How To See Key West in 2 Days

Two days in Key West is the perfect opportunity to explore history, beautiful beaches and exciting activities without feeling rushed. A weekend in Key West allows visitors to enjoy the highlights of the island with time to relax. If you are in the city on a port day in Key West, you can still experience incredible sights and flavors. This guide will help you make the most of your time with suggestions for memorable landmarks, outdoor adventures and local dining.

Day One: Exploring Key West’s Landmarks and Outdoor Adventures

Morning: Smathers Beach

Start the morning of your two days in Key West at Smathers Beach. The beach stretches along the Atlantic Ocean and is known for its soft sand and clear water. Visitors can rent paddleboards or kayaks and enjoy calm conditions perfect for beginners. Volleyball courts are available for some friendly competition. During a weekend in Key West, this beach is a great place to relax in the sun or take a refreshing swim. Vendors nearby sell tropical drinks and snacks. On a port day in Key West, many travelers choose to start here before heading into town for sightseeing.

Mid-Morning: Snorkeling With Fury Water Adventures

A trip to the Florida Keys is not complete without seeing the vibrant coral reef. Fury Water Adventures offers an excellent snorkeling trip that departs from the Historic Seaport. Guests can explore colorful coral formations and spot tropical fish, with occasional sightings of sea turtles and stingrays. For those spending two days in Key West, this is a highlight of the trip. After snorkeling, the crew serves complimentary drinks during the relaxing sail back to shore. It is a perfect way to unwind and enjoy the sea breeze on a weekend in Key West or a quick port day in Key West.

Afternoon: Key West Historic Seaport

Spend the afternoon exploring the Key West Historic Seaport. This area is filled with sailboats, fishing charters and local shops that showcase the island’s maritime history. Stop for lunch at Conch Republic Seafood Company. This open-air restaurant serves fresh seafood, conch fritters and delicious cocktails. Live music often plays in the background, creating a laid-back atmosphere that fits the rhythm of two days in Key West. A weekend in Key West is not complete without a walk along the docks, where you can watch fishermen bring in their catch and pelicans gather by the water. Even on a port day in Key West, this part of the island offers a taste of local life and coastal charm.

Late Afternoon: Visit the Southernmost Point

The Southernmost Point Buoy is one of the most iconic landmarks in Key West, marking the southernmost location in the continental United States. Just 90 miles from Cuba, this large concrete buoy replaced a smaller wooden sign in 1983 and has since become a popular photo stop. Visitors spending two days in Key West often line up to capture a picture with this colorful marker. Across the street, The Southernmost House, a beautifully restored Victorian mansion, now operates as a boutique hotel and offers a glimpse into Key West’s Gilded Age past.

Evening: Sunset Celebration at Mallory SquareSM 

No weekend in Key West would be complete without joining the nightly Sunset Celebration at Mallory SquareSM. This lively gathering brings together street performers, musicians, and local artists. Visitors can watch jugglers, acrobats, and magicians perform with the Gulf of Mexico’s sunset as their backdrop. Vendors serve conch fritters, Key lime pie on a stick and fresh coconuts, giving everyone a taste of local flavors. 

Night: Experience Duval Street’s Nightlife

Duval Street buzzes with energy each night and offers more than just bars. Live music pours out from open doorways, and visitors can stop by well-known spots like Sloppy Joe’s Bar, where Ernest Hemingway once spent time, or Capt Tony’s Saloon, which has its own colorful history. For those spending two days in Key West, the Green Parrot is another must-visit, known for live blues music and a laid-back, welcoming crowd. Walking Duval Street during a weekend in Key West is one of the best ways to experience the city’s fun, carefree side.

Day Two: Culture, History and Hidden Gems

Morning: Breakfast at Fisherman’s Cafe

Start your second day with a visit to Fisherman’s Cafe, located in the Key West Historic Seaport. This small but beloved spot is known for its commitment to fresh, local ingredients and Cuban-inspired flavors. 

Mid-Morning: Explore Key West on the Old Town Trolley Tours®

Old Town Trolley Tours® is the easiest and most entertaining way to explore the island’s history and culture. The fully narrated tour features friendly and knowledgeable guides who share stories that bring facts about Key West to life. Unlimited reboarding allows visitors to hop off and on at top locations. During two days in Key West, you can stop at:

• The Ernest Hemingway Home & Museum, where visitors can see Hemingway’s writing studio and meet the famous six-toed cats.
• Harry S. Truman’s Little White House, offering a fascinating look into the president’s time in Key West. Visitors on a port day in Key West will find this tour to be a unique way to learn about the island’s history.
• The Key West Lighthouse and Keeper’s Quarters, where you can climb 88 steps to enjoy panoramic views.

Lunch: Moondog Cafe & Bakery

Moondog Cafe & Bakery is conveniently located next to the Hemingway Home and is a favorite among locals and visitors. Their tropical-inspired dishes include house-made pastries, gourmet sandwiches and wood-fired pizzas. The café’s relaxed patio makes it an excellent stop for families, couples, and solo travelers alike. For those on a weekend in Key West, it is the perfect spot to recharge before an afternoon of more exploring.

Afternoon: Tour the Ernest Hemingway Home & Museum

The Ernest Hemingway Home & Museum is one of the most visited landmarks in Key West. Visitors can explore the Spanish Colonial-style home, filled with original furnishings, personal artifacts, and photos that tell the story of Hemingway’s life. The lush gardens and saltwater pool offer insight into the writer’s Key West lifestyle. Descendants of Hemingway’s six-toed cats still roam the property. 

Late Afternoon: Discover Mel Fisher’s Maritime Museum

The Mel Fisher Maritime Museum is a must-see when visiting for two days in Key West. The museum showcases an extraordinary collection of artifacts recovered from historic shipwrecks, including the legendary Nuestra Señora de Atocha. Visitors can view gold bars, rare coins and delicate jewelry, all part of the treasure pulled from the ocean floor. Detailed exhibits explain the process of underwater archaeology and the challenges faced by Mel Fisher and his team during their years-long search. Anyone spending a weekend in Key West or enjoying a port day in Key West will appreciate learning how treasure hunting is deeply tied to the island’s maritime heritage. The museum also hosts rotating exhibits on maritime history and pirate legends, making it a rich educational stop for visitors of all ages.

Evening: Dinner at Nine One Five

After a full day exploring Key West attractions, Nine One Five offers the perfect setting for a memorable meal. Set in a charming Victorian home on Duval Street, this restaurant serves fresh seafood, house-made pasta and creative small plates. The menu features highlights like a crispy pork belly with pineapple salsa and Key West pink shrimp linguine. Guests can dine indoors or relax on the balcony, taking in the lively atmosphere of Duval Street. For visitors making the most of a weekend in Key West or a port day in Key West, this dining experience pairs excellent food with a welcoming ambiance.

Night: Experience the Ghosts & Gravestones® Frightseeing® Tour

End your two days in Key West with an unforgettable experience aboard the Ghosts & Gravestones® Tour. This nighttime adventure explores the island’s most haunted locations, with chilling stories about restless spirits and unexplained encounters. Stops often include the Key West Cemetery and the haunted Porter House. Guides combine historical knowledge with eerie tales, bringing Key West’s darker past to life.

Closing

A weekend in Key West or a port day in Key West offers a unique blend of outdoor activities, cultural landmarks and fun local experiences. From snorkeling at the reef to dining at Nine One Five and exploring maritime treasures at the Mel Fisher Maritime Museum, there is no shortage of things to do. Finishing your adventure with a Ghosts & Gravestones® Frightseeing® Tour adds a memorable twist. Old Town Trolley Tours® is the best way to navigate the island easily, with friendly and knowledgeable guides sharing stories about Key West’s past. Unlimited reboarding makes it simple to explore top sites and discover hidden gems during two days in Key West.

FAQs

What is the best time of year to visit Key West?

The best time to plan two days in Key West is between December and May. During these months, the weather is warm and pleasant, making it ideal for beach days, water sports, and sightseeing. This period also brings exciting local festivals and events, like the Conch Republic Days and the Key West Food & Wine Festival. If you are planning a weekend in Key West or a port day in Key West, this season offers the most lively atmosphere and beautiful weather.

Is it possible to see Key West in two days?

Yes, two days in Key West is enough time to visit major landmarks, enjoy delicious local dining and experience the island’s famous Sunset Celebrations. The key is to plan wisely. For visitors with limited time, Old Town Trolley Tours® makes it easy to reach top Key West attractions without hassle. Whether visiting the Hemingway Home, snorkeling on the reef or strolling along Duval Street, two days can feel full and rewarding.

Are the attractions in this itinerary open year-round?

Most Key West attractions are open throughout the year, including the Mel Fisher Maritime Museum, Key West Lighthouse, and the Truman Little White House. The only exceptions are occasional holiday closures or special event adjustments. If you plan a weekend in Key West or have a port day in Key West, it is always a good idea to double-check operating hours, especially for seasonal tours or events.

What is the best way to get around Key West without a car?

Getting around during a weekend in Key West or a port day in Key West is easy. Old Town Trolley Tours® is the most convenient option with multiple stops and unlimited reboarding. For shorter distances, walking or renting a bike is a great way to enjoy the scenery and explore at your own pace.

Is Old Town Trolley Tours® included in any Key West attraction passes?

Old Town Trolley Tours® is part of several combination passes that include popular Key West attractions. These passes are perfect for visitors spending two days in Key West who want to maximize their itinerary. Booking in advance can often save time and allow for easy access to the best tours and experiences.

Are there family-friendly activities in Key West?

Absolutely! Families spending two days in Key West can visit places like the Key West Aquarium and the Butterfly & Nature Conservatory or take a glass-bottom boat tour. These experiences are fun for kids and adults alike and are easy to include in any port day in Key West.

Can you recommend unique souvenirs to bring home from Key West?

Visitors often bring back Cuban cigars, Key lime pie treats or locally made art from shops around Mallory SquareSM. If you are spending a weekend in Key West, plan to stop by the Historic Seaport and Duval Street for memorable and locally crafted items. Locally made items are more genuine to Key West than traditional souvenirs.