What To See in Key West: One Day Itinerary

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.

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!

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!

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!

5. The Gardens Hotel Courtyard and Wine Bar – 526 Angela St
A historical mansion that was built in the 1800’s is the main building of the hotel, but the secret is the beautiful oasis in the gardens and the self-serve wine bar. You can purchase a wine card at the front desk and sip vino in the beautiful gardens. Don’t forget to visit the tortoises and read their story on the garden path. (close to stop 15 on the Duval Loop) They also have live music in the gardens on some nights.

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. 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)

8. Santiago’s Bodega – 207 Petronia St
The white sangria here is the best we’ve 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!

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 (Sheldon Benton is great to listen to when he’s playing!)

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 there is a “clothing optional” Garden Of Eden bar upstairs on the rooftop.

5. Blue Heaven – Amazing music and food! It’s usually a wait to get in here, but worth it.

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.

The Gardens Hotel – 526 Angela St. It is really an oasis!

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!

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!

The Artist’s House– 534 Eaton St. Victorian bed and breakfast in great area. The rooms are lovely here.

A tip for finding the best and cheapest flights on a longer trip to Key West is to use the Skyscanner website to search different combinations and routes. They also have an alert you can set up to be notified when the flight price goes down!

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 listening to the ghost stories of Key West.

Dark Side of Key West Ghost Tour – We had a great time on this 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 our favorite Birkenstocks for travel review to help.