#ziptothekeys: My Roadtrip to Key West with Zipcar

When Alma, my best friend since 10th grade, invited me to Key West for her 30th birthday, I of course happily accepted.  My other BFF Jimmy was flying down from Michigan too, so we decided to do a mini roadtrip from Miami to the Keys.  I first looked at traditional rental car options, but found myself wishing I could just grab a Zipcar instead, like I do in NYC.  A few quick searches later, lo and behold: Zipcar is in Miami!  And my NY membership works there too (along with any other city in the country where they have cars)! This was a pleasant surprise, as the last car sharing service I was a member of did not let me rent outside of the New York Metro area, even if they had locations in the city I was visiting.  A quick price compare showed that going with Zipcar was the most economical for our three day trip to the Keys – I mean, gas and insurance included?  Yes and yes.

Zipcar lot at the Applebaum MRI Center

When I touched down in Miami, I hopped in a cab and 10 minutes later I was at the nearest Zipcar lot.  Instead of waiting in a car rental line, getting upsold on extra insurance I probably don’t need, and getting surprised with random $500+ holds on my debit card, I just walked right up to my ride, tapped my Zipcard on the window, and was ready to go.  I sat in the shade of the palm trees and blasted the AC while I hooked up my iPhone (YAY smart car).  The setting was so pleasant, I was immediately in a better mood.  After a quick drive up to the Fort Lauderdale airport to pick up my friend Jimmy, we were off.  Well, not immediately – we had a required stop to make at Trader Joe’s to pick up a few bottles of Two Buck Chuck 🙂

Key West Tip #1:

Pick up some drinks for your room before you hit the Keys – there’s no island markup in Miami.  

Then we hopped on Highway 1, aka the Overseas Highway.  From there, no more navigation was needed: There are no turns, just cruising down a mostly two-lane road.

Neither of us had ever been to the Keys, so we didn’t know what to expect.  Our first indication that things were going to be different was the blue paint on the dividers – you don’t see that in Michigan or New York.  We were honestly a bit underwhelmed by Key Largo – from the road, it didn’t look nearly as glamorous as Sade made it out to be – but things got interesting when we got to Islamorada. Where else can you see a giant lobster on the side of the road?

The route truly became scenic there too, with the Overseas Highway living up to its name.  We were surrounded by beautiful, sparkling water on all sides, whether peeking through the foliage or encircling us as far as the eye can see.

Idyllic islands and leisure boats dotted the view – everything felt wonderfully laid back.

Though the roadside beaches and turquoise waters beckoned to us, we wanted to get to Key West as soon as possible, as the birthday girl was there waiting for us. It was the first time we were all together since just after my wedding, almost three years ago, and we immediately picked up right where we left off.

Jimmy and I snapped a mission accomplished pic in front of our Zipcar, which got us from Miami to Key West in cool comfort (another Zipcar perk: Because gas is paid for, you don’t have to worry about blasting the AC if needed).

This is also my first OOTD: The perfect travel jumpsuit.  I know, I know, that sounds like an oxymoron, but this BB Dakota jersey jumpsuit is the most comfortable thing in my closet.  It came in my Gwynnie Bee package that arrived right before the trip, and proved to be a lifesaver.  It felt like I was wearing pajamas, but with a pendant statement necklace from Rocksbox, it looked purposeful and pulled together.  The usual drawback of jumpsuits (i.e. that they are a PITA to get on and off for the restroom) is not applicable to this one – the open scoop neckline is both bra friendly and easy to navigate. For running to catch a plane and driving for hours, I knew to go for my trusty Cole Haan flats (hello arch support and Nike Air technology!).  It was hands down the best travel outfit I’ve ever worn – so much so that I wore it again for the flight back 🙂

As we headed in to the cottage, I found myself pining for the crystal waters we sped by on the Overseas Highway. Fortunately, our destination was an oasis in its own right.

The minute I saw this jewel of a pool, I was ready to hop in.  But our first order of business was a quick trip to the grocery store, where I ran into some more Key West charm.  Not literally, thank goodness:


Fun fact: There are chickens EVERYWHERE on Key West.  Wild ones, domestic escapees, tiny hens, giant roosters, and even little chickies.  Seeing them cavort anywhere they pleased was random and delightful. So was shopping in a spacious grocery store (I forget that the cramped aisles of Manhattan are not the norm).

Key West Tip #2:

If you have a kitchen or a grill, utilize it!  Groceries are reasonably priced at the Pathmark on the island (a 5 minute drive from Old Town, but many restaurants have a tourist mark up.  Our favorite meals were the simple ones we ate in the cottage or by the pool.

After getting our supplies for grilling and breakfast, we headed back and parked the car for the evening. (Never drink and Zip!) Fortunately, Key West is eminently walkable, and full of picturesque spots.  This palm tree looked more like a sculpture than a plant, but I can guarantee it was growing out of the ground.

There are also plenty of silly photo opps, perfect for childhood friends reunited and acting a fool together.

After a lackluster Mexican dinner on Duval street (see Tip #2), we all headed back to the cottage and I finally was able to dive in (I am a total water baby and not being in the pool was just torture).  My swimsuit is from last year’s Gabifresh for Swimsuits for All collection.  This year’s fab styles are not going to be on the site much longer, so if you are looking at one, grab it ASAP.

Nightswimming with some of my favorite people in the world was a perfect cap to a day that started almost 22 hours earlier.

Check out my great Zipcar offer below, or use the code CURVILYZIPS for $25 of free driving as a new member!

New Zipsters Get $25 Free Driving. Hourly rates include gas & insurance and 24/7 access. No paperwork, no rental counter, no headaches. Sign up online and be driving in no time at zipcar.com.