Olegana Travel Boutique’s women only Sicily tour: Enjoying the beautiful outdoor pool at Masseria della Volpe in Noto, Sicily, Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
What soft travel actually means
I want to be precise about this, because the term has picked up enough marketing energy that it risks meaning everything and nothing at once.
Sunset over Boca Sami, Curaçao, with sailboats floating on calm waters beneath a colorful evening sky.
Photo©: Olegana Travel Boutique / Baoase Luxury Resort
Soft travel is not about spa hotels and doing less. It's not a synonym for relaxing, though it can include that. It's a specific orientation toward travel: staying somewhere long enough to develop a real relationship with it, choosing depth over breadth, designing a trip around how you want to feel rather than what you want to see.
The woman who takes two weeks in one region of Portugal and leaves knowing it as something approaching a local knows it: that's soft travel. The woman who joins a small group of women for a week in Sicily, cooking, walking, talking, eating things she can't find at home: that's soft travel. The woman who spends a long weekend in Seville with nothing on the agenda except wandering and whatever she discovers: that's soft travel.
Edinburgh Castle rises above the lush green lawns and mature trees of Princes Street Gardens in Edinburgh, Scotland, showcasing the city’s historic architecture and scenic beauty.
Photo©: Anna Fishman / Olegana Travel Boutique
It's intentional over efficient. Present over scheduled. A conversation instead of a checklist.
Most of the women I work with, whether they use this language or not, have been moving toward this for years. They've done the high-pace tour. They've done the ten cities in twelve days. And they come to me saying some version of the same thing: I want to actually be somewhere this time.
I want to actually be somewhere this time.
Why this matters especially for women traveling solo or in small groups
Olegana Travel Boutique’s group tour: Travelers posing together on a scenic outdoor terrace overlooking beautiful mountains and a lush valley in Spain.
Photo©: Anna Fishman / Olegana Travel Boutique
Solo travel, or travel in a small group of trusted women, has its own particular emotional register. You're not managing someone else's experience. You're not compromising on pace or place or how long you want to sit at a particular table. The trip can be entirely yours.
Olegana Travel Boutique’s Women-Only Sicily Tour: Visiting a charming boutique winery on the slopes of Mount Etna in Sicily, Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
That freedom is extraordinary. It's also, sometimes, a little confronting. Soft travel destinations work especially well for solo women because they're places where it's easy to be present, easy to connect with other people, easy to feel safe and welcomed without needing a companion to navigate for you.
The destinations below are ones I know well and send women to regularly, either as part of our group tours or as custom solo itineraries. What they share: they reward lingering. They have a warmth that makes solo travelers feel seen rather than alone. And they offer enough richness, in food, culture, landscape, and human connection, that you come home feeling fuller rather than depleted.
The destinations worth knowing
A note on how I've organized this: Lisbon, Seville, Curaçao, Sicily, and Edinburgh are destinations I know with real depth and recommend from firsthand experience and supplier relationships.
Lisbon, Portugal
Slow mornings, fado evenings, and a city that rewards wandering
Photo: Anna Fishman and her family exploring Lisbon, Portugal, and enjoying its scenic views, historic landmarks, charming streets, and vibrant culture.
Photo©: Anna Fishman / Olegana Travel Boutique
Lisbon is one of those cities that gives you more the less you plan. The neighborhoods are distinct enough that you can spend a week moving between them and feel like you've been to several places at once: the hustle of Baixa, the quiet of Mouraria, the bohemian tilt of LX Factory on a Saturday morning. The light here is particular, golden and warm even in shoulder season, and the Tagus is always there at the end of a walk to give you somewhere to stop and think. Fado, the Portuguese musical tradition that sounds like it was invented specifically for evenings when you want to feel something, is best heard in a small Alfama restaurant rather than a ticketed venue. The food is genuinely excellent and accessible at every level. Sintra, forty minutes by train, offers one of the most atmospheric half-day escapes in Europe. For soft travel, Lisbon works because it never feels like you're rushing to keep up with it.
Seville, Spain
Andalusia at its most alive, and most itself
Photo: Olegana Travel Boutique showcases the beauty of Seville, Spain, featuring its stunning architecture, historic landmarks, charming streets, and vibrant culture.
Photo©: Anna Fishman / Olegana Travel Boutique
Seville is one of my personal favorites, and I've been recommending it for years before it became the kind of destination that appears on every travel list. What I love about it for women traveling solo or in small groups is the scale: it's large enough to have real depth and small enough to feel navigable without a plan. The old city is walkable. The plazas invite sitting. The food, especially the smaller tapas bars that open at 8pm and stay warm until midnight, is the kind of eating that makes you understand why Spanish culture schedules itself the way it does. Flamenco in Seville is not a tourist show. In the right venue, a small tablao with twenty people and performers who have been doing this since childhood, it's one of the most genuinely moving experiences available in Europe. Fall and spring are the ideal seasons. We took our Andalusia women's group trips through this region for exactly these reasons.
Curaçao
Dutch color, calm water, and an island that slows you right down
Photo: Discover the beauty of Curaçao, known for its stunning beaches, crystal-clear waters, and delicious local cuisine. A glimpse into one of the Caribbean’s most captivating islands, filled with colorful scenery, vibrant culture, and unforgettable experiences.
Photo©: Olegana Travel Boutique / Baoase Luxury Resort
Curaçao is the Caribbean island I call my happy place, and it's an easy five hours nonstop from New York. It doesn't try to be a glossy resort island, and that's part of its charm. The coves along the calm side of the island have water you can float in for an hour without thinking about anything. In the evenings, Pietermaai's restored colonial houses hold small restaurants and bars you can walk between, and on Thursday nights Punda fills with music in the streets. The old Jewish quarter of Scharloo and the synagogue, the oldest in continuous use in the Americas, are worth a slow morning. For women who want Caribbean warmth and ease without the crowds of the better-known islands, Curaçao is the one I send people to and the one I keep going back to.
Sicily, Italy
Ancient, layered, and generous in the way only Italy can be
Photo: Olegana Travel Boutique showcases the beauty of Sicily, Italy, featuring stunning coastlines, charming towns, historic landmarks, delicious cuisine, and unforgettable cultural experiences.
Photo©: Anna Fishman / Olegana Travel Boutique
Sicily deserves its own post, and we have one. What I'll say here is that it embodies the soft travel ethos almost by accident: this is a place that has been too many things for too many civilizations to hurry through. Greek temples, Arab-Norman architecture, the best street food in Italy, volcanic landscapes, and a warmth from local people that makes you feel welcomed rather than tolerated. Our women's group trips to Sicily have centered on food, culture, and connection, and they sell out because the destination does something to people. Women arrive expecting a beautiful trip and leave feeling rearranged. We're going back in May 2028.
Edinburgh, Scotland
History on every corner, and a city made for walking
Photo: Olegana Travel Boutique showcases Edinburgh, Scotland, with its historic landmarks, elegant Georgian architecture, and charming streets.
Photo©: Anna Fishman / Olegana Travel Boutique
Edinburgh is one of my favorite cities anywhere. It's wonderfully walkable: you can spend a morning on the Royal Mile, wander down the narrow closes of the Old Town, and be strolling the elegant Georgian streets of the New Town by lunch without ever needing a taxi. The history is everywhere you look, from the castle on its rock to streets that have barely changed in centuries. The food has become genuinely excellent, from cozy pubs to serious restaurants, and the shopping is a real pleasure: cashmere and tweed, independent boutiques, and the curving, colorful shopfronts of Victoria Street. For women traveling solo, it's an easy city to feel at home in quickly. Many of the women on our castles and gardens trip add a night or two here before the group comes together.
Ready to travel somewhere that stays with you?
Our women's group tours are designed for exactly this kind of travel: small groups, curated destinations, real depth. See what's coming up.
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What soft travel looks like in practice when it's planned well
Olegana Travel Boutique’s Women-Only Sicily Tour: Savoring local wines and discovering the unique flavors of a boutique winery near Mount Etna, Sicily, Italy
Photo©: Anna Fishman / Olegana Travel Boutique
The difference between a soft travel trip that actually delivers and one that sounds good in theory comes down to a few things I've learned from designing these itineraries:
Staying in one place long enough to develop a rhythm. Two nights somewhere is sightseeing. Four or five nights is the beginning of actually being there. The most restorative trips I design for women build in real stillness at each stop.
Baoase Luxury Resort and Baoase Culinary Beach Restaurant in Willemstad, Curaçao, offer a tropical beachfront escape with luxurious accommodations, tranquil waters, and exceptional dining.
Photo©: Olegana Travel Boutique / Baoase Luxury Resort
Choosing accommodation that has warmth and character, not just aesthetics. The right hotel for soft travel isn't necessarily the most impressive one. It's the one with a terrace where you want to spend your mornings, a staff who knows your name by day two, and a location that puts you into the life of the place rather than beside it.
Olegana Travel Boutique’s Southern Spain Tour: Enjoying a scenic boat tour along the beautiful coastline of southern Spain.
Photo©: Anna Fishman / Olegana Travel Boutique
Building in unscheduled time. This sounds obvious and is consistently the thing most travelers resist until they've experienced it. The afternoon with nothing on the agenda, where you end up at a table you stumbled into and have a conversation you didn't plan, is often the best part of the trip.
Traveling with the right people. For solo women who want company without compromise, a small curated group of like-minded travelers is often the answer. Our group tours are designed around this: sixteen women at most, shared values, genuine freedom within the structure.
A note on traveling solo versus joining a group
Both work. It depends on what you're looking for.
Solo custom travel gives you complete freedom. The itinerary is designed entirely around you: your pace, your interests, your version of a perfect day. You're alone in the independent sense, with everything arranged and support available, but you're moving through the destination as yourself, without the compromises that even the best travel companions require.
A small women's group tour gives you something different: built-in connection. The friendships that form on well-curated group trips are among the most lasting and genuine I've seen in travel, because you've gone through something real together. The shared table, the unexpected afternoon, the moment of genuine beauty in a place you've traveled to specifically to experience it: those become the foundation of real friendship in a way that a cocktail party never does.
I've seen both change women's lives. The question is which kind of change you're looking for right now.
Anna Fishman, the visionary and soulful force behind Olegana Travel Boutique, orchestrates transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
See our women's group tours
Small groups. Curated destinations. The kind of travel that stays with you. Check here or book a call with me.
Frequently Ask Questions
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Soft travel is an approach to travel that prioritizes depth over breadth, presence over efficiency, and intentional experiences over packed itineraries. Rather than visiting as many places as possible, soft travelers stay longer in fewer destinations, choosing activities that allow for genuine connection with a place and the people in it. It's particularly popular among women and solo travelers who want to come home feeling restored rather than exhausted.
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Destinations that reward lingering, have strong food and cultural traditions, and welcome solo travelers warmly are ideal for soft travel. Lisbon, Seville, and Edinburgh are consistently strong choices in Europe for their walkability, warmth, and depth of local culture. Sicily and the south of Italy offer extraordinary food culture and genuine hospitality. In the Caribbean, Curaçao offers calm water, a slower pace, and fewer crowds than the better-known islands.
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They overlap but aren't identical. Slow travel refers specifically to pace: staying longer in fewer places, often using slower forms of transport, spending weeks or months rather than days. Soft travel is broader and more about orientation: it can be a week-long trip that is intentionally designed around depth and presence, even if the pace isn't slow by strict definition. Most soft travel is slow travel, but not all slow travel is soft.
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Yes, and small curated group tours are often an ideal format for soft travel. The key is group size and itinerary design. Tours of sixteen women at most, staying at each location long enough to develop a genuine feel for it, with unscheduled time built in, and experiences designed around connection rather than sightseeing, produce exactly the depth and restoration that soft travel is about. The addition of like-minded company often deepens the experience rather than diluting it.