Key West

8-DAY Key West, Florida ITINERARY

Key West, a U.S. island city, is part of the Florida Keys archipelago. It's also Florida's southernmost point, lying roughly 90 miles north of Cuba. Famed for its pastel-hued, conch-style houses, it’s a cruise-ship stop also accessible from the mainland via the Overseas Highway. It’s known more for its coral reefs – destinations for diving and snorkeling – than for its beaches, according to Google.

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Must do, must see, must try:


Can you see the fabled green flash said to occur the moment the sun sinks below the water?


Like you 'conked' your head, but these are the delicious kind. Enjoy some conch fritters.


Key Lime Pie is the local cuisine so try a slice or seven. Tip: try with whip cream, and try with meringue.

The Perfect 8-Day Key West Itinerary


AirBnB close to Mallory Square 

Hotel: The Gates Hotel ($$$), Margartiaville Key West ($$$), Old Town Suites ($$)


Avoid the hurricane season (June through November) and visit between March and May. The summer months are nice but can be rainy and humid. 


The itinerary pieces activities together that are walk-able, but Lyft to the outskirts. Don't rent a car, it's too expensive paying for parking.


Language is English

Currency: US Dollar


Great city for an interactive history lesson, that doesn't end with a quiz. Many places to visit, to drink at and eat at throughout the days. Also, this is an American city Bucket List must.

Besides the beautiful sunsets, Key West offers a lively nightlife on Mallory Square, a touch of history featuring Ernest Hemingway and President Truman, and you can't forget the wild chickens and roosters that cause a scene.

Day one

Evening flight; arrive in Key West. Take the shuttle down the 7-mile bridge and check into the hotel

Dinner: Bagatelle ($$, Seafood) and sit outside for people watching

Drinks: any place in Mallory Square, then find a spot to applaud the sunset

Day Two

9 AM Breakfast: Cuban Coffee Queen ($, American & Coffee) and get a picture of the famous crossing arrows

10 AM – Start your day exploring Mallory Square, which is the center of attention

  • If you’re up for it, here is a self-guided tour (PDF) of Key West; time spent is 1-2 hours

11:30 AM - Mel Fisher Maritime Museum (time spent 1.5 hours, $15 USD) for famous pirates, shipwrecks and treasures; lab tours also available

Lunch: local favorite, Sloppy Joe’s Bar ($$, Burgers & Bar)

Get a pineapple drink at The Smallest Bar in the World, inside of the Smallest Bar Inn, on Dunval Street. Save room for some dessert, with a slice of key lime pie at Key Lime Pie Bakery ($, Bakery)

2 PM – Shop the small marketing and mini-malls, The Key West Sponge Market

3 PM – Visit the Custom House Museum with sculptures outside and galleries inside

  • Stay outside and snap some pics with the art, you don’t need to tour

4:45 PM – Close encounters with the Key West Aquarium (time spent is 1.5 hours, $16 USD) or visit the Truman Little White House ($20 USD)

6:30 PM – Venture up to Key West Historic Memorial Sculpture Garden, a free courtyard where you’ll find 36 busts of influential Key West people

Sunsets are a big deal, join the party at Mallory Square overlooking the water and sunset key in the distance.

Dinner: Fogarty’s ($$, American) or Caroline’s Café ($, American) – and you must get the conch fritters

Bar: Irish Kevin’s Bar ($$, Irish Pub) with lively Irish music and dancing

Day Three

Grab a coffee and a light breakfast

10 AM – Have some fun with Fury Key West, Ultimate Adventure (time spent is 6 hours, $140 USD) for parasailing, jet-skiing, mini water park and reef snorkeling on the third largest reed in the world in the Gulf of Mexico

  • Breakfast and lunch provided

  • Bring a bag (water-proof preferred) to store your items, also some extra snacks and water bottles

  • Check the page for a list of ‘What to Bring’

  • Or Barefoot Billy’s Jet Ski Island Tour; 1.5 hours

4:30 PM – Back to the VRBO to clean up and eat some snacks

6:30 PM – Sail with Danger Charters for a Wind & Wine Sunset Sail; time spent is 2 hours, $85 USD

  • Choose from 8 different wines from around the world and choose from 5 domestic and imported beers

  • Heavy hors ‘devours are served

If you’re hungry, hurry over to Gabro’s Grill ($, Tacos & Burgers) for some tacos before they close at 10 PM

Drinks at Capt. Tony’s Saloon ($, Famous Bar – visited by Hemingway, Buffet and more)

Then Hog’s Breath Saloon ($$, Pub)

  • Finally, Bull Bar for a visit to Garden of Eden’s clothing optional bar – fair warning, you cannot un-see what you see ($$, Lounge)

Day Four

Lazy morning: coffee at the local shop and lounge

11 AM – Come hungry and wear comfy shoes for a food tour by Key West Food Tours, Southernmost Food Tour; time spent 3 hours, $75 USD

2:30 PM – Check out touristy spots and landmarks

  1. Start at the Mile Marker 0 on Whitehead Street and Fleming Street

  2. This is a 20-minute walk or 5-minute ride, your choice. If you want to ride, walk down a block to Pirate Scooter Rentals

  3. Grab a drink at Green Parrot Bar ($$, Bar)

  4. Stroll the Ernest Hemingway Home and Garden (time spent is 1 hour, $14 USD) – which is now home to over 40 cats, most with 6 toes

    1. If you need a snack, pop into Nine One Five ($$$, Tapas) for a bowl of Chipotle Conch Chowder

  5. Gaze upon the Key West Lighthouse (time spent is 30 min, $10 USD) – take a picture and move on

  6. Rest at the Key West Butterfly and Nature Conservatory; time spent is 1 hour, $12 USD)

  7. Finish at the Southernmost Point Buoy (in the Continental USA)

Rest up at the VRBO

7 PM Dinner: Antonia’s Restaurant ($$$, Italian), has amazing calamari and seafood

Drink: Virgilio’s ($$, Bar) a fancy martini bar

9:30 PM – Encounter the other side with a Ghost & Gravestones tour; time spent is 1.5 hours, $34 USD

  • Wear comfortable shoes


Quick breakfast or Cuban Coffee Queen again

9 AM – Fun in the sun on the beaches, 4 options below:

  • Higgs Beach (man-made with white sand imported from the Caribbean)

    • Setup on Higgs Beach and enjoy, things to do: walk down the Edward B. Knight Pier aka White Street Pier, visit the historical landmark West Martello Tower, or put a pup at the Dog Park

    • lunch at SALUTE! on the beach ($$, Mediterranean), then continue your day in the sun

  • Smathers Beach (man-made with white sand imported from the Caribbean) – using this one

  • Fort Zachary Taylor Historic State Park ($2 per person, natural beach and slightly rockier)

  • You could also purchase a day pass from Margaritaville Key West Resort for Sunset Key Beach, $40 USD

Setup on Smathers Beach, it has it all. Sunset Watersports Key West offers chairs, umbrellas, rafts and more starting at $10 – relax

  • Bring water and snacks with you

2 PM – back to the hotel to clean up

4 PM – Afternoon rum tasting at Key West First Legal Rum Distillery; time spent 1.5 hours, free tour

6:30 PM - Stumble over to for dinner at The Commodore’s Boathouse Bar & Grill ($$, Bar & Grill)

Stay here to watch the sunset and have drinks (try a passion fruit mojito)

Dessert: Kermit’s Key West Key Lime Shoppe ($$, Bakery) for a frozen chocolate covered key lime pie slice

Day Six

10 AM Brunch: Blue Heaven ($$, American) and order key lime pie slice for dessert

  • Embrace the local chickens run around like they own the joint

1 PM - Explore underwater gardens by snuba-ing with Key West Snuba Diving; time spent is 3 hours, $109 USD

  • You do not need a diving certification

4:30 PM – back to the hotel to get ready for a fancy evening out

7 PM Dinner: Mangoes Restaurant ($$$, New American)

9 PM – prepare for a show at Aqua Key West ($$$, Drag Show) and stay for dancing

Day Seven

10 AM Breakfast: Camille’s Restaurant ($$, American) and savor the Godiva White Chocolate French Toast

Spend the rest of the day at Ocean Key Resort & Spa, Spa Terre and get a day pass to the resort, enjoying the private beach

  • Or ride a beach cruiser, rented from BikeMan Bike Rental Key West, Cruiser Bikes; $10 USD for the day, and explore areas that you may have passed up earlier, or revisit some favorites

  • Or go back to a beach, see Day 5

Dinner: Bliss Restaurant Key West ($$, Seafood), sip on red or white sangria or keep it easy with Duetto Pizza and Gelato ($$, Pizza)

Return to Mallory Square for a final night of entertainment

Day Eight

10 AM Breakfast: Two Friends Patio Restaurant ($$, American)

Clean up and check out of the hotel

Goodbye Key West. Head home.

helpful links
Travel a GO-Go

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Besides the beautiful sunsets, Key West offers a lively nightlife on Mallory Square, a touch of history featuring Ernest Hemingway and President Truman, and you can't forget the wild chickens and roosters that cause a scene.

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Happy Travels, 

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