Between Voyages: A Transatlantic Crossing on Wind Surf

Sailing from Sint Maarten to the Azores to Lisbon, Portugal

There are moments in a life of travel when the next journey is not planned so much as it is necessary.

After years of walking - across Canada on the Trans Canada Trail, across Spain on the Camino Frances and Via de la Plata, across Portugal on the Camino Portuguese and across the United Kingdom on a series of national trails, and through landscapes that reshaped how we see the world, we have come to understand that travel is not always about the physical distance covered. Sometimes it is about regaining perspective. Sometimes it is about finding space to think clearly again.

 

This voyage aboard Windstar Cruises' Wind Surf begins in such a moment in our lives. In a moment full of tensions, decisions and uncertainties, we are setting out in search of direction.

Only days before departure, with little more than instinct to guide us, we found ourselves once again turning toward the Atlantic. Not the result of long-term plans, but out of a moment of recognition that we needed to step away from the noise of daily life and return to something simpler. Something more essential and something slower. Something that has, in the past, helped us regain our footing.

To go to sea is, in many ways, to surrender control. To opt into a stretch of uncertainty.

A sailing vessel does not promise efficiency. It does not guarantee arrival on schedule, nor does it follow a rigid path across the ocean. Weather, wind, and tide shape the journey as much as any charted course. Plans may hold…or they may shift entirely, as we have experienced before. And yet, within that uncertainty lies its value.

Out there, beyond sight of land, we are given time and opportunity to reflect. Thoughts have the chance to settle. The constant urgency of the world and 24/7 news takes a back seat and is replaced by the roll of the ship, the sound of the waves, the movement of clouds, and the presence of seabirds tracing invisible routes across the sky.

This is not our first transatlantic crossing aboard Wind Surf. Our previous voyage carried us not to Lisbon as intended, but to the Canary Islands and Cádiz, redirected by the realities of the open ocean. That experience taught us something essential: that the destination matters far less than the act of crossing itself.

This time, we set out again – acknowledging that this is in itself a new voyage, but hopeful that it can offer the same moments of peace and perspective.

Entries for this Voyage:

Panic Attacks and Plans : An Unexpected Spring Voyage

Packing and Preparing for a Transatlantic Sailing

 

En Route : Leaving the Noise Behind

Wind Surf Day 1 – Embarkation : Returning to the Atlantic and MSY Wind Surf

Wind Surf Day 2 – Atlantic Wanderer

Wind Surf Day 3 – The Art of Slowing Down

Wind Surf Day 4 – Into the Wind, and Not Knowing

Wind Surf Day 5 – Time, Rhythm, and Life At Sea

Wind Surf Day 6 – Ease and Shelter

Wind Surf Day 7 – Travelling by Compasses, Not Clocks

Wind Surf Day 8 – Taking the Helm

Wind Surf Day 9 – Sailing with Dolphins, Whales, and Sea Birds

Wind Surf Day 10 – Embracing the Realities of Slow Travel

Wind Surf Day 11 – Changing Plans: Ponte Delgada Deferred

Wind Surf Day 12 – Navigating Uncertainty at Sea

Wind Surf Day 13 – Final Sea Day

Wind Surf Day 14 – Arrival, Lisbon, Portugal

Wind Surf Day 15 – Disembarkation and Travel 

Reflections on Knot Your Average Crossing on Wind Surf

Return to Land - Birding the Ria Formosa on Foot

Turning the Tide - Birding the Ria Formosa by Boat

What’s Next?

A Voyage Between Journeys

In many ways, this crossing exists in the space between things. Between planned hikes, between past journeys and those yet to come…. and between key decisions in our lives.

This voyage, therefore, also exists between certainty and uncertainty. Between the demands of life on land and the clarity that often emerges on the way or out at sea.

We carry with us the weight of recent years - long-distance trails, changing circumstances, and the accumulation of looming responsibilities that come with time. These are not things we seek to leave behind, but we now face circumstances that we hope to understand more fully. There is a difference.

Travel, for us, has never been about escape. It is about gaining perspective. About placing the challenges of life within a wider horizon, where they can be seen more clearly, and perhaps carried more easily. A transatlantic crossing – as we have discovered on Queen Mary 2 and Wind Surf in the past – are the type of wondrous journey that offers exactly that.

Days at sea transpire according to the conditions at hand – there is no changing this simple reality. There are no roads to follow, no towns to reach by nightfall, no distances that need to be measured. Instead, there is only the steady passage of the ship, the rise and fall of the swells, and the realization that not everything needs to be resolved immediately. As well as the hope that by landfall, there is clarity to what lies ahead.

Some things simply need time. And so it is in the space between continents, a space beyond schedules and itineraries that we have found in the past what we did not realize that we were searching for.

The Journey Ahead

This is not intended as a guide to cruising, nor as a fixed itinerary for what a transatlantic sailing should be. It is a record of a journey as it unfolds: uncertain, weather-shaped, and open to whatever the ocean chooses to reveal. It is about what it means to step away from the noise of land, to cross an ocean slowly, and to notice what remains when distance, wind, and time begin to strip life back to its essentials.

In writing these entries, we hope to share the experience of preparing to leave, almost before the decision has fully settled. We want to capture the mixture of logistics and emotion that comes with setting out: the hurried packing, the unresolved questions, the familiar pull of the sea, and the hope that somewhere between continents, perspective may begin to return.

We also hope to offer a sense of what it is like to live aboard Wind Surf for more than half a month, not as a checklist of amenities, but as a rhythm of days. Mornings on deck, changing weather, meals shared at sea, sails above us, waves against the hull, birds and marine life appearing when they choose - these are the details that shape a crossing far more than any printed itinerary.

And because this is a return voyage, it is also a story of familiarity and difference. The same ship, the same ocean, but not the same crossing. We return with memories of our first transatlantic sailing aboard Wind Surf, but also with the understanding that no journey can be repeated exactly. Wind, weather, crew, passengers, and our own state of mind will make this voyage something entirely its own.

Ultimately, this series is about the long space between departure and arrival: what it feels like to leave one shore behind, to live for a time with only sea and sky around us, and then to approach familiar lands and ports changed, perhaps only slightly, by the crossing itself.

Continuing the Line of Our Travels

Our second Transatlantic voyage on MSY Wind Surf is one part of a much longer slow travel adventure. Beyond our long-distance hikes such as the East Coast Trail and Bruce Trail, and our pilgrimages on the Camino Madrid, the Rota Vicentina, and Via Podiensis. We have travelled across Canada on Via Rail’s iconic trains, the Ocean and the Canadian, and repeatedly crossed the north Atlantic on the world’s last ocean liner, Cunard’s Queen Mary 2.

Each journey connects to the next. Each crossing extends that line a little further.

And while no single voyage provides all the answers, each one offers something of value - if only the space to ask better questions. Whether you are dreaming of your own crossing or simply curious about life between continents, we invite you to follow along.

See you on board.