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2 days in Key West Itinerary: Perfect Weekend Trip

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Located in the state of Florida is Key West which is the southernmost point in the United States. If you are looking for a weekend of watersports, sandy beaches, and historic sites, then this 2 days in Key West itinerary is perfect for you!

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

Key West Florida Itinerary 2 days
Key West Florida Itinerary 2 days

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Planning a trip to Key West: Travel Tips

Here are some important travel tips and information about Key West

2 day Key West Itinerary

  • Day 1: Arrive in Key West. Explore the Historic District attractions, hang out at the Duval Street
  • Day 2: Snorkel tour OR Snorkel & Dolphin watching, beach time, sunset cruise (Food & culture tour for non-water sports activity) 

Key West is a walkable city, and you can enrich your vacation by adding snorkeling, and sailing adventures. 

Getting to Key West Florida:

Key West is served by the Key West International Airport or EYW. You can arrive there via connections or direct flights from a host of Florida cities, the USA, and other parts of the world. The average flight duration from New York City to Key West is about 3.25 hours. 

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

This 2 day Key West itinerary is also perfect if you are road tripping in Florida. Combine a trip to Miami and Key West and make it a Florida Keys itinerary with stops at tropical national and state parks. Miami to Key West is 3.50 hours (one way) by road, or you can also fly.  

View of Key West in Florida
Florida – Key West

Where to stay in Key West for 2 nights

For a short weekend trip to Key West Florida, we recommend staying at the old town or near it. The Old Town is also known as the Historic District, and from here one can easily walk to various sightseeing attractions, and find cafes and restaurants nearby. 

Recommendation for Key West Hotels 

  • Truman Hotel: Truman Hotel is a boutique hotel located in the heart of Key West, and is one of their popular accommodation options. Attractions and cafes are within a 5 to 6 minute walk. The hotel also offers continental breakfast by poolside. Book your stay here
  • Almond Tree Inn: This Key West hotel is located in the downtown area, and is within walking distance to key attractions such as the Hemingway Home, the Lighthouse, and museums. Although based in the heart of all the action in Key West, it is surprisingly quiet and welcoming. However, no kids are allowed at the property. Check availability and prices here
  • Silver Palms Inn: Silver Palms Inn is also located in the downtown area and is about a 9-minute walk away from the city’s iconic attractions. However, this hotel allows children and also has a large outdoor pool. Check out photos, and availability here
  • If you are looking for an apartment, then Truman @ Duval is a good one to consider. 

In the historic district and nearby, you can easily find vacation rentals, and modest hotels to fit your budget. Search for hotels for your Key West vacation here

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

Once you are at the Old Town and settled in, hop on the sightseeing Trolley to explore the major historical attractions in Key West.

Best way to see Key West in a day: We recommend the Old Town Trolley Tour with 12 stops, which is a perfect way to check off all the attractions on day one of your Key West Itinerary. 

Historic Trolley Tours
Historic Trolley Tours

You can grab your tickets here. It is valid for 1 day. In this convenient tour, you can hop on and hop off at about 12+ stops. 

There are other options for transportation and sightseeing in Key West, other than the trolley tours. You can use the free Duval Loop bus shuttle, or get on the Conch Tour Train Tour. 

Here is what you must explore on day one in Key West. 

Wander the Historic District

The Key West Historic District aka the Old Town of the City of Key West) is about 4000 acres and is filled with over 180 historic buildings. In the 1980s, it was expanded to include more areas such as Mallory Square. Today it is home to 2485 historic buildings. 

Spend some day strolling the lanes, and various quarters or admire the district from the comfort of your Trolley seat before getting down to explore.

Key West Cemetery

At the old town, pay a visit to the Key West Cemetery. This cemetery dates back to 1847 and about 100,000 are buried here. There are free walking tours that you can go on to learn about its history and hear all the quirky stories. Here is a  self guided tour to consider. 

Truman Little White House

Truman Little White House is another stop at the Old town. It is located at the Truman Annex, which was the former winter residence of US President Harry Truman. 

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

Mallory Square and the Historic Seaport

A short walk from the Truman House is the Mallory Square and the Historic Seaport

Mallory Square is a lovely plaza located on the waterfront area in the historic Old Town, facing the Gulf of Mexico. The cruise ship port is adjacent to it.  

Stop here for soaking in water views, or rest and grab a bite to eat, before exploring the next set of attractions. 

From the Mallory Square, you can pick 2-3 sites to visit next. They are all located within walking distance from the waterfront. 

Key West Aquarium
Key West Aquarium

The Key West Aquarium

The Key West Aquarium is about a minute walk away. It is the only public aquarium in Key West, and is worth visiting!

Set aside about 45 minutes to an hour at the aquarium. Tickets start at $17 USD for adults, and you are allowed to explore the complex in a day (consecutive) day period. 

Ernest Hemingway Home

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
Hemingway House

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, wandering everywhere in the complex.

Key West Lighthouse

From the Hemingway House, walk to the Key West Lighthouse for a nice snap and exploration. This lighthouse dates back to 1825 and was originally meant to assist ships to avoid the hazardous reefs. 

Find the perfect 2 days in Key West Itinerary to explore heritage sites, beaches, indulge in water sports, sail, & more for an epic weekend! Lighthouse in Key west
Key West Light house

With a history of over 120 years, a visit to the museum (located on-site) is a must to understand the history of Key West and its surrounding areas. 

If you have time on your hands, climb 88 steps to reach the top of the tower for some amazing views.

Fort Zachary Taylor State Park

Fort Zachary Taylor State Park is another spot worth exploring in Key West. It is a historical and a coastal area located at the southern tip of Key West (at the end of Southard Street on Truman Annex). The site is centered around the Civil War-era fort. 

The entrance fee to the park is $2.50 USD, or $7 for two with a vehicle. 

Key West Butterfly and Nature Conservatory

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

The butterflies are kept inside climate-controlled, and glass-enclosed habitat. Tickets start at $10 to $13 USD. 

Other than butterflies, don’t forget to meet the cutest flamingos – Scarlet and Rhett. 

Southernmost Point of the Continental United States 

2 minute walk from the conservatory is the Southernmost Point of the Continental US, marked by an anchored concrete buoy. Don’t forget to snap a photo here!

Southernmost Point of Continental US in the evening - Key West itinerary
Southernmost Point of Continental US

Additional sightseeing attractions to consider: You can easily swap the recommendations above with these options, all located in the Old Town  – Key West Shipwreck Treasure Museum, Key West Historic Memorial Sculpture Garden, Mel Fisher Maritime Museum, and the Audubon House.

Finish the day at Duval Street

Duval Street is the heart of the Downtown area of Key West. It is known for its active nightlife, and here you will find awesome places to hang out and chill – from bars, restaurants, to nightclubs. 

Here are some restaurant recommendations for the evening, 

  • Visit the historic Sloppy Joe’s, which was a personal favorite of Ernest Hemingway. Enjoy cuisine, and live music
  • Sit down at Red Shoe Island Bistro, and try their Key Lime pie and Pork tenderloins
  • Head to Martin’s for a European dinner experience 
  • For delicious seafood, head to Matt’s Stock Island Kitchen in Key West

Day 2 of Key West Itinerary 2 days: Go snorkeling, dolphin watching, beach time and set sailing on a sunset cruise 

For day 2 in Key West, indulge in water sports of your choice, followed by beach time and a sunset cruise to finish the day. 

From snorkeling, jet skiing to dolphin watching, there are a ton of adventurous things to do in Key West. 

We have shortlisted these tours from GetYourGuide (our trusted tour provider which we have been using for the past 5 + years or so). You can easily book them online. If you prefer booking on the spot (when in Key West) then Fury Water Adventures is a good option to consider.

We have also included non water sports activities below, so keep reading!

Snorkeling with breakfast and Mimosas (3 hours)

This 3 hour snorkeling tour comes with a breakfast option. You have to arrive at the port, and then join the cruise. On broad you will enjoy epic views of the coastline and snack on a delicious, light breakfast plus mimosas.

In this highly recommended tour, you get to enjoy some of Key West’s 110 species of coral and 500 species of tropical fish.

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. 

Snorkeling in Key West
Snorkeling in Key West

You can book your 3 hour tour with breakfast here. For snorkeling do remember to bring your swimwear and a towel. 

Dolphin and Snorkel Tour (3 hours)

Here is another alternative where you can combine a dolphin watching and a snorkeling tour too.

In this 3 hour tour, you are taken on a fast catamaran to see Key West dolphins. 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. You can book your tour here (3 hours)

Other tours: 

Beaches in Key West 

If you are not into watersports, consider spending time at the beach, and joining a food and cultural tour. Popular beaches in the city include South Beach, Rest Beach, Higgs Beach, Simonton Beach and the Smathers Beach are great options. 

You will like Rest Beach for a nice time under the sun for a picnic. You will find picnic tables here. 

Food and culture tour 

A food tour is a great way to experience the city’s culture and cuisine. This 3-hour guided small-group tour takes you to 6 tasting locations. 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.  

You will also get to learn about the history of Key West along the way, and also receive a collection of exclusive recipes from your stops and keep them as souvenirs. Book your 3 hour food tour here

Sunset Cruise & Key West Sunset Celebration

Sunsets are mesmerizing in Key West. The ‘See you at Sunset’ phrase summarizes the spirit of the city. Mallory Square is a popular spot to ring in the evening vibes with celebrations, and hop on a sunset cruise with dinner abroad. 

Sunset Celebrations in Mallory Square
Sunset Celebrations in Mallory Square

The Key West Sunset Celebration takes place at the square. This ‘event’ started in the 1960’s and even today just before sunset, spectators get together to soak in the golden hues over the horizon of the Gulf of Mexico. 

Along with natural beauty, you are surrounded by performers from magicians, jugglers, to local musicians, and food vendors for a spectacular evening!

The  sunset cruise is also a lovely add-on to your evening. The cruise begins on “The Party Cat”, and it lasts for 2 hours, where you get to enjoy a buffet dinner and an open bar. 

After dinner, you are welcomed to the upper deck for live music and dancing. Don’t forget to bring a light scarf, and your camera to capture the gorgeous night sky and the waters.

You can book a sunset cruise with dinner here

Sunset sailing in Key West
Sunset vibes in Key West

Day trips from Key West: 3 days in Florida Keys Itinerary or more

To extend your trip from Key West, you can add visits to national and state parks. 

Key West to Miami Road Trip

If Key West is your entry to Florida, then visiting Miami from there, is recommended. 

The road trip from either way is worth it, as it is filled with blue beaches, and leafy trees. It takes 3.50 hours one way, and you get to explore one of the finest cities in the US. 

There are awesome places to stop along the way. Here are some road trip stops to consider, 

  • Big Pine Key: Perfect for outdoorsy activities like fishing, and admiring the beautiful coastal scenery.
  • Marathon: Key to Marathon is about an hour’s drive away. It is set on 13 islands in the Florida Keys and is known for tropical activities. On the southern edge is the Seven Mile Bridge – Overseas Highway. Although it takes 4 hours to complete the drive, you can surely admire the endless blue water views here. The bridge has two traveling lanes, and you can enjoy trails next to the highway or stop for a picnic.
  • Islamorada: Key West to Islamorada is about less than 2 hours. It is a pretty village in Monroe County. It is known for its coral reefs, dolphins, and the Diving Museum. This spot is perfect for a rest spot. The Florida Keys Brewing Co. located at Islamorada (Old Hwy) is a travelers favorite for light beer, fish tacos, and live music. 
  • Key Largo: You can explore Key Largo as a day trip from Key West, or stop as you drive from Key West to Miami. It takes about 2 to 2.50 hours to get there. Key Largo is home to the world’s second largest artificial reef, beaches, and beautiful resorts. Do visit Key Largo Conch House for delicious seafood and key lime pie.
  • Miami

From Miami, do include a trip to Biscayne National Park. (Key West to Biscayne National Park is 3 hour by road, so a day trip will be too much. But you can visit Biscayne National Park and then proceed to Miami instead). 

Day trips from Key West

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 reach there via public transportation (located at mile marker 37 in the Florida Keys). 

Bridge in Bahia Honda State Park
Bahia Honda State Park

This State Park features an award winning beach and historic bridge. 

Dry Tortugas National Park: Dry Tortugas 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. 

At the park, you can explore 19th-century Fort Jefferson and relax at a beach. When traveling from Key West, set aside 4-5 hours at the National Park. 

Everglades 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). 

Well known for its subtropical wetlands, from coastal mangroves, and marshes, the Everglades is home to hundreds of species of animals such as leatherback turtle, Florida panther and West Indian manatee.

There are tons of easy to challenging hikes that you can embark on at the Everglades. On a day trip you can also explore by enjoying short walks and strolls on well marked boardwalks, go on an airboat tour, or join a Shark Valley Tram tour. National Park fees apply. 

What to pack for a trip to the Florida Keys?

Being a tropical destination, we wanted to share a packing list for your trip,

  • Sunscreen and sunglasses: Regardless of the month of visit, you must carry sunscreen and sunglasses to provide against harmful UV rays. Reapply sunscreen when necessary.
  • Walking Shoes: Since the city is walkable, bring in your best and comfortable walking shoes
  • Beach essentials: Don’t forget flip flops, swimwear, shorts, a hat, and a beach bag 
  • Water shoes
  • Breathable clothes: Carry and wear airy and breathable fabrics. Pack flowy dresses in different colors. 

Sightseeing Map with stops for 2 day Florida Keys Itinerary

Additional Key West Travel Tips: Key West Itinerary 2 days

Is 2 days enough in Key West?

2 days are perfect to explore Key West. You can set aside a day for exploring the iconic city attractions such as Key West Historic District – Truman House, Hemingway House, Key West Cemetery and Duval Street. 

Keep the second day for watersports and sunset sail.

How many days do you need to visit Key West?

2 to 3 days are enough for Key West. With an extra day in the city you can either visit one of the national or state parks on a day tour. Or pick more water sports. 

Other than snorkeling and dolphin watching, you can also go on eco tours, jet skiing, and sailing/parasailing, without being rushed. 

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

A minimum of 3 days is necessary to drive from Key West to Florida keys, and check off the prime attractions, and stop/relax too.

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 sightseeing – it is not too hot. Plus the peak crowds (from December to March) would have disappeared during that time allowing for better hotel and flight deals. 

Winters are very busy and crowded here, and it is the busiest time of year to visit Key West. 

Off season months are from June to November, but summers are hot. September and November are the cheapest for hotels and flights.

Is Key West Expensive?

It is possible to travel to Key West on a budget. Booking during the off season is key to save on flights, hotels and tours. The city is walkable, so you don’t have to spend on renting a car. 

City sightseeing doesn’t have to be expensive either, you can walk to various attractions, admire the coastlines/beaches, and opt for self guided tours. In terms of food, there are tons of casual and affordable food vendors that you can rely on for your meals in Key West.

We hope you found this suggested 2 day Key West itinerary useful in planning your next getaway to Florida!

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