PSL Source Baltimore Ravens PSLs
A Guide to Key West

Key West A Guide to Key West

Posted in Key West
Print this article

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 relatively reasonable on Southwest Airlines or AirTran. Some prefer to hop on a puddle jumper into Key West but for me, the drive is like a huge welcoming mat that gradually brings you into a Key West state of mind.

Besides, there are plenty of great things to see along the way and places to stop, eat and have a responsible libation or two.

Driving Directions from Ft. Lauderdale to Key West

Should you decide to drive, 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) until after you go over the causeway outside of Miami Beach and see all of the beautiful homes and emerald waters…before long you are on the Florida Turnpike. About 45 minutes into your drive you will hit Florida City. That’s where what I call “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…

One of my favorite little stops is Hog Heaven at MM 85 which is in Islamorada. The peeps are mostly local and very friendly. Islamorada is very laid back and if fishing is your thing, Islamorada is for you. Marathon Key is great…also laid back and they have these cool little house boats that you can rent that are unique and well worth it. Faro Blanco Marine Resort, Marathon Key, Florida

Get to the 7 mile bridge during daylight hours….Words do not do the drive justice. 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 and the wind through your hair.

A great place to stop for a cool dip is Bahia Honda State Park….it’s beautiful…

Once in Key West, dead-head your convertible at the Key West Airport. Turn it in! You won’t need the car. Save your money and rent a bicycle. Get those cheap old ones….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 less expensive and way more convenient. You don’t have to worry about drinking and driving –parking…there’s really no contest…and you get to see more of the island that way as well….


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 — but very expensive. 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.

And boy do I have the right place for you — a great little place in a quiet part of town just a couple of blocks off Duval Street at 823 Virginia Avenue.
The place features two cottages…one that comfortably sleeps 6 and the other that sleeps 4. All of the modern amenities are included and I can tell you from experience that 823 Virginia Street is priced extremely fair.  And why wouldn’t you want that? Save your cash for the fun and lunacy of Duval Street or the many, many water activities in and around town.
The two cottages share a secluded built in pool that is protected by tropical trees and plants to provide comfort and privacy.If you have an upcoming trip to Key West, do yourself a favor and check out the prices and availability for 823 Virginia Street before you make any commitment elsewhere.*** BUT BE SURE TO MENTION AND GET 1 FREE NIGHT’S STAY WHEN YOU STAY 4 OR MORE NIGHTS. ***
Generally speaking, rates are in the $150-200/night range and trust me, it is a great value particularly when the expenses are shared by 6.Here’s the 411 on 823:Rick Wagner
823 Virginia Street
Key West, Florida 33040
Cell No. 813-695-5490


Some must do’s in Key West and places to party/eat/check out:

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.

2. If you like jet skis, there was once a place next to the Walgreens on Roosevelt Blvd next to the Hampton Inn….rent them there.  A similar tour is described here The Ultimate Jet Ski Tour (Key West, United States of America) Adventure Tour.  We went on a tour around the island that lasted nearly 2 hours and we paid $90 per ski. Other places will charge $65/half hour and restrict you to a certain area. It may be a tad more expensive now but even if it’s $25 more I’d say, “worth it!”;

3. The Hemingway house tour on Whitehead is worthy and I’m not much on those tours…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.  This is a nice thing to do if it’s overcast or if you want to get out of the sun for a bit. HEMINGWAY HOME & MUSEUM

4. Sunsets at Mallory Square are fun…lots of Vaudeville-like acts there….but if you want to hit the best kept secret in town (not anymore) head to La Concha Hotel on Duval, the tallest building in Key West. They have a sky bar and it’s the best for taking in the sunset and for those great photo ops.  I even proposed to my wife there.

5. Once when I took the kids we did a tour of the dolphin playground….they swim up next to the boat…that was very cool… For those that 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.

Places to go to drink and 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

2. 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 mellow which is great in the sunshine while having a cocktail…he’s also very funny….in an extremely dry sort of way.

3. 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.
4. Other places on Duval we’ve enjoyed: , Hog’s Breath Saloon, Bare Bottoms, Flying Monkeys, The Bull…. also check out The GREEN PARROT BAR….a locals’ favorite on Whitehead Ave.

5. Have breakfast at Blue Heaven…a must!

6. 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 Ravens24x7….
7. 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!Side note…..Margaritaville looks like it could be in any shopping mall….it’s a real disappointment but you will undoubtedly check it out 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…



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…..then there’s 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….there’s also a pool at the Southernmost Hotel/Inn near the end of Duval. 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.

Going home….

I used to drive back but lately the puddle jumper back to Ft. Lauderdale or Miami is the way to go. Besides, it’s so hard to leave that we waited to the last possible minute.  You might also consider South Beach for a couple of days after Key West.  It takes the pressure off your flight schedule.

Share your Florida Keys experiences with us at and we’ll post them here.  But some of what happens in the Keys, should stay in the Keys.




I have followed your recommendations to the letter including this great little cottage (and a no-brainer for the money) and the only bad thing that I had to deal with was leaving. I can’t wait to go back! And trust me, I will!!!

Oh and this time I’ll definitely pull out the card for the extra night.

Here’s to KW,

Eddie Vasiliades, Perry Hall, MD


“We found a great place for breakfast this year.  It’s in Islamorada – – click on the link on the left that says Islamorada Restaurant and Bakery.  They had the best food ever!

We also eat dinner at Hawk’s Cay Resort in Marathon every year – Watersedge Restaurant – fine dining but very casual.” ~ Dolores Pucher, Baltimore, MD




Hello Tony,

I’ve read 24×7 for a while, my compliments for a terrific and informative Ravens website.  I happened to stumble upon the link to your Key West suggestions just in time for our trip to Florida .  I printed off your list and took it with us.  We actually stayed in South Beach and drove down to Key West for a couple of days 6/6-7.

Other suggestions for consideration for your informational link and or next trip:

-We had to have lunch at the Hard Rock Cafe (outdoors of course)

-Take the cheesy train tour ride around town (very informative and it will orient you to the town)

-Dinner at the Blue Heaven restaurant (very different – a memorable dinner)

-You have to stop in to have a margarita at the Margaritaville bar (ask for Sherry the bartender)

-Breakfast at Camille’s located at Simonton & Catherine Streets  (outstanding breakfast food)

-Lunch at Jack Flat’s Cafe/Bar on Duval Street – about 495 Duval ??? (excellent food at reasonable prices – great friendly service)

and you were right…

-You must experience the sunset festival in Mallory Square (go early to reserve a seat at dock side or you will be standing). The street vendors, artists and vaudeville type acts are very entertaining.  The sunset “main attraction” is incredible…

-At least one morning you have to get up early to watch the sun rise over the Atlantic … a unique experience

Thanks for the tips…

I also listen to the radio show whenever my schedule permits.  Good Luck with the show!

All the best…

Jack Moore



We have never met but I look at your website on a weekly basis to get updates on Ravens stuff and see what people are talking about. Then today I sign on and found your blog on Key West . Sounds like you have been there a lot. I have a surprise for you. I belong to an elite group of firefighters who crash Key West every year. This year will be our 10th anniversary of crashing Key West . We take anywhere between 80 to 100 people on our trip and it is a blast. We are down there for about 8 days and it is a hoot. We have been going down so long that we now have sponsors who get a shout out on our website in trade for their donations. We also march in the annual Conch Republic Parade host by the Vice General of the Conch Republic Peter Anderson. If you mention us he will most definitely set you up with a passport by mentioning our group.

If you have people who frequent Key West then you must at some point hook up with us as we have Key West to a science. We even have the fire department donate fire pumps for the Bloody Battle that we participate in every year. If you are not familiar this is where the Conch republic re-enacts the battle that took place for the succession of Key West from the U.S.A. Interesting reading.

Our group is known as The Castaway Travel Group and we are a travel group that has only managed to travel to Key West (talk about a state of mind). We fell in love with Key West and they did with us. We walk around Key West with tags on and day time prices on drinks and free cover to all the popular places. You need to check out our website and I am definitely going to shout out your website to them.

Your article sparked interest because a buddy and I are doing the exact thing you talked about and making the drive from Ft. Lauderdale . I am hopeful that your group and ours could possibly merge and really become and force in Key West ….


Keep up the good work on your website?

Wasted away,

AL Brown

Castaway Travel Group

Ravens Fan



The wife and I just got back from Key West on Saturday.  I wanted to say “thanks,” we took your ideas to heart and drove down from South Beach .  Here are some recommendations I have, if you want to post them on your site:

1.  I can’t recommend these two restaurants enough:  Blue Heaven and Meteor Steakhouse.  Blue Heaven is laid back, and has incredible breakfast and dinner selections.  It’s also off the beaten path a couple blocks off of Duval Street.  The Meteor Steakhouse is even more laid back, and has amazing barbecue – they have an amazing “green beans” appetizer that you have to eat and see to believe.

2.  We took a puddle jumper on Continental back to Fort Lauderdale to catch our flight home.  I can’t recommend that enough – it’s $90 each for a 50 minute flight, but you fly over the Everglades and see the Keys as well.  In addition, you avoid any traffic issues and stress on your way back to catching your flight.

3.  Go to for some Bed & Breakfast recommendations.  We ended up staying at The Nassau House (  The owners were very nice, with an impressive breakfast spread each morning that they cooked themselves.  It was a little far from Duval Street – 6 blocks up Fleming Street – but we rented a couple of bikes to make it a little easier.  Next time we’ll stay a little closer.


Darren Weagly


“I too just got back from Key West and had a great time.  I went to a restaurant for breakfast called Blue Heaven— they had had the best pancakes and coffee and when leaving noticed the bricks (see attached).  Baltimore is well represented.

We got to the Keys from Ft Myers on a two hour high speed boat ride.  Ft Myers and the surrounding areas are a nice alternative to the East coast of Florida.” ~ Bruce, Ellicott City




Hey Tony,

Your article on the Keys inspired me!  Heading down May 6-13.  Flying into Miami , renting a Jeep Wrangler and doing the drive thing just like you suggested.  Hope to hit some of your suggested places!

Jen Siler


Jen’s Follow up

Hey Tony,

Had a great time in the Keys!  Would definitely stay at the Speakeasy again, that place rocks!  We recommended it to friends already who want to go to Key West in December.

Thanks for the recommendation!




Facebook Comments
Share This  
Tony Lombardi

About Tony Lombardi

Tony is 24x7 Networks, LLC's founder (the parent of and His work has been featured on various sports websites and he is a regular guest on 105.7 The Fan and CBS Sports 1300. A diehard Fab Four fan, Tony is a frustrated musician who thinks beating on the steering wheel is akin to being John Bonham. Follow Tony's new Twitter @RSRLombardi. More from Tony Lombardi


Your browser is out-of-date!

Update your browser to view this website correctly.

Get More Information