Planning Your Solo Vacation: Getting Started

Congratulations!  You’re ready to get started on your solo travel journey.  Welcome to the club.  It’s filled with amazing, friendly, adventurous, vibrant fellow travelers.

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First things first, you have to decide on the where, when and how.  Don’t worry though, I’ve got tips and tricks for you.

Choosing When

This may seem out of order, but when planning your solo vacation, you need to determine the length of the trip and when you want to travel first.  This will help narrow the where. 

If your schedule is flexible, you can do this the other way around, but with work vacation time and life obligations, few people have that luxury.  Since it’s more common to have the dates determined first, we’ll start with the when.

Length of Time

How many days do you have available for travel?  It’s okay if you only have a rough idea.  There’s a big difference between 5-7 days, 7-10 days, and 14 days.  Knowing your general parameters is the important part.  

When can you go?  This could be a specific date, month, or season.  Are you looking at a week beginning November 4, sometime the month of November, or anytime in the fourth quarter?

Now that you’ve got an idea of the when, let’s narrow down the where.

Choosing Where

I know, you’re thinking “What about my budget?”.  That’s coming up, but first, get inspired by looking at the options available.  You’ll be surprised at how you can modify a trip to meet a budget if you have your heart set on a location.

Be Inspired

One of my favorite tricks is to visit travel company websites to see the tours they offer.  Their sites are filled with inspiration.  

Agencies usually also have previews of the itinerary to help show some of the must-sees in the area.

You may find a location that didn’t occur to you when you started to plan your solo vacation.  It’s also possible you realize there are cooking tours in China or adventure kayaking tours in Mexico that you didn’t know about. 

After a bit of looking, you should start to think about what type of travel you would like and then the location.

Location Tips when Planning Your Solo Vacation

Best Times to Travel

Be sure to look at the best times to travel at a location.  This is why knowing the When is so important. 

As an example, Antarctica tourist season is during their summer months of October through March.  If you only have May available, you’ll want to choose a different destination this year. 

Length of Time Needed to Truly Experience a Destination

The other reason using an agency site is helpful is that you’ll begin to see how long you would need to truly discover a destination.  If you only have 5 days, the Galapagos may not be on your list this year.  Don’t forget to add travel time into your timeline (but we’ll cover this a bit later). 

Once you have a few destinations and ideas identified, hit that search button in your browser.  Check out articles from bloggers and online magazines.  See if certain ideas continue to pop up. Usually, a pattern will start to emerge.

Additional Travel Information for a Destination

Before booking any travel, check the US State Department website. You want to check on safety or any notices for that destination and if there are requirements other than a passport to enter.

This is crucial since some countries require additional paperwork or fees that must be purchased ahead of time.

Now that you’ve narrowed down the location, it’s time to consider your budget.


There’s no getting around it, budget is important. You also have options on how to book your trip.

Planning Your Solo Vacation on Your Own vs A Travel Agency

This is the point where you have a choice to plan the trip on your own or use a travel agency. Check out our article on advice for when using an agency may be a better option.

If you’re using an agency, you may still need to determine additional costs for getting to the location and any excursions not included. They may have additional day trips you can add on, or you may opt to stay at a location longer than the trip. These are costs you’ll need to determine.

If you’re planning the trip on your own, it can be a bit frustrating and difficult to get an exact cost upfront. That’s okay at this stage. All you want to do is get a ballpark.

Getting there

Are you driving, flying, or taking the train?  Look at the overall costs.  If you’re driving, don’t forget to look into any associated parking costs as these can add up. 

Right now, you’re just trying to get a feel for expenses, this isn’t the time to try and secure the cheapest ticket.  You’ll look for those when you go to book the tip. 

Your goal at this stage is to asses if it’s a $500 trip, $1000, or $5000.   Any savings you can secure later are just icing on the cake.

First, check on flights.  You can use a basic website like Expedia for this.  Remember, you’re just looking for a ballpark on the usual price.  It’s also important to see when the flights leave, what layovers are required and how much time it will take to arrive.

If you live near a major airport, this may not be a concern.  But if you’re flying out of a local or regional airport, there could be 1 to 2 layovers that take most of the day.

Are there extra days needed to accommodate flights and will this affect your trip? If the answer is yes, you may need to see if you can alter the itinerary, or if you will need to rethink the destination. 


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Here again, you can use a major website like Expedia, TripAdvisor or Airbnb to check on accommodations in the area. 

What type of housing is available?  What is your preference?  Do you like a shared room Airbnb?  Would you prefer a place to yourself?  Hostel?  Hotel?  Do you want room service and a restaurant? 

Consider your needs and look at the options.  Don’t forget to check a map and see if the location is where you want to be.  Do you want to be in town or have the quiet of an outside area?  Is transportation going to be a concern?

If you’re staying 30 minutes from the area you’ll be spending the most time visiting and you don’t have a vehicle, transportation costs could add up. 

TripAdvisor is a great place to get ideas on convenience and noise.  Do your research.


You’ve got your location, you’ve figured out the basic cost, and you have an idea where you want to stay.  Now, what do you want to do?

This is where travel blogs and TripAdvisor can come in handy.  See what others have done and if there are patterns.  Does everyone like this one attraction?  Are there some ideas that aren’t commonly mentioned but intrigue you?

Don’t forgo something just because it’s popular.  There are reasons some attractions are common and touristy.  Would you go to England and avoid Windsor Castle or The London Eye?  Probably not. 

But maybe there are a few things that appeal to you not on the common tourist list.  It’s your agenda.  You get to do what you want.

Check on admissions, hours, and any particular rules for attractions.  Begin to put together an itinerary based on location and how much time you feel you will need at each location.

Based on my experience, give yourself a little wiggle room.  Don’t forget to schedule time for food!  I’m notorious for forgetting this.  Trust me, you need time for food.

Planning Your Solo Vacation – The Agenda Begins to Come Together

You should start to see the agenda taking shape by now.  Things are looking great!  You’re getting excited about the trip.

Take another look and see if you have friends, colleagues, or relatives that have been to this particular destination.  Have them take a look and offer suggestions. 

Finalize the Cost

Now is the time to check on cheap flights, hotel deals, and coupons.  You know the cost of the trip and any savings you can find are just icing on the cake.

When booking flights, check sights like Expedia, Google Flights, Momondo, and don’t forget the airline sites.  I have gotten better deals directly from an airline before. 

When booking your accommodations, think of ways to save. Do you have hotel points?  Can you cash in credit card points?  Check online for coupons.  If booking a hotel, check their site directly as well as booking sites.  Make sure you’re clear on any cancellation policies. 

If an Excursion is popular, you may want to go online and see if you can get a ticket before you leave.  Don’t do this for too many outings though, or your schedule can become less flexible. 

When you Arrive

Upon arrival, talk to your Airbnb host, or the hotel staff, see if they have ideas.  Also, check out any Visitor Center since they often have coupons you can use. 

Most importantly, go with the flow.  If your itinerary starts to fall apart because locals are telling you there’s somewhere you have “just got to see” and this other item is “super touristy”, roll with it. 

At the end of the day, maybe you want to go to the touristy place.  Perhaps Stonehenge is a bucket list item.  That’s okay. 

If you find yourself enjoying the local ideas, then go with that.  I had my entire itinerary fall apart in Savannah, but it wound up being one of my favorite trips. 

When traveling, you can’t go wrong.  It will always be an experience.  Some good, some bad.  Always something to write home about.

Have Your Itinerary and Other Information Available

I like to keep a paper copy of my itinerary, but I’m a former Project Manager and can’t help myself.  I like to note the date and time and what I’m doing. 

Also included are addresses. I note things like where a tour is meeting, the address for a museum I have a ticket for, as well as any notes. If I’ve already purchased a ticket, I have a printout ready. 

This may seem like overkill, but I’ve had electronics fail me, so I like paper when traveling.  There’s nothing worse than having no signal and your phone is refusing to locate the email with the ticket and bar code.  Good times. 

Final Thoughts

Planning your solo vacation, realize that there are so many places to see and so many ways to travel, you can’t possibly do them all.  Be inspired but realize there’s no wrong way to travel.

My one piece of advice is don’t try to shove too much into a trip.  It’s better to have a relaxed and enjoyable experience than rush from one location to another so you can “see it all”.  I’ve forced a 7-day trip into 4 days before and it wasn’t fun. 

If you really want to do it all, schedule more time, vow to come back, or put this particular destination on the “next time” list.

As long as you’re true to yourself, or willing to stretch out of your comfort zone and laugh about things, you’ll have a great time. 

Happy Travels!

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