All I can say is proceed with caution. We’ve had some good experiences and some bad. The first trip we took with friends didn’t go that well. We knew what they were like ahead of time so we should have known. They have been known to drink too much and get into arguments. Sure enough, it happened on vacation and we weren’t sure if we would still be friends when we got back home.

Last year we went on vacation with another group of friends. It went well because our friend Cara insisted on planning everything a year in advance. You can pretty much trust someone who is a project manager to plan a good trip. All I had to do was show up.

Fast forward to 2020. This year we are planning a spring break vacation with Cindy and her family. We started talking about it last spring. I wanted a commitment by late summer, but didn’t get one until Thanksgiving. By the time I looked at a trip to Disney for 10 people all the deals were gone and nothing was left in our price range. So I started looking at places to stay outside of Disney.

My friend Cindy wanted me to do all the planning. I have the time, plus I am very detailed, organized, structured, experienced traveler who tirelessly thinks about and searches every option. I had no problem with that. I researched flying vs driving. They were pretty convinced they wanted to drive. Again, I looked at all the options. I even called a place that rented out a 12 passenger van. I researched the driving route. Everything. Then I presented it to them and they said they didn’t like the van idea because it had bench seats which weren’t comfortable. Okay.

Then they wanted to fly again. So I searched all the airlines again. Now the prices were sky high, pun intended. They baited you with an affordable flight but once you wanted to return home you had to add on another $250 if you wanted a good flight. What I mean by good flight is not leaving late at night and getting to our destination the next morning, leaving very early morning, or having 2 layovers.

From our home airport the going rate to fly to Orlando was almost $1,000 per person. I flew to Thailand for less than that price. Insane! We couldn’t fly anywhere out of the state of Wisconsin for much less than that. Yes, I checked. Everyday I checked. We could fly out of Chicago for $750 per person which is still pretty expensive. But we were leaning towards doing that.

We are now less than two months from our trip. I asked Cindy to give me a call and we could sit down at our computers to book a flight together. I just sat down to eat supper with the whole family, nothing short of a miracle, when my phone rang. I didn’t answer the phone because I have the boundary that no one is going to disturb supper with my family. It was Cindy.

By the time I was done eating, Cindy had already booked their flight by phone. Yes, by phone! She told me she was able to find a flight for half the cost and wanted us to do the same. I was like, no way! My husband looked up the company they purchased tickets from. The company had several complaints filed against them with the BBB. Some consumers were calling this company a scam. Sure, they got a cheap flight but they are also taking a big risk. They received their ticket confirmation from a gmail account. Geez!

I was very upset. They couldn’t wait until I was done eating to talk about it? They totally circumvented me in the process after all the work I did. But then I realized something. Our friends are very spontaneous, disorganized, and impulsive whereas I probably ruminate the details more than a serial killer. Honestly, I was so upset and hurt that I didn’t even want to go on vacation with them anymore. We’ve had such a rough start before the trip even started. It all could’ve been prevented if they were more organized. But I already knew this about them.

It took a couple of days to feel better. Last night our family made the decision to drive down to Florida. We want an adventure. We want to do our own thing. We will head out after school on Friday and spend the night in Chicago. From Chicago we will drive to Chattanooga, TN. Then we will spend almost a week in Orlando with a couple days at Disney, a day in Universal, and some down time at the beach. Then we will spend a couple of days in New Orleans before heading back to WI.

Today I spent the morning planning out the rest of the trip and I almost felt happy. I love planning trips. I’m glad we are taking two separate vehicles now. We have the option to do different things. We can be structured and they can be spontaneous and hopefully our worlds don’t collide.

Stay tuned…