A weekend of family fun in Orlando: What it cost and how we booked

Recently, the Frequent Miler team met up in Orlando for an annual face-to-face meeting to talk about plans and goals for Frequent Miler. My family decided to tag along with me and spend a weekend in Orlando. It hadn’t even occurred to me to to write a post about the trip, but quite a few people have asked family-travel related questions lately, so I thought I’d share how we booked it, what my family did, and how we saved some money along the way.

Flights

Cost: 14,100 Southwest Rapid Rewards points + $10.20 round trip per passenger x 3 plus $11.20 round trip for Southwest Companion.

We flew Southwest Airlines to and from Orlando. My wife and I have had a Companion Pass for years. My wife is the Companion Pass holder and last year I changed her companion to one of our sons.

In years past, my wife had listed me as her companion. That made sense when it was just the two of us and when the situation was such that if either of us were cancelling, both of us were cancelling.

However, this trip illustrates why I changed our companion strategy. If my kids got sick and couldn’t travel to Orlando, my wife would have had to have stayed at home with them while I still needed to travel to Orlando. If I was her Companion Pass Companion, a last-minute cancellation of my wife’s ticket would have meant that my ticket would also be cancelled (since the Companion can’t travel without the Companion Pass holder). I’d have needed to buy a last-minute full-fare ticket for myself since I’d have still needed to get to Orlando. Since there are situations like that where my wife and kids might need to cancel but I might still need to travel, it made sense to make one of our sons the Companion. Whereas it is possible that there are times when my wife will have to cancel but I’ll still travel, there aren’t times when my wife would cancel and our son would still travel — so he’s the better choice for a companion ticket.

In terms of buying the tickets, we paid a bit less than 6,500 Rapid Rewards points + $5.60 per passenger for my wife, her mother, and our 4yr old son to fly from Albany, NY to Orlando, FL and just over 7,600 Rapid Rewards points + $5.60 in the other direction. We added our 7yr old son as a Companion to each reservation for just $5.60 (my ticket was covered by Frequent Miler). Since our “home” airport is Albany International Airport, we almost always connect wherever we’re flying. This trip was a rare instance where our flights were nonstop both to and from Orlando! I don’t typically put much value on nonstop vs connecting, but I think I’m beginning to understand why people value it :-). Traveling with kids, it was certainly convenient to have one nonstop flight in both directions.

Rental Car: 30% back on Avis via Capital One Shopping (maybe)

Cost: $273 (hopefully $56.39 coming back)

We most often rent through Hertz or National, booking a midsize vehicle and choosing from the rental company’s choice area based on our status (President’s Circle area with Hertz or Executive Selection with National), but this time we rented through Avis. We needed a minivan for this trip and Avis had the best price of the major chains at $273 all-in for 5 days. That deal potentially got a bit better given that I had gotten a targeted offer for 30% back at Avis via Capital One Shopping.

The base rate on the rental was $187.96, so I expected to get $56.39 back. That sweetened the deal further and cemented booking through Avis.

Unfortunately, the rental hasn’t yet tracked successfully via Capital One Shopping. The purchase shows up in my history as “ineligible”. Capital One Shopping terms do note that travel rewards may track as “ineligible” for 30-90 days. I only booked the trip about 22 days ago and completed it ~10 days ago, so I’m still waiting to see if this tracks. Even if it doesn’t, Avis was our best bet, but I’ll be a lot happier if that $56 comes through.

Car seats: Whoops!

Cost: $40

Based on reader recommendations, we have inflatable booster seats that we typically bring when we travel for rental cars & taxis. This is the one that we use (our affiliate link), though you should certainly do your own investigation to decide what’s right for your family.

Unfortunately, we arrived in Orlando and immediately realized that we’d forgotten to pack our inflatable car seats. Most rental car companies charge $10-$15 per day for a car seat or booster (Avis typically charges $13 per day up to $65 per rental). Given that we were renting for four days, that would have come to $52 for each seat, for a total cost of $104. That seemed nutty to me. Instead, we ended up ordering two booster seats from Target via DoorDash. They cost $20 each for a total of $40 — a savings of $60+ over the cost of renting! I intended to just donate those boosters when we left, but my wife was determined not to throw that money away, so she managed to pack them in our bags for the flights home — and now we’re two booster seats ahead.

Hotel: Hyatt Regency Grand Cypress (cash rate + suite upgrade)

Cost: ~$650 plus food

Most of my hotel stays are award stays where I use points rather than cash. However, cash rates in Orlando were surprisingly low across the board during the second weekend of January. There were a lot of very reasonably-priced hotels in terms of cash rates.

My family loves the Hyatt Regency Grand Cypress Orlando to the point where they weren’t really willing to entertain other options. That was fine because the Hyatt Regency was available for a great cash rate — with a Hyatt Leverage Rate, the first few nights were $135.15 and the last night was $169.15 before tax. That averaged out to about $143.65 per night over the four-night stay before tax. That’s an excellent deal for this hotel, which often costs more than $300 per night.

It’s worth noting that the nightly rate shown at first glance in search results looked like it was higher — see here where it says that the average nightly rate was $193.

That’s because Hyatt displays the room rate including resort fees in search results. I love that feature overall because it makes it far easier to compare hotels and to compare the full cash rate against the award rate (since Hyatt waives resort fees on award stays, but most guests have to pay them on cash rates).

However, what creates admirable transparency for most members makes for a bit of potential confusion for top-tier Hyatt Globalists. That’s because a benefit of Globalist status is waived resort fees on both award stays (which is true for all members) and paid stays (which is only true for Globalists). Thus the ~$193 rate being displayed in search results wasn’t accurate — my rate was ~$143 plus tax per night because the resort fee and resort fee tax are waived for Globalists. I try to always keep this in mind when looking at Hyatt cash prices.

Regardless, rates were cheap enough that I was happier paying cash and earning Hyatt points than I would have been redeeming the  18,000 points per night that Hyatt wanted during my dates.

We ended up charging a couple of meals to the room and I earned around 4,400 World of Hyatt points on the $678.60 in qualifying spend, which seemed like a much better deal than redeeming 72,000 World of Hyatt points for the four-night stay.

One of the reasons we like the Hyatt Regency Grand Cypress is because the resort has a ton of suites. The base suite here is basically two regular connecting rooms where one room is furnished as a living room (with a pull-out sofa and a dining table) and the other room is furnished as a bedroom.

I used a Hyatt Suite Upgrade Award to confirm a suite at the time of booking. As a reminder, Hyatt Suite Upgrade awards are milestone benefits that you can earn starting at 40 elite nights and each suite upgrade award can be used to confirm an upgrade to a suite any time from booking onward for a stay of up to 7 nights. They can be applied on either award stays or paid stays (but you can’t combine a Guest of Honor award or a free night certificate+ a suite upgrade on the same stay). I found a standard suite available at the time of booking and that worked out perfectly for us as we ordered from Uber Eats one night and enjoyed having the dining room table and the extra space of a king-sized bed and a full pull-out sofa was perfect for the family. The ability to confirm a suite at the time of booking was a big part of the reason why we booked this property — having enough space to relax in the room in between activities or to eat dinner in the room is a luxury we really value when traveling with the kids.

In terms of the hotel itself, I won’t be publishing a full Bottom Line Review, but a few things of note:

• The breakfast buffet continues to be very good, with the service continuing to outshine what you’d expect at a domestic Hyatt Regency
• Activities continue to abound. My kids enjoyed the rock climbing wall and pitch ‘n putt course and pickleball (which they picked up at the Hyatt Regency Lost Pines in Austin last fall). One complaint: there are no bathrooms anywhere near the pickleball courts, which is inconvenient, particularly with kids. One piece of advice: get your Pickleball pack from the equipment person next to the rock climbing wall — my wife tells me it was a bit of a hike from there to the courts.
• The resort still has “coin” laundry (I believe you pay with a credit card) near the FedEx Office location, but note it’s only 2 washers and 2 dryers.
• If you can’t get a late checkout, it’s worth noting that they have “guest lounges” (rooms with a shower/sink/toilet where you can shower and change before you leave). Those are up an elevator next to the FedEx Office location.
• You can save on the room service fee by picking up at the restaurant if you want to order in and don’t want to deal with Uber Eats / DoorDash / etc.

Legoland

Cost: ~$300 for four tickets.

My family went to Legoland on a Sunday afternoon and had a great time (I didn’t accompany them this time). My kids are obsessed with everything Lego. We’ve been to Legoland New York, the original Legoland in Billund, Denmark, and Lego Discovery Centers in New York and Tokyo, and this was the second family trip to Legoland Florida.

It’s worth knowing that Legoland Florida is a good drive outside of Orlando. It’s a solid hour from the Hyatt Regency Grand Cypress by car. The good news is that the distance probably helps in keeping manageable crowd sizes. Crowds and lines were very manageable, both on our previous visit and on this one. My family reported that lines only ran around 5 minutes long on this trip (without getting the Legoland equivalent of Disney’s “Lightning Lane” add-on).

In terms of tickets, the best deal I found (by a slim margin) was a “Buy one adult, get one kid free” promo that we found in a marketing flyer while visiting a Lego store in New York. Here’s the link for this deal. It slightly beat the “discounted” prices I found through AAA, AARP, T-Mobile “Member Deals” and a few other sources like that. Two tickets came to $144 plus tax. Putting all four tickets (two adults and two kids) in the same order meant that only one kid rung up for free, so I placed two separate orders.

Disney World

Cost: About a net $600 for four one-day tickets plus $128 for Lightning Lane Multi-Pass

Perhaps ironically, people in my close social circles (friends and family) rarely ever ask me about how to travel more for less, but when they do it is almost always about how to save money going to Disney World. I typically tell people that Disney is one of the few travel experiences that is just hard to do cheaply. It is easier to plan a cheaper trip to Hawaii or Europe or even the Maldives than it is to save money visiting the House of the Mouse.

Greg had recently asked in our Frequent Miler Insiders group for tips about doing Disney during the peak holiday travel period, particularly focused on making the experience better even if it meant adding to the cost. One of the tips he found most valuable was buying a Lightning Lane Multi-pass. If you’re staying off-property, this can only be done 72 hours in advance and must be done at exactly 7am if you want to get the best rides and times (you can do it any time within 72 hours of arrival, but everything I’ve read indicates that the highest-demand rides and times go quickly, and that tracks with my experience — whereas I picked two rides in close proximity and one across the park hoping to set them up in a loop, even at just a minute or two past 7am the only times I could get had my family crisscrossing the park in a way that meant a lot more walking). With this pass, you’ll be able to immediately reserve Lightning Lane for 3 rides (three days in advance of your visit!). Then, each time you get off a ride, you can immediately Lightning Lane the next one. Essentially, you’ll always have your next three rides reserved. The cost of this varies based on demand. For our date, it was an additional $32 per person on top of the (expensive) cost of a single-day ticket. That made an expensive day a little more expensive, but it worked out really well. My family ended up busy all day without spending much time waiting in line. It was a hit and well worth the $32 per person. My wife said she wouldn’t go to Disney again without it.

There are some ways to mitigate costs a biit. Buying rarely-discounted Disney gift cards is one method. Just a couple of weeks ago, GiftCards.com had a sale on Disney Gift Cards, offering them for 10% off. Capital One Shopping very frequently has targeted offers for GiftCards.com, and at the time I had an offer good for 10% back at GiftCards.com. That meant that a $100 Disney Gift Card could be purchased for $90 and I would get $9 back from Capital One Shopping. Even if you only value the Capital One Shopping rewards at 75% of face value (since they can only be redeemed for gift cards through Capital One Shopping), that’s still like an effective total rate of around 16.75% back. I believe it is possible to load $5,000 in Disney Gift Cards to your Disney account at a time, so that could have been a great way to save.

I anticipated using that stack to buy gift cards to pay for meals, merchandise, and parking at Disney World. However, I hadn’t realized that GiftCards.com only carries physical Disney gift cards. I waited too long and didn’t have enough time to wait for them to ship.

The good news is that I stumbled something even better. I clicked around on activity-booking sites in the browser where I have the Capital One Shopping extension installed. A day later, I got a targeted offer of 27% back on Klook. For those unfamiliar, Klook is an activity platform much like Viator, but more popular in Asia. It turns out that Klook sells Disney tickets. While many activity-booking platforms only sell multi-day tickets, Klook even sells single-day tickets. The cost was about $10 more per ticket than I’d have paid directly via Disney, but with 27% back, that still worked out really well. I paid $751 for four single-day tickets and got $203 back via Capital One Shopping. Again, if you only valued the Capital One Shopping cash back at 75% of face value, that’s like getting $152.25 back — nearly the cost of a single day ticket! That was huge. On a multi-day ticket, the savings could be really bananas here.

It’s worth noting that Capital One Shopping email offers are capped at a maximum of $250 back per use, but I’ve never run into that limitation when clicking through the website offers. I was pleased to find that targeted rate on the Capital One Shopping website. I was even more pleased that the offer tracked without issue and as expected — I had half expected that it wouldn’t track.

The day in the park was a huge hit. Everyone had a good time and the kids wore out before the fireworks. For those curious, my kids were 4 and almost 7. They’re both very tall for their ages, so they could go on many/most of the rides. Their top picks:

• Buzz Lightyear’s Space Ranger Spin
• Barnstormer (easy roller coaster)
• Pirates of the Caribbean (I thought this might be scary for them, but they loved it)
• Peter Pan’s Flight
• Monsters, Inc Laugh Floor

They also enjoyed plenty of others, but those were the ones I heard most about. The Seven Dwarfs Mine Train was closed for much of the day and then the wait was too long to get a Lightning Lane reservation, which was a disappointment.

My wife packed a bunch of snacks and water bottles. Disney World allows you to bring in outside food and non-alcoholic drinks. We pretty much always travel with a bag of snacks that the kids like, whether on an hour-long car ride or walking around a Disney park. That helped to save some on food.

I’ve never been a Disney specialist, but it feels like we’re slowly getting the hang of it. My preference would still be for Disney Paris or Tokyo over Orlando from a cost perspective, but this trip went more smoothly than past ones thanks to the Lightning Lane Multi-Pass and a bit more planning.

Bottom line

My family had a fun weekend in Orlando, enjoying the great facilities at the Hyatt Regency Grand Cypress and also one day each at Disney World and Legoland. Hyatt was the easy choice thanks to being able to use a suite upgrade award and cash rates that were even better than they looked at first glance. The Disney experience went a little more smoothly this time around and Legoland remains a bit hit in my family. Overall, this was a successful, easy escape from the cold.

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