I first visited Iceland ten years ago as a solo traveler, taking advantage of Iceland Air’s generous stopover policy that allows up to seven days in the country en route to another destination. That visit was brief—just two days—but long enough to explore parts of the Golden Circle and soak in the Blue Lagoon. I found Iceland stunning and always hoped to return.
This time, it was a completely different experience. My wife hadn’t joined me on the first trip due to grad school, and we weren’t yet parents, so now—with our kids in tow—it felt like seeing the country through fresh eyes. Much of our itinerary included places I hadn’t visited before, and we waited until our youngest was steady on his feet before planning a trip filled with hikes and outdoor adventures, without relying on a stroller.
As with many of our travels, we were drawn to Iceland for its natural beauty, mountainous terrain, and abundance of kid-friendly outdoor activities. It’s a magical destination that offers all of that and more. As our children grow and progress in early elementary school, we’re shaping our travels to be both fun and educational. Our hope is that when they open a textbook to learn about volcanoes or glaciers, they’ll recall the places they’ve seen and the experiences they’ve had—turning abstract lessons into something personal and lasting.
In spring 2024, my family and I visited Paris for six days. It was our first trip to Europe in six years, and our boys experienced it for the first time. Having never visited Paris, this was the last major European city on our bucket list. We found spring an ideal time to explore the city—the weather was pleasant, the crowds at major attractions were manageable, and accommodation prices were lower than during peak season. Rain was in the forecast most days, but it was generally a passing shower, which gave way to sunshine and pleasant temperatures. Low 60-degree temperatures made it ideal for walking around the city and exploring the beautiful and diverse neighborhoods that Paris is known for. Since it wasn’t peak season, award redemptions on American Airlines and Air France were plentiful and required relatively few miles compared to the summer. Here is a day-to-day breakdown
Traveling using frequent flier miles and points certainly has many advantages, such as making business class travel attainable for the casual traveler, and regardless of the ticket class you purchased, you’re saving money compared to booking with cash. However, there are instances where you might book using points from one airline in getting to your destination and use points for a different airline during your return. As far as I can remember, I haven’t ever used miles for the same airline going and coming back. For example, I’ve flown on United miles going to Europe while flying on American miles coming back multiple times. I minimized the miles expenditure by planning my itinerary this way. The only issue? Booking international tickets one way will increase the likelihood of getting the dreaded SSSS on your boarding pass. SSSS stands for secondary selective screening selection. For me, thebiggest giveaway that I’ll end up with SSSS on my boarding pass on the return trip is when I’m unable to check in for my flight 24 hours before takeoff. The mobile app will have some variation of the same message, “check-in unavailable,” or I’ll get an error message. For a traveler who is designated SSSS, the only way to check in is at the ticketing counter at the airport. When you receive your boarding pass at the airport, the capitalized SSSS will be highlighted by the ticketing agent. Once you are in line and the customs officer scans your boarding pass, a red light will flash, or there will be a beeping sound, alerting the agent of your SSSS designation. It’s also important to note that other factors may also be in play. Your name (someone with the same name or similar may be on the watch list), the region you are traveling to and from, and your citizenship status could all play a role.
My SSSS designation from Dubai to NYC last summer
Every country differs in its protocol for conducting secondary screening. In Reykjavik, Iceland, I was taken to a separate room, and all the contents of my carry-on bag were removed. All electronics were swabbed and scanned, and the procedure was completed in 10 minutes. The personnel were friendly and explained what they would do in advance. In San Jose, Costa Rica, the security personnel gave me a pat down and searched my bag right at the gate. I hated this experience since almost everyone on my Southwest flight headed to Baltimore was already in the waiting area. 170 pairs of eyeballs glaring at me as one agent thoroughly searched and swabbed my backpack and all its contents while the other gave me a thorough pat down.
There are also instances where you might get SSSS on your boarding pass when traveling domestically. This occurred in 2015 when my wife and I returned from Istanbul, Turkey. Istanbul was deemed a high-risk travel area then, and anyone returning home from that area was getting SSSS on their boarding pass for the ensuing months. Upon returning, my wife and I had a domestic flight from Chicago (ORD) to NYC (LGA), a flight we had taken countless times. This time, we both received the SSSS on our boarding pass, much to our surprise. The TSA officer asked if we had been anywhere recently. I told him we were in Istanbul the prior week, and he explained that everyone returning from that region was being selected for secondary screening. He wasn’t wrong; even people with TSA Pre-check and Global Entry were flagged from secondary screening. In this instance, we were both given thorough pat downs (more like a massage) and had every electronic device swabbed and scanned. Our laptops had to be taken out and powered on. Even The Points Guy (Brian Kelly) had a similar experience upon returning from Turkey around that same time.If you get an SSSS on your ticket, be cooperative and understand that the security personnel are just following protocol and doing their jobs. It will make the process easier and quicker, and you’ll be on your way a lot sooner.
Even though Airbnb has been around since 2008, I never used it to book an accommodation until 2015. For those of you who have never used it, it is a website where homeowners rent out their houses, apartments, condos, cabins, even tree houses. There are filters that allow you choose what type of accommodation you’re looking for such as an entire place or a single room. I have used it seven times since and all but one of my stays were excellent. Five of those trips have been in Europe where I strongly believe booking Airbnb was the better option versus booking a hotel. During our trip to Prague, decent hotels were going for $140+ in desirable locations such as Old Town Square and Wenceslas Square. Nonetheless, there were many excellent apartments and condos near these locations that were listed on Airbnb. These accommodations were just a 5 minute walk away from Old Town Square or Wenceslas Square, which eliminated the need for taxis, Uber, etc. Including taxes and cleaning fees, our total for 3 nights came out to just $67/night. I’ve included pictures of the place we booked below.
There are a few things to keep in mind prior to booking an Airbnb:
1) Make sure the place you’re interested in has a minimum of five reviews that are spaced apart (I ignored this step once and ended up booking a place that had no reviews. This resulted in my one below average experience using an Airbnb.)
2) If the owner has not posted pictures of the interior, that’s a red flag and you should avoid it.
3) Try to book a place that is a short walking distance away from as many tourist attractions as possible. By doing this, you’re saving money avoiding taxis and Uber.
So whether you’re traveling somewhere where hotels might be pricey or if you’re traveling with multiple families and want to rent out an entire house on a beach, Airbnb is a great alternative to hotels. If you use my link here you will also get $40 off your booking of $75 or more. If you have used it before, feel free to share your experience in the comments section below. As always, thanks for reading.