Keys Please


Over the next week, my girlfriend and I will be taking a mini-roadtrip from Orlando to Key West, primarily focusing around the Keys. I’m really excited – the Overseas Highway is something I’ve been dying to visit since…well, since I first saw it get blown up in True Lies, but I digress.

Anyway, you guys have always had great travel tips in the past, so I’ll throw it to you: anything we definitely need to see, do, eat, or experience while we’re down there? Most of the trip will be focused in the Keys, but we’ll be passing through Miami and the Everglades on our way down too.

Thanks in advance!


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  1. Meredith Marciano

    The Hemingway House. Lots of “Hemingway” cats live there too (cats with thumbs).

  2. Meredith Marciano

    And all the art deco hotels/buildings in South Beach if you’ve never seen them before.

  3. Will be going down for the first time in July myself so i look forward to what see what you think of it.

    like I said, I haven’t been, but someone who goes 2-3 times a year gave me the following suggestions that i plan to check out:

    Green Parrot Bar, (Ask for Garry)

    Virgilio’s, (Apparently the only place in the Keys to try Italian food, but good drinks and entertainment)

    Blue Heaven, (Make reservations, great seafood)

    Sloppy Joe’s, (Most famous bar, Hemingway drank here)

    Then of course there’s the Hemingway house, the lighthouse, and I hear the Moonlight Sail and the Glass Bottom boat sails are worth doing. If you like cigars the Key West Cigar Factory is good. Also, I was told EVERYTHING

  4. Sorry got cut off… As i was saying:

    Also, I was told EVERYTHING in Key West is expensive so since you’re driving, if you’re staying in a house and want to buy some food for the time you’re there get it on the way to key west.

    Enjoy the trip!

  5. Two Key West bars that are sort of landmarks, have great live music every night and are always a good time:

    Also, stop at ISLA MIRADA on the drive down and go to the TIKI BAR….It’s the midpoint between Miami and Key West, and is a great place for a cold drink and swim to break up the long drive. Great people watching here, too.

    Also, go see the sunset at MALLORY SQUARE (The Southern most tip of the continental U.S.) – lots of street performers, vendors, wacky tourists and a pretty view.

    Definitely try to go snorkeling. There are several companies that offer inexpensive day trips. They have stands set up all over, so no need to pre-book.

  6. Keys Fisheries in Marathon Key has some wonderful seafood and sandwiches (LOBSTER REUBEN)

  7. If you’re into cemeteries, the Key West cemetery has a rather well-known mausoleum with a marker for B.P. Roberts, with the epitaph “I Told You I Was Sick!”.

  8. I second the Key West cemetery. It was fascinating – and they have a map to help you look around. Very peaceful even though it is in the center of town.

  9. Coral Castle, Vizcaya, the abandon Miami Marine Stadium, the cat man show in key west.

  10. I’d never snorkeled before I went to the Keys this past winter and am now in love with it.

  11. Denny’s Latin Cafe in Key Largo. Amazing cafe con leche.
    Scout, we also stayed at Parmer’s Resort on Little Torch Key – retro but awesome, I think you’d enjoy it. Beats the tourist traps in Key West by a long shot! Have fun, and let us know how it goes!!

  12. I second the Keys Fisheries. It just north of the 7 Mile Bridge. Just south of the bridge is Bahia Honda State Park. It is the most beautiful place I have ever been.
    Key West is expensive, but not anymore so than Manhattan.

  13. The Deering Estate in Miami is wonderful.

  14. Advice from a road-trippin’ Florida kid:

    STAY HYDRATED. No joke. Aim to drink a gallon a day if you’re outside at all. You’ll sweat most of it out. Seriously.

    Flamingo Crossing ice cream on Duvall St (Key Wwest) has spectacular home-made ice cream. Commit to the crazy tropical flavors like passion fruit or guava; you won’t regret it.

    Also in Key West: have conch, if you can find it. It’s delicious. Mind the cats. And the chickens.

    If hitting theme parks, start as soon as the gates open and hit the long-line rides for tickets. Don’t bother with any parades. After 3, go on all the rides that little kids also like, like flumes– the kids will all be cranky and wanting to go home by then, so won’t be in line any more.

    The Dali museum in St Petersburg is amazing and well-worth a day’s detour to the west coast.

    Ditto beaches– gulf beaches are much calmer and generally more pleasant.

    Keep extra water in the car. Again with the hydration.

    Oh yeah: sunblock. No joke.

    Titanic bar & microbrewery in Miami, right next to UM, is excellent for food & beer. This is a rarity in Miami (or was, when I last lived there). It’s a favorite. Might still have karaoke on Sunday nights.

    Take a day to walk around South Beach. It’s a different beast from Miami altogether, and it’s one of the best places to people-watch ever.

    It’s about a 3-hour drive from Miami to Key West, with not many opportunities for bathroom facilities. Take those opportunities.

    Yes, it’ll thunderstorm pretty much every afternoon. Pack shorts and rubber flip flops– go for easy-to-dry as opposed to trying to avoid the water. Less hassle that way. Plus, walking in the rain is the best way to cool off!

    Mandatory photo op #1: the southernmost marker (Key west).
    #2: I-95 mile 0 marker. One day I’ll get the other one in Maine.

    If you can make it work at all, go visit weeki wachee springs in Spring Hill. It’s Old Florida at its best; a small theme park that pre-dates Disney. My dad went there as a kid 45 years ago and met one of the (now retired) mermaids when we last visited 10 years ago. It’s a living landmark, and very special:

    Have fun!

  15. And have key lime pie at the key lime pie factory in key west. It’ll change your life.

  16. Fort Zachery Taylor Beech (often called Elizabeth Taylor Beech by locals)…was my favorite…not many tourists there and in Key West that’s a blessing, the two colors of the water coming together is beautiful. Sunset cruses are nice…take the Conch Train..once…it’s fun, you’ll see the city…and Theatre there is good: Waterfront Theatre, Red Barn Theatre or Tennessee Fine Arts Center.

  17. Before you actually get to the keys there is a fruit stand called Robert Is Here. Stop for a shake. They are amazing. Vizcaya is beautiful in Miami. Just south o downtown.

    • A big YES to Robert Is Here just before you leave the mainland… get a key lime shake and check out the unusual tropical produce. Heard that the nearby alligator farm is fun, too, though I’ve not personally been there.

      Also, Bahia Honda (as someone previously mentioned) is beautiful, and a neat place to check out one of the few parts of the Overseas Railroad that’s left standing.

      For a great place to get a drink and watch the sun set, check out Morada Bay in Islamorada. (You have to do it in Key West as well since it’s on every tourist’s must-list, but it’s totally crowded and commercial.)

      My niece and nephews love feeding the tarpon at Robbie’s in Islamorada (

      Further south, check out the old portion of the Seven Mile Bridge and get over to Pigeon Key, but beware that you’ll have to either walk or rent a bike since the old bridge is no longer open to vehicular traffic.

      And we’ve always loved Louie’s Backyard as a place to eat in Key West.

      Dunno if Key Lime Pie Factory will change your life, but pretty much any key lime pie you get in the Keys will be fabulous, especially if you can find a restaurant that makes their own fresh.

  18. Conch chowder in Key West. And conch fritters. And remember that the “h” is silent!

    I imagine the places I used to go there are all closed (last there in 1986), but the conch chowder we used to scarf down was at a place called either the Full Moon or the Half Moon.

    And key lime pie by the handful. Every time I went down I had key lime pie every single day and never from the same place twice.

    Take a bike ride around the key’s perimeter–it’s not far, and it gives you a wonderful sense of the island.

    Going fishing on a party boat (we used to go on Captain Jack’s Greyhound II, if that’s still around) is also fun. It was never particularly full, you could lie in the sun on the top desk if you liked, and it was really peaceful.

  19. I just saw a piece on CBS Sunday Morning about Fort Jefferson which was built on a sandbar off of Key West. Looked like a fascinating day trip.

  20. When in Miami, go check out City Hall Building at Dinner Key Marina. They converted the original Pan American Marine/Air Terminal into City Hall.

  21. You must stop at the No Name Pub in Big Pine Key!!! I think you will find the history of the bar very interesting. The dollar bills on the walls are a sight to see!

    • Sean P. Fodera

      I’ll second the No Name Pub. I’ve never been, but folks I trust implicitly (including one major science fiction author) are regulars.

      Have a great time!

  22. There’s a Trolley tour in Key West that’s touristy and hokey, BUT they give you a lot of info about the architecture and history of the island while driving you around to the parts that you wouldn’t otherwise see just doing the tourist Duval-crawl/Mallory square thing.
    The Hemingway house and Old Lighthouse are also pretty fantastic.

    As for driving through the Keys, I’ve made the drive a number of times and am always pleasantly surprised at the places I just happen upon. You’ve got a great eye for hidden gems. Definitely use that and just pop in to any place you see. Don’t be afraid to drive off the main road (there is only 1 main road the whole way) and explore a bit.

    Can’t wait to read about it, have a great time!

  23. ALSO, having driven from Ft Lauderdale all the way to Tallahassee more times than I can remember, even though it’s a toll road, I highly recommend taking the Turnpike over 95. Less big trucks, less crazy driving, less accidents, equally visually boring. 😉

  24. I always send people to Pepe’s Cafe, the oldest eatery in Key West. The food and service are excellent, but I particularly enjoy going for breakfast. The courtyard tables are worth the wait.

    806 Caroline Street

  25. You have to stop at Kino Sandal in Key West for leather sandals! They’re all hand made in house and like $13. Total Florida staple.

  26. Okay, there are a lot of comments about Key West and places in Miami, but you must have adventurous start to the Keys.

    On US1, just below Florida City you will see signs for Card Sound road to your left. This is the less traveled and somewhat longer road to Key Largo. Along the way, you’ll pass a now closed Navy listening post, what remains of the old squatters homes that were mostly washed away by hurricane Andrew and then you’ll reach Card Sound Bridge. Card Sound bridge is little used, but is the highest accessible point in the Keys and will give you a great view of Miami. About a 1/2 mile across the bridge, you’ll come to a flashing stoplight (or it was when I used to frequens tthe area). Don’t bother turning left, you’ll end up at the guard gate of Ocean Reef Club and WILL NOT get in. However, turn right towards Key Largo and surprises abound. First, you’ll see the remains of a radr station built during the 60’s. It was actually maintained in a mothball state until about 1984. Very cool. A bit farther down the road, look for a road on the left that has chain link gate. Yes, most roads are gated but this is special. When you see the remains of a guard shack you have found the right one. Behind the gate is the remains of an old missle complex. We used to get in therough holes in the fence, but probalby not anymore. In the 90’s various law enforcement used it for training. The ground was littered with casings from M-16 rounds. The climas is the remains of a development that was shut down due to environemtal concerns after it was started. it is now a nature preserve but you can walk in on the old road. Loook for the entrance on the left. You can’t miss the large structure that was going to be the main entrance. and on the opposite side of the road from this main entrance is the helipad that was built about 15′ above the ground. After driving this empty stretch of raod, you’ll join back up with US-1 and be at the north end of Key Largo.

    If it’s early enough, have breakfast at Mrs. Mac’s kitchen in Key Largo. I have been eating their since 1981 when I first visited Key Largo. Probably not the same owners but you don’t find places like it much anymore.

    Enjoy your trip!

  27. website about preserve in North Key Largo. Breifly mentions the Nike missle site.

    The Port Bouganvillia development that is now a park. Only a 1 mile walk and definitley worth it.

  28. Do yourself a favor & pick up Last Train to Paradise: Henry Flagler and the Spectacular Rise and Fall of the Railroad that Crossed an Ocean by Les Standiford. It will really put into perspective much about the history of what it took to build all those bridges to Key West & why Flagler wanted to do it. You will appreciate the drive that much more.

    Have a safe trip. Enjoy!

    • I second that emotion. No Flagler, no Florida, at least as we know it. I was wondering if anyone would mention this. Great background. On the way down if you have the time visit the Cape. The Saturn V experience is worth it, sure it is touristy but isn’t that what we all are away from home? And I am surprised no one mentioned Ron Jons in Cocoa. Sort of like a Florida version of Wall Drugs or South of the Border.

  29. By all means see Vizcaya in Miami on Biscayne Bay. The house and gardens are unique. The exquisite design and the antiques pit it in a class with the best of Newport and the Gilded Age. It is truly a don’t-miss place, in its way more important than the Art Deco reclamations in South Beach. If you can only see one thing in Miami, make it Vizcaya.

  30. 30 years ago I stayed at the Old Marriot, it felt like Club Casablanca, beautiful old building with newer additions. Don’t miss the sunset and entertainers at the pier

  31. Awesome! I’m looking forward to this! I too dream of one day doing a road trip involving the Florida Keys, and yes, also because of the bridge scene in True Lies!

    As you like that sort of thing, and if you have time to read, try finding some books from the Travis Mcgee series by John D Mcdonald. Mostly set in Florida and the surrounding area and good fun.

  32. On Key West, definitely pick up a bike rental and bike around the island. If you ride the perimeter route, you’ll pass the US 1 mile marker, some non-touristy beaches, a Navy base and giant desalinization plant.

    The Hemingway House was great to see. Descendants of his six-toed cats wander the premises. If you need more Hemingway, there’s Sloppy Joe’s, but it’s not too special and everyone else who’s visiting will be stopping by.

    We took a boat out to the Dry Tortugas, which are a group of tiny islands about forty-five minutes from Key West. There’s a lot of great sea life you can see there if you snorkel or dive. There’s also a great-looking Civil War fort that, unfortunately, was closed when we went.

    Zachary Taylor Beach is a wooded, isolated, non-touristy beach on the residential side of the island. It was nice to visit, but not to go swimming in – the rocks under the water are surprisingly sharp.

  33. If you decide to see South Beach (which I highly recommend for the architecture alone), you should take a peek at the Raleigh Hotel. It’s classic 30’s deco still in top form. If you can, sneak up on it beachside to see the famous pool.

    Have fun!

  34. Another vote for Keys Fisheries in Marathon. Get the Lobster Reuben. Deelish. Walk it off on Old Seven Mile Bridge, then drive over the bridge to Bahia Honda Park.

    Have a drink at the Holiday Isle Tiki Bar in Islamorada. Take a walk on Anne’s Beach, also in Islamorada.

  35. The Dry Tortugas are amazing, but much further than 45 minutes. It’s a little over 2 hours. The islands are 70 miles west of Key West. It’s a stunning piece of history, but it takes a full day to get there and back.

  36. Haven’t been there so I have no suggestions, but I look forward to your updates after the trip. Your roadtrip from a couple of years back is what got me interested in Scouting NY and I’ve been hooked ever since.

  37. i enjoyed visiting the really little things hidden on each key. just turn don some roads and find unexpected joys.

    i loved the bat tower in sugarloaf key, but i am a bit batty

  38. Definitely Vizcaya – one of America’s greatest estates and gardens – when it was being built, it employed 1,000 of Miami’s 10,000 residents!

    Also check out the Miami City Hall, on the wonderfully named Dinner Key. It was originally Pan Am’s Miami flying boat terminal – the southern counterpart to our own Marine Air Terminal, and a fairly early example of adaptive reuse.

  39. emailed you this awhile back, but coral castle just north of homestead is a MUST see. estate built complete out of coral rock by one man who did the entire thing himself. One of the most original and interesting pieces of architecture ever in my opinion.

  40. You’ve already received suggestions for the most popular places in Key West. I have a restaurant suggestion….El Siboney. Cuban food at it’s best. Just Google for the address.

  41. I just saw your post and hope I’m not too late. Five Brothers Grocery on Ramrod Key is a great Cuban food mart/diner, delicious cafe con leche and breakfast — very good value. In Key West, Ana’s Cuban Cafe on South St is another simple, delicious spot. Near Big Pine Key check out Bahia Honda State Park, and see the article in Sunday’s New York Times about the disagreement over hooking No Name Key up to the power grid. Lazy Days Restaurant on Islamorada is a good place to stop for grilled fish and conch fritters. The Keys are very special. I hope you have a great time!

  42. yes to conch anything. Yes to key lime pie. yes to Vizcaya, it’s beautiful. Stop in Little Havana almost anywhere and get some Cuban food. And definitely take a walk through South Beach. Beautiful architecture.

  43. You should visit Cassadaga, Florida! It’s home to a population of 40% psychics and mediums and has amazing history.

  44. Don’t miss the butterfly conservatory in Key West – amazing!

  45. Blue Heaven has THE best pancakes!

  46. The locals drink at the Green Parrot and it’s filled with local color! The Half Moon Raw Bar has the best conch sandwiches. Blue Heaven is yummy and I like Kelly’s for atmosphere. For a reasonable place to stay, don’t miss the Eden House. Have fun 😀

  47. We just took a trip to the Keys and had a wonderful time!

    SIGHTS: *Definitely* stop at the Seat Turtle Hospital in Marathon. It offers 90-minute tours, which includes a 30 minute presentation and almost an hour long tour of the sea turtles in residence! You can get really close to them, many of whom are recovering from boat strikes and weigh over 200 pounds.

    It’s completely nonprofit and a wonderful organization. Call them in advance for tour reservations:

    FOOD: In Marathon (about 2 minutes away from the Turtle Hospital), go to the Keys Fisheries. It’s a hole in the wall short-order setup that has amazing Lobster Reubens for lunch! They sell thousands a month. They also have picnic tables with a great view.

  48. Need to go to the caribbean club in key largo… most amazing sunsets.!home/vstc1=happenings

  49. Scarlett Johanssan

    While You guys are down there in Key West check over at Margaritaville and see if Jimmy Buffett is still serving Anita and Kutchie Pelaez’s famous Key Lime Pies. If he is you had better try some. You surely will enjoy it.
    Hell some people say that Anita and Kutchie’s pie are the best thing that they liked there.
    It’s always a big favorite of ours when we travel to the end of the line.

    Have a great trip and take care.


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