Field Guide No. 03 · Florida Keys · Key West Solo

You gotta start somewhere.

In May I took my first vacation with myself in 16 years. I booked it in one day, on points, with nothing planned but the drive.

Here's that trip as a guide. Fly into Fort Lauderdale, drive the Overseas Highway to Key West, spend three nights in Old Town and a last one on the beach. It's built for wandering, not a schedule.

Aaron smiling under the Alexander's Guesthouse sign in Key West Old Town
Aaron flexing beside the Welcome to the Florida Keys signThe drive
Aaron in sunglasses at the Southernmost Point buoyMile Zero
Flip through it
03 Field Guide No. 03

You gotta start somewhere.

Key West solo. Fort Lauderdale to Mile Zero and back, five days by car.

Aaron under the End 1 and Mile 0 highway signs in Key West

By Aaron Berth · Dopamine Furnace Creative

You gotta start somewhere.DF/c · 03
Before you go

Fly to Fort Lauderdale. The drive is the point.

Flights into Fort Lauderdale cost fewer points than Key West, and the Overseas Highway is half the trip. Drive back up a day early and sleep on the beach, so there's no 5 a.m. scramble for your flight.

Every morning: wake up, have coffee, ask yourself if you feel like water, wandering, eating or drinking, and start there.

Where
Fort Lauderdale to Key West and back
Pace
5 days, 4 nights, by car
Best
Spring. I went in mid-May.
Booked
A week out, flights on airline miles
For
Solo, queer, or anyone who'd rather meander
Day 1 · The drive downDF/c · 03
Day 1 · The drive down

Skip Miami. Feed the tarpon.

Pick up the car at Fort Lauderdale and get on the Florida Turnpike early. I took US-1 through Miami and lost an hour in traffic. Don't be me.

  1. Robert Is HereFlorida City, before the Keys

    A fruit stand since 1959. Get a strawberry-canistel shake and a slice of Key lime pie for the road.

  2. Robbie's of IslamoradaMile marker 77.5, bayside

    Buy a bucket of fish and hand-feed the tarpon off the dock. Keep your fingers together. I almost didn't.

  3. Seven Mile Bridge and Pigeon KeyMarathon

    Watch the old railroad bridge run beside you, broken in places. Yes, that's the True Lies bridge.

A1A road signs and a Tropical Acres sign on the drive south
Day 2 · MorningDF/c · 03
Day 2 · Old Town

Coffee on the porch. Then the cats.

Watch your street wake up before you go anywhere. Then walk to the two literary houses, ten minutes apart.

  1. The Hemingway Home907 Whitehead St

    Six-toed cats everywhere, one asleep on the bathroom windowsill. I cried here, and I was in a hurry.

  2. Tennessee Williams MuseumKey West Art & Historical Society

    Small, yellow, and worth the detour. I cried here too.

Hemingway's yellow-tiled bathroom with a claw-foot tub and a cat on the windowsill
Day 2 · Afternoon and nightDF/c · 03
Day 2 · The water

One reef, one band.

  1. FishMonster & Island JaneSnorkel and sail, Old Town docks

    Three hours under sail with a stop at the reef. Solo tip: sit up front with the other solo travelers.

  2. Sunset PierBehind Ocean Key Resort

    Come for the sunset and stay for the band. You might end up onstage. I did.

  3. Captain Tony's Saloon428 Greene St

    The original Sloppy Joe's, where Hemingway drank, with a tree growing through the bar. Then follow the music.

I followed the music everywhere I needed to go.

Aaron on the deck of the sailboat after his first snorkel, sunglasses on, open water behind
Want a trip like this?

I'll build yours, from the flight to the first sunset.

One trip request, no phone call. Up to 7 nights for $333, with a 30-minute Burn Session included.

dopaminefurnace.org · (708) 414-6945

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Every place in this guideEvery place in this guide Each one links to its own site.
Need to knowNeed to know Getting there, the drive, what I'd do again.
Fly
Into Fort Lauderdale, not Key West. Fewer miles, more choices, and you get the drive.
Drive
About four hours without stops, so leave room for at least three.
Arrive
Aim for golden hour. Drop your bag and walk to the sunset before you look for dinner.
Last night
Sleep on the beach near Fort Lauderdale. Sunrise from the room, then an easy run to the airport.
All of you is welcome

Find Your Intersection(ality) Here

Queer, neurodivergent, traveling solo and loving it: you can be all of it here. Tell me which, and I'll point you to the places that fit.

I'll flag the ones that fit you, and I'll still meet you for coffee. Find your corner of Milwaukee.

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Where to next.

Journeys

Solo trips.

Trips for one, on purpose. I'll plan yours the way I planned mine.

Plan a solo trip
Boiling Point · Reading 003

A Queerdo Looks at 44.

The same Key West trip, told in my own posts and the voice notes from the car. Nothing cleaned up.

Read the zine
Field guide No. 01

Brady is still weird.

Six stops, six places to eat and the hotel I'd book, on the street I've sat with since 2005.

Read the guide

You've got the spark.
I've got the matches.

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Not sure? Start with the room. You can add the trip any time.

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