Perfect 2 Days in Key West (10 Things You Shouldn’t Miss)

Key West is small—only about 4 miles long and 2 miles wide—but there’s plenty to see in a weekend. In 2 days, you can hit the top sights, grab good food, and even squeeze in some water activities. This guide shows you 10 things you shouldn’t miss, where to eat, and practical tips for getting around so you can make the most of your short stay without wasting time.

Old Town is easy to explore on foot or by bike. Biking is often the fastest way to see multiple spots in one day, and there are plenty of rental shops. Some hotels even offer complimentary bikes for guests.

The Hop-On Hop-Off Trolley and Conch Train are convenient ways to visit popular stops like Mallory Square, the Hemingway House, and the Southernmost Point — especially if you want a break from walking or biking.

Choosing the right hotel makes a big difference in Key West. Most visitors prefer to stay in Old Town, where you can walk or bike everywhere. All the places below are our top choices, and always have high ratings for comfort, service, and location.

The Capitana Key West – A modern waterfront resort with a relaxed, boutique feel. It has a pool, small private beach, and a hot tub—plus free parking, which is rare in Key West. Rooms are spacious, and many have balconies with ocean views.

H2O Suites – Adults Only – This luxury, adults-only hotel is perfect for a quiet getaway. It offers all-suite rooms, and some come with private plunge pools. There’s also a rooftop pool and bar. Excellent service and spotless rooms make it one of the best options in town.

The Reach Key West, Curio Collection by Hilton – An upscale resort with its own private beach, oceanfront pool, and on-site dining. Rooms are stylish, and the property feels private while still being close to the main attractions.

Eden House – A great mid-range choice with a friendly, tropical vibe. It has lush gardens, a pool, and hammocks for relaxing. Many rooms have porches or balconies.

Casa Marina Key West, Curio Collection by Hilton – A Key West classic. It offers a long stretch of private beach, two oceanfront pools, and a spa. The rooms are large and comfortable, and the sunsets here are beautiful.

PRO TIP: Book early—especially for winter and spring. Prices rise fast, and smaller boutique hotels often sell out months in advance.

I’ve included a map of Key West showing all the spots in this itinerary. It makes it easy to plan your days, see what’s nearby, and figure out the best order to visit everything.

Start your day at the Key West Lighthouse. Climb the 88 steps to the top for panoramic views of Old Town and the harbor.

Take time to explore the Keeper’s Quarters museum, where you’ll see antique furnishings, navigational tools, maps, and vintage photos showing how lighthouse keepers lived.

The lighthouse was originally built in 1825 and rebuilt in 1848 to guide ships past the coral reefs surrounding the island.

GOOD TO KNOW: Plan about an hour to an hour and a half here. Admission is around $15 for adults.

I have been to Santiago’s Bodega numerous times and always had a wonderful tapas dinner. Every dish is fresh and tasty, and there are so many choices.

My recommendation is to try beef tenderloin, pear and avocado salad, roman meatballs, short ribs, and brussels sprouts. However, you really can’t go wrong with any other choices. Everything is delicious!

Mel Fisher Maritime Museum is one of a kind place that you cannot skip on your first visit to Key West! It is a fascinating place!

“Today’s the day” was Mel Fisher’s mantra and the day was July 20, 1985, when, after 17 years of searching, Mel Fisher and his crew recovered Nuestra Señora de Atocha vessel, which contained millions worth of buried treasure, from the ocean floor just offshore from Key West.

On September 4, 1622, 28 galleon ships left Havana en route to Spain.

Aboard these ships were silver from Peru and Mexico, gold and emeralds from Colombia, pearls from Venezuela, and so much more. The very next day, the fleet was overtaken by a hurricane and eight of these ships ended up on the bottom of the ocean floor.

The most widely known vessel of a fleet of ships that sank in a hurricane was Nuestra Señora de Atocha. At the time of her sinking, Nuestra Señora de Atocha was heavily laden with copper, silver, gold, tobacco, gems, and indigo from Spanish ports at Cartagena and Porto Bello in New Granada (present-day Colombia and Panama, and Havana, bound for Spain. It was a heavily armed Spanish galleon that served as the almirante (rear guard) for the Spanish fleet. It would trail behind the other ships in the flota to prevent an attack from the rear.

Mel Fisher Maritime Museum has several exhibits. No doubt, the 1622 Fleet Exhibit is where you should start. You will see the buried treasures acquired from the Nuestra Senora de Atocha and the Santa Margarita. There are hundreds of artifacts on display that include gold and silver bars, gems, jewelry, coins, and many more.

Another exhibit that you should not skip is Henrietta Marie Exhibit. At Mel Fisher’s Maritime Museum, the Henrietta Marie Exhibit tells the story of an English merchant slave ship that sunk off the coast of Key West in 1700 shortly after selling 190 captive Africans in Jamaica. Discovered by Mel Fisher’s dive time in 1972, the exhibit displays artifacts and information about Henrietta Marie, the Transatlantic slave trade, and Key West’s African Cemetery.

The Southernmost Point Buoy, located at the corner of South Street and Whitehead Street, is an anchored concrete buoy and it marks the southernmost point in the continental United States, the lowest latitude land of contiguous North American states.

Taking a commemorative photo with the Southernmost Point Buoy is a must!

Mallory Square is famous for its fun shopping, great places to eat, fun street performers, and above all it is known for its Sunset Celebration.

It is a perfect spot to take a leisurely stroll, and have a drink while watching the sunset. Life can’t be any easier.

A great way to experience the lively nightlife in Key West is to do a Key West Pub Crawl.

It is a 2.5-hour guided pub crawl during which you will visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street.

The tour includes a domestic beer or mixed drink at each of the five locations, plus you will get a t-shirt to commemorate the event.

If you are up to the crazy and rowdy atmosphere, then venture out on your own.

The most popular establishment includes the famous Sloppy Joe’s Bar well-known for hosting thousands of famous patrons through the years, the most celebrated being Ernest Hemingway.

Another place is Flying Monkey’s, which is famous for its frozen drinks.

Next, put The Rum Bar on your list. It is known for its rum of course, but you need to try a mojito or a painkiller here!

Finally, check out The Smallest Bar in Key West. It is a tiny place, and here you need to try their rum run.

Do an early morning coffee run to Cuban Coffee Queen. Hands down, it is the best coffee you will ever have. It is rich, creamy, and smooth. And then, try out their Cuban burrito, or one of the Cuban sandwiches. Jeez, just writing about it, makes me want to book a flight back!

There are three locations. However, I always bike to the original Cuban Coffee Queen! located at Waterfront, 284 Margaret Street. It is open daily, 6:30 am – 7 pm.

Key West Mangrove Kayak Eco Tour run by Lazy Dog Adventures is great! And, what an incredible way to start off your day.

First off, it is an easy-going and relaxing kayak tour winding through the mangroves. The guides are knowledgeable and entertaining. You will learn about this unique coastal environment and hopefully spot some wildlife.

Departure Location: 5114 Overseas Hwy, Key West, FL 33040, USA (At Lazy Dog Adventures, Hurricane Hole Marina)

Fort Zachary Taylor Beach is my favorite beach in Key West. It is the best place if you are looking for some solitude, to snorkel, or sunbathe. It is like a hidden gem in Key West!

What I like about Fort Zachary Taylor beach is its natural shoreline, which is composed of ground coral instead of imported sand. However, it is tough to walk barefoot on it, so make sure to pack water shoes or flip-flops to protect your feet!

If you like snorkeling then Fort Zachary Taylor Beach is a great place to snorkel.

Also, you can stroll or bike along some beautiful nature trails at Fort Zachary beach. In addition, you can take ranger-guided tours of historic Fort Zachary, which explore the Civil War-era fortifications.

A lot of people come to Fort Zachary State Beach to take photos of the sign that has the distances to different places around the world. So, do not miss it and snap a couple of pictures as well.

One of the most amazing things to do is to end the day with a sunset sail.  

My top choice is Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres operated by Sebago Watersports. It is top-notch! And, they do an awesome job!

Seriously, nothing beats watching a sunset aboard a 70-foot catamaran. To top it off, the appetizers are great, plus there is champagne, wine, a full liquor bar, ice-cold beer, and soft drinks (all included).