Have you ever been to a place where you thought to yourself, “Wow this is a cool place! I like it here.” If so, have you asked yourself, why you had this impression?

What was it that you liked so much about that particular city or town?

Well, as a real estate investor and hedge fund manager, I have always paid attention to what I like and what other people find alluring in a specific city.

In the past, I had the privilege to live in a variety of places around the world like Egypt, the Middle East, France and Switzerland, throughout Europe, various cities in the U.S. (mainly California), Cancun, Mexico and also Old San Juan Puerto Rico, in the Caribbean. I have had many residences for over a decade now and have enjoyed the beauty and uniqueness of all these different places. But I have come to realize that there is a set of criteria, when met, any city becomes attractive to its locals and most of its visitors.

Here is a short list I developed after 3 decades of travels, while always keeping an eye on beauty of architecture and attitude of locals that impact the overall lifestyle in a particular location.

To feel like a great place a city or a town must have:

1. Order: Balance, symmetry and a variety in forms and colors. Its layout must be organized in a way that flows well with nature even in its complexity.
2. Visible life: The streets should be alive with activities, full of life, energy and excitement. It must give you a sense that a lot is going on and you don’t want to miss out on something. You want people walking, talking, sitting in restaurants and cafes enjoying life; not just cars or people hustling and bustling for work. It has to be as much on display as possible.
3. Compact: While you want space, you also want decent density. Having the balancing, moderating influence of living close to other people in an uplifting surroundings. Tightly packed well-ordered cities, with lots of squares, plazas and places where we can hang out. The art of the square is a having good size, symmetry and height of buildings. Having great statues and maybe a water fountain in the center. You want to have a place that is private within the public space, surrounded by cool places to hang out.
4. Orientation and Mystery: You want to get a bit lost in the back streets that are cozy and and quaint. A place that is both cool and warm. Anonymous and mysterious yet personable and familiar. Where you get the sense of the old respected history and the new modern energy. You want to sense the newness of the place as well as some intimate old familiar surrounding.
5. Scale: You don’t want it packed with commercial interest posted on high rises. You want a variety of places of worship, museums, culinary places and shops. No more than 5 stories high buildings are always more welcoming. Sizes and spaces with density that does not make you feel too small or too big.
6. Local influence: You want to immediately feel that there is a uniqueness to the character and feel of the place. You want to see people and architecture that reflect the local customs, way of life and history.
7. Climate: An inviting climate that makes you feel you are at the right place, no matter the time.
8. Safety: You want to feel that you can go venture on your own and discover without having to worry about your own security or well being.
9. Friendly and happy: You want to feel that everyone around you is happy to see you there. Making you feel welcome, appreciated and wanted. I like places where people take time to share their stories and carve time out of their schedules to involve you in what is happening in their surrounding. It is great to feel open and connected. Especially when look you in the eye, smile and greet you and each other which gives you a sense of warmth and welcome.
10. Educational: You want to learn something new to be able to share with you friends back at home. Museums, local customs etc.

In the early 2000’s I found such a city— and it is called Old San Juan, Puerto Rico. It is the oldest historic zone under a U.S. flag. This area features all of the criteria I wrote above and more. It has hotels, museums, churches, restaurants, art galleries and great shopping. This enchanting city is all nestled into some unique and colorful colonial buildings with narrow streets covered by blue stone-casts that were brought over as ballast on Spanish ships in the 1500 and 1600s.

This area is very charming and I have worked hard and invested millions into the area to restore the beauty and integrity of its colonial buildings. My goal has been to make everyone enjoy the history and charm of this Old City. That city offers everyone, locals, tourists, first time visitors (coming off the cruise ships) to returning guests an opportunity to connect with each other and with the historic architecture and the story that is very much part of nature in its design and creation.

Come and visit Old San Juan, PR and you may just fall in love with it as I did back a decade and a half ago.