You’re retired – yay! Now it’s time to choose which European trip you’ll take. Where will you go next? If your first thought was Joe Montana’s, “I’m going to Disneyland!” then you are officially old, like me!

With time and at least a bit of lucre at your command, you’ve options. So, let’s get started putting some plans in place.

We can all acknowledge the “elephant” in the bucket-list room and give the nod to Australia, China, Africa, Antarctica, and good ole road-trippin’ across the USA – all great choices and you should absolutely consider them.

But as a tour operator that specializes in Europe, we are a bit biased. From the living history, architecture, cuisine, and cultural delights that await you in every country throughout this continent, we think you’d be amiss to not trek through a destination or two.

So now that you’re excited and your bags are mentally packed, let’s explore the best European trips to take when you retire!


Nearly every article you read will mention Portugal as a “retirement abroad” destination. Why not check it out yourself? History, friendly people, great food and great wine, a temperate climate, and moderate pricing….when’s the next flight out?

As mentioned, Portugal’s temperate climate makes it a warm destination year-round; however, spring and fall months offer fewer crowds.


Nearly 5% of Americans have Italian heritage which makes Italy a favorite destination for many to trace their roots and walk the paths of their ancestors. A leisurely self-drive trip around the island of Sicily will also give you Greek ruins, volcanoes, fishing villages, and beach resorts – not to mention more amazing food and wine!

If a tour through wine country does sound up your alley, we recommend choosing a private driver tour to provide you with ease of transportation after tastings and vineyards tours.


Speaking of islands, Iceland’s Ring Road is perfect for an extended retirement trip. (It’s on my list, too!) Plan for at least 2.5 to 3 weeks for this drive – and prepare to be flexible. This destination can be truly remote and with the mindset of “ok, we will work with what is available to us as tourists,” you’ll be in for a trip unlike any other you’ve made before!

While not for everyone, Iceland’s Ring Road is completely safe and doable. Your Travel Specialist will help you determine all the components of your trip – from the best time to travel to the type of car – to ensure a successful experience. Plus, all our travelers have 24/7 access to our By-Your-Side ServiceSM TEAM in case of any snafus or last-minute changes.


Of course, you can’t forget Ireland, Tenon’s very first destination! This remains the top choice for our retired travelers. With an ideal 12-16 nights, you can explore the whole island, including Northern Ireland – a place that most of us of a certain age only knew from the Nightly News – and not in a good way. Give yourself 3 to 4 nights in each of the original four provinces and you’ll have a fabulous opportunity to check out heritage sites as well some of the world’s most stunning coastlines.

Browse our inspirational itineraries to help you plan your ideal trip to Ireland.


1. If you’re a seasoned European traveler, why not go back to a place you enjoyed before? You have more time and less of a backpacker budget now. You’ll be amazed at the changes, and it will build your travel confidence as you see familiar sites, but now with the perspective of maturity. (Hmmm, maybe staying out at a disco till 5 am on a remote Greek island wasn’t the best adulting you ever did…cough cough.)

2. Go over Thanksgiving. Let the kids feed themselves for once! For Europe, this will be the off-season which means fewer crowds and better pricing. Sure, some attractions may be closed for the season, but that might be a worthwhile trade-off depending on your priorities.

3. Speaking of “kids,” don’t assume they’ll want or be able to join you on a dream trip. Many wonderful plans have to be scuttled when work schedules/child care/pet sitting/budgets get real. Travel for yourself. Make your kids jealous (while they stuff their own turkey!)


1. Be creative with your car rental. Maybe spring for a Mercedes for a few days? Try out an SUV? We’ll include the insurance, so treat yourselves and have fun!

2. Do something 100% “touristy.” There’s a reason attractions like the Colosseum or the Tower of London are so popular – go see for yourself! But perhaps on a privately guided day tour so you’ll have the best experience possible.

3. To balance that, do something you’ve never done before. Live it up on a beach in the South of France. Blend your own whisky in Scotland. Go ziplining in Wales (I will hold your backpack, thanks very much). Just get out of your comfort zone and spark the element of surprise and delight!

4. A last thought: If there is a trip you really, really, really want to do, please do not sit it out because you haven’t hit your magic retirement age yet. If the past few years have taught us anything, life is for living – and traveling! Don’t put off your dreams when you have the chance to make them real.

Now, let’s get you packed.

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