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Key West Itinerary 2 days: How to spend the perfect weekend

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Disclosure: This post on Key West Itinerary 2 days, is sponsored by Hotels.com to bring forth some of the stunning wanderlust destinations in the USA. As always the opinions and ideas are my own.

Located in the state of Florida, at the southernmost point of the United States is Key West. Known for watersports (like snorkeling), amazing coastlines with beaches, and a lively nightlife to historic sites, here is how you can spend a relaxing yet fun weekend getaway – the perfect Key West itinerary 2 days!

Key West Itinerary 2 days: How to spend a weekend in Key West

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How to spend 2 days in Key West

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Note: As travel today remains uncertain, please keep your safety and the safety of others in mind at all times. If you decide to travel during this time – follow local guidelines, remember to wear a face mask, and wash your hands often. Check official websites before your trip for the latest updates on policies, closures, and status of local businesses.

Before we share the itinerary, here are essential travel tips for your trip to Florida, USA. 

Getting to Key West Florida:

If flying from Canada or the overseas, your best bet is to fly to the Key West. Visitors can fly to Key West International Airport (EYW) via connections or direct flights from a host of Florida cities.The city’s airport is serviced by all major carriers. 

Having said that you can also drive or take a boat to the Key West from within the USA. 

You can combine a trip to Miami and Key West as well. It takes about 3.50 hours to get there by road from Miami; but you can fly as well if you are not renting a car. 

Once you are in the city, you can access ground transportation from the airport, including local shuttle buses and rental cars to get to your hotel or old town area. 

Coastal views of Key West
Key West

What is the best location to stay in Key West?

For a short weekend in Key West itinerary, stay at the old town or near it, so you can easily hop on tours, and explore major attractions by walking. 

The Old Town is also known as the Historic District and it is one of the best areas to stay in Key West. You can easily find bed-and-breakfast, vacation rentals, mid-budget Key West hotels, or luxurious accommodation in and around the Downtown area. 

Once you are at the Old Town, you can enjoy sightseeing on the free Duval Loop bus shuttle, or get on the Old Town Trolley Tours (with a 24-hour validity) or a Conch Tour Train Tour. 

We highly recommend the Old Town Trolley Tour with 12 stops. This is a perfect way to check off all the attractions on day one of your Key West Itinerary. 

You can grab your tickets here, it is valid for 1 day, and you can hop on and hop off at about 12+ stops. They also have a great frequency – of 30 minutes!

Day 1 of Key West Itinerary 2 days: Explore the historic side of Key West, and hang out at the Duval Street in the evening 

As a weekend destination Key West is amazing. For history buffs, there is the winter residence of the former President, a historic seaport, and art, and after a fulfilling and busy sightseeing the coast and the beaches awaits you. 

If you are into water sports, there is nothing better than the Key West!

The Light house Key West: Itinerary 2 days
The Light house Key West: Itinerary 2 days

Best way to see Key West in a day: As we mentioned, the Old Trolley Tour is a great way to explore all of these prime attractions and more. You can stop at any spot as per your personal preference, hang out and take photos! Grab your tickets here!

Here is what you must discover on day 1 of your Key West Itinerary 2 days.

Visit the Key West Cemetery for a quirky start to the day. Covering about 19 acres, the cemetery opened in 1847 and about 100,000 are buried here. It is located in the old town, and you can also opt for free walking tours to hear all the quirky stories about this place. 

Located at the Truman Annex is the former winter residence of US President Harry Truman also known as the Truman Little White House. It is a presidential museum in Florida, and you will find that many pieces of furniture are still in place. You can grab tickets here for the house/museum tour

A short walk from this historic house is the Mallory Square and the Historic Seaport. This square is also best visited in the evening when you can soak in sunsets and enjoy street celebrations. 

In the vicinity, you can also explore the Key West Shipwreck Treasure Museum, Key West Historic Memorial Sculpture Garden, Mel Fisher Maritime Museum, and the Audubon House – dating back to the 1840s. You will also find the tour agency here – Fury Water Adventures – to book your water adventures if you have not already (more details on water sports on day 2 of this itinerary). 

The Key West Aquarium is also located a minute away from Mallory Square. This is the only public aquarium in Key West, and is worth visiting!

The Key West Aquarium in Key West, Florida.
The Key West Aquarium in Key West, Florida.

At the Historic Seaport you can go on sunset cruises or tours for dolphin watching, swimming, or snorkeling to name a few. During your trolley tour, you can soak in the views of the harbourfront and stop for lunch before continuing on. 

Ernest Hemingway lived in Key West for a while and Ernest Hemingway Home was his residence in the 1930s. The home is very well-maintained and showcases the way Hemingway lived there with original architecture and furnishings.

Hemingway House, Key West, Florida, USA
Hemingway House, Key West, Florida, USA

The museum is open all days of the year, and tickets start at $14 USD for adults.One of the coolest things about this museum is that it has (about 57 and counting) cats everywhere in the complex.

From the Hemingway House, walk to the Key West Lighthouse for a nice snap and exploration. This lighthouse dates back to the 1830s (1825 to be exact), and its objective was to assist ships to avoid the hazardous reefs. 

This heritage lighthouse is over 120 years old, and today you can climb the 88 iron steps to the top of the tower for amazing views. There is a museum on site as well. 

Finish the day at Duval Street. Duval Street is the heart of the Downtown area and this is where you will find places to hang out and chill – from bars, restaurants, to nightclubs. 

Also located at Duval Street is the Key West Butterfly and Nature Conservatory which is home to over 60 different species of live butterflies from around the world. 

Duval Street is great for nightlife. You will also find live performing acts to enjoy your day or night. In the downtown area, do visit the historic Sloppy Joe’s, which was a personal favorite of Ernest Hemingway (writer).  

If you are looking for delicious seafood, visit Matt’s Stock Island Kitchen in Key West. 

Day 2 of Key West Itinerary 2 days: Pick a water sports, hit the beach and go on a Key West sunset sail cruise in the evening

Spend your final day by choosing a water activity of your choice. From snorkeling, jet skiing to dolphin watching and lazing at the beach (yea that counts as an activity!), there are a ton of things to do. 

For day 2 of your weekend Key West itinerary, we have included water tours from GetYourGuide. Here we what we recommend for tour combinations for your morning in Key West or a full day adventure

For snorkeling do remember to bring your swimwear and a towel. For the beach it is nice if you have a beach mat with some essentials (like snacks, a book/ipod, etc). 

Beautiful coral reef in the Atlantic Ocean. Located near Key West, Florida, United States.
Beautiful coral reef in the Atlantic Ocean. Located near Key West, Florida, United States.

Snorkeling with breakfast and Mimosas (3 hours)

Kickstart your day 2 in Key West with a 3 hour snorkeling adventure and breakfast. During the cruise, you can soak up epic views of the coastline and snack on a delicious, light breakfast plus mimosas.

At the snorkel site, your guide will provide all the necessary gear and safety briefing. Your instructor will lead you to the impressive coral reef and snorkel as you go in search of colorful marine life. 

In this highly recommended tour, you get to enjoy some of Key West’s 110 species of coral and 500 species of tropical fish. You can book your 3 hour tour with breakfast here

After snorkeling, you may add a 90 minute jet ski adventure

It is a 28-mile tour in which an expert guides through the Key West backcountry, passing remote islands, Mallory Square and the southernmost point in the US. 

Dolphin and Snorkel Tour (3 hours)

You can combine dolphin watching and a snorkeling tour too. In this 3 hour tour, you are taken abroad on a fast catamaran to see Key West dolphins, admitted to the beautiful turquoise waters of the Gulf of Mexico.

After that you will be guided to the Key West wildlife refuge to snorkel in the shallow backcountry waters. The tour guide will be leading the way, so if snorkeling is new to you, no worries as you are in safe hands. 

(This program was put together by conservation agencies, including the National Marine Sanctuary of the National Oceanic and Atmospheric Administration, the National Marine Fisheries Service, the Dolphin Ecology Project, and the Whale and Dolphin Conservation Society). You can book your tour here (3 hours)

You might like this tour: This is a dolphin connection interactive tour

All Inclusive Watersports Adventure (6.5 hours)

If you prefer a one-stop shop for your water sports on day 2 of the Key West itinerary, this is a good one to consider. This 6.50 hour tour takes care of your breakfast, lunch and takes you snorkeling, parasailing, and jet skiing too!

In this tour, you are welcomed aboard on a state-of-the-art catamaran with a lovely breakfast and all you can eat lunch, and countless drinks. You get to snorkel for an hour, and see angelfish, parrotfish, blue tangs and other species. 

You can relax and sunbathe on the spacious deck, and spend the afternoon on jet skis, parasailing, and playing aquatic games. You can book your tour here

Now, if water sports are not your thing, here are some options for you!

We do recommend checking out beaches in the city. Rest Beach and the Smathers Beach are great options. They will be crowded as they are public beaches, but the views are great and worth spending for a few hours here. 

At the Rest Beach you will also find picnic tables to enjoy a nice spread. Another option is Fort Zachary Taylor State Park, where you can check out the Civil War-era fort plus the beach. 

A food tour is also a nice way to experience the city’s culture and cuisine. This 3-hour guided small-group experience takes you to 6 tasting locations, which is perfect for lunch. 

Tastings range from local eateries, tucked-away hidden gems, and a fisherman-owned seafood market. You will be able to truly see, eat how locals do.  

As you stroll the charming side streets and docks, you will also learn about Key West history. 

You’ll also receive a collection of exclusive recipes from your stops and keep them as souvenirs. Book your 3 hour food tour here

When at the southern tip of the country, witnessing horizon sunsets is a must. You can revisit Mallory Square on day 2, or head to the Seaport and hop on an evening cruise with dinner.

Sunset at Key West with sailing boat and bright sky
Sunset at Key West with sailing boat and bright sky

This sunset cruise is done on “The Party Cat”, and it’s for 2 hours, where you get to enjoy a buffet dinner and an open bar. 

After dinner, you can dance the night away or listen to live music on the upper deck. Don’t forget to bring a light scarf, and your camera to soak in the golden hues across the night sky. You can book a sunset cruise with dinner here

Optional day trips for 3 days in Florida Keys Itinerary:

If you have additional time, we recommend the following activities to extend your trip. 

Dry Tortugas National Park: This national park is located west of Key West, and it takes about 2 hours and 15 minutes to get there by ferry. 

Dry Tortugas comprises 7 islands, and coral reefs. You must explore 19th-century Fort Jefferson and hang out at the beaches here. With commute time set aside 4-5 hours at the National Park. 

There are other national parks in Florida that you can visit from Key West, the most popular one worth exploring is the Everglades National park (2.50+ hours by road one way). 

Key Largo: Another day trip or a further road trip option is to visit Key Largo. It takes about 2 to 2.50 hours to get there. Key Largo is home to the world’s second largest artificial reef, and of course you will find beaches and amazing resorts there too. Do visit Key Largo Conch House for delicious seafood and key lime pie. 

Bahia Honda State Park: From Key West, you can also explore the Bahia Honda State Park. It takes about 50 minutes to get there by car. You can also hop on a bus to get there (located at mile marker 37 in the Florida Keys). This State Park features an award-winning beach and historic bridge. 

Bahia Honda State Park in the Florida Keys
Bahia Honda State Park in the Florida Keys – fishing poles in front of old overseas highway bridge on a beautiful sunny day

Seven Mile Bridge and Overseas Highway: If you are looking to do something different and fun in Florida, then drive across the Seven Mile Bridge. It will take you about 4 hours to complete the drive one way, whilst enjoying endless blue water views. 

The bridge has two traveling lanes, and you can enjoy trails next to the highway or stop for a picnic.

Sightseeing Map: 2 day Florida Keys Itinerary

Additional Travel Tips: Key West Itinerary 2 days

Is 2 days enough in Key West?

2 full days or 2 nights in Key West are perfect for city explorers. You can visit the main attractions or landmarks of Key West Historic District and check off the Truman House, Hemingway House, food tour, Key West Cemetery and spend time at the Duval Street. Second day is perfect for indulging in watersports and sailing or time at the beach.

How many days do you need to visit Key West?

If you are into watersports, we recommend at least 3 days in Key West so that you can enjoy snorkeling and eco tours on one day, and set aside another way for sailing/parasailing and dolphin watching, etc without being rushed. 

Of course, one day is essential for exploring the city centre/downtown and the historic district.

How many days do you need to see the Florida Keys?

A minimum of 3 days will be nice. You can drive from Key West to Florida keys.

Is the drive from Miami to Key West worth it?

Yes, absolutely. The road trip from Miami to Key West is only 3.50 hours, but is with it for its views of blue beaches and leafy trees. You get to explore one of the finest cities in the US, and hit the coast at the southernmost point of the country. 

There are awesome places to eat and hang out along the way, including the Florida Keys Brewing Co. located at Islamorada (Old Hwy).

What is the best time to go to Key West?

The best time to visit Key West Florida is from March to May, when the weather is pleasant for water activities and sightseeing. 

Winters are very busy and crowded. Booking hotels, flights and activities will be a pain during this time as it is the busiest time of year to visit Key West. 

Off season months are from June to November. And September and November are the cheapest for hotels and flights. 

Is Key West Expensive?

You can make Key West vacation as expensive as you want, or make it affordable. Flights and accommodation will be pricey if you are visiting in the peak seasons, so if you visit during off season it will be better for the wallet.

City sightseeing doesn’t have to be expensive, you can walk to various attractions, and use one tour (like the Trolley tour). Eat in casual restaurants. For your second day, choose 1-2 water activities (prices start at $50 USD) or just hang out at one of the public beaches to save money.

How to spend half day in Key West?

For 2-4 hours in Key West, you can enjoy a walking tour in the historic district to learn about the city’s past, and check out main attractions.

Read More USA Guides: 

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