🌴
🌴

🛳️ Cruise Port Day · Key West, FL

Key WestDuval Crawl 🦩

Your Self-Guided Island Adventure

📅 Your Port Day 🕘 9:30 AM – 3:30 PM 🚢 Back by 4 PM
🗺️ Crawl Progress 0 of 8 stops

🏆 Crew Score

0

Points — complete stops & challenges to earn more

🚕 Getting Around Key West
🚕
Uber / Lyft
⭐ Recommended
Fastest & easiest. Door to door from the pier. ~5 min ride to the south end.
~$8–12 split between crew
🚌
Duval Loop Bus
Free
Free city bus running the length of Duval St. Runs every 15–30 min. Look for the green bus near the port entrance.
Free 🎉
🛺
Golf Cart
Most Fun
Rent near the port. Perfect for cruising in style. Watch the one-way streets on Duval!
~$50–80/hr (4-person cart)
📍 The Crawl
9:45 AM 📍 Southernmost Point Landmark

The iconic red & black buoy — 90 miles from Cuba. Hit it early before the tourist crush. The perfect group photo to kick off the day.

Free
📍 Open in Maps ↗
📸 Photo Challenge: Get the whole crew jumping in the same shot at the buoy. No one's feet on the ground!
10:15 AM 🏠 Hemingway Home Museum

Ernest Hemingway's legendary estate. 60+ six-toed cats roam free. Guided tours run every 15 min — arrive early to dodge lines.

🎟️ $19/person — pay at door, no reservations needed
$19 Admission Cards OK
📍 Open in Maps ↗
🐱 Cat Count Challenge: Before the tour starts, everyone guesses how many cats you'll spot. Whoever gets closest wins the title of Official Cat Whisperer.
11:15 AM 🟢 Green Parrot Bar Bar · Since 1890

Florida's oldest bar and a Key West icon. No pretense, just great vibes, live music, and free popcorn. A local favorite since 1890.

🍹 Order: Key Lime Margarita — fans call it the best on the island
No Cover Live Music
📍 Open in Maps ↗
🎶 Music Challenge: If there's live music, everyone dances for at least 60 seconds — no excuses. Someone's filming.
12:00 PM 🏴‍☠️ Captain Tony's Saloon Bar · Historic

The OG Sloppy Joe's — where Hemingway actually drank. Dollar bills and memorabilia covering the ceiling, a hanging tree in the middle of the bar. Pure Key West legend.

🍹 Order: Pirate's Punch — the house signature
💵 Bring Cash Live Music
📍 Open in Maps ↗
🩲 Tradition Challenge: Leave something on the hanging tree — a dollar bill with your names on it. You'll know when you see it.
12:45 PM 🦞 DJ's Clam Shack Food · 4.7★

Featured on Diners, Drive-Ins & Dives. Maine lobster, never frozen. The lobster rolls here are legitimately the best on the island — don't skip.

🦞 Order: Maine Lobster Roll ($24) or Overstuffed ($39) + conch fritters
Cards OK
📍 Open in Maps ↗
🦞 Menu Roulette: Everyone orders something they've never tried before — no defaults! First person done eating unlocks the bonus stop 🔓
1:45 PM 🌿 The Cannabis Bar Shop · 4.8★

Hemp-derived products right on Duval — no medical card needed, just a valid ID. THCa, Delta 8, edibles, CBD drinks, and cold beer. Great staff and easy vibes.

🌿 No medical card required — 21+ ID only.
21+ ID Required Cards OK
📍 Open in Maps ↗
2:15 PM 🍋 Kermit's Key Lime Pie Bakery · Iconic

30+ year Key West institution. Get the chocolate-dipped frozen bar on a stick — it's the move. Sample everything first, buy what you love.

🍋 Order: Chocolate-dipped frozen key lime bar on a stick
Cards OK
📍 Open in Maps ↗
🍋 Taste Test: Eyes closed, everyone rates the key lime bar on a scale of 1–10 out loud at the same time. No peeking at each other's reactions!
2:35 PM 🇨🇺 El Meson de Pepe Cuban · Live Salsa

Live salsa band, waterfront patio on Mallory Square, authentic Cuban food & cocktails. The perfect way to close out the crawl — 5-min walk to the pier from here.

🍹 Order: Mojito or margarita + Cuban sandwich or ropa vieja. Dance. Obviously.
🎺 Live Salsa Cards OK
📍 Open in Maps ↗
💃 Final Boss Challenge: The crew has to recreate a group video to whatever the salsa band is playing — even just vibing and pointing counts. Most dramatic performance wins!
🚢 ~5 min walk north to the pier · Aim to be on board by 4:00 PM

🎉 CRAWL COMPLETE! 🎉

You did it, crew! See you back on the ship for the next adventure. 🚢
What happens in Key West...

Want this experience on your cruise?

Cloud Nueve Travels curates custom port day itineraries like this one — tailored to your ship, your crew, and your vibe. Let's plan your next getaway.

✨ Book a Consultation

Tap to mark complete — each earns bonus points toward the crew leaderboard 🏆

+25 PTS
🐓 Rooster Photo
Get a photo with one of Key West's famous feral roosters. No chasing allowed.
+25 PTS
🌊 Southernmost Selfie
Full crew in frame with the ocean visible. Has to go on someone's story.
+50 PTS
💃 Dance With a Stranger
Get a local or fellow tourist to dance with you at El Meson. Video proof required. Extra points for style. 🎺
+50 PTS
🗺️ Full Crawl
Complete all 8 stops and make it back to the ship before 4pm. Legend status.
🔓 UNLOCKABLE · +75 PTS
🍺 Bonus Stop: Sloppy Joe's
Unlock this by winning Menu Roulette at DJ's! The most famous bar in Key West — neon lights, live rock, and the original Sloppy Joe sandwich. Squeeze it in between stops 5 and 6 if the energy is right. 410 Duval St.
💵 Cash Warning: Captain Tony's has a card surcharge — bring some cash. ATMs are on Duval St if needed.
🌿 Cannabis Bar Note: Florida is medical-only for dispensaries, but The Cannabis Bar sells hemp-derived products (THCa, Delta 8, CBD) to anyone 21+ with valid ID — no medical card needed.
🏠 Hemingway Home: $19/person, pay at the door. No reservations needed but arrive right at open to beat the lines. Tours run every 15 min.
🦞 DJ's Clam Shack Hours: Opens at 11am. Don't arrive too early or you'll be waiting outside!
⏰ Ship Cutoff: Aim to leave El Meson by 3:20 PM. It's a 5–10 min walk back to the pier. Don't be the reason the crew misses the boat! 🚢
Key West Duval Crawl · Curated by Cloud Nueve Travels · cloudnuevetravels.com