A Travellerspoint blog

Forty is the new F Word.

A friend's 40th in Key West

People can run around saying “40 is the new 20” and “I’m not 40, I’m 23 with 17 years of experience,” all they want. The truth is, turning 40 sucks giant donkey balls.

I know. It happened to me 5 years ago.

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You have to check a new demographic box every time you fill anything out.

Young adults literally start calling you “ma’am” overnight like there’s a stamp on your forehead that says, “I AM YOUR MOM’S AGE.” The cute boy that was flirting with you at the coffee shop? Yeah, he wasn’t. He called you ma'am as he handed you your change. There was no way he was flirting with you. You remind him of his mom.

You have to start getting mammograms.

Even the DMV takes a crack at you by ensuring that your driver’s license expires on your 40th birthday, forcing you to go get a new one with a picture where you suddenly age 5 years.

It can be uber depressing.

Unless you plan something fun.

Something that makes you look forward to turning 40. Something that gives you an opportunity to look 40 right in the eye and say, “BRING IT.”

My 40th birthday in the Bahamas made turning 40 one of the most fun things I ever did.

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When my friend Alison’s husband was trying to figure out what to do for her 40th birthday, I offered him 2 suggestions: 1) hire Stephen Tyler to serenade her with “Walk this Way” as Channing Tatum provides a personal lap dance or 2) do a destination birthday.

And that is how we ended up planning a surprise trip with her husband and 8 friends to Key West.

(Personally, I was hoping for Channing Tatum)

We spent 6 months planning and scheming….. quietly, carefully. Finally, the big day came. Alison was blindfolded and told she was being taken to see a car. Instead, all of us were waiting to surprise her.

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You have to be careful surprising an almost 40 year old woman like that. At our age, we could lose bladder control. Or spontaneously break a hip.

We expected screams. We expected fainting. We expected tears of joy. Instead, we heard, “You mean I’m not getting a car?”

(I told him he should have gone with Channing Tatum)

It was time to load everyone up in the Chieftan and head south.

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It was Key West or BUST, baby.

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Day One: Key West in June....Hotter Than Georgia Asphalt

My planning was impeccable. I had the perfect place to stay. Groceries and drinks were being delivered before we arrived. A beautiful cake and balloons had been ordered. An awesome itinerary had been planned. Every detail was accounted for.

Or so I thought.

I missed one tiny detail.

It’s really HOT in Key West in late June.

Like…really, REALLY hot.

I have had some hot vacation experiences. Like that time we thought it would be a good idea to go to Texas in the summer and eat tacos with hot sauce from a street vendor on the sidewalk. That was just before we caught on fire.

But Key West in late June? It was like walking through a furnace in a gasoline suit.

Even my fingernails were sweating.

There you are, innocently waiting in line to eat when it happens. One minute, you are smiling and enjoying a beautiful day. The next minute, you burst into flames.

It’s called Spontaneous Key West Line Combustion and it can really happen. It’s science, people.

And there is only one remedy: mimosas!

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We found them at Blue Heaven. We also found lobster & grits with toasted banana bread, BLT benedicts, and PIE.

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It was early in the day, and some of our group had never been to Key West, so we thought we'd do some walking around, maybe some shopping, and let everyone get a feel for Key West.

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Within 5 minutes, we said "Screw it." It was too hot to do much walking, so we only made it as far as the Rum Bar. Bahama Bob was behind the bar doing his thing.

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The group quickly became addicted to painkillers. We had to get them out of there after the 3rd round. We had been up since 4:00 a.m. and we didn’t want anyone passing out before we even got checked into the house.

Palm Gardens was PERFECT. Two, 2 story houses, each made up of 2 independent condominium units with a king bedroom, kitchen, den, bath, and porch. We had rented all 4 which gave us private access to the pool.

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Which was good, because no one else would have fit in that pool.

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We spent the afternoon cooling off before heading to Half Shell for happy hour. It was time for oysters!

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And shrimp.

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And drinks.

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And unfortunately shaped shadows.

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Having done the “booze cruise” with the Fury catamaran a couple of times, I had decided we needed something a little classier for the birthday girl. I didn’t want Alison’s pre-birthday filled with memories of overcooked chicken wings and cheap margaritas.

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I had booked us on the sunset sail with Floridays. It was a smaller boat, a more intimate crowd, and a more relaxed atmosphere.

It was an AWESOME boat. Service was impeccable. The boat was classy and refined. The mood was relaxed.

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But, as we sipped our champagne in the sunset, I couldn’t help but wish I had a couple of those greasy chicken wings.

You can take the girl out of the trailer park, but you can never take the trailer park out of the girl.

To prove that point, I forced tequila shots and tater tots on everyone after the sunset sail.

We had drinks at Agave 308. It’s dark. It’s classy. It’s filled with tequila. What’s not to like?

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Afterward, we stumbled over to Amigo’s. You can’t beat Amigo’s for late night eats.

The pork carnitas nachos were simply a thing of beauty. Not to be outdone by the amazing tater tots and street corn.

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And just to be certain that everyone barfed before they went to bed, we stopped at Better Than Sex for dessert.

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Then we all ate a handful of Tums and called it a night!

Day Two: Happy Birthday!

We’d had enough drinks the day before to give an aspirin a headache.

There is only one remedy for that: mimosas!

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What doesn’t kill you only makes you stronger. This especially applies to alcohol and fried foods, so we headed to Camille’s for a deliciously boozy breakfast.

Every time I walk into Camille’s, I feel like I am visiting 1984. From the orange sherbet walls and colorful vinyl tablecloths to the barbies and fornicating ceramic pigs to the Pet Shop Boys pumping out of the stereo, it screams "Hello, Vicki, this is your adolescence calling." However, despite how awesomely eclectic it is, one does not come to Camille’s for the décor, one comes for the breakfast.

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Matt went snazzy with the chorizo benedict and I went old school with a fried egg, grits, and Cuban toast.

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We had rented a deck boat for the day. Destination: Boca Grande, a small uninhabited island about 14 miles from Key West with a pretty nice little beach. Renting a boat was significantly cheaper than taking a boat out for a day with a captain, and it eliminated the embarrassment of acting like total idiots in front of a stranger. When we act like idiots, we prefer to do it in privacy.

We were armed with sandwiches and adult beverages. It was time to get our boat day on.

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It only took about 40 minutes to get to Boca Grande.

As we pulled up to the beach, I noticed a lot more seaweed than usual. It wasn’t quite a pretty as it usually was, but it still beat any beach on Key West.

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We poured up some beach drinks, found ourselves a shallow spot in the water, and made a day of it.

We proceeded to go through the 5 stages of beach drinking:

Stage 1: SUNSHINE AND HAPPINESS. This is the pre-drinking stage. Everyone is basking in the golden sunshine, cup in hand, marveling at how simply amazing it is to be right where they are.

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Stage 2: LET’S GET THIS PARTY STARTED. There is always that one person that gets a little louder sooner than everyone else. A little rowdier. A little OUT THERE. That person is usually me. This time, it was all 10 of us.

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Stage 3: DUDE, THIS IS AWESOME. This is the full-buzz stage. Everyone is having a killer time. Everything is the most fun thing EVER. Especially more drinks.

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Stage 4: HEY, Y’ALL…WATCH THIS. You have arrived. You are fully intoxicated and it seems really cool to do really dorky things. Like try to put your glass in your swimsuit and try to drink out of it. Or do synchronized swimming. This is the stage where you are most likely to get a black eye or lose a tooth.

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Stage 5: I LOVE YOU, MAN. We’ve all been there. This is the stage where you love everyone. They love you. These people are your BEST FRIENDS EVER. At least one person usually cries. Personal space ceases to exist as everyone talks too close, hugs too much, and generally climbs on top of each other like a bunch of puppies in a too small box. At least this is what happens when women drink.

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It is best to follow the “I love you, man” stage with food, lest you end up in the dreaded 6th stage of beach drinking: Puking like a kid who ate all of his Halloween candy in one sitting.

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We had an amazing lunch spread. We had it all: Champagne, coconut rum, and beer. Sodas. Chicken salad, tuna salad, and turkey and Swiss sandwiches. Chips and dip. Fresh Fruit. Cheese. Crackers.

Know what we didn’t have?

A knife.

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(I realize there is a "cut the cheese" joke just dying to come in here, but it's just not going to happen, folks)

And then, somewhere in the alcohol fueled haze of the beautiful afternoon….we ran out of alcohol. Just. Like. That.

It was probably a good thing. Otherwise, we’d probably still be sitting on that beach.

Time to go!

Back at the house, we had an AMAZING pina colada birthday cake from Key West Cakes. The cake was delicious, beautiful, and they had even delivered it to our fridge before we even arrived.

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Then it was time to head to Alison’s birthday dinner.

I was not about to let my girl spend her 40th birthday somewhere mundane like Jimmy Buffet’s Margaritaville eating a “cheeseburger in paradise” while sipping a watery cocktail and listening to “Fins.”

I wanted her big day to be exceptional and memorial. What better way to do that than with a dinner on the beach at a private island resort?

Ask anyone “Where is the best place to have a special occasion dinner in Key West?” and you will almost always get the same answer: Latitudes. Jet Set dining at its best, Latitudes is located on the private island resort of Sunset Cay, just a five minute ride on their private ferry from Key West.

As we pulled up to the dock, we knew we were in for a very special evening.

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And we were. It was called “Heat Stroke.” And it was very special.

I had made reservations in February so that I could secure a table in the sand about an hour before sunset, knowing that the restaurant was known for its unobstructed sunset view.

“It’s going to be really hot,” the girl on the phone warned me when I made the reservation. “It’s late June and you’ll have literally NO PROTECTION from the sun. It’s brutal.”

I looked outside my office window. It was snowing. I pictured a beautifully set table in the sand.

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“We’ll take the 7:00 reservation,” I said. What did she know? WE LOVE SUN. Sun is awesome. Sun is our friend. Too hot? Pfffffft. There’s no such thing as too hot.

I remembered that conversation as I sat sweating through my tank dress, gulping down a coconut martini as fast as my throat could swallow while silently apologizing to Mother Nature for making all those snide comments about global warming. Then I started sucking down Matt’s frozen bushwacker, promising God that I would purchase some solar panels and trade in my Land Rover for a hybrid as soon as I got home if he would just cool it down a few degrees.

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Heat be damned, we had an excellent dinner. Even though our faces were sliding off into our laps, the food and setting were hard to beat.

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The cool wedge salad was a perfect first course, with fresh Florida oranges and chilled melon topped with gorgonzola cheese and a papaya dressing.

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Matt had the seafood pasta: fresh tagliatelle pasta with Key West pink shrimp, lobster, and scallops tossed in a parmesan pesto cream sauce with heirloom tomatoes and roasted mushrooms.

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I couldn’t resist the honey and ancho chile crusted waygu beef skirt steak, primarily because it was topped with two big, fat onion rings (remember what I said about the trailer park?).

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Finished up with a mango martini, the dinner couldn’t have been better.

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Cooler, yes. Better, no.

We enjoyed the amazing sunset before catching the ferry back to Key West.

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Now that the sophisticated part of the evening was over, it was time to get the party started. In order to protect the guilty, I shall not divulge the intimate details, but there may have been lots of shots, dancing on tables, a couple of male dancers and a significant loss of one dollar bills, and we might have gotten thrown out of a bar by a guy that looked just like Vanilla Ice (but not before I told him how much I loved Ice, Ice, Baby….which he did not seem to think was as funny as I did)…..but I’m not confirming nor denying anything.

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Day 3: Wakey, Wakey, Eggs & Bakey

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We woke up s-l-o-w. I don't mean slowly. I mean slow. We were slow. We had no aggressive plans for the day so everyone slept in and got up at their own pace. It was a perfect morning to do nothing more than lay around in the air conditioning eating aspirin for breakfast.

Everyone finally roused around noon, so we thought we’d take everyone to the Southernmost Point for the “photo op” since some of our group had never been to Key West.

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We severely underestimated how heat can affect a hangover.

There are many who say that heat is a good remedy for a hangover. These people say you should “sweat it out” and get rid of the toxins in your body.

These people are stupid.

And are masochists.

We should not have tried to beat the heat. We needed to sit in the shade and drink a lot of Gatorade. And think about our life choices.

Instead, we were on bicycles, sweating it out on top of pavement that had to be at least 147 degrees. As we pedaled from our place on White Street toward Duval Street, there was absolutely no shade to be found. At the 4th traffic light we were forced to stop at, we started to die slowly.

It was so hot, my biggest bicycle wreck fear was, "What if I fall off my bike and cook to death on the pavement?"

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By the time we reached the Southernmost Point, we sent the strongest of our bunch in search of water while the rest of us lay limply on the sidewalk, begging for a quick and painless death. When Matt returned (did you really think it was anyone else?), we didn’t even bother to drink the water, but simply poured it over our heads. I think I saw steam.

And yes, we got the photo op. Unfortunately, Matt was buying water and I was taking the picture so I had to Photoshop us in. I don’t think you can tell.

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When we realized we were not, in fact, going to die, we made a mad dash to Deuce’s Off the Hook Grill for some lunch in the blessed air conditioning.

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This was a first time at Deuce’s and it was a WINNER. It instantly became everyone’s favorite, and not just because of the air conditioning.

Because of the amazing fish tacos and sweet potato tater tots.

SWEET POTATO TATER TOTS, y’all!

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The food at this small restaurant was outstanding.

Go here. Now.

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We were loath to leave the air conditioning, and the tater tots, but I don’t think Deuce’s was willing to let us stay for the next 7 hours, so we had to pedal on out of there.

It was just too hot for shopping, and no one had seen the beach at Key West, so we took them to Fort Zachary, thinking we might be able to dip in the refreshing water.

Unfortunately, the refreshing water was filled with seaweed and smelled like farts.

So we sat in the shade and ate giant pickles and popsicles instead. Have you ever noticed how many penis shaped foods there are in Key West? I’m just making a point, here, people. Just making a point.

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There was nothing left to do but spend the afternoon in our pool. Even though the pool was heated, it was the coolest we’d been all day.

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Seriously….who heats a pool in Key West in the summer??????!!!!!

It was our last day, so heat or no, we were going to make the most of it. We decided to do a Happy Hour crawl for dinner, starting with oysters and margaritas at Pepe’s.

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Then, it was on to Kelly’s for wings, nachos, and more margaritas (and maybe some nachos and fish dip).

I have a tidbit of advice for Kelly's: Maybe if you let people sit OUTSIDE in your pretty courtyard during happy hour instead of making them sit INSIDE....your pretty courtyard wouldn't be TOTALLY EMPTY.

Just a thought.

Especially considering the courtyard was the only really good thing at Kellys.

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Then we did a little Duval Street Strolling. It was finally cool enough to shop!

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The final stop was at the Little Room Jazz Bar for what was supposed to be one drink. You know, since we were flying out in the morning.

One drink did not happen.

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As a dog returns to its vomit…….

Some of us never learn.

Home again, Home again!

We filled ourselves with doughnuts and bacon before heading home.

I learned that a “side of bacon” at Sandy’s means “a pound of bacon.” It was a thing of beauty.

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It had been a whirlwind, but it had been fabulous. It had been hot, but it had been fun. It had been exhausting, but it had been worth every second.

There was nothing left to do but put the inflatable margarita in the trash and fly home.

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What's next? Why, getting stranded naked in Abaco, that's what!

Posted by vicki_h 12:39 Archived in USA Tagged key_west florida_keys duval_street conch_republic

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Comments

When a blog makes you smile and laugh 5-8 times while reading it, you know it's a good.....wait, check that: GREAT blog!

by rdbaa1286

OMG - I was cracking up reading this!! "enough drinks to give an aspirin a headache"?? Where do you come up with this stuff - I need some lessons!! You are too funny! Loved this one, but I love all your stories, er I mean travel blogs!! :D

by JoanneR

Love your blog!! Who makes the romper you have on in key west on the boat? Love!!

by Lindsey310

Lindsey - it's made by Charlie Jade.

by vicki_h

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