Your First Solo Trip

Planning your first solo trip at 50 or 60

Whether you are newly on your own, recently retired, finally have an empty nest, or have simply decided it is your turn — a first solo trip later in life is a wonderful thing to give yourself. It is also completely normal to feel a flutter of nerves alongside the excitement. This is a gentle, practical guide to making that first trip easy and enjoyable, at your own pace.

Golden tip: For your very first solo trip, pick ONE easy, English-speaking or easy-to-navigate city, stay 4–6 nights somewhere central and well-reviewed, and book one small-group walking or food tour for your first morning. You arrive, settle in, and have friendly company and a sense of the place within a day — without committing to a long, complicated itinerary.

You are in very good company

Women over 50 are one of the fastest-growing groups in solo travel. Far from being unusual, setting off on your own in your 50s, 60s or 70s puts you among a large and growing community of women doing exactly the same thing — many for the first time.

You do not need to be especially adventurous, fit or experienced. The women who enjoy solo travel most are usually the ones who chose somewhere gentle to begin, went at a relaxed pace, and let their confidence build trip by trip.

Choose a gentle first destination

The easiest first trips share a few things: they are very safe, easy to get around on foot or by simple public transport, forgiving if you do not speak the language, and well set up for visitors. Think compact, walkable cities where help is never far away.

Our round-up of the safest, easiest places for solo women over 50 groups destinations exactly this way — from English-speaking and gentle, to warm and walkable, to scenic places with plenty of organised day tours to join. Start there and pick the one that quietly appeals to you, rather than the one that sounds most impressive.

Where you stay matters more than anything

For a first solo trip, choose a central, highly-rated place within easy walking distance of the things you want to see, on a street that feels comfortable to return to in the evening. Paying a little more for location and good reviews is almost always worth it — it removes most of the day-to-day friction of travelling alone.

Book your first night before you fly, and try to arrive in daylight. Knowing exactly where you are going when you land takes a surprising amount of stress out of day one.

Plan a soft first day, then leave room

Resist the urge to fill every hour. Plan one easy anchor for each day — a gentle walking tour, a single museum, a stroll through a famous square with a long lunch — and let the rest unfold. You will see more, not less, by going slowly.

A short, well-paced trip you enjoy is far better than an ambitious one that wears you out. You can always go further next time, and there will be a next time.

Build in comfort and a little company

Small-group tours, cooking classes and food walks are the easiest, most natural way to share part of your day with like-minded people — with no obligation to socialise beyond that. Eat well, rest when you need to, and treat comfort as part of the plan rather than an indulgence.

When you use Wavvia to plan, you can tell it you would like a gentler pace and it tailors everything around that: a relaxed schedule, central walkable stays, safe well-lit evenings, and an optional friendly activity or two where you can meet people if you would like to.

In short

  • Pick one easy, very safe, walkable city to start — not a multi-stop tour.
  • Stay central and well-reviewed; book the first night and arrive in daylight.
  • Plan one gentle anchor per day and leave the rest open.
  • Book a small-group tour early for instant company and a feel for the place.
  • Carry travel insurance, and tell someone at home your plans.

A gentle solo trip, planned around you — free

Tell Wavvia you’d like a relaxed pace and it tailors everything — an unhurried schedule, safe and central places to stay, walkable days, and friendly small-group activities where you can meet people if you’d like.

Plan my solo trip — free

One simple thing worth sorting first

Travelling on your own means no companion to fall back on, so good cover gives real peace of mind — emergency medical care, cancellation and lost luggage. Compare a few quotes and check the medical limits before you buy.

Emergency medical & evacuation Trip cancellation Lost or stolen luggage
EKTAMost popular

Single-trip cover, high medical limits

Get a quote
TripInsuranceGood for groups

Flexible family & group cover

Get a quote

Wavvia may earn a small commission at no extra cost to you. We only recommend cover we trust — compare quotes before you buy.

Common questions

Is 50, 60 or 70 too old for a first solo trip?

Not at all. Many women take their first solo trip in their 60s or 70s and wish they had started sooner. Choosing an easy, comfortable destination and a relaxed pace matters far more than your age.

How many days should my first solo trip be?

Four to six nights in a single, easy city is a lovely first trip — long enough to settle in and feel the rhythm of travelling alone, short enough that it never feels daunting. You can build up to longer trips from there.

Do I need to book everything in advance?

Book your flights, your accommodation and your first day or two. Beyond that, a light plan with room to wander is usually more enjoyable than a packed schedule — and far less stressful if you are tired or the weather changes.

What if I feel lonely?

It is normal to have a quiet moment here and there. Booking the odd small-group tour, staying somewhere a little sociable, and eating where it is easy to chat all help. Solo travel means you choose your own company — as much or as little as you like.

Keep reading

Last reviewed June 2026. This is general travel guidance to help you plan — not medical, mental-health, legal, financial or insurance advice, and not a guarantee of safety. Conditions vary by person, place and circumstance, and can change. Always use your own judgement, check your government’s current travel advice before you travel, and seek professional advice where appropriate. Wavvia is not liable for decisions made from this information.