Travel in retirement: The best time to explore the world

Travel in Retirement: The Best Time to Explore the World

Retirement is the perfect time to fulfill those lifelong travel dreams. After years of working hard, raising families, and saving for the future, many retirees finally have the freedom to see the world. But for some, that sense of freedom comes with a touch of urgency. As health concerns become more pressing, there’s a growing desire to explore while it’s still possible. Others, who may have spent their careers focused on work and family, are now playing catch-up on travel, eager to make the most of this new phase of life. One of my clients even sold her home to fully embrace the joys of travel, determined to savour the fruits of her labour while she still can.

Whether you’re someone who has always dreamed of jet-setting or you’re new to the travel scene, retirement offers a unique opportunity to explore the world. Here’s a guide packed with tips and insights to help you make the most of your retirement travels.

Take your time - there’s no need to rush

Retirement means you have the luxury of time, so why rush? Whether you’re exploring the ancient streets of Rome or the beautiful coastlines of the Amalfi, take things at your own pace. Research your destination in advance, pick the top places you’d like to see, and leave plenty of room in your schedule for spontaneity. Overstretching yourself can lead to burnout, and the last thing you want is to spend your vacation recovering.

Plan for relaxation time, whether it’s a leisurely afternoon at a café or a quiet morning walk through a local park. By slowing down, you’ll have more energy to truly enjoy each experience and absorb the culture around you.

Embrace solo dining - it can be liberating

Travelling alone doesn’t mean you have to miss out on the dining experiences a destination has to offer. Solo dining can actually be a rewarding part of your travels. Find a cozy corner in a restaurant or café, bring a good book, and enjoy people-watching while savouring the local cuisine. You’ll often find that solo diners receive extra attention from waitstaff, who may offer recommendations or engage you in conversation about the area. Don’t be afraid to dine alone—embrace it as part of the solo travel experience.

Consider joining small group tours

Solo travel doesn’t mean you have to be alone all the time. Many retirees join small group tours centred around specific interests like cycling, hiking, or photography. These groups give you the best of both worlds: you get the independence of travelling solo but with the camaraderie of like-minded people. Plus, travelling in a group often opens the door to exclusive experiences that you might not be able to access on your own, such as private vineyard tours or guided safaris.

Hop on, hop off bus tours: A perfect way to explore

One of the most accessible and enjoyable ways to explore a new city—without over-exerting yourself—is through hop-on, hop-off bus tours. These tours offer flexibility, allowing you to take in the sights at your own pace while comfortably seated. You can hop off at places that catch your interest and skip those that don’t, making it the perfect way to see the highlights without feeling rushed.

Some of my favourite hop-on, hop-off tours include:

• Cape Town: The bus tour in Cape Town offers an extraordinary route, taking you all the way to Constantia, one of the world’s oldest wine regions. Sip on South Africa’s finest wines while enjoying spectacular views.
• London: London’s hop-on, hop-off buses take you through the city’s rich history, offering stops at free world-class museums, iconic royal landmarks, and even shopping districts like Oxford Street. For a special treat, try a themed bus tour with afternoon tea—you can enjoy scones and tea while passing by Buckingham Palace!
• Paris: Paris offers one of the most extensive bus tour systems, allowing you to get close to iconic landmarks like the Eiffel Tower, Notre-Dame, and the Louvre. It's a perfect way to enjoy the romance of the city without getting tired from walking all day.

Cruises: A social and relaxing way to travel

If you’re looking for a mix of relaxation and adventure, cruises—especially river cruises—are a fantastic option. Cruises provide the perfect balance of seeing new places while enjoying the comfort of a floating hotel. River cruises, in particular, offer an intimate experience, stopping at charming towns along the way. You can explore Europe’s waterways, enjoy a glass of wine in a picturesque village, and meet fellow travellers.

Cruises are also a wonderful way to meet people, with plenty of social opportunities. The shared experience of cruising—whether it’s an excursion or a night of onboard entertainment—makes it easy to connect with others. And with everything from meals to activities included, it’s a stress-free way to explore multiple destinations.

Bring the family - create lasting memories

Why not bring your family along on your travels? Multi-generational trips are becoming increasingly popular, and for good reason. Travelling with children and grandchildren allows you to create unforgettable memories together. Whether it’s a trip to an all-inclusive resort, a cruise, or a European adventure, the time spent together will be cherished by everyone.

Imagine showing your grandchildren the Eiffel Tower for the first time or introducing them to the wonders of ancient Rome. These moments are priceless, and sharing them with your family will create a legacy that lasts long after the trip is over.

A few top tips for safe and comfortable travel

1. Apply an AirTag to your luggage and carry-on

Even if your carry-on stays with you, it’s a good idea to attach an AirTag or another tracking device to your luggage. These smart gadgets allow you to track your bags using your phone in case they go missing. It’s a simple way to avoid the stress of lost luggage and keep everything under control.

2. Invest in a small under-clothing body purse

A body-worn travel purse can hold your passport, money, and other important items, keeping them secure and hidden under your clothes. Leave non-essential valuables at home. You want to travel light and avoid carrying anything that might draw attention from pickpockets.

3. Carry a copy of your passport separately

Always carry a photocopy of your passport in a different place than your actual passport. This will make the process much easier if your passport is lost or stolen. Keep the original safely tucked away, perhaps in the body-worn travel pouch you just bought.

4. Learn how to use the “Share Your Location” feature on your phone

Before you leave for your trip, set up the “share your location” feature on your smartphone. This way, family or friends can track your whereabouts, offering you both peace of mind. It’s an excellent way to stay connected, especially when travelling solo.

5. Place a shoe in the hotel safe

When using the hotel safe to store your valuables, place one of your shoes inside the safe as well. This handy trick ensures you won’t forget to retrieve your important items when checking out, as you’ll be looking for your missing shoe.

6. Get travel insurance

Travel insurance is a non-negotiable, especially as you age. Make sure your insurance policy covers pre-existing conditions, emergency evacuations, and unexpected medical expenses. If you have health concerns, research hospitals and medical facilities in your destination before you go.

7. Pack light and smart

Packing light is key, especially if you’re travelling solo. Invest in a lightweight suitcase with 360-degree wheels to make navigating airports and train stations easier. Choose versatile, comfortable clothing that can be layered and easily mixed and matched. This will make your travel experience more enjoyable and hassle-free. I always pack several full outfits in my carry on in case my luggage gets lost. 

The world awaits

Travel in retirement is about more than just ticking off places on a bucket list—it’s about embracing freedom, seizing new experiences, and creating memories that will last a lifetime. Whether you’re exploring solo, joining a group, or travelling with family, these years offer you the chance to see the world on your own terms. With thoughtful planning and an adventurous spirit, the world awaits—so pack your bags, set your itinerary, and make the most of this exciting chapter of life…You earned it! 

Next summer, I’ll be leading a small group on one of my all-time favourite ways to travel: an AMA Waterways river cruise through Germany and Switzerland. This trip came about when one of our regulars asked what my ideal summer plan would be for mixed ages. On a river boat holding just 200 passengers, this journey is perfect for solo travellers, couples, friends, and multi-generational groups. Expect stunning views of castles and vineyards, all-inclusive excursions, gourmet dining, and plenty of surprises and extras you’ve come to expect from my hosted trips. Let me know if you are interested. 

Don't forget if you are looking to travel I still own a TICO registered travel agency in Ontario and will be happy to help. Always the best way to reach me is by email as I mostly work remote and I can either set up a time to meet you or suggest a perfect local agent to help you.