Something has shifted in the way people are thinking about travel this year. The world feels louder than usual. The news cycle moves fast, the economic picture is uneven, and the questions that used to live quietly in the background are now front and center: Is this the right time? Will the trip I am planning actually happen the way I imagine it? Is someone going to be in my corner if it doesn't?

*Photo©: Olegana Travel Boutique, Anna Fishman*

And yet, the trips are happening. My phone has not gone quiet. If anything, the conversations I am having with clients right now are richer, more thoughtful, and more intentional than ever before. People are not giving up on travel. They are being smarter about it. And the ones who are traveling the best, with the least stress and the most to show for it, are the ones who decided to stop planning alone.

This is what a luxury travel advisor actually does in a moment like this. Not just book flights and hotels. Not just fill in a form. Build the trip that holds together when the world does not.

And increasingly, the conversations I am having are not just about where to go. They are about who someone wants to be when they get there. The traveler who wants to feel like themselves again. The couple who wants to remember what they built together. The woman who has spent decades taking care of everyone else and is finally ready to take care of herself. These are the trips that matter most to me, and they are the ones I am best at designing.

What the travel landscape actually looks like right now

Before I talk about what working with an advisor changes, I want to be honest about what is happening in travel at the moment. Because if you are feeling uncertain, you deserve a clear picture, not a sales pitch.

Demand is strong. Hesitation is real.

Nearly half of Americans say travel remains a protected line in their household budget. More than 70 percent are actively planning a trip right now, not someday, right now. The desire to travel has not gone anywhere. What has changed is the pace of commitment. People are taking longer to book, asking more questions before they do, and wanting reassurance that they will not be locked into something rigid if life shifts around them.

This is not fear. This is wisdom. And it is exactly the kind of client I do my best work with.

Booking windows have compressed.

What I am seeing across the board is that people are booking closer to their departure dates than they used to. The client who once planned 12 to 14 months out is now calling 4 to 6 months before they want to leave, sometimes less. This matters for two reasons. First, certain experiences, the most sought-after restaurants, the most intimate guided access, the most coveted hotel categories, are already reserved well in advance. Second, it means flexibility has to be engineered into the trip from the start, not retrofitted later. This is where my relationships and my process make a measurable difference.

Some regions are booming. Others have shifted.

Europe continues to be the most requested region I plan. Italy, Spain, Portugal, Scotland, and the UK are all performing strongly. The Caribbean remains a consistent favorite for shorter, warmer escapes. What I am also seeing is a renewed interest in secondary destinations, places that sit just outside the most crowded itineraries and deliver something the overtouristed routes cannot: space, authenticity, and access that feels genuinely rare. Puglia over the Amalfi Coast. The Basque Country alongside Barcelona. The Scottish Highlands rather than Edinburgh alone.

The clients who let me introduce them to these combinations come home talking about them for years.

What an advisor unlocks that you cannot arrange on your own

This is the part that surprises people most when we first speak. They assume working with a luxury travel advisor is about having someone do the logistics for them. That is the smallest part of what I do. Here is what it actually looks like:

Access to hotel categories and room types that are never released publicly. My relationships with properties across Europe and the Caribbean mean my clients arrive to things the online booking rate simply does not include.

Private guided access to places that charge admission to everyone else. I work with local specialists and cultural institutions who reserve private entry, after-hours access, and behind-the-scenes experiences for a small number of trusted advisors. I am one of them.

Curated dining experiences that are not on a reservation platform. Some of the most extraordinary tables in Europe do not exist on any app. They exist because a supplier I have worked with for years made a call on my behalf.

Itineraries built with deliberate flexibility. I design trips with modular structure, meaning if something shifts, your trip adjusts around it, not the other way around. I know which suppliers can move dates, which properties have flexible policies, and how to sequence an itinerary so nothing is fragile.

A human being who answers when something goes wrong. Not a chatbot. Not a hold queue. Me, with the direct lines and the local contacts to fix it.

Multi-generational and group trips where every traveler, from grandparents to grandchildren, has something designed specifically for them, without anyone feeling like an afterthought.

One client described the transfer and logistics experience across her Greece and Croatia itinerary in five words: "mindless and so easy to navigate." That is exactly what it should feel like. Another, returning from Greece, told me the ease of getting to and from every excursion and the airport was one of the things she loved most about the trip. Not the Acropolis. Not the sunset boat in Santorini. The fact that she never had to think about how to get anywhere.

Ready to plan your next trip?

If you have been sitting on a trip idea and are not quite sure how to move forward, this is the moment to reach out. I plan custom European and Caribbean journeys for couples, families, and women travelers who want every detail handled, every experience curated, and every worry off their plate.

Book a consultation at anna@oleganatravelboutique.com

One of my clients said it better than I ever could:

“Anna planned the trip of a lifetime for my husband and I to celebrate our belated honeymoon in Italy and Greece. She balanced the trip perfectly with activities and relax days, booked amazing hotels and private boat tours. She really took our preferences and input to heart and created an itinerary that was so organized, well thought out and fun!!! The app she uses also is extremely helpful when traveling as it had all our travel info, tour vouchers, taxi contact info etc. We had put off planning our trip because we kept getting overwhelmed - but once we found Anna and put it in her hands, all we had left to do was enjoy! Thanks again Anna you’re amazing!”

- Naomi G

When is the right time to start planning

The most common thing I hear from people who reach out is: I wish I had called you sooner. So let me give you the timing picture honestly, because it matters more than most people realize.

12 or more months out

This is the ideal window for complex itineraries: multi-generational trips, women's group tours, honeymoons, and anniversaries that involve specific properties or experiences. The access is better, the options are wider, and you have the luxury of designing something without pressure.

6 to 9 months out

This is where most of my clients land, and it is still a very workable window for custom European and Caribbean travel. We will need to move decisively on certain accommodations and experiences, but the itinerary can still be exceptional.

3 to 6 months out

Shorter windows are increasingly common, and I plan for them. There will be tradeoffs on certain dates and properties, but a well-connected advisor can often do in a week of focused outreach what a traveler cannot accomplish in months of searching independently. Reach out. We will see what is possible.

Less than 3 months out

Do not assume it is too late. Some of my most rewarding client relationships started with a call that began, 'I know this is short notice.' Call me anyway.

What a trip designed this way actually feels like

Because this blog is about the experience of working with an advisor rather than a single destination, I want to walk you through what a well-designed trip actually feels like from the moment you reach out to the moment you come home.

*Photo©: Wanda Crespo, Olegana Travel Boutique Client*

The first conversation

Before we speak, I ask you to fill out a short form so I can come to our call prepared. Then we spend 30 to 40 minutes actually talking about your trip. How you want to feel. What has frustrated you on past trips. What your travel companion needs that you might not have named yet. By the end of that call, I know more about what your ideal trip looks like than any search engine ever will.

The proposal

Within a week or two, I come back to you with an itinerary that reflects what we discussed, with hotels described by character and location, experiences outlined with real specificity, and a clear picture of what the trip delivers. You will not receive a generic PDF. You will receive something designed for you.

The refinement

We go back and forth until it feels exactly right. Most clients make two or three rounds of adjustments. This is where the trip becomes yours.

The journey itself

You travel knowing that I have briefed every supplier, confirmed every detail, and built contingency into every segment. If something shifts, you do not scramble. You reach out to me, and I handle it.

The return

The clients who travel this way come home differently. Not just rested, but genuinely full. Because the trip was designed around what they needed, not around what happened to be available.

Who this way of traveling is for

Couples who want to actually be present

If you have ever spent an anniversary trip managing logistics instead of being in the moment with your partner, you already know what working with an advisor protects you from. My couples arrive with nothing to manage and everything to enjoy.

Families planning something that matters

Multi-generational travel, milestone birthday trips, family reunions abroad: these are the trips that become the stories your family tells for decades. They deserve to be designed by someone who has done this before and knows how to make every age group feel considered.

Women traveling solo or with friends

Women over 50 traveling solo or with close friends are one of the fastest-growing segments I work with, and one of the most underserved by the mainstream travel industry. These are experienced, decisive travelers who know exactly what they want: genuine connection, physical comfort, curated experiences that go beyond the surface, and knowing that someone has thought through every detail before they arrived.

My women's group tours are designed for exactly this traveler. Small groups, five-star standards, and itineraries built around the things women actually want to do when they travel together, not what a mass-market tour operator decided was close enough. For women who prefer a fully custom itinerary, solo or with a close friend, I plan those too. The common thread is this: you should never feel like an afterthought on your own trip.

Experienced travelers ready for something deeper

If you have been to the major European destinations and want to go deeper, the secondary regions, the private access, the local relationships that take years to build, this is the kind of trip I specialize in designing.

Where I am sending clients right now

If you are in the early stages of deciding where to go, here is what I am designing most frequently right now and why each pairing works.

Italy: Puglia and the Amalfi Coast

For travelers who want the beauty of southern Italy without fighting the crowds on the Amalfi headland, Puglia is the answer. The two regions pair beautifully for a 10 to 14-day itinerary that moves from the dramatic cliffs of the south to the trulli villages and masseria estates of Puglia.

Spain: Barcelona and the Basque Country

Barcelona remains one of the most requested cities I plan, but the clients who let me extend the itinerary north into San Sebastian and the Rioja wine country come back with a richer picture of Spain than they expected. One of my current group tours covers exactly this route.

Scotland and England: a castle and gardens circuit

For travelers drawn to history, landscape, and the particular pleasure of a country house hotel, the UK offers some of the most exceptional properties I know. Scotland's Aberdeenshire and the English countryside pair well for two-week itineraries that feel genuinely unhurried.

Portugal: Lisbon, the Douro Valley, and the Alentejo

Portugal continues to outperform expectations at every tier. The combination of Lisbon's culture, the Douro's wine estates, and the Alentejo's cork forests and converted convents delivers a journey that feels entirely unlike anywhere else in Europe.

Why this is different from planning it yourself

I am going to be direct here, because I think the travel industry sometimes dances around this in ways that are not helpful.

The internet gives you access to an enormous amount of information. What it does not give you is discernment, relationships, or the judgment that comes from years of visiting these places, vetting these suppliers, and understanding what a particular type of traveler actually needs.

When my client arrives at a hotel I have placed them in, the property already knows their anniversary is tomorrow, that one of them is celebrating a milestone birthday, and that they prefer a high floor with a view over the city rather than the pool. That information did not come from a booking form. It came from a relationship I have built over years of placing clients there.

The other thing an advisor does that no platform can replicate is absorb the risk. When something shifts, whether it is a flight cancellation, a property issue, a change in local conditions, I am the one who knows who to call, what leverage I have, and how to protect your investment. That is not a feature. That is the entire point.

For the kind of travel my clients are planning, the experiences that mark milestones, the trips that reconnect families, the journeys that feel genuinely transformative, working alone is simply not the same thing as working with someone who has done this hundreds of times.

The most meaningful shift I have seen in recent years is that people are not coming to me with a destination. They are coming to me with a feeling they are chasing, or a version of themselves they want to inhabit for two weeks. What kind of traveler am I? What does a trip that actually reflects my life right now look like? Those are the conversations I am built for. And when a trip is designed around who you are rather than just where you want to go, you come home differently.

One client who had visited Rome twice before told me after her third trip, the one I planned: "We liked Rome a lot more than in the past, which was most likely influenced by your planning." Same city. Different experience. That is the entire argument for working with an advisor, made in one sentence.

Another client, returning from her Portugal honeymoon, put it simply: "The itinerary was essentially flawless." Not because nothing is ever imperfect, but because when you have someone experienced building the structure, the imperfections either don't happen or they get handled before you ever know about them.

**Anna Fishman** is the visionary and soulful force behind Olegana Travel Boutique, orchestrating transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.

Let's start planning

If something in this resonated with you, the right next step is a conversation. Not a form. Not a quote. A real conversation about what you are imagining, what has held you back, and what your next chapter of travel could look like when someone who does this every day is in your corner.

I plan custom European and Caribbean itineraries for couples, families, and women travelers who are ready to stop leaving their trips to chance.

Email: anna@oleganatravelboutique.com

Phone: (917) 345-5792

Schedule a consultation: Schedule Here

FAQ

It is a question I am asked every week right now, and my honest answer is: most of my clients who have traveled in the past six months came home glad they went. The world will always have noise. What I can do is give you the most current, accurate picture of your destination before you book, build flexibility into your itinerary, and stay close to conditions on the ground throughout your trip.
My planning fee starts at $950 for European travel and $500 for Caribbean itineraries. Custom trips start at $20,000 for 10 days for two travelers. The planning fee covers design, research, supplier communication, and full trip support. It is not added on top of what you would pay anyway. It is what ensures the trip is worth what you are spending.
Ideally 9 to 12 months for complex itineraries, 6 months for most custom European and Caribbean travel. That said, if your timeline is shorter, reach out anyway. I will tell you honestly what is possible.
Yes, and multi-generational and group travel is one of the things I design most frequently. The key is building what I call parallel programming: a shared itinerary with activity tracks that allow different ages and energy levels to experience the trip in the way that suits them best, then come together for the meals and moments that matter most.
My core specialization is Europe and the Caribbean, with particular depth in Italy, Spain, Portugal, France, the UK, and Scotland. My team extends to river cruises, Asia, and Africa through our specialist partners. If you are dreaming of a destination, reach out. Between us, we cover a great deal of the world.
You call me. This is not a theoretical reassurance. I maintain direct lines with my supplier partners in every destination I plan, and I build contingency into every itinerary. When something shifts, you are not managing it alone.
Airfare is genuinely variable right now, and I will not pretend otherwise. What I can tell you is that the range is wide. I have seen transatlantic fares well under a thousand dollars and others that are significantly higher, sometimes for the same route within weeks of each other. Part of what I do is monitor this and share real, concrete examples with my clients so the numbers feel less abstract. Sticker shock is one of the most common reasons people delay booking, and a good advisor can usually help you understand what you are actually looking at and when it makes sense to move.
Every trip that leaves this office has been personally designed by me or one of my specialist partners, and every client relationship runs through one of us directly. You are never handed off to a coordinator you have never spoken to. The person who learned what your trip needs to feel like is the same person who builds it, monitors it, and answers when you call.

Why smart travelers work with a luxury travel advisor in 2026 (especially right now)

What the travel landscape actually looks like right now

What an advisor unlocks that you cannot arrange on your own

Ready to plan your next trip?

One of my clients said it better than I ever could:

When is the right time to start planning

What a trip designed this way actually feels like

Who this way of traveling is for

Where I am sending clients right now

Why this is different from planning it yourself

Let's start planning

FAQ

Is now a good time to travel, given everything that is happening in the world?

What does a luxury travel advisor actually cost?

How far in advance do I need to reach out?

Can you plan a trip for a group with very different needs?

What destinations do you specialize in?

What happens if something goes wrong on my trip?

What about airfare? I've seen some alarming prices lately.

What makes Olegana different from other luxury travel agencies?

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