The Year of Traveling Fearlessly: Planning Your First Solo Trip

January 29, 2016

Traveling Fearlessly, Solo TravelThis year I want to encourage everyone to travel solo, and this is why I am introducing a new monthly series on traveling fearlessly! The main focus will be on solo travel, but may also include general travel tips. I have lots of ideas for posts lined up, but I want to hear what you guys want me to write about. What questions, concerns, fears, etc. do you have about solo travel?  Leave me a comment or email me! I will be going in-depth on what my tips are for successful solo travel and tell you some of the mistakes I have made while traveling solo. So let’s get right into it with the first post!

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Planning Your First Solo Trip

You have finally decided to go on your first solo trip! You may be excited, but also nervous. By doing some planning, you will erase some of those fears and enjoy the trip even more. Here are the steps to planning your first solo trip.

1. Decide on how far you are comfortable going. Not every trip needs to be an international trip or even a trip that involves plane travel. The first trip should be about making yourself comfortable with the idea of solo travel, not an epic adventure. Are you willing to go 50 miles, 100 miles or even further? I would suggest this trip be at least an overnight trip, though. This way, if you are nervous about staying alone, you only have to worry about one night. This will be great practice!

2. Pick a destination.  Once you have decided how far you want to go, look to see what destinations are within that area. Maybe there is an interesting historical site or a museum there you want to visit. Pick something in a place that you really want to see. This will help motivate you to go there.

3. Decide on a budget and length of the trip.  Now that you have picked a destination, you should decide how much you want or can afford to spend. This will help you decide on accommodation, meals and activities. If you have decided to stay more than one night, then you can decide on a length of the trip based on your budget. You should consider the cost of transportation, fuel, meals and activity costs.

4. Make an itinerary. Plan each day of the trip, including travel days. For the travel days, plan where you might stop to eat or get fuel, if you are driving. If you are flying, decide how you will get to your hotel from the airport. Then plan what you want to do on what days. While some people, like me, are not big planners, I think for first-time solo travelers, having a plan calms the nerves. Don’t plan every minute of the day, but have a general idea of what you want to see and how long it will take. Plan where you want to eat for your meals. This will lessen the anxiety of eating alone as you can walk confidently into a restaurant and ask for a table. If you vary from the plan, great and if you aren’t comfortable, you can always go back to the plan!

5. Make a plan for emergencies. The chances of something happening to you on a trip is rare. I haven’t had a true emergency on any of my travels. But it is good to decide in advance of what you will do if something does happen. This way you won’t worry about it and in the unlikely event something does happen, you will be calm because you are prepared. Tell family or friends where you are going, where you are staying with contact details and how long you will be gone. Find out where the local pharmacy and hospital is in case you need them. Make note of your hotel address if you are out and need to get back in a taxi. If you have been brave and gone to a foreign country, have the hotel write down the address in the local language. Have a backup credit card and leave some cash locked in the safe in your room in case you lose either one. (This has happened to me. Lost one of my credit cards on my first day in Rome, but had another one, so no big deal!)


These are the basics. I will go more in-depth about several of these topics over the year. If this has inspired you to go on your first solo trip, please let me know! I would love to hear about it. If I get some great stories, I can share them here on the blog (with your permission, of course.)

Friday Favorites will return next Friday. The next post in the Traveling Fearlessly series will be posted on the last Friday of each month. Again, if you have questions you want me to answer regarding solo travel, drop me a note or leave a comment!

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  • Reply vinneve January 30, 2016 at 10:48 pm

    It’s a must to have travel insurance too for overseas travel 🙂

    • Reply Tiffany January 31, 2016 at 6:31 pm

      For some yes. Some people’s companies have coverage and some people’s regular insurance covers them. Always good to do your research! But good tip.

      • Reply vinneve February 5, 2016 at 1:41 pm

        You gave me an idea thanks! I have asked hubby to ask about our insurance if this will cover us traveling 🙂 Last time I took out travel insurance which was worth the effort as PD went to hospital for an overnight stay.

        • Reply Tiffany February 7, 2016 at 8:55 pm

          It is definitely worth asking. That is not fun! I am glad that you had the insurance then.

  • Reply Lauren N Bridges February 2, 2016 at 4:59 pm

    Hi Tiffany! Great post, and I look forward to reading more in this series! I enjoy solo travel, but the one thing that holds me back from certain trips is the fact that I am a female, traveling alone. This is something friends andand family express concern for as well. I’d love to see a post on traveling fearlessly as a girl, alone, with her passport. 🙂

    • Reply Tiffany February 3, 2016 at 9:08 am

      Hi Lauren! Thank you. I am so glad you enjoyed it. I will be covering traveling alone as a woman. I will also talk about making your family feel comfortable with you traveling alone. Thanks for the ideas and I hope you will send more questions.

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