Key West has always been known as a hard drinking town, ever since Ernest Hemingway threw back dry martinis at Sloppy Joes, or Capt.Tony’s Saloon, or both. (The bar debate rages to this day.)
When ships dock in Key West, revelers walk off the boat to find themselves smack in the middle of the world-famous Duval Crawl, where several landmark watering holes are lined up within walking distance: Sloppy Joe’s, Capt.Tony’s, Hogsbreath, The Green Parrot, The Bull and Whistle, Margaritaville, Smokin’ Tuna, Rick’s, Irish Kevin’s……and so, so many more. 
If downing drinks is your primary Key West objective, have at it: you’ve come to the perfect place. With eight hours of shore time you’ll barely make it to a handful of them, so belly up to the bar with the crush of other cruisers. The crush depends on how many ships are in port. A 3-ship day makes for a frantic mess, and I’d run from Duval if I were you; check the Port Schedule here. And you won’t be meeting many locals, unless they’re serving you.
But with a drink in hand, who cares? Just make sure there’s someone there to help you crawl up the gangplank in time for ship departure. Of course, if you just want a peek at the famous bars and don’t need all the drinks, you can always check out the live bar webcams (I watched Hurricane Irma approach on one of these, until she blew out the cams).
Key West’s Duvall-area bars have predictable music (you’ll hear Margaritaville, trust me), but the better bands tune up after 5 pm; most cruise ships head toward the horizon around then. You might catch a band that locals like on a weekend afternoon, though. Best place to check music listings is in the print edition of Konk Life, out on Thursdays, in the What’s Happening section (latest edition here). 
Yet Key West is so much more than its watering holes. We come down for a month or two each winter, and sometimes I’m that lady sitting on a bench near your cruise ship, watching people pouring off the ships or returning after a few too many. I always hope visitors have a fine time, but worry they’ll miss the best stuff with only eight hours and all those tempting bars. So here’s what we’d do on a first-ever trip to Key West.
TRANSPORTATION/TOURS
We’d definitely start with a Conch Train tour. We didn’t do this for years, thinking it was too touristy, and of course it is. When we finally climbed aboard a train (they’re everywhere in Key West – try not to get run over by one), we said ‘silly us’ for not doing so earlier.
Two different companies (Conch Train Tour, and Old Town Trolleys) provide tours to see the sights, with history-packed, entertaining commentary that brings to life the quirky Conch Republic, including Key West’s 1982 “secession” from the United States. (FYI if you visit the CR website don’t spend big bucks on a Conch Republic passport unless you want to help fund the tongue-in-cheek but very fun Independence Day celebration). 
As a first-time visitor, I’d go with the Conch Train’s 90-minute tour (three stops, sticks close to Old Town) to save time for later. On a second visit, try the Old Town Trolley for its hop-on-hop-off convenience. It ranges farther afield around the entire island, to stops such as lovely Smathers Beach. Just understand that if you hop on and off it might eat up your entire day.
An alternative to trains, longer bike tours (3 hours) pedal to similar destinations and provide comparable commentary (Key Lime Bike Tours gets high ratings). While you can rent your own bike, you don’t really need it of you’re only here eight hours; Key West has excellent downtown-area transportation options.
There is the totally free Duvall Loop bus route, which stops every 15 minutes and gets you around Duval, to the Seaport, and the Southernmost Point. (maps and info here). And Uber just arrived in town. All bets are off in terms of whether your Uber driver will provide entertaining, historical commentary or not, though.
After a train or bike tour, walk up to the Chamber of Commerce Visitor Center, 510 Greene Street (ground level directly behind Sloppy Joe’s Bar). Here you will find great maps and information*. Then, it’s time to walk, walk, walk, which is the best way to appreciate Key West’s charming ambiance and architecture (and to get away from Duval Street).
*Some online search advice: It’s difficult locating unbiased sources like Monroe County’s excellent fla-keys visitor’s site or the Chamber of Commerce – click for links. A few KW travel apps exist, but none I’d recommend. If better ones get developed, I’ll update here.
Where to walk? With a myriad of options, what you choose depends on your interests:
ARCHITECTURE AND HISTORY
At the Visitor Center, pick up the map A Walking Guide to Historic Key West: On the Pelican Path. This walking tour takes 1 ½ to 2 hours, although you could easily do some of it and not all of it.
KEY WEST CEMETERY
This is our personal favorite, for its beautiful statuary, historic gravestones, and peaceful quiet (even for the living). A free comprehensive self-guided tour map is available at the cemetery’s front entrance (guided tours also available/check website). Make sure to find the headstone that reads, “I told you I was sick.”
We love to just aimlessly wander the narrow streets and lanes surrounding the cemetery, where you’ll find block after block of brightly colored, historic Conch cottages. If you enjoy strolling past charming conch cottages, cross White Street to the Meadows neighborhood, which many locals say has the most charming historic homes, and wander up and down the blocks.
SEASIDE VISTAS, DOCKS, and BOATS (and maybe a tarpon or manatee sighting)
At the bottom of Duval Street, go right on Front Street, walk to its end, then stroll along the boardwalk of the Key West Historic Seaport. Here, you can catch a ride on a historic sailing vessel, watch the catch come in (or charter a fishing trip), or hang out in more landmark watering holes such as Schooner’s Wharf, The Half-Shell Raw Bar, or Turtle Kraals.
BEAUTIFUL BEACHES
Warning for sandy beach lovers: Not so much here. The Florida Keys make for world-class
fishing/diving due to their reefs, which create rocky, seaweed-strewn beaches. Still, you can reach some lovely sandy beaches from downtown Key West by bus, taxi, conch train, or long walk: Fort Zachary Taylor (closest to pier), Higgs Beach, or Smathers Beach (farthest). At all three, you can rent an umbrella and a chair, and there are glorious ocean views to write home about.
MUSEUMS
For the non-walkers/beachgoers, I suggest a museum or two. Our favorites:
The Custom House. For the history/art buffs, you can’t miss it when you leave the ship (look for the giant couple kissing). Here you will find floors of exhibitions that weave together two centuries of Key West history, art, and people.
Truman’s White House. Winter White House from 1946 to 1952. You’ll get the human side of Harry, who relaxed with his family here while at the same time dealing with Cold War threats. History buffs will appreciate Cold War and naval history insights, and the home has stayed much as it was when Truman lived here, furniture and all.
Mel Fisher Museum This is Padre’s favorite. Educational displays, including stunning gold, silver, and precious gems, trace the life of treasure-hunter Mel Fisher and his discovery of Spanish galleon Atocha, wrecked in the seas off Key West in 1622.
Shipwreck Museum. Glorious fun, especially for kids (or adult kids). Brings alive the world of 1856 Key West, the era of the wreckers, using actors, films, and artifacts from the 1985 wrecked vessel Isaac Allerton.
Hemingway Home Tour. Sometimes the lines are long here, and I’d skip it unless you really love cats, which I do. They’re everywhere and yes, many of them have six toes – and their own cemetery.
EATS AND DRINKS
If you’re still with us, so far you’ve taken a train or bike tour (2-3 hours), completed a walking/beaching/museum foray (2 or 3 hours), and now you’re starved. Thorough recommendations for food and drink will have to be the subject of another post, but we do have a couple favorites to share.
For on-the-go bites, two excellent choices locals like, close to the cruise pier: Get takeout at the Conch Shack on Duval (lobster rolls to die for), or the food truck Garbo’s Grill, tucked behind Grunt’s Restaurant (shrimp tacos, also to die for).
For a final toast to Key West before you go, go right next door to your cruise ship: The Sunset Pier. Hurricane Irma damaged the pier extensively, but they’re up and running, and repairs are underway. So grab a table by the railing to soak up stunning views of boats sailing by in the harbor, and enjoy a local music group playing on the small stage.
A fitting ‘bon voyage’ to one of our favorite little towns on the planet.
