The Trip I’d Plan for a Solo Traveler Who Doesn’t Want to Travel Alone

Solo travel has never meant solitude to me

The point of traveling solo is not to prove that you can be alone. It is to have more say in your own time. I like waking up to a view and deciding what I need from the day. Sometimes that is a beach. Sometimes it is a full day at the spa. Sometimes it is walking a city until my feet hurt, wandering through museums, or having an epic shopping day without anyone asking if I am ready to leave yet.

I have spent hours kayaking around a lagoon in Turks and Caicos by myself. I have had fabulous Michelin-starred dinners alone. I have sat at a bar and talked with someone until late because neither of us was ready to call it a night. Those are not second-best versions of travel. They are often the reason to go.

Traveling solo has also made me more open. I will start conversations in ways I might not at home. I will ask someone waiting for an elevator what they did in port. I will sit at the bar and ask the bartender what they would do in their own city. Sometimes it is as simple as complimenting a stranger in passing and watching them light up.
You do not need a clever line or a big reason to talk to someone. Just notice people.

Sometimes a conversation lasts 10 minutes. Sometimes it lasts years. I have stayed in touch with many people I met while traveling solo, and some of them are now people I travel with. You do not have to make friends to have a great solo trip. You only have to be open to the possibility that you might.

For LGBTQ+ solo travelers, comfort and community can matter just as much as the hotel or itinerary. I pay attention to how a destination feels, where connection might be easy to find, and how to build a trip that feels affirming without turning every moment into a statement. You should be able to take the trip you want, be yourself, and decide how social you want to be.

A balcony hammock, nowhere to be, and exactly the kind of quiet I needed.

I plan around the reason you are going

If you want the freedom of traveling alone without a trip that feels isolating, I first decide which kind of travel best gives you that balance: a city, an adults-only resort, a guided tour, or a cruise.

A resort is not just rest. It is permission to stop performing productivity on vacation.

When I plan a solo resort stay, I choose more than a pretty pool and a nice beach. I think about the energy of the property, the food, the room categories that are worth the spend, the spa, and the ease of getting off property when you want a change of scenery. I want you to have a beautiful place to do very little, while still knowing a great lunch, boat day, local experience, or quiet corner is there when you want it.

A city is not just immersion. It is the pleasure of following your own curiosity without compromise.

You can spend as long as you want in a museum, eat at the bar of the restaurant you have been thinking about for months, shop until you are done, or take a long walk because a neighborhood caught your attention. I take care of the work around that freedom. I choose the right neighborhood and hotel, arrange transportation, book the experiences worth your time, and make sure you know where you will feel comfortable dining, wandering, and coming back to at the end of the day.

A guided or escorted tour is not just convenience. It is company and access without the burden of organizing the trip.

For the right person, a great tour makes solo travel feel easier without making it feel generic. You have people to share the experience with, local knowledge built into the day, and someone else managing the transfers, tickets, logistics, and timing. I look closely at group size, pace, inclusions, and traveler mix, because the right tour feels like access and ease. It should not feel like being rushed through a checklist.

A cruise is not just variety. It is the easiest way to wake up in a different mood every day.

You unpack once, wake up somewhere new every day or two, and decide what version of vacation you want. One day can be a beach day. The next can be an excursion, a late night, a recovery morning, a spa afternoon, a great dinner, or a show. A cruise does not give you the same depth in every destination as a longer city stay. But it can be an excellent introduction. A port you love can become the place you return to later for a longer trip.

I still handle the planning. I help choose the right sailing, ship, cabin, cabin location, itinerary, excursions, dining strategy, and travel days around it. Once onboard, you get a lot of freedom without having to create the entire experience yourself.

Hours spent kayaking a lagoon in Turks and Caicos, entirely on my own schedule.

Why Virgin was right for my solo birthday

Virgin Voyages is not the subject of this story. It is the clearest example I have of the kind of solo trip I am talking about. I had sailed Virgin before, so I knew the ship and knew what to expect. That familiarity helped. Still, I was spending my 40th birthday by myself, and I was not sure how it would feel. It turned out to be one of the best trips I have taken.

The Solo Sailor group gave me an easy place to start. We did a lot together, but I never felt trapped in a group trip. I could join in when I wanted to and do my own thing when I did not.

After an overnight in Ibiza, I took a catamaran excursion and met a few women who were traveling together. We ended up helping each other with a very fun photo shoot and had a great afternoon. Nobody had planned it. It was simply one of those great travel moments that happens when you are open to a day going somewhere unexpected.

I spent time with the Happenings Cast and went to events that genuinely interested me. I met people through the Solo Sailor group and in ordinary moments around the ship. On a longer sailing, you begin to see familiar faces. You run into someone at the bar, at a show, in the spa, or on the way to dinner. The social part starts to happen naturally.

I also had my own space. I could meet friends at the spa, or I could spend a morning in my balcony hammock, looking at the water and doing absolutely nothing. I could have a late night, then take the next morning slowly.
That is the balance I want for a client who is nervous about traveling alone. Connection is available. Privacy is available. Neither has to be earned.

Virgin is right for a traveler who likes an adults-only environment, restaurant-style dining, good energy, and a trip that feels different from the traditional cruise formula. It will not be right for everyone. That is exactly why matching the traveler to the experience matters.

Solo travel has taken me from warm Caribbean water to cold Icelandic skies. The freedom is the point.

You can go alone without being unsupported

The people I most want to encourage are often not afraid of the destination. They are afraid of carrying the whole trip themselves. You do not have to.

Whether I am planning a beach escape, a city stay, a guided tour, or a cruise, I choose the experience that fits your reason for going. I handle the details that shape how the trip feels, share recommendations that match your interests, and make sure you know what to expect before you leave home.

I am also available while you travel. If something changes, if you need a recommendation, or if you simply want reassurance, you have someone to call. You are traveling independently. You are not doing it alone.

Solo travel can be about a milestone, a breakup, a particular event, deep immersion in a city, a real reset, or simply refusing to wait for someone else to go.

Your reason for traveling should determine the trip. A resort offers restoration, a city rewards curiosity, a guided tour offers company and access, and a cruise gives you changing scenery and easy variety.

For LGBTQ+ solo travelers, I plan for both the practical details and the feeling of comfort that lets you be fully yourself.

Virgin Voyages was the right setting for my own 40th birthday because it gave me room to make friends, room to have quiet time, and the freedom to decide what I wanted each day. The best solo trip is one where you feel independent, supported, and completely free to make the experience your own.

For more inspiration and insider recommendations, visit our cruises page.