2 DAYS IN KEY WEST ITINERARY

sunset in Key West Itinerary

Heading to Florida? This 2 days in Key West Itinerary will help you plan the perfect trip to the southernmost point of the United States.

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. Key West is a perfect place for people looking for a laid-back vacation with warm weather, delicious cuisine, and a colourful cultural vibe.

I won’t say that Key West is a cheap place to visit in Florida, especially during peak months it can break your bank. But if you research well before your journey, a relaxing weekend vacation in Key West won’t burn a hole in your pocket. To get the most of your Key West trip, check out this 2 days in Key West itinerary guide.

Aerial view of key west

When 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 less.

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.

Driving to Key West

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 flight 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. Mos tourist attractions in Key West are within walking distance of each other. 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.

directions in Key West

Tip: The crime rate in Key West is higher than the state and national average. I will highly recommend carrying an antitheft backpack to keep your costly belongings safe. If you are unsure which backpack would be the best for you, check out the best 10 anti-theft travel backpacks buying guide

Accommodation in key West

Two Days in Key West Accommodation

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

eden house key west

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.

Ocean Key Resort & Spa key west
Artistic side to Key West

Where to Eat in Key West

Blue Heaven restaurant and bar 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, lobster eggs benedict to 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. 

The stoned crab seafood restaurant in Key West
Sunset over key West

Best Things to do in Key West

There are plenty of things to see and do in Key West. It is not possible to cover all sightseeing and activities in a single visit. I always recommend enjoying the place that you are visiting instead of rushing from one spot to another to mark all the checklist. In this 2 days in Key West itinerary, you will get to know how to get the best of Key West when you have a time limit.

Key West Itinerary for 2 Days

Wondering what you should do in Key West 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 will recommend spending at least 48 hours in Key West to enjoy this charming island city without missing any major tourist attractions and activities. I have split the Key West itinerary into 2 days and prepared a list of the best things to do in Key West in such a way that you would get a mix of it all.

Day 1 in Key West

Ernest Hemingway’s House
Hemingways house in Key West

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.

A guided tour is available in this US National Historic Landmark. During the 30 minutes 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

Rent a bicycle or a scooter and the popular Duval Street. It is filled with restaurants, shops, and entertainment to attract tourists. You can see some historic homes and some of the most popular tourist attractions of Key West along Duval Street. The houses, shops, and hotels are so colourful and unique. This area is full of entertainment and has a lively vibe. It also hosts events and functions throughout the year. If you visit in summer, don’t miss Hemingway Days Festival.

Key West Dog Beach

Some people love to enjoy vacations with their furry friends. Key West Dog Beach is 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.

Key West Dog Beach
Key West Lighthouse  & Keeper’s Quarters Museum
Lighthouse in key west

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. The spectacular view of all of Key West from the top of the lighthouse will leave you awestruck. 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 operate the 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 of Key West Itinerary

Southernmost Point

Key West itinerary is incomplete without adding Southernmost Point. This is one of the most visited and photographed places in Key West. Visit this busy spot as early as possible, else 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.

Southernmost point in the usa Key West
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 snorkelling, 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 really awesome. It’s a great way to explore more of the coast. Jet ski tour offers some unique views of the island. There are many water sports companies in Key West. Sunset water sports is highly recommended for its remarkable service. You can book your tour in advance. They even offer free shuttle pick up from your hotel.

mallory square in key west
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? Key West sunset is one of the best sunsets in Florida and you need to experience one at least once in your life.

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 will recommend reaching here two hours before the sunset to get the best spot. 

sunset in Key West Itinerary

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 own meal 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.

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