The Pirate’s Guide To Travel

What do you want to do? Let’s go to Italy!

30 minutes later our bags were packed and we were cruising through the Bavarian Alps towards Milan, excited for the adventures that awaited us.

Somewhere in Northern Italy

The drive was amazing but our excitement subsided quickly after arriving in Milan. After a 7 hour drive, we arrived tired and hungry. Our phones didn’t work, so we pulled off any exit to look for a decent spot to rest. Unfortunately, as anyone who has visited can attest- Milan is not a car friendly city.

We spent half an hour finding parking (found out later was an illegal spot). Next, because of the time we arrived (between lunch and dinner) we struggled to find an open restaurant. Lastly, it took us an hour and three different stores to buy a Pre-paid SIM card. By the time it was activated, we discovered every hotel under 500€ was booked… Not exactly the best way to start a weekend getaway.

Milan-1 Ayman-0

We ended up calling it quits. drove to nearby Verona, had a blast, and actually saved the weekend. But I still thought about how to prevent this from happening again and hopefully share with you the 10 minutes of planning that could have saved us hours of headache and amplify the joy of travel.

I call this system: The Pirate’s Guide to Traveling

Pirate’s Guide to Travel

Every pirate needs two things to be successful: A treasure map and a pirate ship. Allow me to explain.

Everybody has a list of things they want to see when visiting a city for the first time. Whether it be attractions, museums, clubs, or restaurants.

This is usually stored as a top 10 list blog post or a checklist in your phone. The problem is, most travelers don’t have a clue how all of those “to-do’s relate to each other geographically.

Introducing The Treasure Map

By creating a “treasure map”  with all your points of interest marked down, you can visualize your ideal route and plan out your day.

This way you don’t walk past one attraction to visit another, only to backtrack later so you can mark it off your list (sometimes you have to skip things altogether because you ran out of time). It sounds obvious, but this aimless wandering happens far too often to first time visitors of a city and it wastes precious time that you could be spending getting lost and exploring the hidden treasures not located in any travel guide.

Personally, I use Google maps to create my treasure maps by “starring” locations. It also syncs with my phone so I can see where the little blue dot is in relation to my points of interest:

My Prague “Treasure Map”

I’m not sure of a better service that does this. I know that foursquare and mapquest have tried similar offerings but so far they seem half-baked. I will update if I find something better later.

Pirate Ship

 Once you have your treasure map settled. You need to commander a Pirate Ship that helps you capture the booty.

If you’re anything like me, you probably used to go to Kayak, find a hotel based on its perceived value, (4 star hotel for $100, great deal!) and hope for the best once you arrived.

But now that we’re implementing a location based strategy to your travels, the most important criteria for hotel selection is location. You want something centrally located to the areas you want to visit. This might mean you pay more per night, but the amount of money you save on tram fares and late night taxi rides more than makes up for it. You may even end up saving money when all is said and done.

But most importantly, there is no greater freedom than waking up, grabbing breakfast and walking to your first adventure. So find your hotel/motel/hostel, book it, and screenshot the address so you can show it to the cab driver even when you don’t have internet.

Protip: Once you’ve found your Pirate Ship, screenshot the addresses of nearby Internet cafes or pre paid SIM card stores so you can be mobile again within minutes of checking in.

When you implement this Pirate strategy to your next trip, you can maximize your time,  minimize stress, and actually enjoy your travels.

One final note, travel is supposed to be messy, exciting, and spontaneous. Don’t over-plan  be flexible, and let the city and your intuition guide you as you explore your new surroundings. Some of my favorite experiences were walking down a random alley and finding a popping restaurant filled with locals and the freshest fish this side of the Mediterranean Sea.

Go somewhere where nobody knows your name.
Go somewhere where nobody knows your name.

The Pirate’s Guide to Travel is merely a tool to help you have more of those types of experiences and less time in taxis or aimlessly wandering around a city.

Good luck, and happy pillaging!



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