Ranking our top 5 family trips ever
The List
This past week, we wrote out down all of the trips our family of 4 has taken over the past 3 years on paper and every member of the family got a chance to vote for their top 5 favorite trips. Largely due to points and miles, this list included places like: The Bahamas, Malta, Austria, Disney World, Arizona, Savannah, and eastern France. However, none of those made the top 5.
After some lively debate (at least as much as a 4 and 7 year old can have!), we landed at these as our Top 5 destinations that we’ve taken as a family:
Disney Cruise
In February 2020 (yes, about 3 weeks before the world shut down!), we went on a 5-night cruise aboard the Disney Wonder. Honestly, it wasn’t just the girls who voted this highly. It was all 4 of us! Courtney and I loved pieces of the cruise ourselves: the food, the entertainment, etc. However, we most loved watching our girls light up like every 8 seconds. The cliche is true: it was magical. The lines for characters were never longer than 12 deep. The Kid’s Club gave us periodic reprieve. The stop at Disney’s Castaway Cay was amazing.
So, how did we make it happen? I mean frugal and Disney cruise rarely go together. However, here’s a few steps we took to make sure we didn’t have to forfeit our Frugal and Free Travelers name to make a Disney cruise happen for our family:
I searched prices weekly at https://disneycruise.disney.go.com/ for close to a year. I had a price range in mind and I didn’t budge from it. So, when a 5-night cruise popped up for 2k ($100 per night, per person, which is insane for a Disney Cruise, where the average price I was seeing was between $200-$300 for an inside stateroom), we jumped on it!
We didn’t care when we would take the cruise and where we would go. This was before our 7-year-old Linden was in elementary school, so we had even more flexibility than we do today. So, we were open to jumping on whatever deal we eventually found, no matter the dates or the departure port. Remember: Follow the deal, not the destination.
We ended up booking a re-positioning cruise from San Juan, Puerto Rico to New Orleans, as the ship was changing departure ports. I routinely see re-positioning cruises priced lower per night than normal “out-and-back” cruises, where you return to your same departure port.
This is a small thing, but for the 2-3 years preceding the cruise, we collected Disney gift cards here and there. We would add one to our Sam’s purchase, at a 5% discount. We would ask for them for birthday or Christmas presents. By the time we cruised, we had collected almost the entire amount of the cruise in gift cards!
Costa Rica
In April 2022, we spent Spring Break in Puerto Viejo in southeastern Costa Rica, close to the Panamanian border. We spent most of our days hiking through the rainforest, playing on black sand beaches or taking dips in the pool at our Airbnb. The open-air house, rainforest-lush property was probably our favorite Airbnb we’ve ever stayed at (which we used Capital One miles to erase most of). We used American miles for 3 of us to fly down and back, for a really reasonable rate (24k miles round-trip), while I used a trip credit from a Covid-canceled flight. I had earned American Airlines Gold status by this point and experienced my first complimentary upgrade of my life (which I of course gave to Courtney!)
The hardest part about the trip? By far it was the rental car process at the San Jose airport as we were required to purchase an exorbitant amount of insurance (if you’re planning to rent a car in Costa Rica, make sure to read up on the rental car insurance laws/regulations first!), as well as the drive from San Jose to Puerto Viejo that GPS said would be 4 hours, but because of construction and accidents, took over 7 hours, rarely traveling over 40 miles per hour!
Despite that, Costa Rica is one of our favorite destinations ever! For your first time, we might recommend flying into the second-largest airport in the country, Liberia, and staying in the northwestern parts of the country and/or driving to the western side of the country after flying into San Jose, rather than the eastern/southern parts!
Switzerland
When it comes to sheer beauty and grandeur, Switzerland comes out on top of places we’ve visited as a family. Courtney and I have traveled to Peru together without the girls, and I definitely think the Andes easily is in the same ballpark as the Alps, but I’m glad I didn’t have to make that hard choice to compare them for this!
We loved the culture, the slower pace compared to other parts of Western Europe, the stunning views that just never stopped, the hiking, and the crystal blue glacier lakes. Our girls love to adventure and hike, so there’s no surprise this was on their Top 5 list.
When it comes to the negatives, the obvious is: Switzerland is EXPENSIVE. To stay frugal, we rarely ate out, but instead cooked in our Airbnbs 90% of the time. And, honestly, the few times that we did eat out, Swiss food just isn’t our jam. So, I guess that’s our other negative! However, we found a steal of an Airbnb for just over $100 a night, and simply used some of our travel budget to pay for it, rather than erasing the purchase with Capital One miles (our stash was low!) We also rarely paid for experiences (except for the occasional cable car!), as so much was available for free (hikes, lakes, etc.)
We used American Express Membership Reward points, transferred to Air Canada, to fly on Swiss Air in business class on the way there and United in economy class on the way back. Note: if you’re trying to find business class availability for families of 4+, we routinely find availability for up to 8 on Swiss Air, as they open up way more business class availability than the average carrier!
Venice
Okay, I was the only one of us 4 who didn’t vote for this one, so it pains me a bit to write this up. However, I have to follow the will of the people. :) I think my main reasons for not putting Venice in the top 5 is a sadness (and, to be honest, maybe a bit of shame) around the current state of the city: the fact that the population of the city is 1/3 of what it was in 1970, the effects of mass tourism, and the effects of the city sinking 1 to 2 mm per year. However, we still chose to go, so I shouldn’t over-think it: Venice is magical. Traversing over most of the 150 canals that run through the city, eating the best gelato we’ve ever tasted, sipping house wine beneath the Rialto Bridge; there’s just no city like it!
We used Hyatt points, transferred from Chase, to stay at the Hyatt Centric Murano (a short ferry ride away from Venice), which included a free water taxi to/from the Venice Airport. We used Avianca LifeMiles transferred from American Express during a transfer bonus to fly business class on Turkish Airlines on the way there and Lufthansa on the way back!
Istanbul
I’m so grateful for our youngest, Merritt, bringing in the 3rd vote to get this amazing city into the Top 5. Of all of our travels, we found the people of Istanbul to be the nicest that we have ever come across, by far! The friendliness, warmness of the people sets this city apart in and of itself. However, we also loved the food, the history, the architecture, and just the sights and sounds of the city.
We stayed at an Airbnb near the Galata Tower that was perfect for our family of 4. We also used Capital One miles to reimburse ourselves for the purchase.
Conclusion
The reality is: for most of these trips, we simply followed the deal, instead of the destination. That was especially true of Istanbul, as it wasn’t in our Top 10 list of places to visit in the world, but we simply followed an amazing business class deal. However, it quickly became one of our favorite cities because we were open to where the deal led us! Compare that to the Disney cruise where we searched for over a year to find the cruise that fit within our budget and we pounced when we found it!
It’s fun to reflect on what trips have been most memorable for us and why as we embark on new adventures in the next 6 months, with destinations like Lisbon, Madeira and Patagonia on the docket!
