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Cities Are the Latest HOT Boomer Retirement Destinations… How to “Try Before You Buy”

By Margaret Manning December 26, 2018 Travel

Today, 55% of the world’s population lives in cities. According to the UN, that number is expected to increase to 68% by 2050. By that time, two out of every three people are likely to be living in urban areas. And, millions of these city dwellers will be retirees!

Road Scholar, the not-for-profit leader in educational travel since 1975, recognizes this retirement trend along with the boomer passion for urban travel. In fact, it offers over 500 city learning adventures in cities around the world!

These Road Scholar city discoveries offer retirees – and those considering retiring in a particular destination – many different options for exploring new cities around the world. These learning adventures can help retirees immerse themselves into a new place before they make plans to relocate to one of the world’s fabulous cities… or simply allow them to enjoy the magic of urban life!

Boomers Are on the Move!

Many boomers are moving from their suburban homes to city apartments where they can reduce costs and indulge in their passions and interests. Their nests are empty. They are over the big houses with big lawns that are in constant need of maintenance. Now, for many, it’s time to explore new destinations!

Many women in the Sixty and Me community are downsizing and moving to smaller urban apartments. In fact, in this Sixty and Me article, we highlight the importance of doing a trial visit to a city before making any decisions.

So, in this article, we want to talk about how Road Scholar can help you to research and, ultimately, find the best retirement destination for your lifestyle.

Now planning on retiring any time soon? Or, plan on staying where you are in retirement? No problem, any of these destinations would make great places to visit anyway!

Let’s Start with Road Scholar’s Independent City Learning Adventures!

Road Scholar offers a unique set of 15 Independent City learning adventures in cities across the United States, Canada and Europe.

These independent city discoveries offer a way to combine a group travel experience with time for individual and independent exploration.

Let’s take a look at a few of the more popular independent city discoveries from Road Scholar.

Experience Lisbon on Your Own Terms

retirement destinations - lisbon

Portugal always ranks high among the list of potential retirement locations for Boomers. In this 8-day Lisbon Independent journey you can spend time in stunning churches, art galleries, World Heritage Sites and gardens.

With an expert Road Scholar guide, you can discover the important highlights of this enchanting city and start to feel like a true Lisbon local.

Pick Prague as Your Next Destination

Another European city many retirees consider visiting is Prague. This 9-day offering from Road Scholar gives you a chance to explore a city that has emerged from communist rule with vibrant modern ideas and a thriving music, art and culture scene.

I took this program with Road Scholar myself and absolutely loved the focus on art and architecture.

Here is a short video that I recorded on this trip:


Meet Montreal, an Amazing Retirement Destination!

Retirement Destinations

In Canada, Montreal is often a retiree destination. This 5-day Road Scholar program is led by a local expert who takes travellers on a journey of Montreal’s vibrant art scene and culinary focus that attracts tourists and locals alike.

McGill University offers a cultural perspective and a very “laid-back” francophone culture attracts many Boomers who just want to relax and have fun gaining a little weight in retirement!

Now, let’s look at a few travel adventures from Road Scholar in their “Signature Cities” category.

Find Out Why Portland is a Hot Destination for Boomers

Retirement Destinations - Portland

Portland is often mentioned on the list of best US cities in which to retire. The Road Scholar 6-day program in Portland offers a way to experience the heritage of this very popular “City of Roses” and enjoy the beautiful natural beauty and modern urban benefits.

It includes visits to the historic Portland Art Museum, International Rose Garden and the astounding Lan Su Chinese Gardens.

Visit Dublin, a Country of Energy and Natural Beauty

Retirement Destinations - Dublin

Ireland has very much been in the news lately as a fascinating and forward-thinking country with entrepreneurial spirit and natural beauty.

The Road Scholar educational adventure in Dublin offers an opportunity to experience the history and culture of Dublin’s Viking past and the vibrant modern and friendly and relaxed entertainment focused culture. Theatre and music are at the heart of Dublin’s charm!

See Seattle Like a Local

Retirement Destinations - Seattle

I am not sure if Seattle is the most affordable place for a boomer to retire, but since I lived there for 25 years, I can certainly speak positively about what is has to offer.

The Road Scholar Seattle Signature City Discovery program reveals a beautiful city nestled on Lake Union offering a beautiful fusion of innovation, culture and natural beauty.

Retirement Options for Every Lifestyle

For retirees who are looking to enrich the next chapter of their lives in a new exciting urban environment, Road Scholar offers something for everyone.

The best way to make an educated decision about whether to spend time in new city is to lean on experts who know the place and a company that you can trust to provide a safe and enjoyable experience.

Have you retired and moved from the suburbs to a more urban environment? What city in the world do you long to visit? Let’s have a chat!

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The Author

Margaret Manning is the founder of Sixty and Me. She is an entrepreneur, author and speaker. Margaret is passionate about building dynamic and engaged communities that improve lives and change perceptions. Margaret can be contacted at

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