In 2027, the packed holiday itinerary could be falling out of favour as holidaymakers increasingly reject the pressure to see and do everything in favour of slower, more meaningful trips, according to global yacht charter and sailing holiday provider Sunsail.
Drawing on customer data, online search behaviour and insight from its on-the-ground destination teams, Sunsail has identified five travel behaviours it expects to shape the year ahead, reflecting a wider shift towards holidays that prioritise how a trip feels over how much can be fitted into it.
Sunsail also predicts that the definition of luxury will evolve, with holidaymakers opting for more freedom and quieter spaces that provide enriching and unique experiences.
The company has also identified 10 lesser-known destinations that could benefit from this shift, offering travellers nature, local culture, food, privacy and a slower pace away from better-known hotspots.
The 2027 travel trends at a glance
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Travellers will choose the experience before the destination – rather than starting their holiday planning by asking where to go, travellers are increasingly choosing the experience they want first, then finding the destination that can deliver it.
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The end of the tick-box holiday – travellers will increasingly reject the pressure to visit as many places as possible. Instead, the ultimate status symbol and measure of a successful trip won’t be how many places guests managed to visit, but the quality of time spent there.
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Luxury will be redefined as peace and privacy – the definition of luxury will evolve and will be seen as space and freedom to switch off, access to quieter destinations, nature and experiences that aren’t busy tourist routes.
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The AI vs Sailor conflict – as more travellers turn to technology for holiday inspiration, there is a risk that the destinations with the biggest digital footprint become the destinations that are recommended most often.
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The UK and the US divide – customer data from Sunsail suggests British and American travellers approach holidays with noticeably different mindsets, which is set to continue in 2027.
Andy Crang, Vice President Marketing at Sunsail & The Moorings UK, said of the predictions: “In 2027, we expect to see a shift from holidays being about how much you can see to how much you can experience. Travellers desire meaningful experiences, greater cultural immersion and long-term connection to the places they visit.
“Guests seek a better balance between adventure and relaxation. Rather than feeling pressured to see everything, they want time and freedom to enjoy the places they have travelled to, which is reflected in the requests our on-site professionals receive. Holidaymakers seek activities hosted by local residents, longer anchorages, and want to find quieter, under-the-radar destinations that make their trip feel exclusive and unique.
“This is where local knowledge is most valuable. The best experiences for travellers aren’t necessarily the ones that are easiest to find online; they come from spending longer in one place, having freedom with itineraries and detailed conversations with local people and experienced professionals.”
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Travellers will choose the experience before the destination
Holiday planning has traditionally begun with one question: “Where should we go?” In 2027, Sunsail anticipates more travellers may start by asking “what can we do?”
For the modern traveller, the destination itself is becoming secondary. Instead, they are booking with key moments in mind, including engaging with wildlife, diving in untouched waters, discovering natural landscapes or learning about a local custom.
Sunsail’s customer research and feedback from the on-the-ground teams support the experience-first mindset. Six in ten (60%) of travellers cite discovering and exploring new places as a primary holiday motivator, while 50% are driven by the search for natural scenic beauty.
Online searches reflect a similar appetite, with searches for ‘experience holiday’ up 70% this year. The result could be a shift in how people choose where to travel – with the experience they want becoming the starting point, and the destination coming second.
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The end of the tick-box holiday
For years, the perfect holiday has been measured by how much you can fit into it, and a constant stream of things to see and do became a badge of honour. But in 2027, Sunsail expects travellers to value the opposite, allowing themselves to slow down and place less value on ‘collecting’ destinations.
They will favour slower, more intentional trips, spending longer in places they visit. For sailing holidays, this autonomy can be built into the experience. Future trips can have less itinerary pressure, less obligation to move on quickly, and more freedom to soak up experiences at a destination guests are enjoying.
The trend is supported by Sunsail’s customer data and online searches, with over a third of customers motivated by natural beauty and searches for ‘nature holidays’ increasing by 30% this year. Meanwhile, 35% cite local food, drink and onshore experiences as holiday motivations.
In 2027, the ultimate status symbol won’t be how many places you visited; it will be the freedom of having nowhere else to be.
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Luxury is redefined as peace and privacy
The days of equating luxury with five-star resorts and concierge services are fading. For the 2027 traveller, the status symbol is evolving, with holidays less about what travellers have access to and more about what they feel.
For some travellers, luxury is becoming less about five-star hotels, private pools or high-end dining and more about having somewhere peaceful almost entirely to themselves. Privacy, nature, clear waters, dark skies and encounters with wildlife are becoming valuable precisely because they provide an escape from everyday noise. Online searches reflect this demand, with searches for ‘private holiday’ increasing by 100% over the last year and by a fifth in the last three months alone.
While these ‘destination watchlist’ locations are becoming the new gold standard for travel, they are notoriously difficult to find. This is where local knowledge becomes the greatest asset, according to Sunsail’s Keith Harvey, Dubrovnik Base Manager, and Mirna Jakšić, Sunsail’s Agana Events and Flotilla Manager.
“Our skippers have been navigating these hidden bays, secret caves, and untouched harbours for years. Unlike a resort, which stays put, a Sunsail yacht allows for true ‘Restorative Luxury.’ Yachts aren’t beholden to a schedule. If the weather turns or a bay becomes busier, we move on. We can adapt to the changing landscape, ensuring guests reach these restorative and luxurious places when the conditions are perfect,” says Keith.
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AI could make travel more predictable – not more adventurous
AI is already becoming the starting point for holiday planning. It can suggest destinations, build itineraries, compare travel times and offer holiday inspiration based on the information available online.
Yet as more travellers turn to technology for holiday inspiration, there is a risk that the destinations with the biggest digital footprint become the destinations that are recommended most often. This means overlooking quieter, lesser-known destinations that may not have the volume of online content needed to make them visible to an algorithm.
AI also has its limits when it comes to the realities of adventure holidays, particularly when on the water.
As Sunsail’s Agana Events and Flotilla Manager, Mirna Jakšić, describes: “AI is not a sailor. It can suggest a route based on what it knows, but it doesn’t have the experience of being on the water and understanding how a place can quickly change with the wind, weather, and sea conditions. Knowing where to go, when to move on, and which places are worth discovering comes with years of experience. AI can be a useful tool, but it can’t replace the local knowledge you gain from actually sailing these waters.”
The future isn’t about choosing between AI and human expertise. It’s about using technology for what it does best, while putting real-world sailing knowledge at the heart of the final plan.
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The UK and the US divide
Customer insight from Sunsail suggests British and American travellers approach holidays with noticeably different mindsets, which is set to continue in 2027.
For UK travellers, sailing is often about making the most of the opportunity to discover somewhere new, whereas for US travellers, the emphasis is more firmly on escape.
There are also differences in who holidaymakers prefer to travel with. UK guests are more likely to travel in smaller, close-knit groups, with 19% of customers travelling in a group size of 2 (compared to 8% for the US) and 38% travelling in a group size of 3-4 (compared to 22% in the US).
US bookings show a stronger skew towards larger groups, with 34% of customers travelling in a group size of 5-6 (compared to 26% in the UK) and 30% travelling in a group size of 7-8 (compared to 14% in the UK).
For both, the appeal is stepping away from the usual routine, but what they do with that freedom is where the two markets differ.
10 destinations for a slower, more meaningful holiday
In 2027, the places on travellers’ watchlists aren’t necessarily the ones dominating social feeds or topping the tourist maps. They are the destinations offering something harder to find, championing untouched nature, authentic food and wine, dark skies, local culture and the freedom to experience somewhere at a slower pace.
Drawing on customer behaviour and first-hand recommendations from its skippers and local teams, Sunsail has created a 2027 Destination Watchlist: places that embody the growing demand for nature, privacy, local culture and the freedom to slow down.
Mirna Jakšić, Agana Events and Flotilla Manager at Sunsail, said of the list: “The most memorable places aren’t always the ones everyone knows about. When you’re sailing, you have the freedom to go beyond the obvious destinations and discover somewhere because of how it feels, rather than how many people have posted about it. That’s where you find the really special experiences, featuring quiet anchorages, family-run tavernas, and the bays you have almost entirely to yourself.”
For untouched nature and outdoor adventure:
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Lastovo, Croatia – for dark skies and untouched nature
A protected nature park, Lastovo is the Rising Star of South Dalmatia with exceptional dark skies perfect for stargazing, as well as beautiful surroundings for snorkelling and diving enthusiasts.
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Mljet, Croatia – for adventurers and nature lovers
Also a national park in southern Croatia, Mljet offers a slower, nature-led alternative to busier hotspots. Visitors can explore its saltwater lakes by kayak or take in the views from the island’s hiking and cycling trails.
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Kalamos, Greece – for the natural landscapes
With mountainous terrain, pine forests, and protected harbours, Kalamos’ natural beauty and peaceful atmosphere give it a luxurious feel.
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Elaphiti Islands (Šipan, Lopud, Koločep), Croatia – for the peaceful and restorative feeling
The islands are either car-free or allow limited local vehicles, which adds to the tranquil environment. Surrounded by luxurious swimming bays, the islands are suited to travellers seeking a quiet luxury that prioritises a slower pace for their trip.
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Anegada, British Virgin Islands – for striking reefs and exotic wildlife
Rising just 28 feet above sea level, Anegada is surrounded by striking reefs, underwater caves and pristine beaches. The wildlife is one of the island’s highlights, with dolphins often playing near the shore, flocks of flamingos at the salt pond and rare rock iguanas living at Bones Bight Nature Trail.
For authentic food and wine
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Pelješac Peninsula, Croatia – for fresh oysters
Oysters are a must when visiting the Pelješac Peninsula, which is also a leading region for red wine production. Packed with farm-to-table experiences, the peninsula brings the best of Croatian cuisine to the forefront.
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Sveta Nedelja, Hvar, Croatia – for wine with a view
Wine lovers can enjoy a unique experience here, visiting a local winemaker with a tasting room beneath sea level and dramatic views looking out towards the sea.
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Jost Van Dyke, British Virgin Islands – for classic Caribbean cocktails
A must visit destination for travellers looking to experience quintessential Caribbean culture, especially when it comes to the cocktails. Choose from a range of classic Caribbean bars located on picturesque white-sand beaches, perfect for soaking up the slow-paced atmosphere.
For living history and local culture
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Pučišća, Croatia – for living history
Explore the village’s distinctive white-stone architecture, shaped by centuries of local craftsmanship.
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Meganisi, Greece – for hidden history
For history lovers, Meganisi is home to Papanikolis Cave, which was used as a hideout by Greek submarines during World War II. The cave is only accessible by boat, extending 120 metres into the rock.
More information on the 2027 predictions can be found on Sunsail’s website: www.sunsail.com/uk/blog/2027-travel-trends-predictions
