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A Key West Trip Report

Birmingham, Alabama
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A Key West Trip Report

Just got back from KW…Grateful that we could spend seven days, 12/20-12/27/2010, in one of our very favorite places.

Since we have been to KW several times, and I typically plan the heck out of each day there, I took a more laid back approach this year. I was armed with my spreadsheet of those must-visit places…but did not have a schedule broken down by day and time.

I am also going to be a little less precise in my trip report on this adventure…to stick with my living-on-island-time theme.

Drive to KW:

Finally took repeated, relentless advice for the small detour to the “Robert Is Here” fruit stand near Florida City. I had a key lime milkshake. My wife had a strawberry milkshake. Both were fresh velvety goodness. Geez, I wish I had heeded the advice to stop here on previous trips. “Robert Is Here” is Florida kitsch at its absolute best. A new tradition has begun for our KW drive.

Stopped for our favorite, and traditional, lunch at Sparky’s Landing in Key Colony Beach (Marathon), FL. Try this lunch sometime… The Gratinee (grat-n-a) appetizer (or “Gratinee Thingy” as Arnie has coined it). I had Lobster tacos. My lovely wife had the Frueben fish sandwich. Maybe you have heard the southern compliment for incredibly great food: “That has some count.” Let me tell you that everything that we have had at Sparky’s “has some count.” Did you catch that I had “lobster tacos?” Geez!

Stopped at Mangrove Mama’s to get in the island groove. This stop always reinforces the need to slow down and enjoy the keys experience.

Checked in to:

Angelina’s Guest House. We love it here. Those homemade cinnamon rolls at breakfast are killer. This place is run by a great staff. Very clean. Very friendly. Great Value. Our home away from home.

Where we ate:


Harpoon Harry’s – a traditional favorite that we do not miss. A local diner through and through. Clean and friendly with great hours.

Le Creperie – a new experience that will become a repeat tradition. Watch them make your crepe at the bar. Super fresh and great tasting food. Make this a don’t-miss on your list if you can.

Blue Heaven – Listen, how can you compete with fantastic Lobster Benedict? You Can’t.

Pepe’s – This is KW cool. Their homemade breakfast breads are awesome. A tradition for us. Everything that we have ordered here (breakfast, lunch or dinner), over many visits, has been thumbs-up.


Amigos Tortilla Bar – this is a new place on Greene St. that took the place of Iguana Café. The tortillas are fresh made on-site. Try the pollo, carne, carnitas, and fish fillings. All were tasty as all get-out. Oh, get some “tots” (tater tots) here too. They also have imported Mexican Coca-Cola with pure cane sugar verses corn syrup sweetener. You can taste the difference. We ate there three times because it was soooo good. Please visit this place to keep them in business so that we can eat there the next time we go to KW.

B.O.’s Fishwagon – I’m going to tell you that the fried grouper sandwich is very good. I’ll further mention that the hamburger is awesome. Who would have thought a place with “fishwagon” in the name would serve a great hamburger?

Pepe’s – If you want a good ole fashioned hand pressed homemade hamburger, get one here. No frills genius. This is also my very favorite key lime pie stop. Key lime pie served in a bowl…oh yes.

El Siboney – This is a regular “must-have” tradition for us. We have always been impressed with everything ordered here. The staff has always been very friendly. Feels like you are eating at a friend’s house for lunch. Great food. Great value. Our menu favorites: fried pork chunks, skirt steak, or picadillo.

Cuban Coffee Queen – in a picnic mood?...go to Cuban Coffee Queen…get a down and dirty Cuban Mix samwich (comes with plantain chips) and a multi shot bucci…bike to Mallory Square and enjoy beyond belief. A no frills meal with atmosphere that you won’t forget. The team at Cuban Coffee Queen gets it right.

Upper Crust Pizza – Another great pizza at Upper Crust on this trip. A traditional stop for us. We have never been disappointed.

Salute – You can’t beat the setting of open air seating on a beach. You also can’t beat the fresh ingredient selections here. If you can’t chill out here, you can’t chill out anywhere dude.

Finnegan’s Wake – Always a stop for us. Consistently delivers on food, drink and atmosphere. If you need a break from the madness and crowds on Duvall, do yourself a favor and relax at Finnegan’s. A memorable meal from this trip was Tina’s Tuna…a sushi grade tuna steak on top of baby spinach with wasabi vinaigrette…incredible. The menu is creative. You will need to make several trips to Finnegan’s to sample the many tasty menu offerings.

Blackfin Bistro – a newer restaurant in KW. We ate here twice…lobster bisque, carbonara (pasta dish), old fashioned burger, local mahi-mahi, and shrimp provencal. All were worthy of repeat.

Flamingo Crossing Ice Cream – You want homemade tasting ice cream in KW? Look no further. They make their ice cream with fresh basic ingredients. Try the mangrove honey ice cream. Hoocheemama!

Mattheessen’s Homemade Treats on Duval… not far from Hog’s Breath – incredible chocolate chip and peanut butter cookies. I have a cookie vice that Mattheessen’s supports every visit. I’d call them a cookie junkie enabler.

Where we hung out:

Schooner Wharf – Michael McCloud and your favorite drink at 2pm. Don’t call and bother me and I won’t call and bother you.

Turtle Kraal Tower – Let’s see…an elevated, shaded, open air view of water and boats…quiet reading time in a super relaxed location. Keep this one to yourself. We’ve read many a book chilling out here.

Sloppy Joe’s - I know, I know…a very touristy Duval cliché marquee stop. If the music is good, we really like the vibe here. No apologies.

Grand Vin – Quiet end of Duval. Great place to catch a breather and meet cool people…locals and visitors.

Coffee Plantation – a great coffee shop on Caroline. Local art. Local newspapers. Wifi. Hang out, sip, read. A slice of home away from home if you like hanging out in cool local coffee shops.

Hog’s Breath – if the live music is good, you will be good to waste a little time here.

The Porch – If you like craft beer, or have a craft beer curiosity, please spend some dollars and time here. This place, located in a beautiful historic landmark home, needs to have a very long life in KW. Take a book. Take a friend. Order your favorite beverage…or try a new and interesting one. Sit on the elevated porch facing Duval. Soak in the atmosphere. You won’t be sorry.

Lazy Gecko – went to the Gecko because Caffeine Carl was playing there with Nick Norman. Got lucky to have some tasty Smile’n Bob Fish Dip (came with hot pressed bread pieces)…yes! Count yourself lucky if you have Kristi to serve your table. She was the best.

Music we heard:

Caffeine Carl – a KW native, and a local musical favorite. If you like smokin hot guitar playing, I would put Carl up against just about anyone. Consider yourself lucky if you get to hear Carl play. You will likely see him play with Nick Norman, Raven or his group Caffeine and Pepper. He plays with several other local musicians as well. We plan our day around Carl’s gig schedule.

Michael McCloud – The Schooner Wharf day music regular. If you want a tried and true KW experience, catch MM at Schooner. You will either get it, or you won’t. I feel sorry for you if you don’t.

Zack Seemiller – Zack is an interesting entertainer. Be in the mood for some humor. We always try to catch his gigs on our KW trips. Zack is a part of the KW culture for us. I have to share that we made a special stop to hear some other favorite scheduled artists at SWB. The scheduled artists called to cancel near show time. Zack was called in on very short notice to substitute. We watched as Zack quickly set up to play the set on time. At the last minute, one of the scheduled artists shows up. Zack quietly packed up and bowed out. I felt like Zack should have been able to do the gig because he was quick to bail out someone who was not going to show up…however good the originally scheduled artist is. Just say’in.

Barry Cuda – Great on the piano. Talented singer and entertainer. We make time to see Barry play every visit. Toe tap’n ragtime, honkytonk, Naw’Orleans…you get the idea.

George Victory – We be jam’n mon. Be in a Marley mood for this one.

C.W. Colt – Had an enjoyable afternoon listening to C.W. Colt at Sloppy’s. Memorable for us.

The Doerfels – If you ever get a chance to see this young family play live…anywhere…make time for that. We have been lucky to see them several times in KW. Class act. Extremely talented. Don’t miss.

Recommendation – Ask your favorite KW musical artists if they have a recorded CD with their music. If so, buy one or two. Download to your digital player. Make a KW playlist. My KW playlist brings the sights, smells, sounds, smiles and memories from our KW trips to life every time I hear it.


Birkenstock – Beautiful wife always buys a pair of “Birkies” on our KW trips. Something special about buying her favorite sandals at KW instead of at a hometown shop or mail order.


Make sure to ride bicycles in KW. Make sure to ride those bicycles in the early morning on Duval and side streets. You will not believe how different the “feel” of KW is in the early quiet mornings versus the busy afternoons and nights. Ride your bicycle to White Street Pier to see the sunrise…an almost religious experience.

YBB…if you read this report, I am sorry to report that it looked like the Dennis Island Café closed its business. The lights were out and the interior looked deserted. We had the mollete (moy-ye-te) fried sandwich on our last visit based on your recommendation. We were looking forward to a repeat. Sad about this causality.

Funny t-shirt sighting:

“A good lawyer knows the law. A great lawyer knows the judge.”


Relaxed. Ready for another trip to KW.


I started out to make this an abbreviated report. There is so much to experience in KW. I kept remembering stuff that I wanted to mention. Oh well…

By the way…Alabama had its first snow at Christmas ever. We were in KW and missed it. Life is good.

Chester County, PA
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1. Re: A Key West Trip Report

Bravo! What an excellent report!

Naperville, Illinois
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2. Re: A Key West Trip Report

Great report, thank you! You hit most of our faves and I'm looking forward to trying Amigos. Like you, when we are in KW, its all about the food and music. We have our favorites we have to visit each time and always try to add a few new ones each trip. Makes for a fun and relaxing trip for us every time!

Memphis, TN
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3. Re: A Key West Trip Report

Thanks for the trip report. I'm glad you had a good time. You know how to do Key West right.

Scottsdale, Arizona
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4. Re: A Key West Trip Report

Thanks for the trip report!!! Sounds like you had a great time. I'm still trying to "get" Michael McCoud." I'm really trying hard but he always sounds wasted to me......maybe even a little depressing. Really, I'm trying.......


Key Colony Beach...
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5. Re: A Key West Trip Report

Wonderful report. Thanks for taking time to do the abbrivated version ;-)

"Armed with your spreadsheet"? WTH is with that? At least it wasn't broken down by day and hour . . . . .

A laid back approach is:

- Take your watch off at the airport

- Well that's it. Do whatever, when ever.

Glad you made Sparky's Landing and Robert is Here. We try and stop and grab a new fruit that we've never seen before. It's pretty easy to do there. We get some good ones, and some really bad ones, but it's always fun.

columbus, in
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6. Re: A Key West Trip Report

Yeah, I found Dennis had closed (sadly) on my last trip in May. What a fantastic trip report! You are one of the people that I always look forward to reading your trip report. You always do so many of the things I love and it takes me there. Can't wait until one of our visits overlaps! I would love to meet you and your wife. Once again, what a fantastic job you did on your report. What a great trip you had. Thanks so much for sharing it with us and I know many will be taking notes on this one.

Key West
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7. Re: A Key West Trip Report

Wonderful trip report. Thanks for sharing. I especially like that you included the local musicians!


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8. Re: A Key West Trip Report

Nice report. I added a couple places to my "list" of possible places to hit

Athens, Tennessee
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9. Re: A Key West Trip Report

NIce report! I agree about the bikes. We love riding in the mornings too. :)

Ottawa, Canada
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10. Re: A Key West Trip Report

Thanks very much for taking the time to post such a detailed report on Key West. My husband and I are planning our very first trip to Florida from Canada and are aiming to go during the last week of February and first week of March. Despite my best efforts to research Florida, I am getting overwhelmed with descriptions of the various popular spots and would appreciate your further help.

What we are looking for is an interesting, relatively quiet (not 'dead') place where we can take long walks on the beach, play a little tennis, do day trips to other interesting places and sites, have a coffee/drink and watch the world go buy and have a great restaurant meal occasionally without the bustle of Disney or too many shopping malls. We don't need too much heat - just a little less cold and much more sun! We intend on renting a condo for our two week stay.

Can you give us some idea of the atmosphere of Key West and what you like best about just going there in general? What about the Lower Keys? Do you recommend that area as well?

Any further information you can offer would be greatly appreciated.

Cheers and Happy New Year

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