The Spirited Traveler

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by Kristina Domitrovich
photos by La-Tessa Montgomery and Lindsay Pace

“I wasted a whole lot of time not doing stuff I wanted to do,” La-Tessa Montgomery realized in 2012, in the midst of going through a divorce. It dawned on her that she spent all her time focusing on her relationship, her children and her work, and no time focusing on herself. She promised herself that each year, she would go on an international birthday trip. She waited to take her first trip until her youngest was old enough that Montgomery felt comfortable to leave for a few days. 

“I get really freaked out. As much as I want to go, I get freaked out being away from home,” she said. “It really bothers me if I let myself think about it, so for me, the sweet spot is four days.”

Montgomery is an analyst by day and a fiction writer by night; and, admittedly, she said this can sometimes make her imagination wander. If she’s gone for much longer than four days, she starts worrying about her kids, “my baby might fall out of a tree!” She can laugh about it now that her youngest is 15, and none of her kids have fallen out of a tree while she’s been away.

Determine a Destination

In 2014, Montgomery got her first passport stamp on her trip to London.

Since then, she has gone on a trip each year –– barring 2020, of course –– and has visited seven countries in six years, doubling up one year. So far, she’s been to London, Amsterdam, Paris, Cuba, the Domincan Republic, Prague and Italy.

She’s rather methodical about planning her trips. She has a list of places she’d like to visit –– she said it has over 30 entries, but some countries have multiple cities –– and she goes from there. She has a rule that she can never visit the same city more than once, though “I think I’m going to take my girls to Europe next year. So we’re going to do London and ride the train over to Paris, but it’s not cheating because I’m taking them,” she laughed.

In 2020, she was going to do her first group trip to Zanzibar in Tanzania, but because of COVID, that was pushed back to 2021, which was later canceled. Now, she’s rerouting to Greece this September.

Plan it Out

“I plan my trip so far in advance because I’m a planner. I’m very anal retentive that way,” she laughed. “So the only way for me to be comfortable to leave and go 6,000 miles away, and leave my kids here, is that I have a firm plan. So I have to start early.”

She usually tries to take her trips in March. Mostly because it’s her birth month, but it’s usually still too cold to be tourist season, so “it’s really cheap.” She plans everything out herself; unless she can’t get somewhere in less than five flights, then she reaches out to a travel planner for help getting there. 

For most trips, she likes to visit a single city because she wants to experience the culture and “the spirit of the place.” Sometimes, she’ll catch a train and go to another city –– like when she was visiting a few different cities in Italy and took an afternoon trip to Venice, where she swears she almost died. But more on that later.

Once she chooses a destination, she spends months researching. 

“I need to start planning,” she said, “Because that’s the only way I can be comfortable.”

The first step, as a Black woman traveling alone, is to research how she’ll be treated.

“I google, ‘How are Black people treated?’” she said. “Then, ‘How are women treated?’ Because I’m going to catch hell for both.”

Through her travels, she’s learned that sometimes it’s “not really a race thing, it’s more of a nationality thing.” Like her trip to Paris, where the French are a bit notorious for hating Americans. Montgomery learned that in her experience, the French just aren’t accepting toward the English language. 

“Paris is not very forgiving when you don’t attempt to speak French,” she said. 

She laughed that by the time she got there, she was speaking more Spanish to the Parisians than French or English. This bought her some leniency, so she “got away with a lot of stuff.”

Once she determines how she will be treated as a solo woman of color, as a solo woman in general and as an American, then she starts researching general safety in that country.

From there, she’ll start looking at “must-see” places in the city, and see if there are any neighboring places worth her time. She’ll also look for popular photo spots, because she enjoys taking photos with her “big boy” camera when she’s traveling.

For her finalized itinerary, she has a currency converter, all the information for her hotel (she keeps their number on speed dial and has the location pinned in her phone), and a list of things she wants to see. Unless she’s going somewhere tropical, then it’s a little different.

“When I go to the beach, I don’t want to leave the beach,” she said, laughing. “That’s when I get my butt in the sand, and I want to have drinks and read my book and I sit on the beach all day long.”

If it’s in Europe or somewhere non-tropical, then her itinerary is a bit more full. Actually, it’s chock-full. But she has a rule of threes: She picks the top-three things she wants to do.

“So when it comes down to it, as long as I get to those three things,” she said, “Everything else is gravy.”

Her list is still expansive –– in fact, she says she likes to feel like an encyclopedia about a place, where to go, what to do, by the time she arrives –– but she won’t stress herself out trying to go everywhere and see everything.

“I’m very flexible. I have this plan so I don’t get bored; I don’t have this plan to freak me out and make me go hop around the city like a junkie,” she said. “I think the worst thing you can do is go pay a couple thousand dollars for this trip and get to a foreign city and be bored.”

She also has about 10-15 words and phrases memorized (and written down) to do her best to have a baseline form of communication. A lot of it is directional phrases (right, left, up, down), and some polite phrases and greetings to get her through the trip.

The Flight

Over the years, Montgomery has mastered the timing of international flights, Europe at least. Her goal is to land in-country at about 9 in the morning and get started. She books her international flights to be overnight. She hops on board, gets comfortable and has a glass of white wine with the dinner they serve in-flight. 

“(Then) you get this thing called Benadryl,” she said, laughing.

After taking Benadryl, she’ll watch a movie and usually fall asleep. The next time she wakes up, it’s usually right as the flight crew begins serving breakfast before they land.

In-country Experiences

Through her travels, Montgomery has experienced a lot of highs and lows; but by far, her least favorite experience was Venice.

“I don’t even have anything else that comes close to the holy freaking terror of Venice,” she said. “I even had a guy in the (Dominican Republic) try to pick me up off the street and put them on the back of his motorbike.”

The first issue she incurred was her phone’s wifi didn’t work, which she didn’t realize until she got off the train and started walking. She wanted to get to St. Mark’s Square, but quickly learned there were no street signs; instead, street names were “spray-painted on the buildings with arrows.”

“I legitimately thought I was never going to get out of there,” she said.

She found Venetians less than sympathetic to those who don’t speak Italian, and couldn’t find help for the longest time; though she was stopping in every shop along the way for directions. 

It took her 30 minutes to walk from the train station to the Square, but finding her way back to the station took two-and-a-half hours instead. 

“And that was after I had a nervous breakdown,” she said, which she can laugh about now. “I wrote this whole story on how I was going to die. I was like, ‘I need to find a back alleyway to sleep in tonight, I want to call my kids.’ It was horrible. I got back to the train station, I sat there and a pigeon came up to me and tried to take my pepperoni sandwich I said, ‘Pigeon, do you want to die today?’”

She cut her Venice trip short, after being lost and afraid for three hours straight, she decided to just go back to Paris. While Venice was by far the most terrified she’s ever been, she’s found that the “rule of averages” usually plays in her favor.

Like the time she was followed by a group of men in a small alley in Naples, after an Uber driver dropped her off at the wrong location.

“That’s all my conspiracy mind needs to start writing stories in my head about how La-Tessa got kidnapped off the streets of Naples because she was (victim) of some part of this ring orchestrated by the damn Uber guy,” she said, laughing now, though she wasn’t laughing at all at the time.

Luckily the men stopped following her, and she eventually got to where she was going, only to bump into an English-speaking man who chatted her worries away.

“That was like a palate cleanser,” she said. “Normally, after really dark situations like that, honestly something just uplifting tends to come along. I don’t question it, but I’m happy when it happens because (it) puts me in a much better mind frame.”

One time, a bird pooped in her hair, which she had just gotten braided, at the Vatican –– a sign of good luck in Italy, so no one would help her clean it out. 

Through all the good times and the bad, Prague was absolutely her favorite city, without a doubt in her mind. Though, it’s kind of surprising. Just a few months before her trip, she almost cancelled it. Her grandmother passed away, and just a few days after her death, Montgomery’s relationship at the time unexpectedly ended. But determined to keep the promise to herself, she decided to go anyway. While she was there, she learned a lot about herself and the city, despite being heartbroken.

“I was able to just let it go,” she said, referring to crying at a cafe one afternoon. “But after that, I had the best time! I did a photo shoot over there, I got all these pretty pictures of that, (there’s) so much history and I love the architecture and buildings.”

She fell so deeply in love with the city that while walking 14,000-18,000 each day, she actually tore her hamstring. There was a lot about her Prague trip that should have ruined it: from the hamstring, to having a rheumatoid arthritis flare up that had her bedridden for half of a day, “a swan literally tried to drag me into some water and take me away,” not to mention the fact that the thing she wanted to see most, the Prague Astronomical Clock, which has been on her bucket list since she was in the sixth grade, was closed for construction. 

One thing that helped the trip rebound was Prague’s unexpected cocktail scene; and cocktails are one of Montgomery’s favorite things, hence her blog, The Spirited Traveler, where she writes about her traveling experiences and the drinks she comes across. 

“I didn’t want to do food and travel,” she said, “Because everyone does food and travel.”

Not only was she enamored with Prague, the buildings and the culture, but she said it was the safest she had ever felt. She had no problem staying out until 1 or 2 o’clock in the morning, stopping in at various bars and trying new beverages.

“I hate absinthe with a fervor, but that’s what Prague is known for because you know, the green fairy and all the artistic minds,” she said. “And I made myself try it, and that absinthe cocktail? It was one of the best things I’ve ever had in my life.”

Prague also taught her to slow down and sit when she gets tired. She learned that she has to sit down every day around noon, usually at a cafe, maybe with a good book or a glass of wine.

She said these moments of relaxation are what she has missed most about traveling over the past year, and are what she’s most looking forward to when she gets to resume.  

Montgomery Safety Rules

Over the years she’s crafted more or less a list of safety tips. 

Use your intuition.

“I was walking down the street,” she said, painting a picture of Prague. “And something said, ‘Nope.’ Know what I did? I took my butt right back around and walked the other way. And then one time I was walking someplace and I don’t know what happened, I just felt like the world was closing in on me, so I left.”

She encourages people to trust their instincts, despite the little voice in their head telling them they’re overreacting. 

“Don’t think you’re being paranoid or being freaked out,” she said. “If anybody even rubbed you the wrong way, don’t do it.”

Don’t be a target.

Montgomery encourages travelers to avoid looking like a tourist and to dress nicely. It might be beneficial to even research typical fashion in an area, to blend in as much as possible. She’s a big fan of walking around with earphones in without anything playing to discourage people from chatting with her, too.

Don’t carry a lot of baggage.

Wear cross-body bags or purses, keeping the zipper or opening flush to your body and keep your arm over it, in case “they come cut your strap.” 

Never look at a map.

“I hate Google Maps,” she said. “Google Maps is demon seed; but it works really well in Europe.”

Before leaving any location, Montgomery sets her Google Maps to the next destination, then puts her phone in her pocket and doesn’t look at it again. She’s learned that if she uses a combination of earphones — without music playing, solely Google Maps giving directions — plus the directions on her Apple Watch — three vibrations for a left turn, two for a right — she can confidently trust she will arrive safely, without looking like a lost tourist.

Befriend the concierge. 

But “use your judgement,” she warned, “Because you don’t want to get snatched.”

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