Is going on vacation alone fun?

Ingrid van de Loo · 30 Apr 2026

Going on holiday alone is something many people think about, but it also comes with doubts. Will it actually be enjoyable? Will you feel lonely? And what will others think? These are understandable questions, but they paint a distorted picture of what a solo holiday can truly be. For a growing number of travellers, travelling alone is a deliberate, enriching choice that offers freedom and self-discovery — something you rarely find on group trips.

In this article, we answer the most frequently asked questions about going on holiday alone, so you can make a well-informed decision for your next trip.

Is going on holiday alone actually enjoyable?

Yes, going on holiday alone is, for many people, one of the most rewarding travel experiences they have ever had. You set your own pace, your own agenda and your own choices, without having to compromise. That gives you a sense of freedom you rarely experience on group trips.

That does not mean it suits everyone. Those who naturally crave shared experiences may need a few days to adjust to the quiet. But most solo travellers quickly discover that travelling alone actually makes you more open to connecting with other people. You approach strangers more readily, you are more accessible to locals, and you get to know yourself better.

A solo holiday does require the right preparation and choosing a destination or travel format that suits you. That is what makes the difference between a wonderful experience and a disappointing one.

What are the biggest advantages of travelling alone?

The advantages of travelling alone are concrete and tangible. You have complete freedom over your own itinerary, you grow as a person, and you meet people in a way that rarely happens on group trips. Below are the key advantages at a glance:

Complete freedom: You decide when you get up, what you eat and how long you stay somewhere.
Greater openness to new connections: Solo travellers are more approachable and connect more quickly with other travellers and locals.
Personal growth: Navigating a new environment on your own strengthens your self-confidence and problem-solving skills.
More deliberate choices: Without group pressure, you make choices that truly suit you.
Rest and reflection: You have space for yourself — something that is scarce in our busy daily lives.

For people who are used to always considering others, the first solo holiday can be a real revelation. You discover what you actually want and what genuinely appeals to you in a destination.

What should you pay attention to when travelling alone?

When travelling alone, preparation and safety are the two key words. A good solo holiday starts with conscious choices about destination, accommodation and communication. Keep the following points in mind:

Choose a solo-traveller-friendly destination: Not every destination is equally suitable. Popular travel routes and destinations with an active traveller scene make it easier to meet other people.
Sort out your insurance: Make sure you have good travel insurance that covers medical costs and cancellation.
Let someone know where you are: Share your travel itinerary with a trusted person at home.
Always book your first night in advance: Arriving somewhere new without a reservation creates unnecessary stress.
Stay alert to your belongings: Solo travellers have no one to watch their things, so stay aware of your surroundings.
Trust your instincts: Situations that do not feel right often are not. Do not be afraid to say no or walk away.

With the right preparation, most challenges of travelling alone are very manageable. It is not about eliminating all risk, but about setting off in a conscious and confident way.

Is going on a cruise alone a good idea?

A cruise is an excellent choice for solo travellers, provided you choose the right one. On a cruise, logistics, meals and activities are organised, which makes it easier to enjoy yourself without constantly having to make decisions. You also find it easy to meet other travellers on a cruise in a relaxed setting.

The downside of large cruise ships is the anonymity. With thousands of passengers on board, you can feel lost, and contact with other travellers often remains superficial. Small-scale cruises offer a clear alternative: a limited number of guests creates an intimate atmosphere in which you quickly connect with fellow travellers.

A luxury sailing cruise on a historic clipper ship combines the organised comfort of a cruise with the intimacy of a small group and the adventure of authentic sailing. For many solo travellers, that is an ideal combination.

How do you prevent loneliness during a solo holiday?

You prevent loneliness during a solo holiday by consciously choosing social activities and travel formats that encourage contact with others. Most solo travellers who feel lonely have built too little interaction into their trip.

Practical ways to make connections:

Stay in social accommodation, such as boutique hotels or small ships with shared spaces.
Join organised activities, such as day tours, cooking classes or snorkelling excursions.
Eat at the bar or at a shared table rather than alone at a small table.
Choose travel formats where you join a group, such as a sailing trip with a small group of like-minded travellers.
Stay open to chance conversations and dare to take the first step.

Loneliness is rarely about being alone — it is about not feeling connected. The right travel context makes that difference considerably smaller.

Which destinations are ideal for a solo holiday?

Ideal destinations for a solo holiday are places where the infrastructure for travellers is good, where it is safe and where you can easily meet other travellers. Think of destinations with a lively traveller scene, a pleasant climate and plenty of activities.

Popular choices include Portugal, Thailand, Colombia, Japan and the Caribbean islands. The Caribbean combines stunning nature, a warm culture and a relaxed atmosphere that perfectly suits the needs of solo travellers looking for both adventure and tranquillity.

For those looking for something more adventurous than a standard beach holiday, a sailing trip through the Caribbean offers a unique way to visit multiple islands without having to repack each time. You sail from bay to bay, discover places that cannot be reached by tour bus, and do so in the company of a small group of like-minded travellers.

How Clipper Stad Amsterdam helps create an unforgettable solo holiday

If you have had enough of the anonymity of large cruise ships and want a solo holiday that truly stays with you, we offer exactly what solo travellers are looking for: adventure, connection and comfort in one exceptional experience on board an iconic three-masted clipper ship.

What you can expect on board:

A maximum of 28 passengers, spread across 14 cabins, meaning you quickly connect with fellow guests.
A young, friendly and dedicated hospitality team available to you throughout the entire cruise.
Daily breakfast, lunch and dinner prepared by our chefs on board.
Activities such as snorkelling, day excursions and relaxing on secluded white beaches in the Caribbean.
An intimate, down-to-earth atmosphere that invites genuine conversations and new friendships.

Our luxury sailing cruises depart to the most beautiful Caribbean destinations. Rates are tailored exclusively to season, cabin category and trip duration. Would you like to know more about what a solo holiday on board the Clipper Stad Amsterdam could mean for you? Feel free to contact us for a personal quote — we would be delighted to tell you more.