The wife and I with the youngest just got back after 5 days on a Disney Cruise – on the Disney Dream to Bermuda. They seem to have a lot of cruise liners, and with this, lots of different places they go. Given the fact that I live 3 hours from NYC and had a 3 year old, I didn’t like the idea of flying somewhere to get on a boat. More on that later.

Before the trip

My wife used a travel agent, who gets paid something by Disney to do this. I also put $250 down on my next cruise, while on the trip, to get 10% off the next one I book within 24 months. So I think that’s what the travel agent is paid. We had some issues with the process, and the travel agent people were nice, but mostly was “call Disney”. The one real problem here was it was an October cruise out of NYC for a Halloween cruise – going to Bermuda. The only thing the wife wanted to do was go to the beach there on the excursion. Wasn’t going to happen with the temperatures in the low 60s and windy.

She had to stay up until midnight, then things opened up for the excursions. Because we are first time cruisers, we are at the bottom of the list, and the ONLY thing open we could do with a 3 year old was the glass bottom boat trip for one hour and 45 mins for $200. I didn’t know this when I paid $4200 for the cruise. We thought we could do what we wanted – no – these things fill up by those on the cruise before. And, it might again.

I was also prepared for my youngest to go into a daycare situation a decent amount to play, and the adults could do things like wine tasting, go to shows, and the wife could lay on the deck by the pool. Figured we could take junior to the pool. None of the “things to do” like win tasting were even open to us – all of those things booked up too. Quickly, I became frustrated. Then, you realize those items are also upsells of perhaps $100 an event for a couple.

Well, everything I thought this was going to be – changed. But, read through the whole thing. I believe this will give everyone a good idea of what to expect, the pros and the cons, and learn from our mistakes. Overall, it was a really good experience that has me wanting to go on more cruises. However, if you are going to break the seal on a cruise, do a shorter one to get the lessons learned so you can get into the higher tier.

The night before

So the night before, I drove the family into the NYC area, stayed across the street from the Meadowlands in north Jersey. That was pretty smooth, but the problem then was the drive the next day. I had to drive to NYC. We had missed the booking window for the Disney parking lot (our fault), and I was stressed about the parking. My brother is a savant with travel, cruises, etc and pointed me to a parking lot for about $180 for the 5 days. The main issue was – do NOT use Waze when in NYC. I was about to make a left at the street they told me (42nd street), and suddenly it flipped the script and said make a right. It was a 5 lane road, and zero hope of ever thinking about getting over. So that stressed me – then I missed the turn at 56th (and 12th) to get to the 58th street parking garage, and went way up the highway. STRESS!! Eventually, we parked. I believe I invented curse words when I missed that turn. Good thing we left WAY in advance. There was to not be sitting in the car and waiting – you have to hand your keys over to the parking attendant at the garage.

We then had to take all of the luggage from the parking garage to the boat, which, by my estimates, was about a mile to 1.5 miles. If you are not in good shape or are up there in years, this is a no go. Because we had the 3 year old in an umbrella stroller – dad (me) had two giant suitcases I was wheeling. Mom had his suitcase and his carry on around the stroller arms, and a backpack filled to the brim on her back. You NEED luggage with wheels, this is not an option at this point in your life.

We get there to the port, and don’t know what to do. We never got a Disney package we were supposed to get that had luggage tags, and presumably, a lot of directions that we needed to do. The staff taking our bags was helpful, and I gave him $5. I have NO idea how to tip for this stuff, so I will give a few tips here.

Once in there, we had a boarding time of 12:30, but we parked the car at 11:30 and got there around noon. Not an issue – they waved us through, as we spent the next 30 mins or so in line and finally started walking onto the boat at 12:30.

Whew. The BIGGEST stressors I had with the whole trip were driving into and out of NYC, and having all of those bags. I had WANTED to try and do some sort of car service or Uber, but with the 3 year old, and needing a car seat, the wife and I threw up our hands not knowing what to do. Certainly, people with children take taxis in NYC? IF I had to do it over again, I’d try and find a place I can park at for 5 days, then take a car service to and from the drop off. The parking/tips were like $190. Certainly a car service there and back could be a little more, but worth not having to drag your child across 8 lanes of traffic to cross over with 30 tons of luggage. Definitely take more time than I did to figure out how to get to NYC from a nearby hotel.

Day 1

We got on the boat at 12:30, and they didn’t take off until like 4:30-5:00. Meaning, you have all of day 1 to enjoy the cruise amenities. Had no idea. Figured you got there and the boat left, so you were just dropping off your luggage and going to dinner. With this, there was some exploration of the ship.

Of note, the boat was taking off at 4 on the schedule, and by 3, the luggage was not yet brought to my room and we were getting nervous. I talked with our cabin guy Pat, and he told me they get everything on the ship first, then it can be until 6PM that it takes until all of the luggage get to the rooms. Luckily, by 4 we had it.

We went around a bit looking at things. Remember, I have a 3 year old, so this next section is important. I didn’t know this.

There are two types of childcare. One is for potty trained 100%, the other is for not potty trained 100%. When I booked this, I was hoping my kid was fully potty trained by now. My boy is 90% of the way there, and with this, he was in the 3 and under nursery for options. You can only use at most 10 hours total for the trip for this, and it costs extra (not a lot). I think we used 6 hours. This is to avoid people showing up on the ship, dumping their kids off, and leaving them there for the whole trip. The “potty trained” daycare is more like a really cool giant plays pace with things to do. The kids disappear there and love playing there. THIS is when mommy and daddy can do things like wine tasting.

My kid still naps, so the first day was some exploring, then getting him down for a nap a bit. This also kind of cut into our ability to do virtually anything early afternoon. Additionally – there were three main forms of visual entertainment on the ship – movies in a giant movie theatre, live shows in another big theatre, and a big screen playing things in the center of the ship, top deck, outdoors. Almost all of this stuff was 2 hours long, and my boy don’t sit still for 5 minutes. I’d say this Halloween cruise is probably best for 5+ who do not mind colder cruises.

We got back to the room – stayed in a state room with ocean view. MUCH bigger than I thought it would be, so that was a bonus. For some reason, women feel the need to nest here and decorate doors. Decoration is not in my DNA. Still – it makes it feel a little like a temporary home.

Also – we had some issues booking the nursery before hand. A big thing my wife wanted to do was having him meet characters. Uggh. OK – but she didn’t know where Mickey would be, when, on what day, so we didn’t book any nursery until there. Surprise, day 1 was booked up.

You then have an eating time, early or late, and there are three different restaurants to eat in. We think there’s an upscale one that charges more, but we stayed with the meal plan given. The early is at 5:45, and with this, anything that starts at 6 or 6:30 was out. Given his normal bedtime is 7:30 to 8, my 3 year old would have trouble staying up for anything that started at 8. But, the other option then I guess is a 7:15 or so dinner, and with that, we would not have been done until 8:30. So I think 5:45 was ok. Again – a child 5+ might have been better suited for this with staying up later.

But they also had a space up on the top deck (11) that was where they had pizza, cheeseburgers, hot dogs, fries, and sandwiches almost 24×7. So right after we got on there, we headed for some lunch. Maybe by now it was 1:30 to 2, and I think I had pizza that was sitting there for quite some time. Had a cheeseburger too. The food quality for this when fresh was much better than after it’s been sitting out for even 10 mins.

There are also other dining options called “the cabanas” which are some of the above food – with extensions. Meaning, there were all kinds of cultures on this cruise, and with this, more food options there were dealing with rice and all kinds of other food that I might consider Asian. However, here it was really busy a lot. The pizza/burgers/dogs were like “poolside snacks” and the cabanas had a more complete offering.

For dinner – they assign you to a restaurant and a table, and you have the same servers each night. I left a $20 spot each time we ate dinner there, and $20 when we ate breakfast in the restaurant. Most of the time we were eating breakfast in the cabanas after sleeping in, as the breakfast time in the restaurant was 6:45 and we were sleeping to 7:30 to 8.

One last note here – I paid for 2 connections to the Ferrari internet. I could do just about anything on it other than watch YouTubeTV – which I felt was important to see my Eagles and Phillies. But internet was blazing fast, and I was able to go to sleep with YouTube videos every night.

Day 2

The big problem we had here was we booked daycare from 9-11. And, we ended up showing up at 10. Why? Because the ship’s captain announced about the time change late on day 1, and the wife and I assumed our phones would flip the time for us, automatically. No. You have to go in and change this manually. So when we woke up at 7:30, it was really 8:30. The wife and I wanted 2 hours to get fancy coffee on deck 4 and plan out what to do.

So we pick up junior at 11, and I’m not going to get into the nuance of each day, but he met 4 characters. Each one, you are looking at lines wrapping around the elevator and 30-60 minute lines. With a 3 year old, who can’t sit still, it’s torture. However, his face would light up when the moment came and there’s great pictures with him hugging the characters.

You find that you spend a lot of time waiting in lines for characters or waiting for the elevators. And, half the times the elevator doors opened, it’s packed with people.

Day 3 – BERMUDA!

Well, lessons definitely learned here!!

I THOUGHT we were going on a Disney trip to the private Disney Island. Which is in the Bahamas. We were in Bermuda. So this is what I thought we were going to see.

Nope. Wrong country. The wife did the planning, so this was also a selling point to me. Turns out, no, this isn’t where we were. And – I told my brother about the trip months earlier, so he was insisting we can cancel our glass bottom trip and WALK to the beach. On day 2, the wife and I went to the excursion booth and said we wanted out of the glass bottom thing ($200 cost). They told us, that unfortunately, it’s a 72 hour cancellation period and we could not be refunded. I had in my mind we were walking to this beach. The guy said we can go on a wait list, and only if someone wants to buy it, would we get our money back. A few hours later, we got notice that it was cancelled due to inclement weather.

At this point, mind you, it’s been not really higher than 66 degrees, and the pool was mobbed. The wife didn’t want to go to the pool because “it was freezing” and “people soup”. There was an adult pool she found later, and had a drink by it, but didn’t go in. OK – back to Bermuda. It was about 80 degrees and overcast, with sporadic rain the entire time we were there. They had a “horseshoe bay” beach excursion for like $20 per head. You get off the boat and they have buses there to take you to it. But, you get off the boat at like 10:30 and they set sail at 4:30. Anytime you want to get off the boat with that many people, it’s a 30 minute endeavor. We eventually got off at 11:30 or so.

Now, I didn’t want to get off the boat and go into town with a taxi (no child seat) and get lost or unable to get back and we are stranded there. We COULD have just paid a taxi to take us there for like $25. Keep in mind it seems to be a super simple option to do, that I overthought.

Above is more accurate as to what Bermuda looked like. The top right is “snorkel park beach”. Yay! Beach! We can walk there in 5 minutes!

This is what it looked like.

Tourist trap.

When going in there, it cost $75 for 2 chairs for the day. But…inflation I guess….and the lady told me $95 when $75 is clearly on the sign. We go in there, and cannot find two open chairs. One. Great. It is painfully obvious this is a money grab, and many there from the ship didn’t pay for chairs and took them. Pretty crowded. We had no towels. Apparently, they cruise line let you take them, but we didn’t do this. Hot dog and fries at this place was $19. Just no.

The beach itself was interesting – with a cliff to the right where an old fort was. Rocky bottom, so glad I had swim shoes. The water was a little chilly, and we had no sand toys for the kid. Had I been there myself, you can rent snorkel equipment and the turquoise water was beautiful. I would have gone out and snorkled with an underwater camera. But, it was the wife, me, and junior with no equipment. I took the boy out for about 30 minutes in the water, and it started raining.

The beach started clearing, and $95 less for an hour at the beach, we headed back. We stopped at a gift shop, and I saw silver!! I wanted to get a Bermuda 1 oz silver coin – the guy wanted $100!! No way!! So I settled for some Bermuda change for $4 to add to the coin box for junior and me.

Remember – this wasn’t the beach that the excursion was supposed to be to. That was $20 I think per head, and they took you on a bus there and back. This was what us folks who never cruised came up with since we didn’t want to take our chances with a taxi there and back. Remember, no car seats.

The highlight of day 3 for me was going to see Beauty and the Beast. It was one hour and 15 minutes, and a fantastic live show.

Had me a few drinks earlier, could not say no to this view!

Day 4

Day 4 was sailing back, and just only now did we start to feel comfortable knowing where everything was. We did a little shopping when he was in daycare. Got the below to celebrate our 10 year anniversary to put on the mantle.

There was a Disney Vacation Club meet for 30 minutes that if you sat through it, you got a $50 credit. I did. Not for me, as it seemed an entry level 200 point membership was $43,000 and $1600 per year to maintain. This would get you “free” rooms at resorts around the world each year based on how many points you have. They didn’t discuss cruises, but the hint was that they points didn’t stretch as far – meaning you probably needed 300 points to get any real cruise rooms worth it, if not more. There was a booth there on the ship for this, and I tried asking about what it was. The lady pointed me to the 30 minute talk. When someone cannot tell you what something is, in 10-20 seconds, and has you go to a seminar, you know you need to really understand there’s a real pricey product here coming. Look – if I went on a LOT of vacations each year, maybe this would be interesting. All of our vacation time is spent visiting the in laws 4.5 hours away, so not for me. But could be for you.

Side note here is that while shopping, I saw a ring my wife liked. $8000. I looked at a Rolex. $37,000. Not my thing. But it begs the question: who goes on a Disney Cruise and buys a $37,000 watch? Meaning, I think a lot of this type of gift shop was TOO upscale for a majority of the people on the ship.

We tried the “Little Mermaid” movie from 2023 in the theatre, but only maybe 5 others were there, and around 9PM, the kid was done. Time to pack it up.

The pros

Having never been on a cruise, ever, I was apprehensive. I didn’t know what to tip to who. They have an “auto gratuity” with the cabin attendant and your servers – it came out to something like $150 billed directly. You put a credit card on file, and anything you want on the ship, you use your ID and it’s “billed to your room” so there’s no real need for cash much. Like I said, for the dinners/breakfasts at the restaurant, I added an extra $20 in cash. The service is like nothing I have ever seen in my life – absolutely amazing. You never met these people, and within seconds of meeting them you feel a warmness. The first night we needed a booster seat, so every night we showed up and the booster seat was already there.

There was an “all you can drink soda and water” situation, but that machine was on deck 11. I had one sprite. The wife bought these 32 oz cups that were Disney trick or treat cups – which we filled maybe once a day with water. I saw people bringing cases of water, OR you could order a case of water delivered to your room. I think in hindsight, have the case of water billed to your account and get it sent to the room. I could not have lugged the case of water with the luggage from NYC.

There was as much ice cream as you wanted, soft serve. One day, I had a cup of chocolate, the next day, a small cone of strawberry.

As much food as you wanted, you could eat at the hot dog/hamburger/pizza place. I just really was never really hungry on the cruise. Ever. Most of it I think boiled down to eating eggs for breakfast. I never eat breakfast. On the cruise, I’m eating eggs and hash browns at 8:30ish, I didn’t really WANT to eat at 12-1, but figured I’d get ravenous by 2 if not. So I would force a cheesburger down at noonish, with 1-2 tiny slices of pizza. Then, at dinner I’d never be hungry, so never really ate a ton at dinner. The beef I ate for dinner each night was good, with the prime rib the last night being the best. Very tiny portions on sides, but I didn’t really care.

The service was fantastic. The “room ninjas” would clean your place when you left. I left him an extra $40 when I left, but it was the last 2 twenties I had, or else I might have given more.

This was a 5 days cruise (4 really, with the last day being breakfast and getting off by 9-9:30). The first day was maybe a half day. So perhaps this is like 3 full days of a cruise, with a half day to start and a 1/10th of a day to end. This was long enough to “get away”, but short enough to learn a LOT.

When possible, I also used the stairs to burn a few calories.

Also – I got to see the statue of liberty for the first time – however, it was at the time of our first dinner and we had to go down before it was really close to see. When leaving out of the NYC port at 4, it was 5:41 I left to go down and it was perhaps a mile away.

Day 5

Late edit, almost forgot this. We had to leave our luggage out the night before to get loaded for disembarkment. Or, we could have kept our luggage and taken it off ourselves. We had a breakfast first, so many people left their luggage outside the restaurant. Then, it was like a 1 hour process to get off the ship and go through customs. LINES!! Driving OUT of NYC was a little stressful as well, but not on the clock anywhere to be at a certain time, so less stressed.

The cons

Most of what I write here goes into lessons learned, and is a function of me rather than a reflection of the cruise line.

  • The travel agent wasn’t entirely useful. That being said, I’d recommend them for a FIRST TIME cruiser until you can learn your own lessons. We used “Say Magical” vacations and they were super nice, but there wasn’t a lot of bonus material with this. We did get a $75 credit to the account from them, I assume to book with them again.
  • The NYC situation. Not good. That being said, if you are comfortable with the area, more the power to you.
  • a 3 year old. I think he was a challenge and a tough age for this.
  • The food. While the service was fantastic, the food at the restaurants were perhaps average. The bread service was like trying to eat rocks. Hard.
  • Excess costs. I paid $4200 for the three of us for a state room. The room was AWESOME. I just wasn’t expecting to spend perhaps an extra $1000-$1500 in tips, drinks, excursions, etc.
  • While a “Halloween cruise” was cool, it was really too chilly for swimming for the wife. It was 60s and breezy. Not the best time of the year to go out of NYC IF you want beach and sun. I didn’t care about that, but it was a major issue for the wife.

In the future – lessons learned

  • I think the NYC situation would be handled by looking more at a park/fly/ride situation OR flying into Florida at port Canaveral in Orlando and taking the Disney service over directly to taking you to the boat. No real luggage to deal with other than getting on the plane. The drive in and out of NYC completely wiped me out, which of course the wife doesn’t appreciate.
  • a 3 year old is difficult to travel with. He isn’t 100% potty trained. The idea of a child having to go at inopportune times waiting in line for an hour gives me great anxiety. He could not sit still more than 45 minutes for a show/movie. I’d have waited until he was 100% potty trained and could make it through a movie decently. 4.5-5 might be a better age for this. He was a monster at dinner.
  • Budget in the extras. The cruise was $4200. All in, I think with the parking, hotel, gas, tolls – I think I’m in for nearly $6k. Had I understood a lot of this upfront, it would have been a lot less anxiety when going through it. I did get the room free though as part of my Hilton Rewards, so that was nice.
  • Get the bottle water package sent to your room. Suck up the $50. The wife and I are so dehydrated.
  • Take a 7 day cruise from Florida at a warmer time – idea here is to visit the Bahamas private island. This might be a few thousand more, but it took me until perhaps day 3 until I understood the boat and how to even navigate what to do and where things were. We also wanted time by the pool to tucker out the little one, and the wife wanted to catch some sun.
  • Use Disney points on CC. I got Disney’s credit card, and will probably use this for all purchases rather than my Discover. I pay for everythin in credit card to preserve cash, and a few times a month I pay my bill off 100% so I don’t get finance charges. But I did the math and I might be able to get $500 or so perhaps each year in Disney rewards.
  • Take turns. Because the little one is tough, the wife needed me with her, with him 100% of the time. I think on day 3, after we got back from the beach, the wife went to the pool for 90 mins to get a drink. When she got back, I went and got some beers and sat on the top of the boat and took in the scenery. Felt relaxed for the first time in days. I think the totality of time I had alone was maybe 90 mins. With the wife alone, perhaps 4 hours. The hope is that we go when he is older and can play in the kid’s club and the wife and I can have a bit more down time.
  • On day 4, there was what seemed to be 50 mph winds and the ship rocked a lot. I didn’t get seasick but many did. The wife did take sea sickness patches, just in case – so it’s a lesson for many of you. I was….a little concerned with the rocking.
  • On the disembarkment, it’s one of 2 options. Leave your luggage out the night before, go to breakfast, and then they usher you out based on your tags. That was perhaps a one hour event from after breakfast until off the ship. Others did “express” who just took their stuff and got off the boat. With the 3 year old, I had fears of him being hungry and miserable without a breakfast. It might make sense to leave some snacks in the car and do the express get off. The upscale coffee shop was open, so I could have gotten coffees and then headed off the boat. I didn’t want to get stuck in NYC traffic when a laxative effect happened either. So it might make sense to wake up early, get your coffee, let the little ones sleep in, then head off a bit later with the express.

I hope that helps all of you! There were quite a bit of speed bumps. Not everything you see on social media is true – where everyone has this perfect life. The wife and I had moments. The 3 year old was a little monster at times. Life isn’t perfect. Embrace your form of dysfunction, but in the meantime, I hope you got something from this to minimize the speed bumps!