Tailbox Blog
Insights and tips on AI-powered travel planning, destination guides, and industry trends
Travel Planning for Couples: How to Make Sure You’re Both Happy
Planning a trip with your partner? Here are 7 real tips to make sure you're on the same page and actually enjoy the journey together.
What Makes a Great Trip? It's Not What You Think
A great trip isn’t about checking boxes or going viral. Learn what truly makes a travel experience meaningful, and how to build it around your vibe, energy, and rhythm.
Top 5 Free Tools to Plan a Trip That Don’t Require a Travel Agent
There was a time when planning a trip without a travel agent felt like a chore with endless tabs, conflicting information, and booking stress. But in 2025, a handful of free, smart, and easy-to-use tools give you all the power to plan a trip that fits your needs — no middleman required.
Introducing Tailbox: Your Personal AI Travel Concierge
Tailbox is a voice-based, visual AI travel planner that transforms trip planning from a 5-10 hour research marathon into a 15-30 minute conversation. Instead of asking "Where do you want to go?", it starts with "What are you looking for right now?" - helping you define your travel vibe before building a personalized itinerary with real-time visual planning, interactive maps, and live budget estimates.
How to Build a Realistic Itinerary That Doesn’t Burn You Out
A realistic travel itinerary balances activities with downtime to prevent burnout by understanding your energy, using the 3-5 hour rule for daily activities, scheduling soft days, and leaving room for spontaneity—ensuring your trip energizes rather than exhausts you.
Travel Planning Is Finally Changing. Here's What You Need to Know
Tailbox is revolutionizing travel planning by shifting from chaotic, fragmented processes with dozens of open tabs to an integrated, AI-powered approach that starts with your personal intentions and energy rather than generic destination lists.
10 Questions to Ask Yourself Before You Even Choose a Destination
Stop stressing over where to go—discover how you want to feel first with these 10 essential questions to unlock your perfect trip vibe.
Why Planning a Trip Is So Stressful (And How to Make It Easier)
Travel planning should be exciting, but decision fatigue, information overload, and scattered tools turn it into an overwhelming mess — here's how to fix it and make planning fun again.
The Right Way to Start Planning Your Trip in 2025 (Even If You’re Still Just Dreaming)
Discover how artificial intelligence is revolutionizing the way we plan and experience travel, making it more personalized and efficient than ever before.