What To See in Key West: One Day Itinerary

Visiting Key West is an amazing experience and you could easily spend a week doing and seeing different things, but what if you only have a day to fit it all in?

We’ll help you plan your perfect one day in Key West Itinerary by answering some frequently asked questions (FAQ) and giving you a sample one day itinerary to help you plan your own perfect Key West adventure.

A great day trip (or cruise port stop) in Key West is totally achievable if you know where to go, what to see, and how to get around in Old Town.

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Tip: check out this handy and inexpensive 👉Key West walking guide map card on Amazon that can be worn on a lanyard during your Key West Trip!

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Sometimes you only have a day, so it is great that the best spots to visit in Old Town Key West can easily be done in a day!

Our itinerary and FAQ will give you a small taste of the epic experiences that Key West has to offer and you can start planning your next longer visit. Let this one day itinerary be your guide.

Why is Key West called the Conch Republic?

In 1982, Key West declared itself the Conch Republic, a sarcastic idea that was a joke on secession from the United States. This bold move was started because a U.S. Border Patrol roadblock set up on the only highway (Hwy. 1) leading into the island, caused a major traffic disruption and hurt the Keys financially.

Frustrated by what they saw as a blockade, local officials decided to take action. On April 23, 1982, Key West’s mayor symbolically declared the island’s independence by “seceding” from the U.S., and proclaimed Key West as the Conch Republic. The act was a publicity stunt to draw attention to the island’s issues — and it worked.

The roadblock was removed, and the Conch Republic became a much-loved part of Key West’s quirky identity. In fact, locals use the conch as a gauge for when a person can consider themselves a local with some different conch levels (saltwater conch – true born in Key West local, freshwater conch – lived there for 7 years or longer).

If you are short on time JUMP ahead to the One Day Key West Itinerary Here then read the FAQ’s later

Key West Trip Frequently Asked Questions (FAQS)

What to do in Key West in One Day:

1. Where should I park in Key West if driving in?

One of the easiest places to park is the Old Town Parking Garage on the corner of Grinnell and Caroline Street. The cost is $5.00 per hour or $40.00 per day.
This location is great because the Free Duval Loop Hop on Hop off Bus has a stop (stop 1) just outside the parking garage.

It’s also close to the Old Town Trolley hop on hop off paid tour stop which is another great way to get around!

Pro Tip:
This garage is also just one block away from Old Town Bakery [930 Eaton St] which (in our opinion) has the Best Key Lime Pie in Old Town. They do tend to run out before the end of the day and close at 3:00 p.m.

2. What if I am visiting for one day on a cruise ship port stop and looking for Key West activities?

If you are visiting Key West on a cruise, then you will probably be docking at the privately run Pier B, which is close to Mallory Square.

The Duval Street area is easily accessible by walking from Mallory Square or the Free Duval Loop Hop on Hop off Bus has a stop (stop 4) on Whitehead and Greene St.

Taking a Cultural Food and Walking Tour of Key West is a great way to experience a lot in a short time!

Depending on the time that you’ll be in town a 3-hour reef and snorkel tour with open bar is a great idea!

3. What are the “must-see” places in Key West Old Town on a one day itinerary?

There are tons of “must-see” places to visit in Key West, but some of our favorites are:

1. Museum of Art and History at Key West Custom House – 281 Front St
It is convenient to Mallory Square and it’s fun to visit and cool off (in the a.c.) in the summer.

2. The First Legal Rum Distillery – 105 Simonton St
They always have a line it seems, but offer a nice tour and free rum tastings. It is located near stop 3 on the Duval loop and a short walk from Mallory Square. There is also a Mojito class!

3. Fort Zachary Taylor State Park – 601 Howard England Way
The beach and water here are wonderful. You can swim to the rock formation just off of the shore near the beach too. We have a beautiful photo from the Fort further down on the page. The sunset is also amazing from this point. (stop 7 on the Duval Loop)

4. Hemingway House – 907 Whitehead St
If you haven’t been, it is a must-see to experience the beautiful grounds and Hemingway’s famous polydactyl (six-towed) cats who reside there. It is located at stop 8 on the Duval Loop (Whitehead Street) and you can easily walk to the next must-see location. (note: admission was cash only) There’s also a Hemingway Food Tour to check out too!

4. Key West Lighthouse – 938 Whitehead St
Just down from Hemingway House is this amazing lighthouse. You can purchase tickets online before you go to save time and visit the keeper’s quarters and climb the stairs to the top of the lighthouse for an amazing 360 degree view.
tip: there’s also a sunset lighthouse experience that you can book and have it all to your group in the evening complete with wine and cheese!

5. Key West Garden Club at West Martello Tower – 1100 Atlantic Blvd
This historical tower was transformed to a tropical garden paradise that you can walk through and experience. We never miss it! (it’s a several block walk from either stop 11 or 12 on Duvall Loop, but worth it!)

6. Clarence S. Higgs Memorial Beach Park – Next to the Garden Club at W. Martello Tower is a vibrant cultural memorial to those whose lives were lost on slave ships coming into the port at the time. It is a solemn reminder of the lives lost there.

7. Sunset Sail from the Harbor Walk marina (near Mallory Square) – If you have time, this is an amazing sunset sail that has a small group so it is not overly crowded and includes wine. It is one of our favorite ways to experience the Key West sunset!

4. Where should I eat and drink in Old Town Key West on a one day itinerary?

1. The Koffie House on Greene – 602 Greene St
If you are parking at the Old Town Parking Garage the Koffie House is not a far walk from there. The inside is a tropical jungle paradise complete with swings. The coffee and pastries are amazing too! Starting with coffee is a great Key West activity so you have lots of energy for the day!

2. Blue Heaven! – 729 Thomas St
This wonderful place is probably on most lists, but it is because it is that good and they have live music too! It gets really crowded so it is better to go early, but they will take your name down and you can walk the area or sit across the street in the waiting yard area until a table is ready. (close to stop 7 on the Duval Loop) Also, it’s the only place we know with a rooster graveyard.

3. Mangoes Key West – 700 Duval St
An amazing Caribbean restaurant with even more amazing Mojito’s (there’s a whole menu just for them). We love the conch fritters here and the shrimp loaded pineapple! (close to stop 6 on Duval Loop)

4. El Siboney Restaurant – 900 Catherine St
Great Cuban food close (about 2 blocks) to stop 12 on the Duval Loop. We went here on a Key West Food Tour the first time and the food was so amazing we don’t miss it every trip now. The Cuban bread dipped in the Cortadito (hot espresso drink) is delicious! They get crowded so get there early.

5. Better Than Sex – A Dessert Restaurant – 926 Simonton Street
If you’re craving a truly unique and indulgent experience in Key West, head to this amazing dessert restaurant. This adults-only spot offers a playful and sultry twist on dessert dining, with an intimate, dimly lit sexy atmosphere perfect for date nights or special occasions. What sets this restaurant apart is its creative menu of decadent desserts and chocolate-dipped drinks. Try the “Cookie Nookie Pie” or the “Peanut Butter Perversion”, paired with a glass of wine or beer served in a rim dipped in chocolate. The experience goes beyond just dessert — it’s indulgent and fun. Make sure to book Better Than Sex well in advance because it books up over a month out during popular months. It will definitely be a memorable part of your Key West adventure!

6. The Southernmost Point – Your trip wouldn’t be complete without seeing the famous buoy, but there is always a huge line waiting for that perfect pic. Don’t be one of those guys wasting precious vacation time for this pic! A great alternative is to see the point then head to the Southernmost Point Bar (1327 Duval St) across and down the street for great tropical drinks and their own replica of the buoy that you can photograph without the lines! (stop 10 on the Duval Loop)

7. Seaside Cafe and Ocean Bar at the Mansion – Just across from the previous stop is this amazing cafe overlooking the Atlantic Ocean. The pizza is fantastic and the Mojito’s are the best that we’ve had in Key West. We never miss stopping here! (it is in the first picture on this article) Our top pic is the Lobster pizza, but all of the pizzas and drinks we had there were perfect! It is also a great spot to watch the sunset!

8. Santiago’s Bodega – 207 Petronia St
The white sangria here is the best we’ve ever had! The small plates are also delicious. Make sure to make a reservation here because it fills up quickly.

9. A Cultural Food and Walking Tour is a great way to hit several of these amazing restaurants! This is how we first came to eat at El Siboney and we have made sure to return as much as possible on each trip!

10. The best way to sample all of the great places for drinks and meet people is on a Craft Cocktail Key West Bar Tour! There’s even a Jimmy Buffet spots walking tour with Key Lime Pie!

5. Where can I find live music in Key West Old Town on a one day Key West itinerary?

• 1. Irish Kevin’s – It gets crowded, but the music was great!
• 2. Hank’s Hair of the Dog Saloon – Great courtyard with live music and food truck (Garbo’s) which was featured on the show Diner’s, Drive-ins and Dives!
• 3. Schooner Wharf Bar – Always had live music when we were there recently. We also did a New Years Eve party there and loved it!
• 4. The Bull and Whistle Bar – Great live music and be warned there is a “clothing optional” Garden Of Eden bar upstairs on the rooftop (no participation necessary).
• 5. Blue Heaven – Amazing music and food! It’s usually a wait to get in here, but worth it.

6. What are other ways of getting around besides walking and the Duval Loop for all of the Key West Activities that require transportation?

Scooter rentals are a great way to get around quickly.

Bike rentals are great too and you can park the bike easily. (a lot of hotels in Old Town have bike rentals or free bikes for guests)
Taking a Key West Bike Tour is a great way to get aquainted with the area too!

Electric carts (like golf carts) are a great way to get all around, though sometimes parking is hard to find. We always find parking however, but sometimes several blocks away. In the Summer heat an E Cart is really a big help getting around!

Key West Conch Train – Nice narrated tour sitting in the motorized train. It is not a hop on hop off, but nice Key West activity tour if you want to just ride and listen.

7. What are the Best Hotels Options if I return for a longer visit to Key West?

Casa Marina and The Reach Resort are both beautiful properties that you can use Hilton points or reward nights on (these are our first choice if we have enough points). Casa Marina has recently been fully renovated and the new rooms are lovely! Both of these hotels also have their own private beach area (an amazing perk!) which is not common in Key West despite its tropical setting.

We have a hotel review and comparison of Casa Marina and The Reach. Read here! If camping is in the plans we also have a guide with the best camping spots in the Keys too.

Other great options:

• Blue Marlin Motel – 1320 Simonton St. This budget-friendly Key West hotel is a great budget option and the location is just off of Duval so it is easy to get to all of the popular spots by walking. There is also a free breakfast each morning and free parking at this hotel which is a major perk!
• Old Town Manor – 511 Eaton St. Beautiful Victorian Bed and Breakfast in a great location!
• Hyatt Centric – 601 Front St. In the center of the Mallory Square area with their own little beach. We love this hotel and saw a manatee, stingrays, and shark from the balcony on our last trip! There is also a great snorkel spot right from the dock at this amazing hotel!
• The Saint Hotel – 417 Eaton St. Located in the center of it all on Duvall area. It is a small, but unique hotel with a great bar and balcony overlooking Duvall. We have the only other Saint Hotel here in New Orleans and it is equally amazing. (We also reviewed The Saint Hotel in New Orleans recently)
• Southernmost Beach Resort – 1319 Duval St. Beautiful hotel on the Atlantic side near the Southernmost Point. We love the location and quaint feel here!
• Best Western Hibiscus – 1313 Simonton St. Economical, but still in a great location. Nice rooms and they have free parking which is great if you have a car or rent a cart to get around!
• The Artist’s House– 534 Eaton St. Victorian bed and breakfast in great area. The rooms are lovely here.

8. What are some other unique Key West activities and tours if staying longer?

If you have longer than a one day Key West Itinerary consider these other great tours. There are many fun things to do in Key West!


• The Dry Tortugas Day trip by Catamaran was one of the best tours we have ever done and we want to do it again! The water is beautiful. It was a long day, but totally worth it for the views and snorkeling.
• The Ghosts and Gravestones Trolley Tour is a lot of fun and it is nice to sit and ride in the purple bus listening to the ghost stories of Key West.
• Dark Side of Key West Ghost Tour – We had a great time on this walking tour!

Also, check out our Summer Travel guide article for some Key Largo ideas if you will be in the area.

All of this walking will need some great travel shoes! We have a review of our favorite Birkenstocks for travel to help.

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One Day Key West Itinerary

This itinerary is easiest with an electric cart rental, but can also be done with the Free Duval Loop bus or just walking. If you are walking you may have to nix the Ft. Zachary Taylor stop because it is a bit of a walk.

Breakfast at Blue Heaven – 7:00 AM – 8:45 AM

Start your day off with a delicious breakfast at Blue Heaven, known for its island-inspired dishes like Lobster Benedict and Banana Pancakes. Enjoy the eclectic atmosphere and the local roosters and chickens roaming around the outdoor dining area (they have a unique rooster graveyard too). The gift shop here is also a great place to find unique gifts. It’s also a great spot for Key Lime Pie!

Hemingway House – 9:00 AM – 9:30 AM

Visit the Ernest Hemingway Home and Museum, the former residence of the famous author. Explore the beautiful grounds, take a guided tour, and meet the famous six-toed cats that live on the property. The grounds are really beautiful and worth a visit. If you have time book the Hemingway Food Tour too!

Key West Lighthouse – 10:00 AM – 11:00 AM

Climb the 88 steps to the top of the Key West Lighthouse and enjoy panoramic views of the island. Learn about the history of the lighthouse and its keepers through the exhibits on display. Also, see our Key West Lighthouse sunset experience review!

West Martello Tower & Gardens – 11:30 AM – 12:30 PM

Discover the West Martello Tower, an unfinished Civil War-era fort and museum run by Key West Garden Club. Wander through the beautiful gardens throughout the tower and take in the unique garden displays. This is an underrated gem and we think it is worth a visit!

Lunch at El Siboney – 12:45 PM – 1:45 PM

Savor a Cuban-inspired lunch at El Siboney, a popular local eatery known for its authentic dishes like Ropa Vieja, Picadillo, and Cuban sandwiches. Don’t forget to try their refreshing mojitos! We love El Siboney and first discovered it on a Key West food tour! Since then, we visit on every trip to Key West!

Key West Harbor Walk – 2:00 PM – 3:30 PM

After lunch, take a leisurely stroll along the picturesque Harbor Walk along the Historic Seaport, where you can watch boats come and go, see tarpons being fed, visit the Waterfront Brewery, take in the historic seaport atmosphere, and browse through the many shops and galleries that line the waterfront. Some other places near the harbor walk that are worth a stop if you have time are Koffie House on Green, Cuban Coffee Queen, and the best Key Lime Pie at Old Town Bakery!

First Flight Island Restaurant & Brewery – 3:45 PM – 4:45 PM

Visit First Flight Island Restaurant & Brewery, the birthplace of Pan American World Airways. Explore the history of aviation in Key West and enjoy a refreshing craft beer or a glass of wine in the unique, aviation-themed setting. They also have some pretty cool souvenir t-shirts on the way out.

Relax at Fort Zachary Taylor State Park – 5:00 PM – 6:30 PM

Unwind on the beautiful sands of Fort Zachary Taylor State Park. Take a dip in the crystal-clear waters, snorkel, soak up the sun, or relax under the shade of a palm tree. You can also tour the fort from here and then walk back to the beach area afterwards.

Dinner and Music at Hank’s Hair of the Dog Saloon (amazing Garbo’s Grill Food Truck) – 7:00 PM – 8:30 PM

Enjoy a delicious casual dinner, music, and fun at Hank’s Hair of the Dog Saloon from Garbo’s food truck, a local favorite for its laid-back atmosphere and tasty comfort food. Try their famous fish tacos or indulge in a juicy burger while you listen to live music. Garbo’s was featured on Diners, Drive-Ins and Dives and a stop on our food tour!

Other places close to Hanks that are worth a visit if you have time are General Horseplay, Bull and Whistle, Mel Fisher Maritime Museum.

9:00 PM onwards: Sunset Celebration at Mallory Square (of course may need to adjust depending on sunset time)

If you still have some energy and time left, head to Mallory Square for the Sunset Celebration, a nightly art market with street performers, local artisans, and food vendors. Watch the sun set over the water and take in the vibrant atmosphere as you conclude your day in Key West with a tropical cocktail.

Plan your next Key West visit and do it all again!

Essential Packing List for a Key West Trip

1. Comfortable Walking Shoes – Travel walking can mean 8-10 miles a day without even realizing it. Make sure to pack comfortable, supportive shoes to prevent foot pain and blisters. Look for breathable sneakers or walking sandals with arch support that can handle a full day in the parks. Our comfy shoe pics are these comfortable Sketchers go-walk ones or our favorite Birkenstock Gizeh sandals from Amazon!
2. Reef-Safe Sunblock – Protecting your skin from sun damage is important and protecting the important reef that surrounds the Keys is a must! This Jellyfish sting blocking, reef safe, SPF 50 sunscreen from Safe Sea is great! Find it on Amazon here.
3. Portable Phone Charger – Between taking amazing sunset photos, using the map app, and getting around, your phone battery will drain quickly. Bring a portable phone fast charger (amazon has this great inexpensive one) to ensure you stay connected and don’t miss out on all of the Southernmost Point Photo Ops!
4. Refillable Water Bottle – The weather in Key West is warm most of the year, but at times it is really hot. Staying hydrated is important. Pack a refillable water bottle that’s lightweight and will keep you hydrated. You can usually get free water at restaurants and bars in Key West so you won’t need to buy bottled water. Check out this inexpensive collapsible water bottle 2 pack on Amazon!
5. Travel-Sized Cooling Towel – Key West sun can be intense, even in cooler months. A cooling towel can help keep you refreshed during those Duval crawl days. Just wet it, wring it out, and drape it around your neck for an instant cool-down. This budget-friendly 4-pack travel cooling towel set on Amazon can be clipped onto a bag or belt loop!

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