What You Should do at Disney’s Old Key West Resort

The grand dame of Disney Vacation Club culture is Disney’s Old Key West Resort, which DVC originally named the Disney Vacation Club Resort. That says it all, really. 

Everything we do today stems from the genesis of this hotel more than 30 years ago. Still, times change, and the program evolves. So, let’s say that you’re at Old Key West now. What should you do?

Go Fishing

When Disney envisioned the DVC program, the perspective of timeshare-style vacations looked much different. Hospitality businesses targeted older traveling couples enjoying their retirements, while Disney also sought to entice younger families.

So, you’ll find a fascinating mix of onsite activities here, some of which appear asymmetrical…but in a good way. For instance, Old Key West is one of the resorts that updated its tennis courts for pickleball play. 

Still, you’ll find a fair share of aquatic activities here, and I’d suggest the obvious one. You’re on vacation, so go fishing! Disney promises a “guided bass-fishing excursion” that is “perfect for amateur anglers and seasoned sportsmen alike.” 

Somehow, I doubt seasoned sportsmen would agree, but I doubt you’re a pro fisher. Instead, you simply want a day on the lake to enjoy the tranquility of Disney. Fishing is perfect for that!

Hang Out at Conch Flats

Several DVC locations offer community halls/centers, and we all have our favorites. Mine are at Disney’s Hilton Head Island Resort and Conch Flats at Old Key West. 

Conch Flats offers the typical assortment of hobbyist games like pool, shuffleboard, foosball, and ping pong. There’s also an arcade in the area if you’re a gamer, and there are some arts and crafts. 

Sometimes, you’ll even notice they’re doing tie-dye shirts here, which is always fun. It’s a great place for your kid(s) to hang out if you’d like some adult time, too. 

Head to Olivia’s 

I’m a loyalist and a longtime owner at Old Key West. As such, I believe in the essentials, and one of them is absolutely a meal at Olivia’s Café.

Located at the Hospitality House across from the hotel lobby, Olivia’s serves legendary fried chicken, seafood, and a wall of memories. Previous DVC members have dined here and left their photos on the walls, creating a living monument to the program itself. 

Whenever you stay at DVC, a cast member welcomes you home. That statement never feels truer than at Olivia’s. 

Play a Round of Golf 

I mean, you can probably see the golf course from your room. If you can’t, you’ll almost assuredly notice it when walking in and out of your building. 

Disney’s Lake Buena Vista Golf Course covers part of the campus. You can book a round on GolfWDW, and then the rest of your traveling party can either join you or watch part of your play from the hotel room!

Rent a Surrey Bike

This one’s delightful. You can watch one second of this video and know that you want to do it.

A handful of DVC resorts offer Surrey Bikes as a rental option. I’m devout in the belief that you’ll discover the best experience at Old Key West. The laid-back vibe and beautiful surroundings make this a bike ride to remember. 

Ride the Boat to Disney Springs

I feel a bit guilty recommending this one, but it’s also one of my favorite things to do at the resort. Old Key West shares a Disney Springs Friendship Boat system with Disney’s Saratoga Springs Resort & Spa.

When you hop on this boat, you’ll enjoy a relaxing 15-minute boat ride with a quick stop at Saratoga Springs. So, you can hop off there if you want to visit another DVC resort while you’re in the area. Otherwise, your boat will take you to Disney’s mecca of shopping and dining.

The reason I feel guilty suggesting this involves what’s hopefully a temporary issue. A lack of rain in Central Florida has led to the disabling of the Disney Springs boat system on some days. It’s the same thing that has shelved the amphicars at The BOATHOUSE. You’ll want to ask at check-in whether the Disney Springs boat is running. 

Swim at the Sand Castle

Whenever the subject of DVC pools comes up, I’m the evangelist for Old Key West. That’s because the pool’s speaker soundtrack has Jimmy Buffett in heavy rotation, which is a positive for me that you might see as a negative. 

Still, we all agree that the sandcastle at the pool here is an unforgettable landmark, as are all the other sandcastle elements on display. The (not so) Hidden Mickey serves as the final tunnel for the accompanying waterslide, which makes the entire experience feel more Disney.

This pool is simply a fun place to spend a couple of hours. It’s the perfect balance after a hectic day at the park.  

Visit the Gurgling Suitcase

One of the most beloved bars in the DVC catalog even comes with a backstory. In case you didn’t know, the theme at this bar is that it’s only 90 miles from Cuba.

So, during the Prohibition Era, Cuba would import pirate whiskey – which just has to taste better – to Key West. Then, Americans would travel to this bar to load up on alcohol, which they would pack in their suitcases. Yes, there’s a reason why the suitcase gurgles!

Anyway, one of the drinks here is beyond legendary. I’m, of course, referencing the Turtle Krawl, an intoxicating mix of rum drinks. Sites like Food.com even post the recipes for this drink!