Solo Travel After 50: Where to Go and How to Get Started
Solo Travel: One of Life's Best-Kept Secrets
There's a moment in many people's lives when the timing is finally right to travel — but the people they imagined traveling with aren't available. Maybe a partner has passed or doesn't share the wanderlust. Maybe friends are tied up with grandkids or work. Maybe you've simply realized you don't want to wait anymore.
Welcome to one of the fastest-growing segments of travel: solo travelers over 50. And here's the good news — it's never been a better time to go on your own. The infrastructure for solo travel has expanded dramatically, with more group tours, friendlier pricing, and destinations practically built for solo exploration.
If you've been considering it, this is your guide.
Why Solo Travel After 50 Is Different (and Better)
Solo travel in your 50s, 60s, 70s, and beyond has real advantages over solo travel in your twenties:
• You know yourself. You know what kind of traveler you are, what you enjoy, what you don't, and what's worth spending money on. That clarity makes for better trips.
• You're financially established. You can afford comfort — better hotels, private transfers, occasional splurges — that make solo travel more enjoyable.
• You have more time. Whether retired or semi-retired, you can travel during shoulder seasons, avoid crowds, and take longer trips.
• You're a great traveler. Decades of life experience translate into adaptability, perspective, and the kind of social grace that opens doors abroad.
Common Concerns (and Honest Answers)
"Won't I be lonely?"
Solo doesn't mean alone. Most solo travelers are surprised by how social travel actually is — striking up conversations at hotel breakfasts, joining group tours, meeting people on cruises. Plus, time alone is part of the appeal: reading on a balcony, lingering at a café, taking a walk on your own schedule.
If you're worried about loneliness, group tours and cruise lines that cater to solo travelers offer instant community.
"Is it safe?"
Many destinations are extraordinarily safe for solo travelers, especially with smart planning. Iceland, Japan, Portugal, New Zealand, and most of Western Europe are excellent starter destinations. Travel advisors can help match you to destinations that suit your comfort level.
"What about the single supplement?"
This is the one real frustration of solo travel — many tours and cruises charge a "single supplement" because pricing assumes double occupancy. The good news is that more cruise lines and tour operators offer reduced or waived single supplements, especially during shoulder seasons. A travel advisor will know who's running these promotions.
"What if something goes wrong?"
This is where good preparation matters. Travel insurance with medical coverage and emergency assistance, registration with the Government of Canada, and a travel advisor as your point of contact back home all give you backup if anything happens.
The Best Destinations for Solo Travelers Over 50
Iceland
One of the safest countries in the world, easy to navigate, with English widely spoken. Whether you join a small-group tour or rent a car for the Ring Road, Iceland's landscapes, hot springs, and friendly culture make it a near-perfect solo destination.
Portugal
Portuguese cities like Lisbon and Porto are walkable, safe, and welcoming. The food and wine culture is solo-friendly (no shame in dining alone), and the country is small enough to explore on your own pace.
Japan
Japan is one of the most rewarding solo travel destinations in the world. Incredibly safe, immaculate, and culturally fascinating. The trains are easy, the people are kind, and dining alone is completely normal — many restaurants have solo seating built right in.
Italy (Especially Tuscany or the Amalfi Coast)
Italy rewards travelers who linger, and solo travel lets you do that. Cooking classes, wine tours, and small-group walking tours offer easy social connection while still letting you set your own pace.
River Cruises (Anywhere)
River cruises are arguably the single best vacation format for solo travelers. Small ship, friendly crew, structured social time, and shore excursions where you don't have to worry about transportation. Plus, several river cruise lines offer reduced or waived single supplements.
Group Tours (Specifically for Solo Travelers)
Several tour companies — including major operators like G Adventures and others — run tours specifically designed for solo travelers, with no single supplements and built-in community. These are amazing for first-time solo travelers.
Tips for Your First Solo Trip
1. Start with a guided tour or cruise. If solo travel feels intimidating, a small-group tour or river cruise gives you community, structure, and built-in logistics. Many travelers "graduate" to fully independent solo trips after a tour or two.
2. Choose a manageable destination. First solo trip is not the time for a complicated, multi-country itinerary. Pick one country, one or two cities, and give yourself time to settle in.
3. Stay in well-located hotels. Don't save money on a remote hotel and then feel isolated. Pay a bit more for a hotel in a walkable, safe neighborhood near things you want to see.
4. Plan your first day carefully. Arriving solo in a new city can feel disorienting. Pre-arrange airport transfer, choose a familiar-feeling first dinner, and don't pack the first day with ambitious plans.
5. Bring a real book or two. There will be quiet moments — long flights, slow lunches, evenings in your hotel. A great book is solo travel's best companion.
6. Talk to people. Hotel staff, café owners, fellow travelers. The more open you are, the more interesting your trip becomes. You'd be amazed how many great solo travel stories start with "I was eating dinner alone and the couple at the next table struck up a conversation..."
7. Eat at the bar. Solo restaurant dining is much more comfortable at the bar. You can chat with the bartender, watch the kitchen, and never feel awkwardly seated at a table for one.
8. Use a travel advisor. Especially for your first solo trip. An advisor handles bookings, flags safety considerations, and is a phone call away if anything goes wrong.
Practical Considerations
• Travel insurance is essential. Solo travel means no one to help if you fall ill. Comprehensive insurance with emergency medical and evacuation coverage is non-negotiable.
• Tell someone at home your itinerary. Share your hotel info, flight details, and a rough plan with a family member or friend back home. Check in periodically.
• Keep digital copies of documents. Passport, insurance, credit cards — accessible from your phone in case anything is lost.
• Pack lighter than you think. You're carrying everything yourself. A medium-sized suitcase plus a carry-on is plenty for trips up to two weeks.
• Consider a money belt or hidden wallet. Especially in tourist-heavy European cities, where pickpocketing is the most common travel crime.
The Joy You're About to Discover
Solo travelers consistently say the same thing after their first trip: "I should have done this years ago." The freedom of moving entirely on your own schedule, eating what you want, lingering where you like, and proving to yourself that you can handle a foreign city alone — it's quietly transformative.
And here's the secret: you'll come home more confident, more curious, and probably already planning the next one.
Our GOwithHIPPO travel advisors love helping solo travelers plan their adventures — whether it's your first trip or your fiftieth. We know which tour operators take great care of solo travelers, which destinations are easiest to navigate, and how to build a trip that fits your style.
Ready to start planning? Connect with a GOwithHIPPO travel advisor today. Our independent advisors across Canada are passionate travel experts who handle every detail — from flights and accommodations to insurance and insider tips — so you can focus on the fun part: getting excited for your trip.