How to Plan a Self-Guided Walking Tour in Your 50s and Beyond

There comes a time in life when travel becomes less about ticking boxes and more about meaningful experiences. For many travellers in their 50s, 60s, and beyond, the joy of slowing down, savouring each moment, and connecting deeply with a place is far more rewarding than rushing from one destination to another. A self-guided walking tour offers exactly that - the chance to journey at your own pace, soak in the beauty of your surroundings, and feel the freedom of adventure, all with the reassurance that an experienced team of travel professionals has your back.

If you’ve always loved the outdoors but never thought of yourself as the “backpacking” type, a self-guided walking tour might surprise you. These trips are designed for active travellers who want flexibility and independence without the stress of planning every detail. Your accommodations are booked, your luggage is transferred, and your routes are mapped out, leaving you free to enjoy the pure joy of walking.

And here’s the best part: you don’t have to be an expert navigator or a tech wizard to do it. Self-guided walking tours are created with accessibility in mind, making them a perfect option for those trying something new in their 50s and beyond.

Self-Guided vs Guided Tours: What’s the Difference?

If you’ve travelled on a guided group trip before, you might be wondering how a self-guided walking tour compares. With a guided tour, you’ll have a leader who takes the group along the route, sets the pace, and provides insights along the way. This is a great option for those who enjoy a social group atmosphere and prefer having every step explained.

Self-guided hiking tours, however, offer a different kind of freedom. You choose when to start your day, how long to linger over coffee in a village square, and whether to pause for a spontaneous photo… or two, or ten! There’s no pressure to keep up with a group, and no compromise on what you want to see and do. Behind the scenes, a support team makes sure your accommodations are ready and your luggage is delivered, so you can simply enjoy the journey without the hassle of logistics. It’s independent travel with a safety net.

Navigating Made Easy

One of the biggest questions we hear from first-time self-guided travellers is: “But how will I find my way?” The answer is simpler than you might think. Nearly all modern self-guided tours use a GPS navigation app that you can download onto your phone. These apps work offline, so you don’t need to worry about data roaming or losing connection. You’ll see your route clearly marked, along with points of interest, cafes, and villages along the way.

In addition, most tours come with detailed route notes and sometimes even physical maps, so you’ll always have a backup. Gone are the days of juggling a binder full of printed directions or trying to decipher a vague guidebook. Today’s tools are intuitive, user-friendly, and designed for walkers of all experience levels. Many of our guests tell us that after the first day, they feel completely confident navigating on their own.

Need more convincing? Check out our blog post on How to Navigate With a GPS on Your Adventure Holiday to learn more.

Popular Self-Guided Walking Tours for Beginners

If you’re ready to dip your toes into the world of self-guided walking, here are a few beginner-friendly tours that balance gentle walking with incredible scenery and cultural immersion:

5-Day Cotswold Villages Walking Tour

• Difficulty: 2/5
• Duration: 5 days
• Season: March–October
• Accommodation: Comfortable inns and charming B&Bs

The Cotswolds are the classic image of the English countryside: rolling hills, golden-stone cottages, and village pubs waiting to welcome you at the end of your walk. This short itinerary is ideal for first-timers; it’s relaxed, scenic, and full of history and charm.

Learn more about the 5-Day Cotswold Villages Walking Tour

7-Day São Miguel Island Tour (Azores, Portugal)

• Difficulty: 2/5
• Duration: 7 days
• Season: Year-round (best in spring and summer)
• Accommodation: Boutique hotels and guesthouses

This walking tour reveals the volcanic landscapes, lush forests, and dramatic coastlines of São Miguel in the Azores. Each day offers a different perspective on this Atlantic island paradise, with plenty of time to enjoy hot springs, fresh seafood, and charming towns.

Learn more about the 7-Day São Miguel Island Tour

Lake Como Self-Guided Walking Tour (Italy)

• Difficulty: 2/5
• Duration: 7 days
• Season: April–October
• Accommodation: Lakeside hotels and family-run guesthouses

There’s no better way to experience the glamour and natural beauty of Lake Como than on foot. Stroll through lakeside villages, climb gentle paths with sweeping views, and indulge in delicious Italian cuisine. The daily walks are manageable yet rewarding, making this a wonderful choice for first-time self-guided travellers.

Learn more about the Lake Como Self-Guided Walking Tour

Your Self-Guided Adventure Awaits

Planning a self-guided walking tour in your 50s and beyond isn’t just possible, it’s an incredible way to travel. With the right balance of independence and support, you’ll gain the freedom to explore at your own pace while enjoying the security of knowing everything is taken care of behind the scenes.

Whether you’re drawn to the rolling English countryside, the volcanic beauty of the Azores, or the timeless charm of Italy, there’s a self-guided walking tour waiting for you. And remember, you don’t have to figure it all out alone. Our 10Adventures travel advisors are here to help you choose the perfect itinerary and take the first step toward your self-guided walking journey - all you have to do is get in touch!