Discover. Plan. Go. — All with AI ✨
Turn your travel dreams into reality with AI-powered planning. Discover hidden gems, design personalized itineraries, and organize every detail — from flights and stays to activities and dining. Whether it’s a quick getaway or a once-in-a-lifetime adventure, everything you need to plan and go is right at your fingertips.
ABOUT US
Discover your perfect vacation with Where Should I Vacation. Our AI and partners analyzes thousands of options to deliver custom itineraries, hotel and flight deals, and experiences tailored just for you. We make travel planning effortless, personalized, and fun, while keeping everything else simple, intuitive, and hassle-free.
How does it work?
Tell Us About You
Share your travel dreams, preferences, and ideal vibe. The more we know, the more personalized your adventure becomes.
Generation Begins
Our intelligent system analyzes thousands of destinations, hotels, and experiences to find perfect matches for your style.
Your Perfect Trip
Receive curated recommendations with the best hotels, flights, and experiences—all tailored specifically for you.
Your Trip, Designed for you
It’s not about where everyone goes. It’s about where you belong.
Tired of the same old postcard destinations and pre-packaged tours? We are too. That’s why we built a smarter way to travel — one that puts you at the center.
With our powerful itinerary builder, every plan is crafted with utmost personalization. No cookie-cutter experiences. No trendy spots just for Instagram. Whether you crave hidden photo spots, indie bookstores, night markets, or serene escapes, we’ll build what you want, where you want it.
Coming from another country? No worries — we’ll match you with flights that align with your schedule, comfort, and budget. We’ll even pair them with hotel options that suit your taste, from cozy boutiques to premium stays — all seamlessly integrated into your itinerary.
Say goodbye to generic. Say hello to a journey that feels personal, intentional, and entirely yours. And if you want even more personalization? You can freely edit the itinerary as you wish.
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A pricing structure that is friendly
No subscriptions, no monthly fees — just pay for what you need, when you need it. Simple, transparent, and commitment-free.
Free
For the light-footed and curious. You like to keep things simple — maybe planning one getaway at a time or just trying things out. No rush, no pressure, just smooth exploration at your own pace.
- Personalized itinerary builder
- 10 AI-Powered Generations (refreshes to 10 per day if used)
- 1 Itinerary (refreshes to 1 per month if used)
$10
For the seasoned traveler or the trusted planner. You plan for yourself, sometimes for others. You're all about depth, detail, and having a solid lineup of trips — because one journey is never enough.
- Personalized itinerary builder
- 45 AI-Powered Generations (resets to Traveler if used)
- 12 Itineraries (resets to Traveler if used)
$5
For the thoughtful wanderer. You enjoy comparing ideas, checking multiple routes, and making sure every trip is just right. You’re open to possibilities, and always have a few options ready to go.
- Personalized itinerary builder
- 20 AI-Powered Generations (resets to Traveler if used)
- 5 Itineraries (resets to Traveler if used)
Frequently Asked Questions
Got questions? We've answered the most common ones below to help you plan with confidence — clear, honest, and upfront.