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.

After the lighthouse, head to Santiago’s Bodega for lunch. This local tapas spot is known for fresh dishes that are perfect for sharing.

Favorites include beef tenderloin, pear and avocado salad, short ribs, and Brussels sprouts. The restaurant has indoor and outdoor seating, and walk-ins are usually fine.

Next, visit the Mel Fisher Maritime Museum to learn about Key West’s famous shipwrecks and treasure hunting. The most famous find is the Nuestra Señora de Atocha, recovered after 17 years of searching.

Highlights include the 1622 Fleet Exhibit with gold, silver, gems, and coins, and the Henrietta Marie Exhibit, which tells the story of a 1700 English slave ship.

GOOD TO KNOW: The museum is open daily from 10 a.m. to 5 p.m. Tickets cost about $17.50 for adults. Plan 30–60 minutes to explore.

After the museum, stop for a photo at the Southernmost Point Buoy, which marks the southernmost point in the continental U.S., just 90 miles from Cuba.

In the evening, head to Mallory Square for the Sunset Celebration. Arrive 45–60 minutes before sunset to secure a good spot.

Street performers, local vendors, and the sunset itself make this a relaxing, fun experience.

A great way to experience the 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.

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.

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

After coffee, do the Mangrove Kayaking Tour with Lazy Dog Adventures. Their Key West Mangrove Kayak Eco Tour winds through mangroves and is described as easy-going and relaxing, with guides who share local nature and wildlife info.

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

The shoreline is natural ground coral rather than imported sand, so walking barefoot can be tough. So, bring water shoes ot flip flops.

There are nature trails and ranger-guided tours of the historic fortifications available. Many people also take photos of the sign that lists distances to places around the world.

One of the most amazing things to do is to end the day with a sunset sail. The top choice is Key West Sunset Sail by Sebago Watersports.

GOOD TO KNOW: The cruise includes appetizers and a full selection of drinks (champagne, wine, full liquor bar, beer, and soft drinks). Cruises depart from the Historic Seaport area.