We turn a Boston positioning flight into a mini trip and share what worked for our family of five, from points bookings to kid-friendly sightseeing. We also give our unfiltered take on the Hyatt Regency Boston, the Boston Tea Party Museum hype, and the airport logistics we’d handle differently next time.
• why positioning flights can feel stressful or feel like a bonus trip
• booking a nonstop Phoenix to Boston flight with American Airlines points and Main Cabin Extra seats
• the Chase lounge wait and the $90 backup meal lesson
• using Amex Platinum Uber credits for rideshare
• Hyatt Regency Boston on free night certificates, upgrade request and junior suite realities
• breakfast highlights, late starts and planning activities around the time change
• Freedom Trail tour pros, pacing and what keeps kids engaged
• Boston Tea Party Museum expectations and what the experience is really like
• dinner at Legal Sea Foods and a lobster roll worth ordering
• using Blacklane for airport transfers and navigating terminal construction
• a reminder to stay kind when airline disruptions overwhelm staff
If you'd like to see the photos, there's one on my Instagram story on the on the Boston highlight, so you can go take a look. Um, and then let me know your thoughts. What do you think? Explosive diarrhea or murder toilet? You you let me know.