1. You’ll do less cramming and planning, and do more relaxing and having fun.
Sure a full itinerary seems exciting before you reach your destination. Planning is half the fun right? But once you arrive at your destination, you’ll find yourself over-scheduled and overwhelmed. How can you possibly see everything and do everything in the time that you have? Short answer: you can’t. So let it go, and just focus on seeing the city or town you’re in. Spend your first day in any city simply by being there. Soak up that feeling of being somewhere new, being away from work, your city, and being carefree. Eat different stuff. Talk to strangers. Stop and really see things and their beauty.
2. You’ll have time to search out some authentic local experiences rather than visiting places that have been so completely tourist-ized.
Staying away from the most major tourist attractions will also put you in places where more locals are (since they stay away from crowded spots with long lines when at all possible). For instance, staying at an agriturismo or monastery in a small town in Italy, often yields a far more unique and rewarding experience than staying at an expensive hotel in an area crowded with tourists. Moreover, by staying in places a bit off the beaten path, you’ll be able to visit places and take photos without as many people photo bombing all your candid shots.
3. You’ll eat better and drink better.
The farther away you stray from the main sights, the better the quality and prices get. Forget plastic menus with photos and low quality food churned out by the bucket to appease un-discerning tourist palates. Head for the shrinking price-tags and dishes you can’t pronounce to get a real taste of the country or city you’re visiting. For example: When I was in Croatia, I befriended a local restaurant owner and asked his advice for great seafood spots (we were in Dubrovnik). He recommended I get away from Dubrovnik completely (overall lackluster restaurants with high price-tags), and visit the nearby small village of Ston (and it’s counterpart Mali-Ston). He had some friends who ran an unofficial ‘restaurant’ from their house. What followed was the best meal I had during my three week vacation in Croatia. Six courses of seafood pulled straight from the sea, a stunning view, no crowds, and a price tag that was a 1/3 of the price my friend and I would’ve paid for 1/2 as much at any restaurant in Dubrovnik. Plus we stumbled across an amazing crumbling 15th century wall and stairs, that led up over mountains on the way back to Dubrovnik. That’s a day we’ll never forget, and we’d never have known those places existed without throwing away our guidebooks and just chatting with the locals.
4. To be able to truly say that you have ‘experienced’ a place, it is important to meet and talk with locals and discover things for yourself.
Rather than walk blindly from place to place following your guide book, walk the streets, grab coffee or drinks at random bars, and get lost. Discover things you weren’t looking for. Seeing the same things every person sees, and having no memories other than racing to and from top attractions, standing in lines, buying tickets, and then taking too many unnecessary photos, isn’t the best way to create true and lasting memories. Dare to veer away from the crowds and figure things out on your own. Get lost in a pitcher of good wine on a sunny porch and find yourself leaving a place with only a photo or two of the landscape– only because you had such a good time you forgot, for once, to pose in front of everything. Live.