Hey Reader, If you’ve ever used online reviews to search for the perfect hotel or activity, you’ve probably run into this:One reviewer calls it a hidden gem. Another says it’s overrated. A third found bugs in their bed. The next reviewer says they’re booking again next year. I love planning our trips, but I often spend way more time researching than is necessary. When that happens, I usually end up in analysis paralysis. It happens when comparing hotels, destinations, vacation rentals, tours...
4 months ago • 2 min read
Hey Reader, Both Skyscanner and Global Hotel Alliance, in partnership with Skift, recently released their 2026 travel trend reports. One of the clearest themes they agree on: travelers are still spending, but they’re being more intentional about it. Skift calls this trend selective splurging. In their joint report with GHA, they found that 34% of travelers expect to increase their travel spending in 2026, with most prioritizing better room types, more convenient locations, and personalized...
4 months ago • 2 min read
Hey Reader, It’s hard to scroll through travel content these days without feeling like you’re doing something wrong. My Instagram and TikTok feeds are obviously travel-heavy. Lately, it feels like every post is a creator flying first class to bucket-list destinations, staying in luxury hotels, and booking aspirational round-the-world trips for what looks like $1.86, despite rising costs. If you don’t have a travel credit card, or don’t use it the way influencers say you should, it’s easy to...
5 months ago • 6 min read
Hey Reader, It is the time of year when travel plans start stacking up, schedules tighten, and every store pushes out a wave of deals. I actually love this stretch. Travel gear gets cheaper, and I get to share a few things that genuinely make trips easier, lighter, and more enjoyable. I just published a new post with my favorite travel gift ideas for this year. Since many people are shopping for gifts right now, I pulled a handful of my favorites to share here. These are gifts that make sense...
5 months ago • 2 min read
Hey Reader, If you have been watching the news, you know airports have been a mess for weeks. The government shutdown lasted 43 days and forced the FAA to cut flights at 40 major airports due to air traffic controller shortages. Those restrictions were just lifted, and airlines are now racing to get back to normal ahead of Thanksgiving and the rest of the holiday crush. That is the good news. The less fun part is that the system won't bounce back overnight. Airlines are rebalancing schedules,...
5 months ago • 4 min read
Hey Reader, Air travel in the U.S. remains in crisis even as Congress moves to end the government shutdown. The FAA has ordered airlines to reduce flights by 10 percent at 40 major airports, resulting in more than 2,000 cancellations and 7,000 delays recorded on Sunday alone. Controllers have been working without pay for six weeks, and up to 20 are retiring daily, worsening the staffing shortage. TSA lines at major hubs now exceed two hours, and several checkpoints have temporarily closed....
5 months ago • 5 min read
Hey Reader, Most people think they need more vacation days to travel more. What they really need is a plan. Strategic PTO planning helps you stretch limited days into long weekends, full getaways, and even extended trips without burning through your balance. Here’s how to make the most of what’s left in 2025 and get a head start on 2026. Use the Remaining 2025 Holidays Wisely Thanksgiving (Nov 27): Take Nov 28 off for a four-day weekend, or add Nov 26 to create a five-day trip. Christmas (Dec...
6 months ago • 1 min read
Hey Reader, Because my wife teaches and our kids attended public schools, we’ve always been tied to school breaks for travel. Traveling during peak season taught me how much timing matters when it comes to booking and budgeting. Here is a quick guide to when it usually makes sense to start planning and booking your next trip. Book early ✈ Flights: About 1 to 3 months ahead for domestic trips and 2 to 8 months for international or peak season travel.🏨 Hotels: Around 3 to 5 months ahead for...
6 months ago • 1 min read
Hey Reader, I shared a post on Instagram this week about something I’ve been working through. It’s about a recent health issue, how it affected me physically and mentally, and what’s helped me move forward again. If you’re curious, you can read the full post here. But this email isn’t really about the post. It’s about the bigger takeaway: Sometimes what’s best for you is what actually works for you. Not what’s trending, not what’s optimal, and not what everyone else is doing. For me, getting...
11 months ago • 2 min read