When I think about our family vacation a couple of months before I came out, I think about the amazing firsts and the wonderful sights and experiences. But I also think about the trials that our marriage went through. We put ourselves in an awkward position at a time when I was in transition limbo. There were bound to be some arguments and misunderstandings.
Prior to the trip, I had a hard time focusing on anything other than the opportunities that I personally was about to experience. We had gone shopping for summer outfits. Picked out all the clothes we would wear every day and night. I had practiced getting my hair and makeup ready. I knew that I had to get more comfortable being out as myself. All these things were very important to me. At the same time, I had to remember that this was a family trip first. We were going to experience a part of the world that we hadn’t seen before. We were all very excited to get the most out of the vacation.
Early trip
We did the best we could for the first part of the trip even though we were hot, exhausted, and inexperienced with international travel. I was stuck in male mode for the flight and the first couple of days. We experienced Rome and hit many of the key touristy spots. We could have easily spent a few extra days, seen more, and reduced the opportunity for conflict. There was not as much value for me to present as I wanted to, especially when this was part of the trip that we were going to be very busy. There was no need to add additional complications. I wonder sometimes though if that is why we struggled more at those times of the trip. I didn’t really want to be the guy in the relationship but I was being forced to be by default. Maybe I was projecting my disappointment.
Boarding the ship
The first chance that I got to really be myself came on day 3 when we boarded the cruise ship. On that first day of the cruise, we started off exploring the ship and then we hit the pool. We knew I wouldn’t be ready at first or have our luggage in our room. So, we planned to take it slow. By this point in my transition, I couldn’t really go topless either as I did start to develop a little. So, a tight compression rash guard would have to do. That night for dinner and for the rest of the evening, I got to be me, the way I wanted to be. I remember taking a long time getting ready. I was so worried that I would give someone a reason to look at me with a funny look. When I finally got myself together and stepped out of the cabin, I was thankful that the hallway was empty. It seemed that every step was so loud in that hallway though, with the clip-clop of my sandals. Then came the elevators, which were not as empty. Those close quarters just invited people to get a closer look which didn’t help my comfort level. I didn’t make any eye contact as we went down the few floors to the dining area. Luckily, it was a short ride.
The First Night

When you sit down to dinner, you are assigned a seat. This will be yours for the rest of the cruise. Unfortunately, you have to give the servers your cruise card which had my wrong name and gender on it. It was a bit of an awkward moment, but the server handled it well. The rest of the meal went fine except for me constantly looking around to see if anyone was staring. When we were done, we continued touring around the ship and made sure we got some good family photos with some sunset shots.
One of the strange parts of a transition, is this phase when you need to switch back and forth between how you present. At the end of that first night, taking all of the makeup and wig off, was hard. It was always hard actually. Just when you are feeling right about yourself. You are happy and comfortable with how you look, you have to undo everything. You are reminded that you are not there yet. Some nights it felt like the journey still had miles to go.
The Second Day
The next day I could be myself for the whole day as it was a sea day. The first thing that I did was go down to customer service to see if they could help me with my cruise card. They did not have the ability to change my name on the card as it had to match my passport. They were able to add my chosen name and gender on the card though which was a great relief. It didn’t always work, as sometimes the servers or bartenders would only look at the name on the physical card instead of the system, but it was better than nothing. There was one meal I can remember where the server not only misnamed but misgendered me a couple of times through the meal. After the 2nd time though, Cathy showed the courage that I couldn’t, and made sure that the server used the correct gender going forward. I’m so thankful to have her on my side.


That second day was a day of many firsts. After lounging on the decks and taking it easy most of the afternoon, we decided to go find a pool. This time, I was ready to stay as myself and get on my swim suit. There is a lot of rearranging that is required to feel comfortable but thankfully the suit also has a small skirt on it to cover up. The first time being myself in a swimsuit in public went very well. The afternoon drinks might have helped with the courage too.
Throughout the day, I would keep running back up to the cabin to use the washroom. It was a little inconvenient, but using the women’s washroom for the first time is one of those challenges that trans women need to overcome at a time that is right for them. It’s an illogical fear but I couldn’t help but think of all of the restrictions in the US and ridiculous reactions you read about. All it takes is one person to say something because they claim they feel unsafe. That fear of being accused is what made it such a challenge for me (and I guess that is what the transphobes are trying to do). That night at dinner though, Cathy mentioned that she was going to use the washroom and I really needed to go too, so I asked if she would mind if I came along. It was a quick decision and a very nerve-racking moment. Just imagine going into an area that you have been told to never go into your whole life. If you go in, there would be serious consequences. And then all of a sudden, you just have to go in. I remember finding the first empty stall I could find, using the washroom, and then Cathy saying from the other side of the door that there’s no one else in here, so you’re all good. It was really uneventful and there was no reason to be worried, but when it was all done, there was so much relief. I used the women’s washroom on the ship a few more times on the trip and even a couple of times on my own. By the end of the trip, I was more comfortable, and it really became less of an issue.
Rest of the trip

The next day, and the rest of the days on the cruise, I would get up in the morning and get ready in male mode to leave the ship. Because my passport hadn’t been changed yet, it was just safer to make sure that I matched my presentation with my documentation. We had some really good days off the ship, seeing so many sights and eating so many amazing foods. Once I got back on the ship though and we prepared for dinner, I got to be me again. We had some good nights on the cruise ship too. Getting all dressed up was so much fun. We would try some interesting drinks and find some activities or shows, and inevitably, find an open table and play cards with our boys – a family vacation tradition for us.
The vacation was memorable in many ways. The food was amazing, and we weren’t afraid to try some new things. Obviously, some of the sights and cities that we explored were better than we could have imagined. But Cathy and I also struggled with our relationships on a few occasions which tainted the overall experience. There were times on those hot days when we were exhausted, and we would say some hurtful things. We learned from these challenges though and ultimately, we are a better couple because of them. Thankfully, when I think back on that vacation, I don’t really think of the tough times, I only think of the good.
4 responses to “First Family Vacation From My Perspective”
This reminds me so much of my first real vacation after coming out. We went to Florida, before it became the dumpster fire it is now. The first time I went to the beach in my swim wear was at night.
Thinking back, maybe a swimsuit at night would have been a bit safer. We briefly considered going to Florida this year for vacation, but then thought better of it.
I am so proud of you. No for me my first major vacation as myself was to universal studios in Florida and one of them was the water park where I had to wear a bathing suit. And I remember how nervous I was and thinking everybody was looking at me. And unfortunately for me too late did I realize no one was looking at me except to see the woman I was and I’m sure it was the same way for you. I so enjoy reading about your journey of self-discovery and on your way to what I call the glory of living your truth.
I remember talking with my therapist about the nerves related to going on a beach. The best advice is that “There’s no point being concerned about what you look like at the beach. No one has time to look at you. They’re too busy thinking that everyone is staring at them too”. I did try to enjoy the moment but it was tough.