For the 50+ Traveler

Cindi Conley started traveling later in life, which led to her blog Traveling Later. She grew up reading books about faraway places and idolizing a world-traveling uncle. She dreamed about travel and knew her life would evolve around it sooner or later. Her first big trip was to Fiji at 26 but another eight years passed before she left the U.S. again. Now Cindi travels wherever and whenever she can, always looking for five-star luxury on a 3.5-star budget. She's a "check my bag" kind of traveler blogging about making travel easy and falling into the story.

Cindi was kind enough to answer our questions below.

TA: How many years have you been traveling and what got you hooked?

Cindi: I've traveled outside the U.S. for the past 35 years, but early on there were big gaps for things like motherhood and the corporate life. I wish I'd chosen a career that included international travel, because that's what I cared about most in the end. Out of my entire family, only one uncle was a world traveler and I thought his life at that time was magical. I kept a mental vision board alive with books. I knew I would travel some day.

TA: Do you specialize in a particular type of travel?

Cindi: I like to think I specialize in easy travel. I want convenience and comfort bordering on luxury -- ok I'll say it: a lot of LUXURY! Like I said before, I check my suitcase and go without a set itinerary. Instead, I learn as much as I can about a place before I go, creating outlines of days with a lot of alternatives. But, I let the weather, the place, and a little spontaneity dictate what actually happens.

TA: What is the best vacation you've ever taken?

Cindi: Four years ago, my soon-to-be-husband and I spent three weeks in Italy. He'd never traveled to Italy and I wanted him to have the best experience. A lot of pressure! We started in Milan, then to the Amalfi coast for five days. Next, we rented a car in Sorrento drove to Tuscany and stayed in a small agriturismo outside Montepulciano for a week. The car was perfect for exploring all the villages and towns in Tuscany and Umbria. We left it in Florence and hopped a train to Venice. It was romantic, interesting, beautiful, and one of the best trips I've ever planned!

TA: What's one place you've always wanted to visit?

Cindi: Morocco! When I'm daydreaming, I find myself navigating to all things Morocco on the interwebs!

TA: What's one thing you ALWAYS pack when you travel?

Cindi: Snacks that I can eat with my gazillion food allergies. I'll bring enough to carry me through a long flight. Return flights can be challenging, but I can always find something in a local store or airport shop to keep me going.

TA: If you could only give a traveler one piece of advice, what would it be?

Cindi: Bring a portable phone charger. When you're out and about during your trip, and away from adaptors, your smart phone can be your lifeline with either Google maps or a rideshare/taxi app. The last thing you want to have is a dead battery.

Gondolier in Venice.
Gondolier in Venice. Photo Courtesy of Cindi Conley.

TA: What are some of your favorite travel blogs and communities?

Cindi: Wanderful is a great community focusing on women travelers and I also like the NomadicMatt community where I can get great info. I love both The Everywhereist blog and the A Traveling Life blog.

TA: Do you have any good airport or flight hacks for people traveling by plane?

Cindi: Somehow, someway, get to a lounge at any airport you have a long enough layover in that doesn't require a sprint to a new gate. Access is free with some credit cards and it's worth the time to check and see if you have one that will work for you. Quiet, comfy, and free food and drinks! If I'm flying overnight, I always go for the window seat: props up my travel pillow the best.

TA: What is the best piece of travel advice you've ever been given?

Cindi: Get Google Maps set up before you arrive at your destination -- with all the essential sites, restaurants, and museums already laid out. You can create layers in the maps with each category (museums, cafes) and save it on your smartphone. Then pull it up when you're ready to head out for a day of adventure.

TA: Is there something you think most travelers worry too much about?

Cindi: I think most travelers worry too much about things not going exactly as planned. Let it go, let it go!

TA: What's a travel scam travelers should be wary of? And if you've ever had someone try to pull a scam on you while traveling, please share the story!

Cindi: Be very wary when you get off a cruise ship in a port of call without a plan. You'll likely be set upon by tons of locals with as many schemes laying in wait for a likely target to wander off the ship.

Sunset at Roche Harbor, San Juan Islands
Sunset at Roche Harbor, San Juan Islands. Photo Courtesy of Cindi Conley.

TA: What was the most romantic place you ever visited with a partner?

Cindi: It's a toss up between everything at the small, all-inclusive resort of Eastwinds in Saint Lucia and sitting at a table drinking wine in San Marco Square, Venice, at twilight as the lights slowly come on in the cafes around the square and the orchestras begin to play.

TA: What is the most beautiful and affordable city you've ever visited?

Cindi: I have this thing about putting beauty way ahead of affordable on my criteria to sift through places to travel. I think I happened to land in a place that fits both those descriptions when I traveled to Krakow, Poland. A very cute, convenient, and large two bedroom Airbnb cost $45 USD/night there. There's a lot of wonderful Medieval architecture because it avoided Warsaw's fate (bombing) in WWII by being a Nazi headquarters.

TA: What are the best places to travel solo and why?

Cindi: I've only solo traveled during the day. By that I mean when traveling with others, I've taken my own path for the day, meeting up with my companion at night. It was easy to do within many European cities, using walking tours, food tours, and wandering aimlessly. You can always find people who speak english to help if you need it, and you can strike up conversations with others easily when you're on your own.

TA: What's something that other tourists do when traveling that drives you crazy and why?

Cindi: Not being aware of their personal space. Fingernails on a chalkboard for me when someone suddenly steps or stands millimeters from my nose/toes.

TA: What's one piece of advice you'd give to travelers your age?

Cindi: Figure out a way to travel now and not wait for retirement by using all the great travel hacks to save money! And start going to the gym or walking regularly so you can easily navigate on your travels.

Learn more about Cindi:

Visit her website Traveling Later.
Follow her on Twitter here.
See her photos on Instagram here.
Read her CV on LinkedIn here.
Or connect with her on Pinterest here.