2 Days in Key West Itinerary (2025)

This 2 days in Key West Itinerary will help you plan the perfect trip to the southernmost point of the United States, including where to stay, eat & play.

Key West is Florida’s southernmost point and a small island city in Florida but it has a lot to keep you busy. This sub-tropical town features a unique combination of cultural influences. We love spending time exploring Florida, with Key West being the best place to visit when it is colder elsewhere in the US!

When we moved to the US, Key West was one of our first vacation destinations. It is a perfect place for people looking for a laid-back vacation with warm weather, delicious cuisine, and a colorful cultural vibe. Especially perfect when we are trying to escape the bitter Chicago Winter!

2 Days in Key West Itinerary

Wondering what you should do in your Key West itinerary in 2 days? It is a great place in southern Florida full of attractions and outdoor activities.

Key West can be visited in two days if you are running out of time, or you can take a week if you are flexible with your time and budget. 

I recommend spending at least 48 hours in Key West to enjoy this charming island city without missing any major tourist attractions and activities.

Day 1: Explore the historic sights and downtown area

Day 2: Visit the waters nearby; whether you choose to take a day trip or go snorkeling

Day 1 in Key West

Ernest Hemingway’s House

After your breakfast, head to the Ernest Hemingway House where this literary legend spent more than 10 years of his life. The house is not only significant but also such a beautiful Spanish Colonial-style mansion that it has now become one of the best places to get married in Florida.

Your Key West itinerary needs to include a guided tour is available in this US National Historic Landmark. During the 30-minute tour, the guide will take you through the home filled with Hemingway’s original furniture and share some stories from Hemingway’s life. 

Opening time: Daily from 9:00 am – 5:00 pm. 

Walking Tour in Key West

Next, rent a bicycle or a scooter and explore the popular Duval Street. The street is filled with restaurants, shops, and entertainment to attract tourists.

You can pet sharks at the Key West Aquarium located along the street, or visit the interesting Mel Fisher Maritime Museum. Take a relaxing stroll through the Audubon House and Tropical Gardens or take an Old Town Trolley Tour to see the sights.

There are some great bars and restaurants along the street too, perfect for lunch. Our favorites include Hogs Breath Saloon and Sloppy Joes.

It also hosts events and functions throughout the year. If you visit in summer, don’t miss the Hemingway Days Festival.

If your Key West itinerary is longer than two days, we recommend spending an extended period around this area, as there is plenty to see and do!

Key West Dog Beach

After a busy morning exploring and a bite to eat along Duval Street, it is time for some beauty in the Key West.

If you have brought your dog along for the journey, you can head to the Key West Dog Beach; one of the best dog-friendly beaches in Florida, where your canine friends can run through the water and enjoy the splash on this small beach. 

After enjoying the beach, check out Louie’s Backyard; a fantastic dog-friendly restaurant where you and your furry friend can enjoy a tropical drink.

Alternatively, you can head to the Clarence S.Higgs Memorial Beach, one of the best beaches in the city in our opinion, or take a stroll along Smathers Beach.

Key West Lighthouse  & Keeper’s Quarters Museum

Finish the first day of your Key West itinerary, with a bit of history.

Built in 1847, it is one of the most beautiful lighthouses in Florida. It is also a unique one as the first keeper was a female which was rare at that time.

Watch the beautiful sunset from the top and enjoy a romantic evening with your loved one in the evening.

The Key West Art and Historical Society operates a museum where you can see the original furniture, household items, and photos of the keepers. Don’t miss the video presentation that gives an insight into the history of the Key West lighthouse.

Day 2 Key West Itinerary

Southernmost Point

No Key West itinerary is incomplete without adding Southernmost Point. This is one of the most visited and photographed places in Key West.

TIP: Visit this busy spot as early as possible, otherwise the lines can be very long to take photos.

This iconic landmark which is marked by a red, yellow, and black concrete marker can be found at the intersection of South and Whitehead streets. You will see street vendors and performers around this lively spot to sell souvenirs and show their talents.

Nearby sights

Next on your Key West itinerary is up to you to choose!

Not far from the Southernmost Point, are a few historic and interesting sights that you can choose to explore. The Key West Butterfly and Nature Conservatory is a fun option for families, as is the Florida Keys Eco-Discovery Center.

History enthusiasts can enjoy a tour of the Truman Little White House, home to the former President Harry S. Truman, and then take a stroll around the Fort Zachary Taylor Historic State Park.

The Key West Shipwreck Museum is also a unique place to explore whilst in the city.

Lunch

There are plenty of places you can choose from for lunch in your Key West itinerary, and we do recommend some more spots below, but our favorites include:

• Blue Heaven for a Florida, Caribbean Fusion meal.
• Bistro 245 for tasty dishes with a fantastic view of the sea.
• Jack Flats for surf-and-turf whilst catching some sports (we love this as a dinner option too!).

Enjoy Watersports Activities

If you love adventure water sports, Key West is an ideal place where you can spend an entire day on fun adventure activities.

From snorkeling, and kayaking to jet skiing, banana boat riding, parasailing, and many more – Key West has an abundance of water activities. 

Jet skiing in Key West is a fun choice too; it’s a great way to explore more of the coast. The jet ski tour offers some unique views of the island.

Sunset at Mallory Square

What can be more beautiful than ending your 2 days in Key West trip with a stunning sunset at Mallory Square?

A Key West sunset is one of the best sunsets in Florida and a sunset from Key West needs to be on your US bucket list.

The Mallory Square is a lively area filled with craft markets and small food stalls. You can watch the street performance before the sunset. I recommend reaching here two hours before sunset to get the best spot. 

Things to Know Before You Go to Key West

Best time to visit Key West

Summer is hot and humid in Key West and it is also the season of deadly hurricanes. Most tourists avoid visiting Key West in Summer.

On the other side, the Winter months are the peak time in Key West. Most people love to visit Key West between November and March when the weather is perfect to get around the city and the chances of rain are very low.

However, if you are on a budget or looking for a peaceful vacation with the least crowds, Spring (March to May) is the best time to visit Key West. The Winter crowds disappear, the sun is bright but bearable, the temperature hovers between the 70s and 80s and the best thing is that you can get some amazing hotel and flight deals during these shoulder months.

How to Get to Key West

Key West International Airport which is located directly on the island is the closest airport to this city. Major Florida cities like Miami, Orlando, Tampa, and Fort Myers have non-stop airline service to Key West.

You can also get non-stop flights from New York, Boston, Chicago, Washington DC, and many other major cities.

If you rent a car from Miami International Airport, take the US Highway 1 that connects mainland Florida to Key West. Ferry service to Key West is only available from Ft. Myers.

How to Get Around Key West

It is very easy to get around Key West as the city is very small – it’s only 2 miles wide by 4 miles. It is not recommended to rent a car to explore Key West. It is an unnecessary expense when the city can be explored by foot or bicycle. Finding parking can be a daunting task and there is no free parking lot near the main city area. 

You can take the advantage of public bus service of Key West. But my recommendation will be to rent a bicycle.

Bicycling is the best way to discover the narrow streets and you can easily access the bike stands at the attractions. Just make sure to use the traffic rules and use the lock that will be provided by the rental shops.

Where to stay in Key West

Duval Street is one of the best places in Key West where most people prefer to stay. You will find plenty of options from luxurious resorts to mid-range hotels and budget-friendly hostels for all types of travellers. 

Eden House Hotel

Located in the historic market town of Grantham, Edn House Hotel is the oldest hotel in Key West. They offer clean spacious rooms with comfortable beds at reasonable rates. If you want to upgrade, they have deluxe rooms with all modern facilities while keeping the original character. 

Eden House also features a heated pool, hot tub, Jacuzzi, hammocks, porch swings, and elevated sundeck that give the vibe of the tropical landscape and offer pure relaxation. A complimentary breakfast is included too. Take the advantage of complimentary happy hour held by the poolside daily. 

Ocean Key Resort & Spa

This luxury resort is located in the heart of Old Town Key West at Mallory Square. It features waterfront rooms with balconies overlooking Mallory Square and the Gulf.

Their on-site spa features an oceanside pool. If you are looking for a romantic weekend getaway in Key West, look no further than Ocean Key Resort & Spa. Pamper yourselves with massage therapies, and other spa treatments.

You are within walking distance of some amazing Key West restaurants, shops, and that splendid Key West sunset.

Where to Eat in Key West

Blue Heaven

No restaurant can beat Blue Heaven when it is time for breakfast. It is one of the best places to eat in Key West. From lip-smacking pancakes and lobster eggs benedict to a special Key West shrimp omelet, they have a wide range of delicious food that will make your tummy happy. Besides their yummy dishes, you will also love their tree-shaded courtyard where cats and roosters roam freely.

The Stoned Crab

Another popular restaurant in Key West for lunch or dinner. They have dedicated fishing boats and serve fresh-caught lobster, stone crab, and other fishes. Seafood lovers must visit this restaurant to taste their incredible dishes. 

Best Things to do in Key West

There are plenty of things to see and do in Key West. There are many beautiful beaches in Florida offering crystal-clear waters, perfect for some relaxing and unwinding.

Spend time at the museums and gardens listed in the Key West itinerary above and make sure to eat as much of the local food as you can.

2 Days in Key West Travel Tips

• Book your accommodation 3-4 months before your journey to avail of the hotel discount.
• Book a hostel or Airbnb with a kitchen to cook your meals to save some money on food.
• Renting a bicycle is the best way to explore Key West. It is eco-friendly, cheap, and perfect for a laid-back city like Key West.
• Never leave your room without carrying a hat, sunglasses, and sunscreen to avoid getting tanned.

Things to Know Before You Go to Florida

Key West Itinerary F.A.Q

How many days do you need for Key West?

You will need at least 2 days in Key West to see the best sights but if you can, aim to have 3-4 days, giving you time to relax and enjoy Key West at your own pace. 

What should I not miss in Key West?

Make sure to visit Hemingway House, tour Truman’s Little White House, and visit the Shipwreck Museum. 

Is it worth visiting Key West?

Yes, if you want to enjoy beautiful beaches and stunning sunsets, make sure to visit Key West. 

What is the best month to visit Key West Florida?

The best time to visit Key West is between March and May, with hotel prices being lower than the Summer months and the weather being a cool and pleasant temperature. Winter is the busiest time to visit Key West, so avoid if possible. 

What is the cheapest time to go to Key West?

Visiting in the off-season is the cheapest time to visit Key West; so hear here from June to November to save money on accommodation. 

Is Key West expensive?

A trip to Key West will cost just over $1000 per person for a week’s vacation. If you book your accommodation in advance and stick to cheaper cafes and restaurants, then Key West doesn’t have to be too expensive. 

How long is the drive from Miami to Key West?

Driving from Miami to Key West will take approximately 4 hours, covering a distance of 159 miles (256 KM).