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Solo Vacations: Why You Shouldn’t Be Afraid to Take One

June 13, 2018 by Crafty Teacher Lady +

“I love to travel!” In my experience, this a sentiment that many people express but fewer actually take the initiative to plan a trip. Money, time off of work, family obligations, or fear of leaving the comforts of home are usually the reasons that hold many back. For me, it was lack of a travel companion (for all of the reasons just mentioned) that was making me hesitant to take the trips that I’d always wanted to take. But why, exactly, was I reluctant to travel alone? Was I afraid I’d be unsafe? Was I afraid to dine alone? Was I afraid I’d be bored without anyone to talk to? After asking myself these questions I realized, that with proper planning, there really wasn’t any actual legitimate reason I couldn’t or shouldn’t travel alone!

traveling alone

I’ve been lucky enough to have traveled extensively over the years and have taken some smaller road trips within the country by myself, but had yet to travel internationally alone. A few months ago I decided it was necessary for my mental health to escape the long, cold New England winter by heading somewhere tropical over April break. I was also looking forward to having some time to read, relax, and recharge away from my house and the never ending project ‘to do’ lists! So, I booked my first solo international trip to the Dominican Republic!

The Logistics

All-inclusive

Book ground transportation in advance

Look for a small resort

One of my colleagues mentioned she had booked a trip for her family to the Bahamas through Cheap Caribbean so I decided to take a look there as well. Because I was traveling solo, I wanted to stay somewhere all inclusive so I didn’t have to leave the resort for every meal or really for anything at all. I ended up finding a great deal that included roundtrip airfare, lodging, food and drinks at the VH Gran Ventana Beach Resort in the Dominican Republic. When booking the trip, Cheap Caribbean also had the option of paying for transportation from the airport to the resort. I would highly recommend this as it took away any of the uncertainty of trying to arrange ground transportation and traveling alone while in a foreign country. As soon as I left the airport, the transportation company had clearly marked signs and I took a small van with a few others vacationers to our respective resorts. It was really easy, safe, and seamless!

The resort itself was the perfect place for a solo traveler. It was small, which made it feel safe both during the day and at night because I didn’t have to walk a long distance to access the beach, the pool area, or the dining room/restaurants. I spent most mornings on the beach, then after lunch, headed for the pool! There was entertainment at the resort each night, which was right next to the main pool area so again, I didn’t have to walk far alone at night! Choosing a safe place to stay (be sure to read lots of reviews) and planning your transportation in advance will alleviate some of the hesitation/fear that comes with traveling alone.

The People

Vacationers are friendly

Book excursions early

Whenever I’ve traveled alone, there are usually so many opportunities to meet and connect with other people. I have found this to be true on any of the solo trips or outings I’ve taken. It seems that people on vacation are usually very excited and interested in hanging out with people from all over the world- chatting about where people are from and usually finding lots of commonalities. My trip to the Dominican Republic proved to be no exception as I met lots of people from all over. There was the woman from the Bronx who was sharing the shuttle bus to the resort, a mother-daughter duo who I ran into all over the resort throughout the week, the couple I met on an excursion who actually live in the next town over from me in Maine (I’m telling you, it’s such a small world), a group from Germany who I hung out with at the pool, and even a group of teachers from Canada, one of whom recognized me because she follows me on Instagram and happened to be staying at the exact same resort!!

Booking excursions is a great way to meet other people as you are usually put into a small group and are sort of ‘forced’ to talk! It’s even a great idea to take an excursion toward the start of your trip because you could end up meeting a group of people you can then hang out with the rest of the week, if you so choose! I met another woman who was traveling solo who ended up hanging out with a group from Canada for most of the week as they were all on an excursion together and were staying at the same resort. I took a city tour of Puerto Plata part way through the trip and met some really fun people! So, while you may think you’ll feel lonely if you travel alone, you will most likely meet more people than you could imagine, some of whom may become life-long friends and travel buddies!

The Benefits of Solitude

Set your own agenda

Build confidence

Reconnect with yourself



While it’s great to meet new people while traveling and it’s always fun to take a trip with friends and loved ones, one of the benefits of solo travel is you are free to make your own agenda and can elect to NOT talk to or meet other people as well! I decided when I wanted to eat, when I wanted to skip out on the evening entertainment and go to sleep early, what excursions I most wanted to take, and whether I wanted to be on the beach or poolside…I made my own agenda with no one to please but myself!

When I told my students I was taking this trip alone, many expressed that they could never do that because the thought of dining alone and having others ‘judge’ them was too embarrassing (I think they may have some negative school cafeteria experiences)?! I feel like many adults let the fear of being judged by others hold them back from experiences as well. Why not dine alone? Why not travel alone? In my experience, most people aren’t feeling pity for you they are actually envious and impressed with the choice to travel and experience life solo! In fact, whenever I told my colleagues and friends about my solo trip to the Dominican, almost all of them were like “What? That’s awesome! Good for you…I’m totally jealous!!” Not a direct quote, but the sentiment was usually the same nonetheless.

Most people who I met while on vacation assumed I was there ‘with my husband’ (which I guess maybe I should take as a compliment?). I would just politely correct them (or sometimes just nod politely) and go about my business! Dining alone was no problem…I even met a stray cat who I fed some delicious mahimahi (true story)! The other diners were not judging me, in fact I’d say it’s pretty narcissistic to think that in a dining room full of 100+ people, any of them were paying attention to me, so there’s really no need to feel self-conscious. In fact, dining and traveling alone only builds self-confidence!

The other benefit of taking a trip alone is time to read, reflect, and do some things to feed your soul. I chose a variety of books (self-help, memoirs, and fiction) all of which offered introspection and relaxation. I watched the sunset, fell asleep to the sound of crashing waves, and reflected on the goals and dreams I have for my life. I’m not sure one has as much time to do these things when traveling with others. Solitude offers a unique opportunity for calm and connection with oneself.

As I was posting stories from my Dominican vacation on Instagram, I received so many messages from women asking if I was traveling alone (not in a creepy way but more in an inquisitive way), then expressing that they had always wanted to do the same but felt too nervous to do so. I’m truly hoping that you’ve read this post and will feel confident and inspired to book that solo trip! With some proper planning (or even no planning but just winging it if you’re brave like some of my super adventurous friends), the willingness to strike up some conversations with new people, and the desire to reconnect with yourself, you’ll end your trip with lots of new memories and certainly feeling a new sense of confidence! What are you waiting for??

Filed Under: life, Life & Leisure, Uncategorized Tagged With: Travel

Hello! I’m Kelly-Anne!

I’m an avid DIY and home decor enthusiast, wife and new mom, teacher of 15 years, and a Mainer now living on a farm in Virginia. Here you’ll find creative endeavors of all sorts!

Now offering Interior Decorating Services at  Dirigo & Dogwood

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