Itinerary Boss Insider Hey Reader, (⏱️ 45‑sec read) Back in 2019, I visited Split and Dubrovnik Croatia for a week and it quickly became one of my favorite places ever. Dubrovnik is still my #1 city I’ve visited. We paid cash back then, but if you’re planning a trip now, here’s how you can do the same trip using points and miles. How to Book Flights to Croatia with Points Fly into Dubrovnik (DBV) or Zagreb (ZAG) Use transferrable points → transfer to Aeroplan or United Pro tip: Fly direct to...
about 1 month ago • 1 min read
Itinerary Boss Insider Hey Reader, (⏱️ 1‑min 38‑sec read) In September 2024, I spent 11 days exploring Greece with my wife, my best friend, and his wife and it was epic. We visited Athens, Mykonos, Milos, and Santorini, and I wanted to simplify the planning process for you with this Ultimate Greek Islands Guide: when to go, what to do, where to stay, how to get around, and a few of our favorite ferry, food, and activity recs. Let’s dive in 👇 When to Visit Greece If you’ve been around here for...
about 2 months ago • 3 min read
Itinerary Boss Insider Hey Reader, (⏱️ 1‑min 37‑sec read) This past Sunday I was deep in travel planning mode and wow, Gondola AI saved me so much time. Here’s what I booked: Wichita for TBEX — to connect with other travel content creators Portland for FinCon — paired with a side trip to Cannon Beach Chicago for the Points & Miles Seminar (🤞 hoping to speak!) All flights and hotels were booked through my brand new Chase Ink Business Preferred card that just arrived in the mail. If you’re not...
2 months ago • 3 min read
Itinerary Boss Insider Hey Reader, (⏱️ 1‑min 35‑sec read) Last weekend was action-packed celebrating Father’s Day, my mom's birthday, and attempting whitewater rafting which promptly reminded me I'm not in my 20's anymore (hello, pulled groin). It’s been nice this week having some downtime to brainstorm and recover, and reflect on recent wins we've had helping travelers like you. Here's what's coming your way this week: 🎉 Community Win 💎 Deal of the Week 🎧 Podcast Spotlights ✅ Actionable Tip...
3 months ago • 3 min read
Itinerary Boss Insider Hey Reader, (⏱️ 1‑min 20‑sec read) This past week has been fun.. We've had 8 new calls and coffee meetings with business owners & sales pros who thought their expenses were “just bills.” We also attended a cool concept at Chilly Coffee Club – sauna ➜ cold plunge ➜ espresso ➜ repeat, a Charlotte Knights game and a good friends 35th-birthday party with a live band who plays a great Sex on Fire by Kings of Leon. This Week, Here's What We're Breaking Down: 🎉 Community Win 💎...
3 months ago • 3 min read
Itinerary Boss Insider Hey Reader, (⏱️ 1‑min 50‑sec read) Over the weekend I scored a few trips using my Capital One Miles → Qantas + the 25 % transfer bonus (OneWorld Alliance). It landed me a one‑way to Las Vegas for $0 on an American‑operated flight and the same move cut a Ohio round‑trip down to just 12, 640 Qantas points using Capital One Miles. 🙌 I booked 4 flights and saved $1,695 using 40,084 miles taking advantage of the 20% bonus. This ended on May 31st, 2025 but since you're...
3 months ago • 2 min read
Itinerary Boss Insider Hey Reader, Happy Memorial Day! 🇺🇸 Summer has officially arrived, and we kicked it off celebrating with friends at a pool party birthday bash and got to connect with other like minded entrepreneurs looking to learn more about points and miles. I hope you enjoyed your long weekend too! This week is packed with valuable tips and highlights designed to help you travel smarter, earn more points, and avoid common pitfalls everyone makes when traveling at some point in their...
3 months ago • 3 min read
Itinerary Boss Insider Hey Reader, This past weekend was packed with fun—catching the PGA Championship right here in Charlotte and cheering on Charlotte FC made for an exciting few days! Speaking of major events, I recently recorded a special podcast episode (coming soon!) on how to save thousands on flights and hotels when traveling to bucket-list events like the Rose Bowl or big Michigan football games. You'll discover exactly how strategic points planning can unlock experiences you'd...
4 months ago • 2 min read
Itinerary Boss Insider ⏱ Estimated read‑time: 2 minutes Hey Reader, We’ve been busy behind the scenes creating tools to simplify points and miles and I’m excited to share the first big one with you today. If you’re feeling overwhelmed by travel rewards, or just don’t know where to start, you’re in luck... 📚 Introducing: Your Points & Miles Cheat Sheet I’ve put together a simple, easy-to-follow cheat sheet that covers: Points & Miles Basics: Explained clearly, step-by-step. Points Multipliers:...
4 months ago • 2 min read