There are some experiences you quietly file away as “probably not for me.”

Not because you don’t want them.

Usually because you want them so much that you almost don’t want to ask the question.

Will this work?

Will it be safe?

Does anyone know what to do?

Will I be able to enjoy the moment, or will I spend the whole time managing the fact that I’m there?

For me, being on or in the water has always been one of life’s great joys. Ever since I was a little girl, I’ve gravitated towards it. Swimming pools, oceans. Glass-bottom boats on Mediterranean holidays with my parents. The feeling of looking out across the sea and somehow feeling both tiny and completely held by it.

That love didn’t disappear when I became a disabled adult.

If anything, it became stronger.

I have been on boats since becoming a wheelchair user. I’ve cruised around the white-beached islands of Cuba and snorkelled over shipwrecks off the coast of Mexico. I’ve done some extraordinary things on the water, and I’m grateful for all of them.

But I’d be lying if I said they always felt easy.

More often than not, it was made quietly clear that I was joining in at my own risk. That the team weren’t really geared up for me. That they would help, of course, but the help was improvised, with the caveat that it was ultimately my responsibility.

A few hands.

A bit of goodwill.

A moment where everyone hopes it will be fine.

And usually, it is fine.

But it usually comes at the expense of extra physical and emotional energy being spent, when it shouldn’t be required.

That isn’t the same as a guest experience.

That is me making it work because I want the experience enough to accept a level of risk and discomfort that, from a safety perspective, I probably shouldn’t always accept.

There’s a particular feeling in those moments. A combination of gratitude that people are willing to help, discomfort because you know they are nervous, and a quiet wish that there was simply a system. A way for the experience to include you without it becoming a conversation about whether it can.

That isn’t pleasant for anyone involved.

And, honestly, I don’t want to be the person who causes the issue.

That is where so much of accessible travel still sits. Not in outright refusal, but in uncertainty. In people wanting to help, but not having the structure, confidence or experience to make that help feel seamless.

And then there are the experiences that make you realise it doesn’t have to be that way.

The experience we nearly wrote off.

Last year, during the honeymoon part of our Santorini wedding trip, Martin and I saw a private caldera cruise and dining experience in the excursion list.

It caught our attention immediately.

A private catamaran. The caldera from the water. Lunch on board. A slow, beautiful day after the wedding, just the two of us.

It sounded like exactly the kind of post-wedding date day you imagine when you choose Santorini.

So we enquired.

It was politely explained that it wasn’t available as one of the accessible experiences, and they weren’t aware of anything suitable for a wheelchair user.

And that was that.

We didn’t push it any further.

Partly because we were already in the middle of a wedding trip and there is only so much emotional energy you can spend asking whether the dream version of something might include you.

But those are the moments that stay with me.

Not because anyone was unkind. They weren’t.

Because this is exactly why The Inclusive Edit exists.

The belief that luxury travel, beautiful experiences, living well and celebrating life’s biggest moments should not sit just beyond reach because someone moves through the world differently.

The finest things in life are for everyone.

That doesn’t mean every experience will work for every person. It would be dishonest to pretend otherwise.

But it does mean the conversation should begin with possibility.

Not assumption.

Why a private cruise mattered to this series.

When I began building The Inclusive Edit’s Santorini milestone travel series, I knew a caldera cruise had to be part of it.

Santorini is an island of big moments.

Weddings. Honeymoons. Anniversaries. Proposals. The kind of trips people plan carefully, save for, and talk about for years afterwards.

And so much of the island’s beauty is seen from the water.

The cliffs. The volcanic beaches. The colours that change as the sun moves. The feeling of being close to the island, but also far enough away to understand its shape.

I had looked at a private Santorini cruise as a disabled newlywed and thought, “I’d love that, but I don’t think it’s for me,” then I knew other people would be thinking the same.

So I started looking for a private catamaran experience that could offer a caldera cruise for two with lunch.

I expected that to be the hard part.

It wasn’t.

From the first email with Sail Away Santorini, the conversation was warm, open and welcoming.

They didn’t specialise in accessible cruises.

But they did specialise in creating beautiful experiences at sea.

And from the beginning, that was the experience they wanted to create for us.

Choice before the journey began.

We booked a morning cruise with lunch, leaving from Vlychada Marina.

The route would take us past the Red Beach, White Beach and Mesa Pigadia, around the volcanoes of Palea and Nea Kameni, with the option of stopping at the hot springs or extending the cruise to include swimming spots.

But for this trip, we wanted something slower.

A few hours on the water.

Santorini sunshine.

Time to take in the coastline.

An intimate setting, without needing to chase every possible stop.

What I really liked was that the trip came with choice. It wasn’t fixed to a rigid brochure version of what a Santorini catamaran cruise should be. There was freedom to shape the experience around how we imagined it, and that mattered.

We had originally booked the cruise for the Saturday, but as the day approached, we could see the weather forecast changing. Just as we were discussing it ourselves, we received an email and message from Sail Away asking whether we would like to move the cruise to the Sunday, when the forecast was much better.

They wanted us to get the best from the experience.

I know that kind of flexibility won’t always be possible, especially in high season or with other bookings around it. But the fact they offered it before we even had to ask meant a lot.

That is part of the guest journey too.

Not just what happens once you arrive, but whether someone is paying attention before you do.

The experience can begin with an optional private transfer from your hotel or residence, and one of Sail Away’s vehicles is a minibus-style van that can accommodate a larger non-folding wheelchair. That detail matters, because access rarely begins at the experience itself. It begins with how you get there.

Boarding with dignity

When we arrived at the marina, Chief Captain Peter was waiting for us.

He explained the itinerary for the day and talked us through how I would board the catamaran. Calmly. Clearly. Without making it feel awkward or dramatic.

That is always the first test.

Not whether someone can help.

How that help feels.

It felt considered and thoughtful. At one point, Peter smiled and told me, “We don’t look for the problem, we look for the solution.”

That was philoxenia, right there.

The Greek spirit of hospitality. Not grand gestures or performance, but the quiet warmth of being welcomed properly.

As an ambulant wheelchair user, we decided I would board from the back of the boat on foot, with assistance from Captain Giannis and crew member Karim, who I would soon discover was also a very fine chef. Peter watched carefully and carried my wheelchair on board.

What I appreciated most was that they weren’t expecting Martin to manage the situation. They weren’t waiting for me to direct every movement. They simply helped me board with the kind of polite, steady assistance you would hope for as any guest.

It didn’t feel like “getting the disabled girl on the boat.”

It felt like boarding.

That distinction is everything.

Before we set off, we also spoke about how the experience could work for a wheelchair user who isn’t ambulant. Peter was clear that, with notice and the right information during the booking process, they would plan differently. The boat could be turned so boarding could happen from the side rather than the back, using larger ramps.

There are, of course, space restrictions on a catamaran. Moving around freely in a wheelchair would be limited, and I don’t want to pretend otherwise.

But this is where honesty matters.

For this particular experience, I’m not sure how much moving around anyone would need to do once settled.

Because the point wasn’t to rush around the boat.

The point was to sit with the person you love, look out across the caldera, drink locally sourced wine, eat beautifully prepared food and let Santorini unfold from the water.

I love an action-packed date day.

This wasn’t that.

This was about being present.

And it allowed me to do exactly that.

A wedding playlist, volcanic beaches and the joy of not rushing.

The weather was perfect.

Twenty-three degrees. Blue sky. No clouds worth mentioning.

And because this was still our anniversary trip, our wedding day playlist was connected to the boat’s Bluetooth.

I’m not saying every catamaran cruise needs a soundtrack from your wedding day.

But I’m also saying, it doesn’t hurt.

We continued to a place we had only seen in the dark, on horseback, before: the Black Beach.

Seeing it in all its glory from the water was another compelling perspective. The cliffs were still pale and dramatic, with old cave houses and syrmata built into the side, leading down to the black volcanic pebble beach below.

Every part of Santorini seems to carry another version of the same story.

Eruption. Impact. Legacy.

Beauty shaped by disruption.

Maybe that is part of why I love it so much.

From there, we sailed away from the main island towards Palea and Nea Kameni. Palea, the older and smaller of the two volcanoes, is dormant. Nea Kameni is larger and active, with a visible sulphur cloud.

We sailed between them and around the hot springs, where people were bathing in the mineral-rich water and sulphuric mud.

We decided to spend more time sailing than stopping for a dip.

The part Santorini doesn’t always tell you is that the mud can discolour your skin for a day or two, and you can probably say goodbye to your swimsuit too. Luckily, we already suspected this, and Giannis confirmed it with the kind of honesty I always appreciate.

So we stayed on board, let Karim top up the refreshments, and enjoyed the journey instead.

Sometimes choosing not to do something is what makes the day better.

Lunch on board Tionna

We decided to have lunch in the coves of White Beach, so we headed back towards the main island, taking in views of Thirasia and Aspronisi along the way.

Then Karim prepared what can only be described as a Greek feast for two aboard Tionna.

Seafood pasta.

Greek salad.

Fava beans.

Stuffed vine leaves.

Bread, olive oil, conversation, sunshine and the kind of stillness that makes you realise you are exactly where you are supposed to be.

I have no idea how he created all of that in the small kitchen on board while also looking after us so carefully, but he did.

And it was beautiful.

Even though we were on a catamaran with a crew, lunch somehow felt completely private. Giannis and Karim gave us space without disappearing. They understood when to step in and when to let the moment belong to us.

That is an art.

We fed the fish overboard and watched hundreds of them gather in the calm, clear water below. Martin and I sat there, eating lunch in the sunshine, holding hands across the table, realising that we were living out the dream we had imagined a year earlier and quietly assumed might not be possible.

That is what I will remember.

Not just the cliffs.

Or the food.

Not even the boat.

The feeling of being in the middle of something I once thought I might have to watch other people do.

The part that mattered most

After coffee, it was time to make our way back to the harbour and take in the last of the caldera from the water.

We honestly didn’t want it to end.

As the harbour came back into view, Peter was waiting to guide us in. Martin and I were both beaming, and we told him everything. The route. The food. The views. The volcanoes. The fact that we had been able to enjoy the experience exactly as we had hoped.

What struck me was that Peter was genuinely interested.

Not just in whether we had enjoyed ourselves, although he clearly cared about that.

He wanted to understand how it had worked in practice.

That is the part I keep coming back to.

Because this experience wasn’t perfect in the sense that every access need had been designed out of the equation. There were limitations. The toilet, for example, required support, and I managed happily with help from Martin and Karim. It was calm, dignified and completely can-do.

But I also understand that this won’t be possible for every single person.

That matters.

The Inclusive Edit is not interested in pretending that an experience is universally accessible when it isn’t.

That doesn’t help anyone.

What matters is clarity. Honesty. Conversation. Understanding what is possible and where the limitations are, so people can make informed decisions before they book.

And what Sail Away Santorini showed, in abundance, is that a dream private caldera catamaran cruise for two, with lunch on board and views worthy of a milestone moment, is possible for many more people than I once thought.

That is powerful.

Access as part of the experience

There is a tendency to speak about accessibility as though it sits separately from the experience.

First, we ask whether something is accessible.

Then, if it is, we ask whether it is beautiful.

But luxury travel doesn’t work like that.

Not really.

The access is part of whether the experience feels beautiful.

Because if you are worried, rushed, embarrassed, unsafe or constantly having to manage the practicalities of your own presence, it doesn’t matter how blue the water is.

You are not fully in the moment.

On board with Sail Away Santorini, I was.

Not because every possible barrier vanished.

Because the team approached the experience with care, confidence and solutions.

They didn’t begin with the barrier.

They began with yes.

Why this matters for milestone travel

A private catamaran in Santorini is not a small thing.

It is the kind of experience people choose for proposals, honeymoons, anniversaries and once-in-a-lifetime celebrations.

It is the kind of experience that becomes part of the story.

For disabled travellers and guests who move through the world differently, these moments can so often feel like they come with an asterisk.

Yes, but.

Beautiful, but.

Possible, but complicated.

What happened with Sail Away Santorini felt different.

It felt like the experience itself.

Not a reduced version. Or the accessible version of someone else’s dream. Not something we were lucky to squeeze into.

The dream itself.

And for this series, that matters.

Because The Inclusive Edit’s Santorini work is not about proving the island is effortlessly accessible for everyone. It isn’t.

It is about showing what becomes possible when the right hotels, venues, suppliers, experiences and local knowledge understand the guest journey properly from the beginning.

Sail Away Santorini understood that.

Not perfectly.

Honestly.

Warmly.

Practically.

And with a level of hospitality that made access feel like part of the service, not a separate issue to be negotiated.

That is the standard I’m looking for.

Not perfection.

Possibility handled well.

Because luxury is not only the private boat, the caldera view or the lunch on deck.

It is whether the experience has been thought through well enough for you to relax into the moment you came for.

And on that morning in Santorini, sitting on the water with Martin, with the island rising around us and the dream we almost wrote off unfolding in front of us, I did.

Completely.