Itinerary Boss Insider Hey Reader, (1 minute 7 second read) Hope everyone had an incredible Thanksgiving and got some well-deserved downtime with the people who matter most. We kept it low-key in Charlotte, amazing sides, plus steak and lobster for Thanksgiving dinner, which was definitely a fun twist on the usual. Friday night we caught Marlon Wayans at the Comedy Zone (yes, the legend from White Chicks and Little Man), and he did not disappoint. Saturday was all about football, Ohio State...
9 months ago • 4 min read
Itinerary Boss Insider Hey Reader, (32 second read) IHG just brought back some of its strongest elevated offers, including a massive 200,000-point bonus on the business card. Whether you’re planning your next trip to Lisbon, Costa Rica, or anywhere in between, these limited-time bonuses can stack you with enough points for multiple free nights. 🏨 IHG One Rewards Premier Business Credit Card Offer: Earn up to 200,000 Bonus Points — 140,000 points after $4,000 spend in 3 months, plus 60,000...
10 months ago • 1 min read
Itinerary Boss Insider Hey Reader, (⏱️ 100‑sec read) This past weekend was packed with family, friends, and points‑and‑miles conversations. 🏡 We spent time with some commercial real estate and real estate service business owners, talking through how to turn their everyday spend into free flights & hotels. The weekend ended with a quick trip through Dulles, where we enjoyed Etihad’s Priority Pass Lounge (also a Sapphire Lounge) a nice perk for Sapphire cardholders passing through IAD. 🎉 A...
about 1 year ago • 2 min read
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 year 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 1 year 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...
about 1 year 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...
about 1 year 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 💎...
about 1 year 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...
about 1 year ago • 2 min read