The Bull…. also check out The GREEN PARROT BAR…a locals’ favorite on Whitehead Ave, emphasis on “local’s bar”. It isn’t uncommon to be ignored by a snooty bartender who dishes preferential treatment to the locals. But the music is usually worth the temporary snubbing that is quickly squashed by a healthy tip.

6. Have breakfast at Blue Heaven…a must! Look for the Baltimore connection. You’ll be walking on it.

Blue Heaven

7. For raw bar….check out Turtle Kraals or Half Shell Raw Bar down near Schooner’s in Old Town…..ask for Greg from Baltimore…he’s a great bartender and partial to The Land of Pleasant Living…he’ll remember us….in fact, last time we saw him, he said “I heard you were coming down.” When I asked how he heard, he said he read it on Ravens 247! The power of social media.

8. If you are down in KW during football season, I recommend Dante’s. It’s a great pool bar and they have NFL Ticket. We once watched the Ravens and Dolphins there. Sunshine, libations, beautiful pool and a view of the harbor. Can’t wait to do it again!


Other places to watch NFL games include:

• Jack Flat’s
Sandbar Sports Grill
• The Lazy Gecko

Parrothead Warning

Margaritaville looks like it could be in any shopping mall and is a real disappointment, unless you frequent Ruby Tuesday’s or Applebee’s. Then you will feel right at home. But despite this money-saving warning, you will undoubtedly check it out because you can’t help yourself, and then you will tell everyone else exactly what I’m telling you now. Unless of course you happen to be lucky enough to catch a rare Jimmy Buffett sighting, but then again if you are lucky enough to be in Key West, well, you are lucky enough.

Fine Dining

If you are willing to plunk down about $125-150 per couple (including cocktails), my recommendations include:

Hot Tin Roof
La Trattoria
Nine One Five
Louie’s Backyard

Louie's backyard

Rip Off Alert

Latitudes will lure you in with its setting and awesome sight lines. It’s very pricy and at the end of the day you will conclude that the juice wasn’t worth the squeeze. The wait staff was hardly accommodating after issues we had with my wife’s dinner which was eventually served when the rest of us (party of six) were already on to our desserts and after dinner drinks. You might think that they would have done something for the major inconvenience and party pooper antics, but nooooo. It was as if they knew others would get sucked in by the allure of Sunset Key (it’s on a small island just across from Mallory Square). They just didn’t care.

Do yourself a favor! Get better views from a sunset cruise and eat at a place that is not only better, but less expensive and snob free. They should change the name of this place to Attitudes!



Key West doesn’t have a lot of great beaches….in fact they have no “great” beaches. You can always crash the small ones at the hotels near Mallory Square or at Casa Marina Resort…no one really cares in Key West. (At least that’s what I tell my friends when we sneak in.)

Casa Marina has a nice ocean side bar. Grab yourself a couple of chairs, be discreet and willingly tip the bartender, wait staff and the guys who will drag your comfortable beach chairs to your desired location. The hospitality directly parallels your generosity. They might even offer you a refreshing, complimentary popsicle.

Key West

There’s also Higgs Beach or Ft. Zachary Taylor beach. ZT is a bit better but Higgs has a little restaurant nearby with friendly bartenders to “hydrate” your system. Oh, and if ZT’s is your choice, take some old sneakers or something to protect your feet. Admittedly I have wussy feet but given my self-awareness, those old shoes allowed me to wade comfortably instead of stepping on broken coral and shells. Without the shoes, I look like a man walking across molten lava.

There’s also a pool at the Southernmost Hotel/Inn near the southernmost end of Duval (Atlantic side). It’s open to the public for a daily fee of $5 or $6 and they have a bar there as well….usually they offer a free drink with your admission fee. Directly across Duval is the Southernmost Beach Cafe. That’s a favorite spot of ours, with a friendly local flare (pictured below).

Key West

Going home…

I used to drive back from the Keys to Lauderdale but lately the puddle jumper back there or to Miami is my preferred way to go. Besides, it’s so hard to leave that we opt wait to the last possible minute. You might also consider Lauderdale by the Sea for a couple of days after Key West. It takes the pressure off your flight schedule although it adds pressure on your wallet.

Please share your Florida Keys experiences with us in the comments section below. Feel free to send along pictures too and we’ll create a Key West gallery (

That said, as others who have traveled to Key West can attest, some of what happens in the Keys, stays in the Keys.

Tony Lombardi
Besides his work here at Thumbs Up 247, Tony is the founder and His work has been featured on various sports websites and he hosts The Russell Street Recap. Among his favorite things in life are his wife, kids, family, friends, The Beatles, Breaking Bad, Gladiator, The Godfather, Guinness, orange crushes, meatballs and Key West, not necessarily in that order. Follow Tony on Twitter @RSRLombardi. Drop him a note at

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