10 Things To Do On A "Look-See" Trip
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July 20, 2015 - Updated February 20, 2017


When deciding whether or not to relocate, many people take what is known as a "look-see" trip to thoroughly investigate a particular location before moving there.

During my lifetime, I have taken two "look-see" trips, one in 2002 and one in 2009, both to Hong Kong.

Why two? Because locales, like people, tend to have a life of their own and change over time. The marriage between the two, where you are in your life and where your destination is in its own, will ultimately determine the success of your union. 

Although I spent nearly three years living in Hong Kong between 2003 and 2005, I visited a second time seven years later before deciding whether or not I would return. Based on the due diligence I collected during that trip, I decided against it.

Though the concept of the "look-see" trip generally applies to the future expat (someone who resides overseas), the same principles can also be applied to anyone investigating a city or town they are considering as a potential second residence or as a new home.

Over the past few years, I have traveled to several U.S. cities, including both Austin and Houston, each with an eye toward my future. At the time of this writing, I am visiting beautiful Savannah, Geo'gia.

What differentiates this trip from the others is that I am treating my visit to Savannah as a "look-see" trip. That doesn’t mean my Eat, Pray, Love cravings for a more meaningful existence are not being satisfied. They most certainly are. And that’s a good thing because I firmly believe if I am ever to feel truly comfortable living somewhere, they must.

That said, there are other, equally as important, criteria to consider before committing to a move. Here are 10 things I recommend doing on any "look-see" trip, whether domestically or abroad, to ensure your visit is a worthwhile one

1. Live. A "look-see" trip is not a vacation, as tempting as it may be to make it one, especially if you are visiting a place you have never been to before. In fact, I have been working ever since I stepped off the plane a week from last Friday. Remember, you are visiting your location for a reason -- to see what life is like.

To mimic real life conditions, I opted to rent an apartment for the duration of my two-week visit instead of staying at a hotel. There are several reputable services that can assist with this process, including VRBO and Airbnb.

For a true "look-see" trip, I recommend staying no less than two weeks in one location, preferably three, in order to thoroughly research your surroundings.

2. Tour. Of course, it is okay to be a full-fledged tourist and engage in vacation-type activities while you are visiting. Actually, I highly recommend doing so, especially as a way to get your bearings. It is important to discover what makes a particular city unique and why it is “on the map,” so to speak.

So far during my stay in Savannah, I have been on a trolley tour around the city, visited the Sorrell-Weed House for a ghost tour, taken a tour of a local synagogue, visited Savannah’s City Market, walked, shopped, and dined along the Savannah River, and met with a psychic for my first ever Tarot card reading.

There are other destinations still on my list, and I plan on hitting a few more of them this coming week as time allows.

3. Locate. Find the places you need to make your stay a comfortable one. Supermarkets, pharmacies, banks, dry cleaners, coffee houses… whatever. This should be your top priority.

When I first visited Hong Kong, my children were only 27 months and 15 months old. During our three-week stay, I scoured supermarket after supermarket searching for the products my family liked and what they (and I) were familiar with. It took some time, but eventually I found (almost) everything we needed. Domestically, doing so may not present as much of a challenge. But, I have to confess, finding Starbucks on my second day in Savannah did put a big smile on my face.      

4. Calculate. How much will it cost to live in your city of choice? From housing prices to the price of milk, it is important to create a realistic budget for yourself. The cost of living varies from place to place, and from item to item. Do your homework so you are not surprised later. I remember the first time I bought a gallon of milk in Hong Kong. The then price of $16 USD per gallon made it an experience I will never forget!

5. Eat. Eat some meals in and some meals out. If you are going to live somewhere, behave like it. I am not suggesting you cook yourself a five-course meal during your stay. But try handling the banality of everyday life by eating a bowl of cereal at your kitchen table or frying up some eggs. You will not only save money but likely a few calories, too, especially here down south.

When dining out, also be sure to try the local cuisine. Food is an important part of any location’s charm and appeal. One caveat, though. If on a "look-see" trip overseas, do be mindful where you are eating. Stay away from street vendors and places whose cleanliness you cannot vouch for. And always be sure to abide by directives and advisories from U.S. agencies that pertain to your specific destination.    

6. Pray. Even if you are not religious, you may be surprised to discover what an important role religion can play when living somewhere new. One of my biggest regrets while living abroad is not having become more active in Hong Kong’s Ohel Leah Synagogue. Though my middle child attended preschool at the synagogue’s Carmel School for one year, I did not fully immerse myself in Jewish life and, as a consequence, missed out on the sense of community organized religion potentially offers.  

During my first week in Savannah, I toured the city’s reform synagogue, Congregation Mickve Israel. I was fascinated to discover this congregation dates back to 1733 and is the third oldest in the United States. I had the privilege of attending Shabbat services at Mickve Israel this past Saturday, and was welcomed afterward to a kiddush luncheon sponsored by a local family in honor of their daughter’s first birthday. At lunch, I had the opportunity to meet and converse with other visitors like myself, as well as local congregants, most notably the synagogue’s eldest member, a 98 year-old descendant of one of the synagogue’s founding families. What could be a better testament to the cohesiveness and devotion of Savannah's Jewish community?    

7. Love. If you are looking for that special someone, it is important to investigate what single life is like in the city you are considering.

Approximately one week before my arrival, I changed my home city to Savannah on both my JDate and Match profiles. Though I received a good deal of inquiries on Match (mostly from non-Jewish men), JDate was much slower than I had originally anticipated.

Despite a strong Jewish presence here in Savannah, I did not feel that same presence online. It seems that it is with good reason because when I searched for men in my preferred age range on JDate, I discovered only three! Networking, it appears, is a more effective way to meet Jewish singles in Savannah, though I have been told that, too, presents its own challenges.

As I have come to realize over the past three plus years since I first began dating, it is important for me to be with someone of the Jewish faith. Although I never rule anybody out solely based on religion, I do consider religion to be an important factor in my search for a life partner. Had I not investigated Savannah's social scene now, I would remain unaware of the challenges I could possibly face later.

Walk. I find it fitting that Savannah is home to Chippewa Square, the place where the fictional character, Forrest Gump, memorably sat on a park bench in the movie bearing the same name waiting for a city bus, telling everyone who sat beside him what his momma always said: “Life was like a box of chocolates. You never know what you’re gonna get.”

Forrest's momma was right. Sometimes.

Immediately after my unforeseen separation, I became a veritable Forrest Gump, walking on average eight and a half miles daily either on my treadmill or around my neighborhood as the weather allowed. Like Forrest Gump, walking was the way I cleared my mind, and my walks have stayed near and dear to my heart (and head) ever since.

Having lived in New York City and several of its surrounding suburbs, as well as in Boston and Hong Kong, I know I want to be somewhere that I can walk for extended distances. It is one of the things I loved most about living in Manhattan and Boston, and least about living in Hong Kong. Although a picturesque city, Hong Kong was not necessarily a walking city, and I missed that during my time there.

Which is why I deliberately did not rent a car during my stay in Savannah. Armed with my Nike app, I have chosen instead to explore the city on foot, sometimes walking a whopping 10 miles per day! Not only has walking enabled me to learn my way around, but I have had no regrets indulging in a yummy southern-style dessert whenever the mood strikes me.

9. Talk. Speak to the locals. Almost every meal I have eaten so far has been either at the counter or in the bar area of the restaurants I have frequented. From bartenders to patrons, I have gotten more local flavor than I would have if I sat at a table by myself. I also talk to tour guides, store clerks, and people on the street whenever the opportunity arises. Trust me when I tell you that I am NOT an outgoing person by nature (that is, until you get to know me). But, as I have gotten older, I realize everyone has something to say. And, wouldn’t you know, people are more than happy to hear from me, too!

10. Connect. During any "look-see" trip, it is important to connect with others. Exchange business cards, email addresses, and phone numbers. You never know when you may need advice from someone who is familiar with your place of interest or have a question.

If at the end of your investigative trip you have done your job well, you should be better able to answer for yourself the most pertinent question of all: Have I connected with the place I am visiting?

It may take more than one visit to determine how deep that connection is, and that’s not only okay, it’s preferable. Relocating is a big step.

Though I am happily settled in my current hometown and have no intention of uprooting my children while they are still attending school there, I know Savannah and I have embarked on an exciting new relationship together, and I look forward to all the city has to offer and all I am gonna get.

What have you discovered on your travels post-divorce?

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