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!

PORTUGAL’S COAST

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.

SICILY, ITALY

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.

ICELAND’S RING ROAD

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.

ISLAND OF IRELAND

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.

OTHER THINGS TO CONSIDER

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!)

AND ONCE YOU’VE DECIDED WHERE TO GO, HERE ARE A FEW MORE THOUGHTS ON THE WHAT.

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.

How We Travel

Learn More
  • Motorcycle

    Ride your way: custom tours built for adventure, created by motorcyclists.

  • Self Drive tour in Europe
    Self Drive

    Hit the road your way: itinerary, car, accommodations, sights, and tours. But let us do all the heavy lifting.

  • Chauffeur 1
    Chauffeur

    The freedom of your own private car, the luxury of your own personal guide. And the very best hidden secrets.

  • funny mural of school children in uniforms
    Scheduled Tour

    For travelers who prefer to join a small group tour, we offer scheduled tours.

  • Train going over bridge next to waterfall
    Rail

    Convenient, comfortable, oozing with charm. With a front-row seat to some of the most beautiful scenery in the world.

  • Young people overlooking scenic area in Europe
    Private Group

    The trip of a lifetime, personalized just for your group of friends, family, or organization down to every last detail.

  • Honeymoon coupe drinking wine by ocean
    Honeymoon

    Every tour is different, perfectly matched for every couple. Crafted by a team who is as excited about your honeymoon as you are.

Mid distance low angle view of male and female tourists in 20s and 30s holding hands and walking through Barcelona park near Sagrada Familia.

Barcelona and Costa del Azahar Discovery: The Solar Eclipse Experience

6 Days | 5 Nights
Outdoor
Adventure
Family
City

Discover the vibrant heart of Catalonia with our 6-day itinerary through Barcelona and Castellón de la Plana. Experience the awe-inspiring Sagrada Familia and the historic Gothic Quarter in Barcelona before journeying to Castellón de la Plana. Here, amidst medieval charm and stunning coastal vistas on the Costa del Azahar, witness a rare solar eclipse—a celestial spectacle to enrich your cultural and natural exploration. Perfect for travelers seeking a blend of urban excitement and seaside tranquility.

 

Starting From $3,225 per person based on double occupancy
Great pond and monument to Alfonso XII at the Retiro Park (Parque del Buen Retiro) in Madrid in early Spring. Long exposure.

Spain Spectacular: Witness the 2026 Solar Eclipse in Madrid & Burgos

6 Days | 5 Nights
Outdoor
Adventure
Family
City

Embark on a mesmerizing 6-day Spanish adventure, culminating in the awe-inspiring experience of witnessing a solar eclipse in historic Burgos. Enjoy private, guided tours of Madrid’s iconic landmarks, including the Royal Palace, and explore Burgos’ rich history with a visit to its stunning Gothic Cathedral. With comfortable private transfers and ample leisure time for optional excursions, this journey promises unforgettable moments under the Spanish sun and stars.

 

Starting From $3,365 per person based on double occupancy

Witness Iceland's Wonders: Experience the 2026 Solar Eclipse & Golden Circle - Group 1

6 Days | 5 Nights
Outdoor
Adventure
Family
City

Experience the rare total solar eclipse on August 12, 2026, in the stunning landscapes of the Snæfellsnes Peninsula. This exclusive journey combines the eclipse viewing with highlights of the Golden Circle, thrilling whale watching excursions, and immersive local experiences. Explore historical sites, marvel at majestic waterfalls, and venture into the captivating Víðgelmir lava cave. Prepare for an unforgettable Icelandic adventure of a lifetime!

 

Starting From $5,195 per person based on double occupancy
By-Your-Side

By-Your-Side Service℠

Our personal concierge service and mobile app

Europe Experts

Custom Europe Experts

Experts in planning truly customized trips

Without Compromise

Value without Compromise

High-touch inclusions and customized experiences

Consistency with Individuality

Consistency with Individuality

You’ll always be met with the highest standards

Let's Get Social

@tenontours