top of page

4 Day Key West Itinerary— What to See, Where to Eat, + Where We Stayed!

If you are planning on making a trip down to Key West this post contains a full 4 day itinerary and details on all the must see's, things to do, restaurant recommendations, and where we stayed! I also have a Key West highlight saved on my Instagram (click here)!

PS, if you're new here my name is Stephanie and I am a wanderlustin, fashion obsessed, spicy margarita enthusiast. Follow me along on instagram @sugaredstilettos to see all that and a big dose of my daily life… I love new friends!

Key West was the first stop on our honeymoon before we took off to Turks and Caicos (Turks blog post is coming soon!). We were in Key West from July 20th-July 24th and let me just start off by saying it was HOT + HUMID. If you could avoid planning your trip to the Keys in the summer months I definitely would, but if it's unavoidable let me just reiterate we still had an amazing time there… it was just a bit sticky.

Here is a summary of what is below in case you want to skip ahead!

  1. Iconic Insta-Worthy Photo Stops

  2. Best Spots to Eat

  3. Things to Do

  4. Where We Stayed— The Marker Hotel

  5. Our Exact Itinerary— if you want to follow exactly what we did!

OUTFIT DETAILS— All my outfits from our Key West trip are linked here! If you can't find something feel free to message me on Instagram and I can send you the exact link!


Southernmost Point Buoy—Located on the corner of Whitehead + South St.

  • This buoy marks the southernmost tip of the continental U.S. and is 90 miles from Havana, Cuba!

Mile 0 Marker— Located on 490 Whitehead Street

  • The Mile 0 marker is another must see photo op because it marks the beginning of U.S. Route 1 which is a 2,369-mile stretch that runs north to the Canadian border!

Sunset Pier— Located on Duval Street

  • Known for their rainbow sprinkle colored benches and tables that overlook the water. Basically it's the cutest photo op with an explosion of color!

Rainbow Road— Located on Duval Street

The Marker Pillars— Located at the Marker Hotel (where we stayed!)

Key West Bumper Sticker Wall— Located by the piers near Conch Republic


Of all the places we ate on our itinerary below these ones were our absolute favorites and I highly recommend them! I also suggest booking reservations ahead of time for lunch/dinner because restaurants in Key West book up fast!

Donuts are literally one of my favorite things so I always try and scope out at least one good donut place from anywhere we travel to. Glazed Donuts DID NOT disappoint. They had so many amazing flavors to choose from and they were SOOOOOOO freaking good. We tried the Cherry Jelly and the Blueberry Glazed Sprinkles— HIGHLY recommend if you are a donut fanatic like me.

If you are planning a trip to Key West and you are reading articles on where to eat I can almost guarantee Blue Heaven will pop up on that list. It is a true Key West staple and their breakfast is out of this world. The vibe of the whole restaurant is amazing, it's set outside behind the main building and has massive trees growing out of the patio area, chickens running around, and live music!

Blue Heaven is known for their key lime pie and eggs benedict. I personally tried the key lime pie and compared to the other one I tried in Key West I'd have to give it second place! It's still absolutely delicious but the one from Bagatelle in my opinion is UNREAL.

We came here for brunch one morning before the beach and it was DELICIOUS! They also do lunch and dinner and I have heard it's amazing as well! We ordered the fried chicken waffles and the deviled eggs and they were legit mouthwatering.

We came here for a drunken happy hour late lunch in between leaving the beach and heading out for the night and it was such a cute little spot.

We ordered the seafood tower with some wine and the seafood tasted SO fresh. I am literally craving that ceviche so badly right now looking at this picture!!

The views from this place were so gorgeous and the setting was very romantic… perfect little spot for a nice dinner and to see the sunset from. I wish I had remembered to take pictures of this little spot because it was truly a little hidden gem!!!

We ate dinner here one night outside on their second story balcony that overlooked Duval Street and it was such a great vibe and ambience. The food + drinks were incredible and packed with so much flavor. This was definitely one of my favorite restaurants that we ate at! AND PLEASE get the Key Lime pie from here it's hand downs my favorite in Key West.

Before I even get into talking about this place BOOK IT…. seriously just book it!! This was honestly one of my favorite things that we did in Key West. It is strictly a dessert cocktail and gourmet dessert restaurant and when I say the combinations of flavors are out of this world I mean it sincerely. The vibe is like a speakeasy and you most definitely need a reservation ahead of time.

We ordered the Love Potion shots to start and the Super Soaker and Exhibitionist as our cocktails. For dessert, we ordered the double stuffed and the Naughty by Nature. Everything was sooooo good!! They truly do an exceptional job here, such a unique spot!

This place isn't fancy, but if you are thoroughly obsessed with all things Mexican food then you need to try it out! You also don't need a reservation to go here so it's the perfect place to eat the night you fly in if you are looking for somewhere to go eat in a crunch. All I have to say is their tacos are SO dang good and their street corn is freaking BOMB!!!!

Latitudes is also a TOP rated place in the Keys, but you need to book a reservation WAY in advance. We weren't able to eat here, but we have had friends eat here and they said it was phenomenal. It's a super romantic vibe and right on the water. So if you're into that, book ahead!!



Key West is such a bike friendly place and it makes checking off all the things from your itinerary SO much easier because you can get around a lot quicker than by foot. Shaun and I literally rode bikes every single day we were there and it's how we were able to do so much in such a small time frame.


If you are a beach lover we did two beach days while we stayed here. I will be honest the beaches aren't anything crazy and they are quite small, but if you want to just pencil in a day of relaxing by the water then it's worth it!

We went to Smather's and Fort Zachary and if I had to pick one of the two beaches to suggest, it would definitely be Fort Zachary. The pictures below are from there!

This place is a quick 1 hr max little excursion, but it's so cool to check out! I will let the pictures speak for themselves.


I'm going to be absolutely honest with you, this was merely a checking off the box kind of excursion for us. We booked our tour through Sebago and they overpacked the boat so much. We don't like crowds in general, so we typically like to book things in smaller groups or privately, but we were crunched on time and it was one of the only tours available so we just booked it. We both agreed it just was not worth it. We didn't even have a spot to sit on the boat because it was so packed. The amount of people on our boat also definitely impacted our snorkeling experience because there was just to much movement in the water and it was way to crowded. I think we may have seen like 3 fish. If you do snorkel in the keys go with a SMALL group or private tour or as the locals said, go to the other parts of the Keys to go snorkeling rather than right in Key West where it's more touristy!

Go to sunset pier to watch the sunset! It's SOOO beautiful!!! They have a bar and live music playing there, so it's such a great vibe.


We stayed at the Marker Hotel in downtown Key West which location wise could not be better in my opinion. It's tucked away in a harbor view corner just steps away from all of the restaurants, shopping, and major Key West staples. Let's put it this way Duval Street is only three blocks away!

The vibe and decor of the hotel is a cross between boho meets tropical, it's just adorable! One of my favorite things about our room was our private balcony, we would end most nights sitting out there enjoying a glass of wine before bed.

There are three sparkling pools on site, one of which has a full service bar… I mean you just can't beat a poolside pina colada!!


I personally love creating insanely mapped out itineraries for our vacations because I love making the most of every single second when traveling. I know itineraries are not for everybody, but if you're somebody like me who needs organization when traveling then this last paragraph is for you!

Below you will find our exact itinerary for Key West. I figured I would take the guess work and stress out of your planning in case you want to replicate it on your next trip! It's a great base to start with and it includes all of the "must sees" in Key West!

DAY ONE (arrival day)

11AM— Arrive in Key West

12PM— Check into Marker Hotel (Address: 200 William Street, Key West)

1PM— Lunch at Conch Republic Seafood Company (no reservation needed; 800 ft from hotel)

7PM—Dinner at Mexican & Margs at Amigos Tortilla Bar (No reservation needed)

9PM—Explore Downtown + Duval Street


9AM— Iced Coffee + Donuts from Glazed Donuts

1030AM—Brunch at Firefly Key West (0.8 miles from hotel)

12PM— Beach Day at Smathers Beach

4PM— Apps + Cocktails at the Thirsty Mermaid

7PM—Dinner at Hot Tin Room (0.5 miles from hotel)

8PM— Sunset at the Pier


830AM— Southernmost Point Buoy Photo Op!

9AM—Brunch at Azur (0.4 miles from hotel)

11AM—Beach Day at Fort Zachary Taylor Historic Park (1.5 miles from hotel)

230PM— Lunch at the Lobster Shack

6PM— Dinner at Nine One Five

9PM— Dessert + Cocktails at Better than Sex Dessert Bar (0.7 miles from hotel)


8AM— Breakfast at Egg Co

9AM— Key West Butterfly Farm

11AM— Mile 0 Marker Photo Op!

12PM— Snorkeling Excursion (3 hrs) (500 ft from hotel)

8PM— Dinner at Baglatelle

10PM— Key West Ghost Tour

DAY FIVE (departure day)

10AM— Breakfast at Blue Heaven

Follow me along on instagram @sugaredstilettos to come along for the ride!

With Love Always,

Sugared Stilettos

By Stephanie


bottom of page