Solo Travel: How to plan your first trip

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Matt Dawson, Travel Agent in Orlando, FL

Matt Dawson

Orlando, FL Travel Agent
Super Agent

Matt Dawson

Orlando, FL · 6 Years of Experience

Adventures By Matt, an independent agent with WorldVia, a Travel Leaders Agency
5.0
(31)
100% Recommended
He was awesome to work with, very professional and quick to respond when I needed anything. Read More >
About
Reviews
Certificates & Awards
My Places

Areas of expertise

Destinations:

United Kingdom, Thailand, Ireland, Iceland, Germany

Interests:

Adventure, Solo Travel, European Culture

About Me

Matt solo traveling in Asia
Matt solo traveling in Asia

Your first solo trip will be one of the most exciting and rewarding experiences of your life. However, the planning process, in the beginning, can be quite frightening. It's a lot different than taking trips within a group or as a family. Being solo, you are on your own, and in charge of each and every aspect of the trip. You’re probably thinking, “where do I even begin?”

Pick a Destination 

One of the first things you need to do when planning your first solo trip is to choose a destination; better yet, a destination that's right for YOU. YOU are the one taking the trip, go somewhere that will make you comfortable, happy, and safe. While the location and destination you choose should be based on personal preference, there are some places better suited than others, and specific factors to keep in mind, such as: 

  • Language
  • Culture & religion
  • Safety
  • Helpful locals
  • Tourism industry

Keep in mind, your destination can make or break your trip. You want to have a positive and memorable experience on your solo adventure, not one that keeps you stressed or constantly worried. Some of the best locations for first-time solo travels are:

  • United Kingdom
  • Thailand
  • Ireland
  • Iceland
  • Germany
  • Spain 

Get Travel Insurance

If you don’t take any other advice from this list, do yourself a favor and be sure to get travel insurance for your trip. Travel insurance is essential when unfortunate events or accidents occur. Whether you need medical attention, lose your luggage, or if there is a natural disaster or, in previous cases, a global pandemic, travel insurance is really important. World Nomads is one of the most trusted travel insurance companies in the world, with various different plans and packages to suit your needs, from sickness, injuries, disaster, or other mishaps along the road.

Use A Travel Advisor 

Planning a solo trip for the first time, especially with no prior experience or knowledge, can be very overwhelming and cause fear ad stress before the trip even begins. Using a travel advisor to help plan your trip is a great idea if you are a newbie to the solo traveling world. A travel advisor can guide your whole process, book reservations and tours, educate you on safety tips and be a direct point of contact in case something goes wrong. Additionally, they may have direct connections on the ground in specific locations, assist you when flights are canceled, or direct you to networks or opportunities you wouldn't have tried to do alone. 

 

Practice Solo Travel at Home 

Before heading out on your first solo adventure, consider practicing solo travel at home. Take yourself out on dinner dates, walk through unfamiliar parts of your hometown, and take weekend road trips to nearby destinations. Learning to be confident on your own is one of the best ways to stay safe, and learn more about yourself and what you are capable of doing. Once you are comfortable enough with your own company at home, traveling solo in unfamiliar places becomes much easier and more enjoyable. 

Set Intentions & Have Fun

Solo traveling for the very first time is a life-changing experience; anything could happen. Make the most of it while it lasts, set intentions, and have fun. What do you want to accomplish? How do you want to feel? Having intentions will give you more direction, clarity, and purpose, making your trip even more exciting and successful. And above all have fun! This trip is all about you. You are setting out in the unknown alone, ready, maybe a little scared, and excited for what's to come. Smile and be proud of yourself, solo travel is all about the journey. Enjoy every moment.

REVIEWS

Rating: 5.0
31 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 31 reviews

The best trip ever!
Reviewed By Cher - Fircrest, Wa | Traveled to Disneyland ~ California ~ USA
He was awesome to work with, very professional and quick to respond when I needed anything.
I would recommend this agent to my family and friends.
4 of 5 people found this review helpful. Was this review helpful to you?YES|NO
The best first experience in Europe!
Reviewed By T - Phoenix, AZ | Traveled to Germany ~ Europe
Matt was super helpful in helping me plan and prepare for my first international trip! He answered all of my questions and made sure I was fully prepared for my trip. 10/10 would work with Matt again!
I would recommend this agent to my family and friends.
2 of 2 people found this review helpful. Was this review helpful to you?YES|NO
Best Company Trip I’ve Ever Been On
Reviewed By Ana C - Reno, NV | Traveled to Las Vegas | Nevada | USA
From the moment we landed in Vegas, everything felt effortless. Flights, transfers, and hotel check-in were smooth, and it was clear this trip was extremely well planned. The private dinner at Bourbon Steak was next-level — incredible food, amazing service, and such a special atmosphere for our team. Renting out Swingers Mini Golf for the after-party was such a fun and unexpected touch. Huge credit to Matt for creating an experience that felt both luxurious and genuinely fun. He gave plenty of communication about which flight I was placed on along with a detailed itinerary.
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Amazing Holiday Incentive Trip
Reviewed By Lydia.P - Austin, TX | Traveled to Las Vegas | Nevada | USA
We cannot say enough great things about Matt and the experience he created for our annual holiday incentive trip in Las Vegas. Planning travel and events for 80 people is no small task, but Matt handled every detail with professionalism, creativity, and total confidence from start to finish. He coordinated all flights, hotel accommodations, and airport transfers seamlessly, making the entire process effortless for our team. The highlights of the trip were absolutely exceptional — a private dinner at Bourbon Steak that felt truly elevated and special, followed by an unforgettable after-party where Matt arranged for us to rent out Swingers Mini Golf. It was the perfect balance of upscale and fun, and our attendees are still talking about it. Matt was proactive, responsive, and always one step ahead, which gave us complete peace of mind throughout the planning process and during the trip itself. If you’re looking for someone who can deliver a flawless, high-impact corporate experience while making it enjoyable and stress-free, Matt is the person you want. We’re already looking forward to working with him again for future trips.
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Awesome taste of Italy
Reviewed By BV - Pheonix, AZ | Traveled to Italy | Europe
We can’t thank Matt enough for helping make our post-cruise trip to Italy so special. There were six of us traveling together, and he coordinated everything flawlessly—from our car service after the cruise, to train tickets, hotels, and unique experiences like a Vespa tour and a golf cart tour through Rome. The hotels in Rome and Tuscany were beautiful, and every part of the trip ran smoothly thanks to his planning. I have used Matt before and recommend him to my group of friends. We’ll absolutely be using Matt again for future friend trips and recommend him wholeheartedly!
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO

Certifications & Awards

ASTA is the leading global advocate for travel agents, the travel industry and the traveling public.It is the world's largest association of travel professionals.Our members include travel agents and the companies whose products they sell such as tours, cruises, hotels, car rentals, etc.Expand your world. Go with the pros.
The Book with Confidence logo tells you that this Travel Advisor has direct access to comprehensive resources for safe and healthy travel, available at their discretion for sharing with clients.  This includes vetting the details on the health and safety protocols implemented by each travel provider in order to recommend the ideal itinerary for each client’s unique needs.
Trusted Travel Advisor: A Trusted Travel Advisor credentials, resources and global connections translates to today’s consumer in respectful interactions, confidentiality, knowledge, and client advocacy of travel services provided in parallel with building long lasting client relationships that builds with each interaction.  A Trusted Travel Advisor knows their client better than the client may know themselves and puts those polishing touches on each travel collaboration.

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
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