To Key West (and back)

A 48-Hour Getaway to the Most Famous Key

The furthest and most popular Key is filled with a myriad of shops, restaurants, historic sites, attractions, and activities — making it hard to choose what to cram into a two-day getaway. We’re breaking down how we maximized 48 hours in Key West.

Location is key. We chose the Marquesa in the center of Old Town. This quaint hotel is a block from Duval Street, and a short walk from most tourist sites. The picturesque complex is a historic property, originally the James Haskins House built in 1884. Last year, Forbes declared it the Best Boutique Hotel in Key West.

It feels like a hidden oasis, with three pools surrounded by lush tropical gardens. A fine place to sip wine on your private porch. It also has onsite parking (critical for Key West), access to a nearby fitness center, and dining at the celebrated Cafe Marquesa.

Day 1: Jet Skiing, Hemingway House, and Sunset Sail

Day one started with a jet ski trip by Barefoot Billy’s. This 90-minute tour around the island, guided by a knowledgeable local who keeps you moving, is a unique way to sightsee landmarks, like the always-popular Southernmost Point Buoy. The few minutes of free play on the water will add to the adrenaline rush of cruising at 45 miles per hour. The two-person jet ski rental ($160) includes complimentary pickup and drop-off at your hotel.

After refreshing at the Marquesa and stopping for a bite at nearby Clemente’s Trolley Pizzeria, we were ready to cruise the rest of Old Town. Stopping by The Hemingway Home and Museum is a must, whether you’re a literary fan or a cat lover. Arrive by 4 pm for the last guided tour, where you’ll get all the gossip on Hemingway’s time in Key West. Don’t forge to peer into his preserved writing studio where many of his works were born. The friendly (and unbothered) felines throughout are mostly descendants of Hemingway’s six-toed cat Snow White.

We closed out the day with Danger Charters’ two-hour Wind and Wine Sunset Sail ($109 per person). This romantic experience is shared by a small group of about 20 guests, all taken care of by friendly staff who serve a wide range of eight wines paired with delicious charcuterie bites. You’ll leave the dock moderately buzzed and deeper in love with your partner.

If you still have energy, hit the nightlife on Duval Street. We opted for hopping on a Ghosts and Gravestones trolley tour. You’ll hear tales of the haunted places in a town built on burial grounds with two centuries of shipwrecks and untimely deaths. The occasional pedestrian will shout, “You are doomed!” in which you are cued to respond with, “Yes, we are the doomed!” A chilling experience for $38.

Day 2: Snorkeling, Dining, and Key Lime Pie

Let’s hope you didn’t drink too much the night before, because day two starts bright and early with morning snorkeling by Sunset Watersports. This three-hour trip ($40.95 per person) provides gorgeous views through the pristine blue waters of the world’s third-largest living coral reef. An hour-long snorkeling session above coral ecosystems, thriving with colorful fish, is more of a workout than you think. Luckily, you can cool off with complimentary mimosas and beers as you sail back to shore.

In the afternoon, we took refuge from the summer sun in the old Key West Aquarium ($22 adults, $13 children). If you get there by 2:30 pm, you can catch the last stingray and nursery shark feedings of the day, filled with neat facts about marine animals.

If you’re a foodie it’s tough to go wrong in Key West, especially if you like seafood. For lunch, we stumbled upon Rams Head Southernmost. This family-owned establishment has a vast, shaded outdoor patio as well as an air-conditioned indoor dining room. Great stuffed avocado, chicken tacos, and a tender steak au poivre.

For dinner, we selected a beautiful waterfront spot: One Duval Restaurant. We had a great white conch chowder, a mushroom spinach pasta, and a New York Strip (okay, so we love beef ). Bonus: another beautiful sunset.

You can’t leave the island without a slice of Key lime pie. We got ours from Kermit’s Key West Key Lime Shoppe. The founder, Kermit Carpenter, has been selling pies for over 30 years at the original shoppe at 200 Elizabeth Street.

Pick up a slice (or a whole pie) and enjoy it in their charming courtyard. Or eat it on the drive home — which we did, slowly remembering we had to return to our busy city life 150 miles away.

READ MORE: A Weekend in Key West