Our Walt Disney World Trips Throughout the Years

Tinker Bell is leading the way to help us tell the tale of our wonderful trips to the magical world of Disney!

With fall just a few weeks away and the days getting shorter, I can feel the Walt Disney World nostalgia creeping in. Mama D and I are already talking about planning our next Orlando vacation but we have to pace ourselves and try to focus on our upcoming trip in a couple of weeks. 2018 WDW Resort deals won’t be out until at least October so instead of focusing on future Disney trips, why not this time focus on past trips? How many times have we been to Disney? It’s hard to keep count so I will summarize it for us all on this page. We’ve never been to Disneyland, only to Orlando’s parks but even though Disneyland was the original one, Orlando is so close and convenient, and having 4 parks with so many onsite resort choices, it’s an unbeatable Disney destination.

Our First Visit To Walt Disney World in Orlando, Florida
DD in 1987 in front of the Thunderbird Motel in Treasure Island near Tampa, Florida.

Our first time to WDW was in 1987. I was 16 and Epcot had just opened 3 years before. My best friend Annie lent me a suitcase full of summer clothes, including accessories. She was such a good friend, I miss her. I don’t remember much of that trip except little tiny bits. Mama D and I had a rental car and we stayed a few days in Treasure Island, near St Petersburg and a few days in Orlando. We visited Epcot one day and Magic Kingdom the next. One of my favorite attractions at the time was Space Mountains that I rode 2-3 times in a row, and The Carousel of Progress. There was no FastPass system then and we must have missed many rides because we didn’t want to wait. I vaguely remember 20,000 Leagues Under the Sea but I remember being impressed by the restaurant reservation system on the big screens called WorldKey Information System. This was the most advanced technology of the time. I’m glad they finally announced lots of much needed new projects for EPCOT.

In 2009, after 22 years since my first visit, Dami got the crazy idea to send me to Walt Disney World for his birthday! I don’t think he meant to be alone on his birthday (he’s got such a big heart!), it’s just that it was a super quiet week at my job at the time and it was the perfect time to take a trip but unfortunately Dami’s job required him to stay. It was a little surreal as we usually plan our trips many months in advance and this was a trip that was happening in a couple of days. He booked my flight and hotel for 4 nights for 3 days visit. He drove me to Burlington, Vermont and I flew to Orlando with a transfer in Washington, DC. I arrived late in the evening by taxi at the Residence Inn Lake Buena Vista. 3 day tickets with Park Hopper was $279.03 usd. ($1 can=0.815769) Today the same would costs 371.69 usd ($1cad=0.793159). The full details are her, here and here. (add links)

Third Visit Staying for First Time at Port Orlean Riverside with mama D
DD in our favorite section of the Columbia Harbour House at Disney’s Magic Kingdom in 2011.

My 3rd visit was with Mama D this time, from January 16th to 22nd 2011. We were meeting at our gate in Toronto and poor Mama D’s flight was late but she made it 10 minutes before our departure. We stayed at Port Orlean Riverside in the Magnolia building, room 8927. We used the luggage service with the Magical Express although our suitcases arrived late. On subsequent trips we took our suitcases ourselves for quicker access. Our meals were so large at The Riverside restaurant that we had lots of leftovers to bring back to the room. Everyday we had breakfast in the room with fruits, cereals, milk and juice. We brought lots of snacks from home including oatmeal and cup a soups. I had a portable cup heater for our coffees and teas which was so convenient to have in the mornings and evenings. It was then that we found our now favorite spot to have our packed lunch at the Columbia Harbour House in the Magic Kingdom; there is usually a table for two waiting for us on the second floor facing The Haunted Mansion.

4th trip with second stay at Port Orlean Riverside
Tamu Tamu restaurant at Animal Kingdom is a quiet place away form the park madness.

My 4th trip was in 2013, with Mama D again, from January 13th to 18th. It was a last minute trip that we booked 4 days in advance and we were so excited! We stayed at Port Orlean Riverside again, in room 8253 in the Acadian House building . We pretty much did the same for our meals as the last trip, buying stuff for our breakfast at the Riverside Mill with a quick meal in the parks. On the 16th, the weather was nice enough for a swim! We had lunch for the second time at Seasons in the Land Pavillion at Epcot. The details of the trip are here (link)

A Dream Come True For You And Me
One Man’s Dream is an an amazing Museum about Walt Disney at Hollywood Studios, WDW Orlando.

My 5th trip, again with Mama D was from January 12th to 19th 2014. This time, I flew with a transfer in Montreal where Mama D met me at our gate. This was a much better option.  We stayed in a studio (5061) at Boardwalk with a view of the Spaceship Earth ball and had food delivered at the resort by Garden Grocer. We had an amazing time once again! You can read the details here (link)

20 days of WDW Magic in February 2015

My 6th and 7th trips to WDW were in February 2015 when I rented a condo in Kissimmee for the whole month. Dami spent the first two weeks with me and then he flew back home on the same flight Mama D embarked on to come join me for the second half of the month. This time an annual pass was without question the best option for me. While Dami was with me, we had a rental car that made it convenient to load up on bottled water and non perishables. With Mama D we took the Lynx bus on the corner that brought us to Magic Kingdom. I must have spent at least 12 days at Disney. With both Mama D and Dami I toured the resorts. I brought Dami to Port Orlean Riverside taking the boat taxi from Disney Springs. It was so much fun to be with Dami for his first Disney experience. You can read more about Dami’s impressions of Magic Kingdom, Hollywood Studios, Epcot and one of his favorite ride here.

My 8th trip with Mama D
Mama D is ready to try to beat my score throwing darts, loops and plates!
Mama D was the slow bunny :))

My 8th trip was with Mama D from January 9th to 18th 2016, staying at Floridays in Lake Buena Vista. Staying outside of the World was not the same. We did have a super nice condo but I seem to only remember the condo, the shuttle ride and not WDW.

Our last trip to WDW
What a great time we had with the Memory Maker! We waited in line many times but it was so much worth it, like for this picture with Chip and dale at Magic Kingdom.

My 9th trip and last visit was with Mama D from December 6th to 15th 2016. We split our vacation between WDW and Universal which we visited for the first time. It was our first time visiting Walt Disney World during Holiday season with all the decorations and music. At Disney we stayed at Boardwalk in a One Bedroom Suite, having our grocery delivered from Garden Grocer. It was so far the best trip to Disney and combining it with Universal made it exceptional.

My next trip with Mama D will be my 10th visit!
Mama D and I at Epcot in December 2016

The next trip will be my 10th time! I just can’t wait! It should be pretty awesome as well as we plan to stay on site again and go with the Deluxe Dining Plan at Disney. The Universal Dining Plan is not as interesting so we’ll skip it. We should be using Garden Grocer again, although only at the end of our stay to bring food with us at Universal. Looking back at the pictures we had with Memory Maker at WDW, having pictures at Universal would be pretty awesome as well. I am so grateful for having such a generous mother: Mama D you are the best mother!