Escape To Key West: It Only Takes A Weekend

Each year before Hanukkah, Jim and I have a discussion about budgeting for the holiday overall as well as specifically how much our budget is for each other’s gifts. When the holiday rolled around last month, Jim (once again) proved himself to be quite clever, as he came up with a gift that was not only way below budget but was romantic and pretty awesome: plane tickets to Key West.

No, our budget was not THAT high. He bought the tickets with airline miles: it only cost him twenty bucks! See? Clever!

With a little research and some more budgeting, we found a nice, very reasonably-priced guest house where we could stay, and chalked up that expense and the rest of the trip to a belated anniversary gift to each other. Loopholes, you know.

ANYWAY, it was a glorious weekend and much-needed getaway for both of us. I was especially looking forward to it after hearing about Momo’s December trip. Jim and I also ended up connecting with Toni, who is now Momo’s and my southernmost mutual friend. (You can read about how it was that Toni and Momo came to meet on her blog: click here)

Toni, by the way, is awesome. She’s a concierge in Key West and the daughter of “Captain” Tony Tarracino, who was the mayor of Key West at one point, the owner of Captain Tony’s Saloon on Greene Street, and a very fascinating character overall.

The agenda that Jim and I planned for our weekend was very different from what Momo’s family did: we weren’t as interested in parasailing (yikes), jetskiing, trolley touring…we just wanted a quiet, lazy weekend. I went against my typical pre-vacation protocol by NOT scheduling anything for us.

I know; I still can’t believe it myself.

The only advance research I did was to ask Toni for a recommendation on the one thing we thought we might want to do: a sunset cruise. (She recommended one of her favorites and we loved it!)

We basically tooled around the island on bikes all weekend, just exploring. One of the highlights was meeting up with Toni after our sunset cruise, walking over to her Daddy’s bar and enjoying some drinks together while she told us about him. She told us what turned out to be one of my favorite stories when I asked her why there were thousands and thousands of business cards stapled to the walls and ceiling of the bar. Apparently her dad used to tell people that if they could find Jimmy Buffett’s (who used to play there, and later immortalized Captain Tony’s Saloon in his song “Last Mango in Paris”) business card on the wall, their drinks would be on the house that night. The best part is that they would never find it: there was no business card from Jimmy Buffett anywhere on those walls! Toni said that people used to sit around and drink all night while they looked for that card. I thought it was hilarious, and genius.

Momo listed some great tips for enjoying a Key West trip, and I thought I’d add my own, here:

1. Rent bikes. You don’t need a car in Key West. We rented bikes for the entire weekend and thus gave ourselves total freedom to get around the island (which is only about seven and a half square miles!) on our own schedule, without having to worry about the cost of cabs or parking a car. There are bike racks everywhere, and there’s just something lovely about pedaling around paradise.

2. Get up early to see the Southernmost Point alone. Everyone who goes to Key West typically heads down to the Southernmost Point to get a picture. The problem is, it’s a bustling, busy corner of town. We rode by there several times but never wanted to stand in line just to snap a quick picture or two. On our last day, we rode down there at 7:30 a.m., and since everyone else was out late partying (probably), they were still in bed and we got to take several pictures there, all alone. (But we were grateful that another couple showed up after a few minutes, so we could ask them to snap a picture of both of us!)

3. Don’t eat at the restaurant chains. This is true for any destination, really. There is a Denny’s on Duval Street, and we saw a Five Guys and a Subway, but we can eat at any of those places here in Chicago. Enjoying the local restaurants is one of the joys of going on vacation. Our favorite place in Key West is Ricky’s Blue Heaven, where you can eat outside with roosters (roosters are everywhere in Key West!). In fact, we ate there for two breakfasts, which we normally wouldn’t do but the crepe place across the street where we originally intended to eat was “cash only” and we were trying to conserve our cash. It didn’t break our hearts to eat there twice, though. We immensely enjoyed the RoofTop Cafe and El Meson de Pepe, too.

4. Pace yourself. There are drinks everywhere on Key West. While my Facebook friends probably thought Jim and I were staggering around the island because I kept Instagramming our drinks (more than, say, the scenery), that wasn’t the case. Jim and I aren’t the stay-out-late-and-party types (and frankly, we retired relatively early each evening because we were tired from riding bikes all day!), so we enjoyed our tropical drinks every now and then throughout the day. Bonus: no hangovers. (Specific recommendations: have a Goombay Smash at Hog’s Breath Saloon, Pirate’s Punch at Captain Tony’s Saloon, a mojito at El Meson de Pepe, and a Jimmy’s Boat Drink at the RoofTop Cafe. But not on the same evening.)

5. Wear sunscreen. Momo said this, but it’s worth repeating. Even if you don’t think you need it, you do. Seriously. We literally forgot it was January when we were there because it felt like July.

6. Don’t stick to the busy tourist areas. Another bonus of having bikes is that we could just ride down any old street and check out the pretty houses and other scenery. Riding down quiet streets was much preferable to taking a bike down Duval Street. We also enjoyed visiting the Key West Cemetery, where we found some headstones that said “I told you I was sick” and “I’m just resting my eyes”, as well as Ft. Zachary Taylor State Park, which has one of the prettiest beaches I’ve ever seen. Higgs Beach is home to the Key West AIDS Memorial, and Smathers Beach is (I think) the longest stretch of public beach on the island. (Note that Key West is NOT famous for its beaches: we just sought these out so we could dip our feet and take some pretty pictures.)

7. Relax and enjoy island time. We were reminded that we were out of the big city the second we arrived at Key West International Airport, when the baggage handlers took nearly thirty minutes to bring the bags in from the plane. While Jim and I just laughed about it (truly), some of our fellow passengers were having mini-meltdowns at how long it was taking. Everything is more relaxed in Key West: the sooner you can relax into the island attitude, the better. It’s what you go there for, anyway, right? (Right.)

Anyway, we’re back now and though it’s always nice to come home–even in the middle of winter–we have nearly 500 pictures to look at as we remember our trip fondly. Only about ten of them are drink pictures, by the way.

Here are a few for your enjoyment. Sigh.

Key West drinks

This heron was obviously used to be followed by paparazzi.

At the Southernmost Point

Another beautiful Key West sunset

B'nai Zion

Captain Outrageous

Smathers Beach

Ricky's Blue Heaven

Blue Heaven

Captain Tony's Saloon

Sunset cruise

Ft. Zachary Taylor beach

At Ft. Zachary Taylor beach


Sunset at the Rooftop Cafe

Unicycle at Mallory Square


    • Melisa

      I looked up the Goombay Smash recipe. If you’ve got the four kinds of rum that it requires, I’ll be right over to serve you one.

  • Toni

    What wonderful pictures! So loved meeting you both, looking forward to next time! Cold front coming through, supposed to be 64 degrees tonight…Brrrrrrrr! XO Toni

    • Melisa

      64 and “brrrr”? HOW DARE YOU. 🙂

      But you made me laugh, so I forgive you. We miss you and Key West! Sigh. xoxo

  • Liz

    Hey, I’ve seen that place with the bras hanging from their rafters on som travel-eat-here-type show. Then again, there may be more than one place with bras hanging from the rafters, or so I’ve heard (ahem). Great captures of your weekend away, thanks for sharing 🙂

  • DaddysFishBowl

    Haha, I was about to write how awesome Key West sounds, especially dealing with these fridget temperatures, then I looked at the next post and saw that you’ve pretty much covered that. So I’ll just leave it alone and look at your pictures to try and forget the current climate.

  • Candy Kay

    So glad you loved Key West!! Capt Tony’s is awesome!! Very good friends own Angelina’s Guest House in Key West. Great place to stay and they are wonderful! Glad to have found your blog!!

    • Melisa

      Hi Candy!
      I may have to check out Angelina’s next time… 🙂
      We’re trying to make it a January tradition!

      Thanks for stopping by today!

  • Marianne

    I am green with envy. Or perhaps as a result of all this season affect nonsense that hits me this time of year. You did it right! I’m googling Key West and will be encouraging my husband to pick up a third job before Spring Break. Thanks for sharing – the pictures are amazing.

  • Toni

    I’m so glad you guys got to get away. Every year, I vow to try and budget in money for getaways…seems like something else always comes up or gets in the way. Thanks so much for sharing!!!

  • tracey

    So, did you hang your bra on that bar?

    And that pic by Southernmost point made me scratch my head until I realized that Jim was standing on that cement block.

  • As Cape Cod Turns

    Fantastic pictures Melisa!! I cannot belive that you did NOT PLAN!! Congratulations! THat is a big milestone for you!!! Don’t pull that in July though for Blogher, ok? I need a plan to follow 🙂