Solo Travel Trip Planning Detailed Guide for Planning a Solo

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solo travel trip planningGoing somewhere? Here’s how to plan your solo trip.

You may well be the ultimate travel planner, perhaps you prefer an organized tour, or maybe you just like to go, wander and see what happens. Regardless of your travel style, some solo travel planning is a good idea.

Planning a solo trip may require more attention than any other kind. After all, it’s all up to you. So, for your own safety and peace of mind, it’s good to have some planning done in advance.

I like to have some planning done but not too much. I like to have a general knowledge of where I’m going and why. I like to have my first night and possibly more booked. But the details of what I’ll do is pretty well left to the whims of my mood and recommendations from people I meet along the way.

This post is for both independent solo travelers and those who prefer taking an organized tour or cruise. It assumes that you know where you are going and why and that you’re ready for the planning stage. If you haven’t yet decided where to go please have a read of Best Solo Travel Destinations: All Solo Traveler Tested and Best Budget Destinations for Solo Travelers: the 2020 Shortlist.

solo travel budget trip planningClick here to get a Travel Budget spreadsheet.

Table of Contents

Trip Planning? Start with Your Travel Budget

Travel, money and happiness are connected.

According to happiness theory, when money is spent on travel happiness grows over time. However, when money is spent on things, the happieness from the expense tends to diminish over time. So, yes, it’s a good idea to spend your money on travel but it’s advisable that you have your budget planned and money saved before you go.

Rather than rewrite all the budgeting tips I have for you, please check out this post on how to set your solo travel budget. In this post you’ll learn how to create a budget for any trip and how to plan a trip based on the reality of a tight budget. Then it gets into the details of budgeting.

But getting back to happiness, if you pay for your trip on a credit card, try to pay off the card before you leave. This approach to money not only relieves painful money woes after a trip (which often negate some of its joy), it also makes the anticipation of the trip that much sweeter.

Save it for later on Pinterest!solo travel planningCome and go as you please from the ship-just make sure you’re back well before departure time.

Solo Travel Planning is Affected Your Travel Style

There are two main ways to travel solo: independently and on an organized tour. Ah, but within those categories there are many options as well.

Independent travel can be placed in many categories. Here are a few for you to consider.

  • On the Move, short term. My rule of thumb is a minimum of three nights per location. Any less and it’s just too rushed. Longer is better. For example, on a 10-day trip you can cover three destinations. With more time you can cover more. For details on planning your trip read
  • On the Move, long-term. Long-term travel can be anywhere between 3 months to forever. The pace of long-term travel needs to be somewhat slower than short-term travel. Otherwise, it can be exhausting rather than exhilarating. Read Solo Travel for a Career Break: Tips and Resources for Long-term Travel.
  • Hub & Spoke travel. In this style of travel, you settle into one place for your accommodation and use it as a base from which to explore. Your accommodation is your hub, all the places you want to visit from your hub are your spokes.
  • Slow travel. In slow travel, you really sink into a location. You get to know the rhythm of a place and visit the same stores and coffee shops on a regular basis. People start to recognize you and take time for a chat. It’s deep dive travel. Read Slow Solo Travel: Connecting to Yourself and the World.

Organized Travel comes in many forms. The caveat with all organized travel is the single supplement. To avoid the single supplement, use our Deals page and read 10 Tips to Avoid the Single Supplement.

  • Escorted tours. On an escorted tour, you and 10-30 other travelers follow a guide and a pre-planned itinerary. It’s an efficient way to travel and see a lot and ensures that you have companions along the way. Read how to choose a solo tour.
  • Resorts. Relaxation is what resorts are known for, however, they can also be used as a base for exploring an area in a similar manner as Hub and Spoke travel. Read Alone at an All-Inclusive: 10 Tips for Going to a Resort Solo.
  • Self-guided. On a self-guided tour, everything will have been organized for you but you still travel independently. These are great for walking or cycling tours as not only will everything be booked for you but your luggage will be moved for you as well. Read Travel Solo on a Self-Guided Walking Tour: Seeing France Slowly.
  • River cruises. River ships tend to be smaller than ocean cruise ships and, as a result, somewhat more friendly to solo travelers. It’s easy to get to know people and have alone time. Read Solo on a River Cruise: Enjoy Both Social and Alone Time.
  • Ocean cruises. The ocean cruise companies have turned their attention to the solo market in recent years. While the norm is to charge 100% single supplement, if you play with your dates you can usually get a very good deal.
  • Untours. This is a more recent entry into the organized travel market. The untour is planned for you–hotels are booked, pick up and drop off at airports are organized, an introductory tour is given, and optional tours are available– but you travel on your own. Read Rome & Paris the Easy Way.

The Lake District of England in the fall may mean more likelihood of rain but it also means lower prices and less people on the paths.The Lake District of England in the fall may mean a greater likelihood of rain but it also means lower prices and fewer people on the paths.

The Question of When

Because you’re traveling alone you don’t have to accommodate other people’s timetables when planning a trip. This can be to your advantage because when you travel will affect how much your trip will cost, how busy your destination will be with other travelers and what the weather will be like. While the weather will probably be a compromise you’ll likely win financially and encounter fewer crowds if you go in the shoulder season.

According to our 2018 Reader Survey, the most popular months for solo travelers to travel are October, September, May and April. Read: How to Save on Shoulder Season Travel: Top Tips.

solo trip planning organizationPinterest is a great place to research travel and to organize the information you gather. You can follow Solo Traveler on Pinterest here.

Trip Planning is Best When it’s Organized

The research stage of trip planning can be a lot fun but you can also be swamped with information. Whether you like to work on a computer, on paper, or use an app, find one place where you’ll keep all the information you gather on the trip you’re planning. See an interesting article on the web? Add it to your file so that you’re able to find it when you’re ready. There’s nothing more frustrating than knowing you’ve seen exactly the information you want and not being able to find it again. So, step 1, set up a place to store your research in whatever format works for you.


  • When you rip articles out of a magazine, you may put them in a file or pin them on a bulletin board. Pinterest is like a pin board for saving articles you find online.
  • Create a free Pinterest account.
  • Create a board for your destination.
  • Search Pinterest using the name of your destination and perhaps the time of year, the type of things you want to do or places you may want to stay at. If you come across an interesting article, pin it to your board.
  • Create a second board for your destination and call it “Destination other possibilities,” or something to that effect.
  • Go through you first board and move anything that is not really valuable or high on your list to that second board.

Your desktop.

  • Open a bookmarks folder in your web browser and a file folder on your desktop for storing all online information you find on your destination
  • Make subfolders if necessary for things like accommodation, things to do, restaurants, clubs, etc.
  • Get a portfolio or actual paper file folder where you can keep hard copies of the most important information you find online as well as articles and brochures you’ve collected.

The view of Sedona from Airport Road. I took this on my Arizona road trip.The view of Sedona from Airport Road. I took this on my Arizona road trip.

Solo Travel Planning: How to Get There

Planes trains and automobiles. I’ve done them all.

How To Select A Flight

Everyone has their favorite OTA site (Online Travel Agent) for booking flights. I use Skyscanner and Flightnetwork. Here’s my optimal booking process.

  • I check Skyscanner and Flightnetwork for the best deal I can find.
  • I choose the option that best suits my schedule and involves only one airline unless, of course, the price difference is more than I’m willing to endure.
  • I then check with that airline for the same price or sometimes better and book directly with them

There are two reasons for giving preference to booking with the airline directly.

  • If there’s any issue after booking, it’s much easier to deal directly with the airline than with an OTA website that is an intermediary. The OTA may have additional fees as well.
  • If getting to your destination involves a more than one flight, the airline takes more responsibility for delays and missed connections than if you’re connecting with another airline.

If there’s a significantly better deal that involves a number of airlines, I will book with Flightnetwork. Read Save on Flights: Booking Tips, Stopover Deals & Bumping, Checked Baggage: Top Planning and Packing Tips, and  Make Flying Easy: 32 Tips.

How to Book a Train

Trains and how they are booked vary greatly from country to country. The number one tip is: book in advance. Booking early can usually save you quite a bit when taking the train. Depending on the country you’re in, there may be standard savings for booking 7 or 30 days in advance. They will sometimes have sales as well. However, if you’re not under severe time constraints, local trains may be a cost-saving option.

Read Train Travel: Best Way to Book Tickets – Europe, British Columbia by Train: Budget or Luxury. It’s Your Choice, and A Blues Highway Itinerary by Train.


Oh, how I love a road trip! But taking a road trip alone does require some planning. A Road Trip Alone: Top 10 Tips to Prepare is consistently one of our most popular posts on Solo Traveler. Check it out for details.

solo travel planningThis was my lovely room at the Drysdale Guest House in the Lake District a few years back.

Planning Where to Stay

When you’re not sharing a hotel room, the price can seem very high. Accommodation can be a big-ticket item for solo travelers. Here’s some advice.

  • Check out at least two hotel booking sites. I’ve had most luck with Frommers tests the hotel sites every year and consistently says the is #1.  Trivago ranked #9. Yes, you can’t believe what the ads say. ranked #8. However, that’s not to say that another site won’t have a better deal on occasion. I check two sites before booking and go with the less expensive one. If you have a loyalty program with an OTA or a specific hotel chain you may be better off booking directly with them.
    • A note about – Most hotels on give you the option to cancel a number of days before your arrival. I always check the cancellation policy as a few hotels don’t offer this service. I’ve never been caught but I don’t want you to be either. Also, if you book through our link, you’ll be supporting Solo Traveler. You’ll pay the same but we’ll receive a small commission.
  • Consider a resort, apartment or home rental through VRBO or Airbnb. I have found some great options on and Airbnb. You can read about it in the post about Kauai mentioned in the next bullet and in Discover Canada: 60 Tips to Plan Your Solo Adventure.
  • Review our recommendations for certain destinations. Check out Best Places to Stay in London: Accommodation for Solo Travelers, Budget Accommodation in Kauai: Four Ways to Stay, and all our 32 tips posts on the more expensive cities: New York, Paris, Sydney.
  • Use Google Streetview. To get a ground view of your accommodation and what’s nearby. To use Google Streetview:
    • Open Google Maps and put in the address of your accommodation.
    • In the bottom right, click the yellow Pegman. Then, drag Pegman to the area you want to explore.
    • Unclick to drop Pegman on a blue line, blue dot, or orange dot on the map.
    • When you’re done, go to the top left and click Back .

how to travel alonePlanning an itinerary is important so that you have enough time to relax, learn, explore…

Plan Your Itinerary

Below you’ll find generic advice for solo travel trip planning for just about any destination. However, it’s worth having a look at our in-depth Destination Tips posts which have very specific advice, including free and low-cost tips, for the following destinations:

  • Canada – Toronto, Cape Breton, Nova Scotia, New Brunswick, Whistler/Blackcomb, Prince Rupert,
  • Europe –  London, Paris, Northern Ireland, Dublin, Bologna, Italy
  • United States – New York, Chicago, Nashville, Kauai, Hawaii
  • Elsewhere –  Sydney, India, Japan, China, Patagonia, Chile,

Now, here’s how you focus in on your actual itinerary.

  1. Do basic research.
    1. Review the itineraries of a number of tour companies. Doing so may entice you to go with a tour company. If so, read Solo Travel: 10 Tips to Avoid the Single Supplement and check out our Deals page. If you want to travel solo independently, use tour sites as part of your research. You will learn what route most companies take, how much ground they cover in a day or a week and what your destination costs are at the high and low end. But remember, as an independent traveler you won’t be able to cover as much ground as you do with a tour company.
    2. Decide what you must see. The itineraries of tour companies will usually hit the highlights but reading websites and blogs will help you find the less common must-see sites, restaurants and activities at your destination. Have a look at the destinations section of Solo Traveler. Most of these posts were written by readers excited to share their experience with you.
    3. Use This is a fabulous site for determining how to get from one place to another. Whether you’re hopping to a different country or just want to get to the center of a city from the airport, it has the information for you in terms of time, money, and all possible modes of transportation. I use this resource all the time.
    4. Study maps. Whether you’re planning to walk in one direction for five days or take on a city like New York, study a good map to develop a workable plan for the time you have available and what you want to do.
  2. Plan an itinerary. This is the most difficult part as it includes where you’ll go when, how you’ll get there and where you’ll stay. I would never suggest for a minute that your itinerary be set in stone. I like to be flexible but there are some basics that need to be in place in order to get the most out of a trip of a few weeks.
    1. Set your own pace. Whether I’m traveling by train or car, I like to plan at least three nights in every location. This gives me at least two full days to explore. Even if travel time is only a half-day, less than three nights just makes trips too rushed for my liking. Consider what pace feels right for you. Then you’ll be able to begin to sketch an itinerary.
    2. Consider a hub and spoke itinerary. This is where you stay in one location for your entire trip and take day trips from there. This is what I did in Bologna, Italy. It’s a great city and was the perfect place from which to visit small villages as well as Florence and Venice.
    3. Integrate your priorities. Once you have a general itinerary, integrate the must-see sites you’ve already identified. Then see whether it still makes sense.
    4. Take advantage of freebies. Read Solo Travel with Fabulous Travel Freebies and learn about:
      • Greeter programs
      • Free walking tours
      • Backpacker’s tours (often cheaper, smaller and more fun)
  3. Organize the logistics.
    1. Decide how you’ll move around at your destination. is good for this as well. You’ll want to think about how to…
      1. Get to and from the airport. If you’re flying in you’ll have to get yourself to and then from the airport. I usually take local transit and do very well – everywhere that is, except for my hometown. Toronto’s transit to the airport is terrible. But, in London, England and in Santiago, Chile, in Nashville, Tennessee and New York City, I’ve found local transit great for getting me into and out of the city.
      2. Travel within a city. How does the local transit system work? What does it cost? Should you use it at night or should you budget for taxis. How expensive are the taxis? I usually save a lot of money by using local transit.
      3. Travel between towns/cities. Intercity transport is often buses or trains.
  4. Plan to pack right. I’ve met many a traveler with luggage regrets because they packed too much. If you have a lot of bus-to-train-to-plane logistics, a backpack is likely a better choice than a roller bag which suits me on most trips. A backpack lets you have your hands free. Whichever you choose, packing light is important. Here’s a link to Bare Minimum Packing that includes a packing list and Bare Minimum Packing: Urban and Luxury Travel. Also, about a week before leaving I add my destination to my weather app on my phone and track the forecast so that I can pack the appropriate clothing.

Taking a cooking class is one way to have a great few hours, meet new people and, often, have dinner.Taking a cooking class is one way to have a great few hours, meet new people and, often, have dinner.

Where to Eat as a Solo Traveler

Whether you’re a utilitarian eater like myself or you travel to enjoy the flavours of the world as Tracey does, here are some tips on where to eat.

  • Choose a restaurant and eat at the bar.
  • Take a cooking class where everyone shares a meal at the end.
  • Find a chef’s table.
  • Choose the lunch hour for a fine restaurant for the same executive chef’s influence but a less romantic setting and a less expensive menu.
  • Dinner with a local through sites like VoulezVousDiner or EatWith.
  • Join a foodie meetup using for your destination city.

For more details here are two posts full of ideas Eating Alone is Easy When You Know How and Solo Travel: You Don’t Have to Eat Alone.

Trip Planning for Solo Travel Safety

  • Plan to stay in touch. For safety reasons and for the peace of mind of friends and family, it’s especially important to stay in touch when you travel alone. There are many ways of doing so, each depending on where you are traveling and your access to data through your phone. I often travel with a skyroam. With a skyroam you cross a border and your access to the Internet (within a few minutes) crosses with you. You don’t need to mess around with SIM cards and unlocked phones. It’s super easy and relies on the same data networks that are used on phones. But I don’t always use skyroam which costs $8/24 hours. I use a lot of free WiFi options as well. Read: Use Your Phone Anywhere in the World: Free and Low-cost Options
  • Definitely get travel insurance. I consider this an absolute must. For an explanation of what solo travelers should look for in travel insurance read: Going Alone? Travel Insurance is a Must.
  • Plan to keep your identity secure. Using free WiFi is great for regular surfing but you certainly don’t want to book accommodation or bank online with it – unless, of course, you have a VPN. In addition to protecting your identity, at my last test (September 2016), StrongVPN allowed me access to my Netflix account when I was out of the country. Not all VPN services can do this. We have a discount code for Solo Traveler readers. Read VPN for Travel: What, Why and an Easy Setup Guide for details.
  • My favorite travel apps. There are many, many apps you can use for travel. Read 5 Top Travel Apps Plus a Few Essentials for Every Trip for a few more.

If money is your obstacle, consider going to a place that is inexpensive. This ashram in India was about $20 per day for food and accommodation. The flight was expensive but at that daily rate a two-week trip could come in just slightly under $2,000. This is Anand Prakash Ashram in Rishikesh.

Getting Past the Obstacles for Solo Travel

Who among us has unlimited funds, unlimited time and no responsibilities? Who can travel anywhere, anytime, for any length of time and as luxuriously as desired? A rare, rare person to be sure.

When it comes to trip planning, most of us have to be realistic about our limitations while pursuing our travel dreams. To successfully balance life and travel, here are three different approaches to trip planning. One of these may be right for you.

Don’t Have Enough Time for Travel? Here’s What You Do.

Time is a huge issue for most people. We live in busy times. With mobile phones, social media, and texting we are (if we allow it) accessible 24 hours a day, seven days a week. By nature, most people will fill all the time available. If a responsibility falls off, we’ll replace that commitment with another.

So how can you deal with the issue of time if you want to travel? It’s all about setting priorities and designing your travel to fit your lifestyle. When the issue is time, travel will fall into four possible categories.

  • staycations
  • micro-vacations
  • short getaways
  • a week to yourself

When planning to travel, start with the category that fits your life. Then choose destinations that are appropriate. Staycations cause you to approach your town as a tourist. On a micro-vacation you might get out of town for an afternoon. A short getaway may mean going only a few hours away, whether by car or plane, for a weekend. And, if you’re lucky, you might get a week away. Maybe you’d prefer to travel longer, but it’s not always possible within our personal constraints. The bottom line is that you may have to save your bucket list destinations for when time is less of an issue.

Read:  When Travel Is the Goal, Not Destination

Don’t Have Enough Money for Travel? Here’s What You Do.

Money is a challenge for many people but unless you are in very serious financial difficulties, it should be one that you can get around. There are three possible ways:

  • Save to take your dream trip.
  • Choose a trip that matches your budget.
  • Schedule your trip when the prices are lower.

Let’s talk about saving for your dream trip first. It can take time. It requires delayed gratification – not something that our credit-laden society is particularly good at. But it can be very sweet to reach your dream destination this way. Research shows that the satisfaction of having saved for a trip, the planning time that this allows, and the lack of stress from not being financially in debt after the trip, all contribute to getting more happiness from your travels.

Of course, the second way to deal with money issues is to travel to destinations within your budget or at a time that makes a destination within your budget. Consider:

  • Places you don’t have to fly to.
  • Destinations that are less expensive such as South America or Southeast Asia.
  • Traveling on the off or shoulder season.


Too Many Responsibilities for Travel? Here’s What You Do.

Personal responsibilities are a more difficult challenge than either time or money. Family or work commitments can definitely get in the way of travel. But it’s important to remember that you will live up to those responsibilities better if you are a happy, satisfied person. So set aside any guilt, make yourself a priority, and plan the solo trip you want.

Once you have your head around the balance of your travel desires and your responsibilities, communicate clearly with family, friends, and work to negotiate your personal time and travels. Be confident that taking time for yourself is good for everyone.


For every trip, check out our Trip Planning Resources page. It has the recommended links above plus many more.

Last updated: 3rd March, 2020


Categories: Jaipur


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