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A ’Pirates and Cowboys’ Kind of Park Day: A Walt Disney World Planning Article
Sandy Symianick, PassPorter Guest Contributor

On our last trip to Walt Disney World in December of 2015, we included a few ‘themed’ days as part of our touring plans.

We scheduled a Knights & Princesses Day, A Jedi Day, and a Pirates & Cowboys Day. One of the lovely aspects of a Walt Disney World vacation, is that it lends itself to being a super planner or a limited planner. Either way, you’ll have wonderful time no matter what! Theming a day out of the parks can be a patience saver for those days when crowd forecasts are high.

For our Pirates & Cowboys day, we decided on the following itinerary:

• Pirate Adventure Cruise for the kids at the Grand Floridian Resort
• Touring Adventureland, Frontierland and Liberty Square at the Magic Kingdom
• Dinner at the Hoop-dee-doo Revue

As our first activity of the day was at the Grand Floridian Resort, we decided to start the morning off with a breakfast reservation at 1900 Park Fare at the Grand Floridian Resort and Spa. It’s not very Pirate or Cowboy themed, but it’s a great way to squeeze in some character interaction. Following our visit with Winnie the Pooh, Tigger, Mary Poppins, Alice and the Mad Hatter; it was time to head off to the Pirate Adventure Cruise which we had left as a surprise for the kids.

After filling out a bit of paperwork; the kids were suited up with life vests, and the story telling began. Essentially, the story is that the two cast members are the granddaughters of a mischievous pirate who has buried his treasure somewhere around the Seven Seas Lagoon. They recently discovered a letter and a map that he left for them, and ask the kids if they would like to join them as pirates on their treasure hunt. As this is a kids only cruise, the information from our kids about the cruise and where they went was a bit jumbled. They remembered going to the volcano at the Polynesian resort and seeing a marooned pirate ship on an Island; but getting more details out of the 6 and 4 year old was a bit difficult. They did come back to port with pirate bandannas and necklaces, and mentioned a snack and potty break along the way. The treasure map led them to a treasure chest hidden near the Gasparilla Island Grill at the Grand Floridian Resort. It was very fun to be there to watch the kids’ excitement at seeing the treasure chest and getting their ‘cut’ of the pirate booty!

Pirate Adventure Cruises sail from the Grand Floridian, the Caribbean Beach Resort, the Beach Club, and Port Orleans Riverside; and are offered for children ages 4-12. Kids must be potty-trained. As we were staying at the POP Century Resort, and planned to visit Magic Kingdom for some park touring after the activity, we decided on the tour that starts at the Grand Floridian Resort for ease of navigation with the Walt Disney World Resort Transportation System.

While some might suggest adults getting a spa treatment at Senses Spa at the Grand Floridian Resort, while the kids are off on their adventure, I would advise against this. By the time the kids are boarded onto the boat and you factor in returning back to the docks 15-20 minutes before the end of the cruise to see the treasure unveiling; you only have a bit more than an hour to yourselves. We used that time to go explore the Grand Floridian’s shops and sat in the sun outside the Gasparilla Grill with a cup of coffee. The atmosphere of the Grand Floridian Resort is very relaxing, and we were happy to share some quiet time together sitting on a shaded bench just looking out over the Seven Seas Lagoon.

Following the cruise, it was off to the Magic Kingdom. We caught Tinker Bell on our way into the park during the parade – no line because of the Parade! With the kids all dolled up in Pirate gear, Tinker Bell played the skeptic as to whether or not she should be meeting with Pirates, because of her experiences with Captain Hook and all… The kids managed to convince her that they were in fact only children playing dress-up and then they all got on like old pals.

Then, it was off to Liberty Square to go to the Haunted Mansion, followed by exploring Adventureland. We had Dole whips for lunch (hey, it’s vacation!), a ride on the Magic Carpets, a trip to the Walt Disney's Enchanted Tiki Room, and a meltdown by our daughter over Mickey Bars that lasted a good 45 minutes (which ate up our time to ride Pirates of the Caribbean ironically). We ended with Splash Mountain, which was a nice way to finish our touring. I had been hoping to make it to Tom Sawyer island, but the crowds were quite large and it took us much longer than we had hoped just to maneuver through the hoards.

Next up was the Hoop-dee-doo Revue! We got in line for the Ferry over to Fort Wilderness, and changed the kids into their Western digs while we waited for the boat to arrive. When Disney suggests you leave an hour or more for transportation – listen. We arrived at dinner with just enough time to go to the restrooms and then be seated. The PhotoPass photographers that are there to take a commemorative photo had already packed up, but were nice enough to still take a photo of us with a little bit of smiling and two little, excited cow folks asking nicely. The food and the show are wonderful. We were seated right beside the pianist and the banjo player, and had lovely conversations with them. Our server was awesome, and full of western puns. The sangria was yummy, and our four-year old daughter who is a picky eater, asked for two helpings of the fried chicken! The show is very interactive, and the main characters walk all around Pioneer Hall throughout the course of the meal, which gets all the guests very involved.

We took our time leaving the restaurant and Fort Wilderness knowing that the first round of Ferries would be very crowded. We found a play structure close to the docks for the kids while we waited for the ferry queue to peter out, and then hopped the bus back to POP Century. All in all, a delightful, jammed packed, themed day!

Other suggestions for Pirate theming:
• Dress up in Pirate gear – Dress-up the kids in their favourite Jake or Zarina gear!
• Make a reservation for the Pirates League in Adventureland -
• Attend the Jack Sparrow pirate tutorial in Adventureland.
• Play the interactive A Pirate's Adventure - Treasures of the Seven Seas that runs through Adventureland -
• Take the Pirates & Pals Fireworks Voyage and meet Captain Hook, Smee and Peter Pan

Other suggestions for Cowboy theming:
• Throw some Cowboy flair into your outfit, like wearing a checked shirt
• Visit Woody and Jessie
• Make a trip out to Tom Sawyer’s island
• Catch the Frontierland Hoe-down in front of Country Bears Jamboree
• Attend Mickey’s Backyard Barbeque

Other links to activities mentioned:

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About the Author: Sandy caught the Disney bug back in 2014 while visiting Walt Disney World on her family’s first vacation there.  Mom to Jakob (7), Evey (4) and wife to Thomas (~); she’s constantly researching for the family’s next trip to a Disney Resort, especially since becoming Disney Vacation Club Members!  She loves to talk about Walt Disney World to anyone who will listen, and regularly gets asked by friends and family to help them with their trip planning.

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