Single Travel In Retirement – Consideration and tips


By Louis Horkan
Reviewed by Nathan Kattner

Table Of Contents

    Solo travel sounds like a dream of a lifetime. While it can be, it does involve smart planning, which can make all the difference in terms of the experience you can expect it to deliver.


    You’ve definitely seen movies and probably heard stories about characters or people you know setting out on their own to travel to far corners of the world.

    Some are wonderful and inspire you to set out as soon as you can to create your own adventure.

    Who can forget “Under the Tuscan Sun?” Or how about “The Bucket List?” Wasn’t exactly solo, but it was two peeps who hardly know one another who set out for ultimate adventure.

    Or the people in our own lives? Like the guy who decides to sell his own company while still relatively young so he could go solo, sailing around the world on his beloved blue-water yacht. (That’s a true story involving one of my own family members. Spoiler alert: ended up being a 20-plus year amazing adventure)

    Others though…not so much. You can fill in your own nightmarish solo travel movies…there’s plenty.

    Whatever the case, often the outcome is a direct result of planning and making good decisions in advance. Or not…

    Today we look at important tips and strategies to take into consideration if you’re thinking about getting away on your own to satisfy that long-standing itch for solo adventure.

    Travel today is different – it can be easier

    In terms of differences, the biggest is the amount of information and services that are available at the tip of your fingers.

    You can look up all kinds info on almost any place in the world to learn all you might want, in mere seconds. This includes stories and experiences and ratings from others who’ve visited, as well as things such as best value or cheapest restaurants and accommodations, things to do, where to avoid, and more.

    You can also learn what’s required, such as documentation needed. This can include things like travel visas, passports, shot records, masking requirements, et. cetera.

    You can also get airline, auto rental, train, and housing or hotel accommodation info in a flash. And book those things instantly. Also book your tickets for events, sporting matches, tours, museums, galleries, and more.

    In the past each one of these things was time-consuming and far from easy to accomplish. And often much more expensive. Given competition and price transparency via the web, you can now be an informed customer and can select the best options for you and your schedule at the best prices available.

    Ultimately, just as in your retirement planning, information is empowering, so the more informed you are, the more likely you are to make a good decision.

    Assess yourself

    You should do a self-assessment.Let’s face it, there a places that are well-suited to who you are as a person and others that are not.

    In order to start the process of determining whether you will be comfortable doing solo travel and where you might want to go, you should do a self-assessment.

    Start with your physical health. Are you able to walk more than very short distances? And do you want to do so? How about hiking? If the answers to those questions are no, then you need to avoid travel opportunities requiring such activity.

    What about general mobility? Do you require the assistance of a device to get around? Are there other health issues and conditions, dietary concerns, et. cetera? If so, hitting a tropical beach will be more difficult. Otherwise, there are plenty of places you can visit, but it’s probably best to do so with a companion.

    Then there are practical issues, such as languages spoken. If the population in the area you wish to visit primarily speaks little English, travel could be tough on a solo basis. Unless you’re the type who enjoys exploring and learning something new, such as a new language. Then travel to a non-English speaking country probably sounds pretty hip.


    You also need to consider your income and the costs associated with travel to places you are considering. Obviously the more it might cost, the less you might have to spend on the trip.

    Also, the fewer places you might be able to travel over the course of your retirement. You definitely need to ensure you travel within your budget…and your overall retirement plan.

    Basically, you need to determine the type of travel and the places to go to in order to make sure what you are considering really makes good sense for you financially. If you spend too much on travel then you might have to cut back on your standard of living in retirement. Ouch…

    Find a balance!

    Why is solo travel worth considering?

    So, if you’re still reading and haven’t been scared off or have talked yourself out of the urge, then you must have a real appetite for the single-travel experience. Good for you.

    What are some of the good reasons to do so. First up, if you’re married or have a significant other, fact is you must have some things for yourself in retirement, just as your significant other must as well.

    Chances are you’ve always traveled together in the past, which often means either you or the other (sometimes/often) has sacrificed.

    Single travel allows you to address that major issue. You get to be you and do what you want – the same holds true for them.

    Both parties are more likely to enjoy and feel satisfied, versus one or the other feeling once again like they are being forced to sacrifice for the other. This can cause serious problems in retirement, which is one big reason why you see high divorce rates in retirement.

    Aside from that, taking a trip once you retire is liberating. It’s like throwing off the shackles of your old life and all the restraints and rules that life imposed on you during all those year.

    This doesn’t mean you didn’t like or love your work and past life, but instead that you are engaging the adventure of the second half of your life.

    Now it’s about you and what you want to do – what you want your retirement to be like. Face it, if you don’t do for yourself now, you never will. And you’ll likely live the remainder of you life regretful…maybe even bitter.

    Determine where you “really” want to go

    When it comes to retirement, you finally have a lot more time to yourself. But the reality is that doesn’t necessarily translate to time available to travel or do other things.

    The age at which you retire matters quite a bit.

    If you do so at 65, you might have five to 10 years left for unassisted travel…if that. If instead you retire in your 50s, you probably have a fair amount of time left for potential solo travel.

    As a rule of thumb, the older you are when you retire and seek to do so, the opportunity to realistically travel solo does decline.

    Quote from blog: "You definitely need to be practical when deciding how many trips you really want to do in retirement.."As such, it makes sense to be very selective when it comes to solo travel. There may be a ton of things on your bucket list, or that you’ve always thought of, but you need to prioritize, with the most important at the top of the list.

    If you prioritize and determine there are four trips you’d like to do at all cost, and if at all possible, definitely start with them first.

    This determination should include your health and budget. If you want to go do the infamous Camino de Santiago walk in Spain or ride bicycles through the countryside in Ireland (both very cool trips), then place those first while you’re still younger and able to do so. A year or two later and that might not be the case.

    Also, you might want to go to experience a certain destination, but they have a major event like the Olympics in two or three years. If you aren’t interested in the Olympics and don’t want to deal with the influx of extra tourists at that time, you may want to go before versus waiting to go afterwards.

    You definitely need to be practical when deciding how many trips you really want to do in retirement, where to do so, and when it makes best sense. And be sure to consider which of those trips you can and probably can’t (or shouldn’t) do solo.

    Determine how you want to travel

    The manner in which you want to travel is a huge issue nowadays.

    In the past cruising was a typical choice for older couples, but today it is much more than some shuffleboard and laying around on a deckchair sipping “foo foo” drinks.

    Destinations in the States, Europe, the Far East, South America, New Zealand and Australia, et. cetera. You name it and you’ll find cruises available. This includes ocean, river, paddleboard, economically-oriented, luxury, and more.

    There’s obviously also airliners, which as previously mentioned you can now book for yourself. And do so to multiple locations across assorted continents, all within one trip.

    Trains are another popular manner of travel here in the States. They’ve always been there, but have become more comfortable and popular in years recent. Same for train trips in other parts of the world. Anyone for the Orient Express?

    There’s also cool auto trips here and abroad. Think about some of the famous drives up the West and East Coast. But you need to decide if you want to put the miles on your own auto or do so with a rental, which entails added expense. Peeps do the same overseas after flying to those countries. But you do need to consider whether you are up for all the driving by yourself.

    How about getting out in an RV you might own? Or that you can rent? Doing a trip over a couple of weeks or for months-on-end is perfect for couples, as well as those looking to go the solo route.

    Lastly, there are the mash-up trips that involve different means of travel. If you really want to make it interesting, you can enjoy travel utilizing a mix of the aforementioned “means” of transportation to get to many places and engage in different experiences, all in one trip.

    Working with a tour organizer

    Working with a professional that is experienced in trip planningWhile it’s great to put together your own adventure, doing so involves a lot of work. Just doing the investigation and learning all you can about an area can be daunting. And even then there is much you won’t know or will likely miss, which could diminish your trip or potentially cause real problems.

    For many, the thought of the hard work involved in putting together a trip (solo or for a couple) is not something they want to have to do.

    Either way, working with a professional that is experienced in trip planning, and who knows the local areas your wish to experience, can make all the difference in the world.

    They can ensure you experience the things that are important, get you discounts, book your accommodations according to wishes and budget, steer you clear of places you should avoid, and more.

    By taking the work out of putting the trip together, and going loaded with all the information and insight that’s needed (from a qualified advisor), you can relax and travel confidently while enjoying your solo tour or trip.

    Should you travel with a group

    Group travel may seem like an oxymoron when you are contemplating solo travel, but the fact is there are some benefits that make it worthwhile to investigate.

    First up, group travel can reduce the costs of transportation. Many domestic airlines offer discounts for 10 travelers or more in a group. Trains, busses, boats and cruises also do so with larger groups. This can also be the case for excursions during your travel for things like day-trips and even those sojourns that are overnight.

    Most group tours generally allow for some flexibility to get off on your own in most of the area visited, so you get to explore on your own on a regular basis.

    There is also the issue of greater opportunity to meet new people, even though you are doing solo travel. New friendships and perhaps a future travel-mate may come of a group trip.

    Lastly, even though you wish to do a solo trip, that doesn’t mean you should throw all caution to the wind. As in many aspects of life, especially when you are venturing out of areas you are familiar with, it makes sense to do things in groups. Even more so when you are in unfamiliar surroundings.

    Areas you might want to avoid

    Quote graphicThere are counties in the world you probably can’t go to as a U.S. passport holder (there are limited exceptions), according to the U.S. Dept. of State. Counties such as North Korea, Cuba, Syria, Iran, Libya, and Somalia are examples. And there are plenty of others where the State Department discourages travel. That list constantly fluctuates due to geopolitical issues, as well as local events and crimes against tourists.

    As a solo traveler, it goes without saying that you should pay attention to travel advisories in general – especially what the State Department has to offer.

    Beyond those places, there are areas in even the safest countries or cities you shouldn’t go into or stay. You can generally find lists of such places well in advance of your travel with simple web searches of any city/country you plan to visit.

    Even if an area seems pretty safe, you have to remember that Americans tend to stick out like sore thumbs when traveling overseas, so you have to be cautious as locals with bad intentions might target you. This is especially true when they realize you are potentially traveling on your own.

    Same holds true here. Domestic locales are replete with bad actors as well. When solo traveling you have to be on higher alert as you don’t have someone with you watching your back. That’s another reason to consider group travel or trips.

    Definitely need travel insurance

    While sparing no expense on elaborate travel and trips, many people decide to go into cheapskate mode when it comes to insuring their vacation. That’s right – travel insurance is meant to ensure the investment they are making into travel.

    Such a decision can leave the money invested into travel in jeopardy. Not to mention that skipping travel insurance can imperil your health and safety as well.

    On the practical side, travel insurance can protect you against the norms, such as lost baggage, expenses due to delays (e.g., missed flights and the need for rebooking), the need to change dates for your trip, and outright cancellations due to health, work, emergencies and other issues.

    And then there is primary reason for travel insurance – things that can happen while you are on your trip. Most health insurance policies you have domestically won’t cover incidents and accidents that arise while in foreign locales.

    If you fall and break an arm while in Portugal, your domestic insurance probably won’t do you any good. You will literally have to whip out the credit card when you get to the hospital before they will begin to work on you.

    And hopefully you won’t have a health incident, such as a heart attack or stroke. You’ll possibly need to be evacuated (it’s unlikely you’ll be placed on a regular airline flight), in which case you or your family will have to pay (in advance) a huge amount of money to get you home.

    Fact is there are literally all kinds of issues and calamities that can befall you while traveling in a foreign country, especially when engaged in solo travel.

    Failing to pay a relatively inexpensive fee for a travel insurance policy is an avoidable and serious mistake – one a smart traveler knows they can’t afford to make.

    Create a detailed plan

    Make a plan!Yeah, yeah, yeah… make a plan.

    Doesn’t it get old hearing that dated advice? Well, there’s a reason you hear it. Failing to put a plan together can keep you from achieving goals, leave you poor in retirement, and when it comes to travel it can ruin your vacation or even leave you in a lurch in some backwater town in the middle of nowhere.

    So, yeah, you do need a plan for your travel. All of the aforementioned tips and suggestions/strategies are important and can keep you safe and make for a well-organized, wonderful experience…or you can end up with a lousy, nightmarish experience.

    Which translates to the need for diligent planning. In today’s day and age there are plenty of tools and resources available to be able to put together simple to even complicated travel plans on your own. Or you can work with a pro to ensure every last detail is meticulously planned out in advance, providing you with invaluable peace of mind.

    Whatever route you take, the key is to plan, just as you do with other important elements in your life.

    Oh, and be certain to share those plans with family so they know where you are and how to reach you while you’re out and about engaged in your solo travel adventure.


    No doubt some of the aforementioned info can be a bit of buzz kill, especially when you have been excited just thinking about the prospect of setting out on your own for travel once you retire.

    Who can blame you for feeling a bit down in this moment. New horizons, the possibility of meeting new friends, experiences you could only dream about while working all the years in the past. Now it’s your time. And now we mention the need for caution….

    Unfortunately, while metaphorically speaking it’s fun to throw all caution to the wind, in the real world you can’t do that. You need to be cautious, meticulous and plan in order to ensure your solo travel experiences will be all you want them to be.

    There’s lots of considerations and the list above is simply a start.

    Bottom line – you have to plan and you definitely want to rely on as much expertise as possible.

    That’s much like retirement – rely on expertise and have plan. There is simply too much at stake to avoid doing so.

    Do you have a retirement plan?

    If you do (either your own or one created for you), our team would be happy to review it to determine if it is capable of adequately and securely meeting your goals.

    Or we can assist you by creating a customized retirement plan capable of helping you to retire with confidence. We can build a holistic, comprehensive retirement plan addressing relevant issues, utilizing strategies that cover travel in retirement, Social Security, taxes, income, spending, healthcare, legacy, and more, customized to your family’s specific needs.

    A plan created with the goal of ensuring you can successfully live out the retirement you envision.

    If you are ready to take the next step and talk to a team of retirement planners who can advise on all your retirement needs, and who will put your interests first, Schedule a call today!


    Related Content

    6 Tips On Saving And Planning Extended Travel When Retired

    Can I Retire at 64 with $800K in Savings? I want to Spend $6K / Month & $15K per Year Travel Budget

    9 Things You Wish You Knew Before Retiring

    Getting Ready To Retire? Follow This Checklist

    What’s a Dynamic Spending Plan and How It Can Help You Through Retirement

    Let Us Help You Achieve the Retirement You Deserve!

    Investment Advisory services are provided through Oak Harvest Investment Services, LLC a Registered Investment Advisor. Insurance services are provided through Oak Harvest Insurance Services, LLC. Oak Harvest Investment Services, LLC and Oak Harvest Insurance Services, LLC are not affiliated with the U.S. government or any government agency. Information presented is for educational purposes only intended for a broad audience. Not an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies.
    “Peace of Mind,” “Safety,” “Principal Protection,” “Lifetime Income, “Guaranteed Income,” or other guarantees are associated with fixed insurance products. No such language refers in any way to investment advice, investment advisory products, securities, or recommendations provided by Oak Harvest Investment Services. Investing involves risk. Rates of return are not guaranteed unless otherwise stated. All guarantees are dependent on the financial strength and claims-paying ability of the issuing insurance company. Annuities have limitations and are not appropriate for all circumstances or individuals. They are not intended to replace emergency funds or to fund short-term savings or income goals. Lifetime income may be available on certain products through an optional rider, at no cost or for an additional cost, depending on the contract. Insurance products are not insured by any federal government agency and may lose value. By contacting us, you may be offered information regarding the purchase of insurance and investment products.
    Oak Harvest has a reasonable belief that this marketing does not include any false or material misleading statements or omissions of facts regarding services, investment, or client experience. Oak Harvest has a reasonable belief that the content as a whole will not cause an untrue or misleading implication regarding the adviser’s services, investments, or client experiences. Please refer to for additional important disclosures.