Planning a vacation can be simple. Log on to Expedia or Booking, find a package that fits your budget, and you’re off to the races. When you want something more tailored, in a place that doesn’t offer all-inclusive packages, that can turn into a minefield. In a world of online hotel reviews and social media, you can whip up an AI-generated itinerary in a couple of minutes and spend an afternoon pinning ideas to a Pinterest board, and that’s a great start, but those resources can’t tell you if your plan will work in practice: if the “quick” drive between two hotels is on a winding, potholed mountain road that will take a whole day, or if the prettiest beach you have saved on Instagram has a dangerous riptide. Or, the most common one we see: you haven’t given yourself enough downtime, and you’ll get home needing a vacation from your vacation.
Travel advisors are here to help. We can plan your itinerary around the activities you want to do, gently remind you not to overbook, and tell you what to skip so you can savor the rest. We know when expectations won’t match reality (we’ve all seen those Santorini pics filled with cruising crowds, right?), which hidden spots are worth the detour, and what issues you might encounter. If problems arise while you’re away – a road gets washed out, a transfer is late, a flight gets cancelled – we can help you take care of them while you’re still in transit (especially valuable when you’re somewhere with limited service).
Honeymoons, milestone birthdays, multiple generations of family members traveling together, and multi-stop itineraries are the types of trips where an advisor is worth it. For budget trips, open-ended trips where you want to go with the flow, and simpler trips (think one place for a week, no activities, no transportation required), you may not need one, though advisors can often get perks at resorts that you might not be able to access yourself. But the days of advisors being able to get dirt-cheap packages are long gone – more on that later.
Different agencies offer different types of service. Some operate like booking platforms, selling standard packages with airfare and hotel stays, all-inclusive deals, or cruise packages. Other agencies create custom-designed private tours based on your interests: culture, art, nature, culinary, wildlife, adventure, or a mix of all of the above.
Before you reach out to an advisor, take an hour or so to sit down and figure out what you really want. An advisor can help you narrow the landscape and hone in on your perfect fit, but if you come in without a starting point and don’t know your priorities, any recommendation we make might feel a little off.
Ask yourself:
- What interests you most: food, nature, history and culture, scuba diving, relaxation, or simply doing nothing?
- How busy (or not) do you want to be on this trip?
- If you can only have two of these three things: quality, time, and budget, which do you choose? In this context, quality might mean five-star properties and service or special amenities like private plunge pools. Time: do you want more days away, or would you cut your trip shorter to have a nicer trip and stay within budget? Budget: is it flexible, or do you need to keep to a specific number?
- Are there any non-negotiables? This may be air conditioning, adults-only, a king-sized bed, or maybe an activity you must do on your trip.
Then, when you connect with advisors, they should ask you more questions, deeper questions, to dig into the core of what you want for this trip. A honeymooning couple looking for a relaxed vacation to recuperate after a stressful wedding planning season needs something different than a family with young kids who wants to national-park-hop and spot wildlife on their trip. To some people, luxury travel means private villas and helicopter arrivals, but for others it’s about waking to waves and birdsong rather than traffic, having excellent local guides, and staying in secluded accommodations where spotty cell service gives you no choice but to unplug. Any advisor worth their salt should ask tons of questions before making a single suggestion. They shouldn’t put the onus on you to research the country and come to them with a list of things you want to do.
Look for destination specialization, not a global catalogue
The most important role of a travel advisor is to do what AI and a search engine can’t: give you the real lowdown on the region, beyond reviews and forum searches. We can tell you why there are no real beachfront hotels in a specific region in Costa Rica (even if the hotels themselves say they’re beachfront), or which hotels in Mexico are more prone to sargassum seaweed. We’ll help you avoid popular tourist destinations that aren’t worth it, in favor of more authentic experiences, and we’re able to accommodate special needs, food preferences, mobility challenges, and the like. Details you won’t find in any online listing.
Questions to ask your travel advisor before you book:
- Which countries or locations do you focus on?
- Have you stayed at the properties you refer people to?
- How frequently do you visit this area?
- Do you have long-term relationships with local guides and suppliers, or do you book through a wholesaler or DMC (destination management company)?
- Can you tell me about any seasonal trade-offs for my dates?
Someone who really knows the area can tell you why they’d recommend a specific destination or season, and they should be honest if the timing isn’t great for one reason or another. It’s not uncommon for clients to come to us after speaking with another agency, only for us to tell them that their destination is in peak hurricane season for their dates, and this is the first time anyone’s mentioned it to them. That’s why we stick with Latin America and the Caribbean. It’s the part of the world we know best and where we can confidently give advice you can feel good about following.
Read the reviews
Look for specific information about the advisor’s services, the level of personalization in trip planning, where they went above and beyond, and how (or if) trip problems were resolved.
Always read the worst reviews – these can offer more insight than hundreds of great reviews can. Personal stories about an advisor who addressed issues are more important than positive five-star reviews with little context.
Ask specifics about customization
Some agencies use trip templates, and others start with a blank slate. Test the waters. If your advisor can speak to the benefits and trade-offs of specific spots in your country of choice, they can probably put together a route that meets your needs. If they can only speak to two or three locations, that’s a red flag.
If your advisor doesn’t ask you during your consult, make sure they’re aware of any dietary restrictions, mobility challenges or religious considerations. Advisors need to understand special considerations like these when customizing your trip.
Ask about supplier relationships
The hotel star rating system is subjective at best, and two hotels with the same rating may be nothing alike. We’ve often had clients comment on the range of five-star stays they’ve experienced.
Beyond ratings and reviews, your advisor should be thinking about safety, service, guide quality, how their partners treat staff and the environment, and how responsive they are to issues on the fly or last-minute changes. Don’t be afraid to ask your advisor why they’d recommend one property over another – they should be able to give you a confident, transparent answer.
Find out how they deal with things that go wrong
Delays and cancellations due to weather, a tour guide calling in sick, road closures, a bout of food poisoning, border delays, something meaningful being left behind at a hotel or in a transfer – issues can arise on even the most meticulously planned itineraries. So get a sense of how your advisor helps when something goes wrong. Will you have to call suppliers and figure out next steps, or do they offer 24/7 support to help you turn things around?
Ask them:
- What support services are available when I’m traveling?
- Who do I contact if I have a problem, and how quickly do you provide support?
- Do you keep me updated about flight and travel plan changes, or do I need to ask?
This type of assistance matters most for remote destinations and multi-stop trips where a missed connection can snowball into missed reservations and mounting costs down the line.
Red flags to watch out for:
- Vague or general responses to questions about a specific location
- Recommendations that appear to be a generic template or AI-generated list of recommendations
- No questions about your interests, experiences, travel preferences, and special requests or needs (at a minimum)
- A travel destination suggested to you without first getting to know you a bit
- An itinerary with little or no free time
- No information provided about logistics or what happens if something goes wrong
- Advice without any transparency about trade-offs and drawbacks
A good advisor will tell you when your first choice isn’t a great fit for you, and can explain why. If you end up booking it anyway, that’s fine, as long as you go in with your eyes open! If a property has a downside, like seasonal sargassum, ongoing construction, or long distances from local attractions, it’s better for you to know that up front. We’d rather lose your booking than send you somewhere you won’t be happy.
Price is not the same as value, and “most expensive” doesn’t automatically mean “best”
Two trips with the same price tag might look similar on paper, but feel different in practice depending on where the money gets spent: accommodation, guides, or logistics. This comes back to budget, quality, and time. If you’ve got a long trip planned, you may not worry about long transfer days on a shuttle bus, but someone with only a week might benefit from a puddle-jumper flight instead. Some honeymooners might want to splurge on a resort with an in-room jacuzzi, while another couple would rather spend most of their budget on costly adventure activities.
A good advisor helps you use your money wisely: booking a private guide rather than a tour, booking a shorter stay rather than stretching it out, or booking travel during the shoulder season rather than the high season for similar experiences at a friendlier price point. In some cases, a good advisor may recommend that you spend more to get what you want.
All that said, don’t conflate “most expensive” with “best”. Just because a property costs more, that doesn’t automatically make it the best fit for you, or even the best overall experience. Sometimes, you end up paying for brand-name recognition, which often doesn’t mean much once you’re there.
What’s better: boutique agencies or large travel companies (including OTAs like Expedia and Booking)?
Large agencies have more extensive inventories. Boutique agencies, including ours, serve a limited number of clients and have more selective geographic and vendor relationships. The benefits of using a boutique agency include more individualized service, faster response times and a trip that is more tailored to your tastes and less likely to be a cookie-cutter experience.
Find a boutique advisor who gets your travel style, and chances are you'll keep coming back. Each trip gets easier to plan, because they already know your pace, your favorites and what didn't work last time. After more than 450 trips planned, that's our favorite part of the job.
Frequently asked questions
Do high-end travel agents charge fees?
Most companies will, so ask about costs, whether it’s a flat fee, a percentage of trip costs or some other compensation. Professional advice won't be free for a complicated, several-week trip. Osaviva charges a flat $75 fee for planning services, which is applied to your trip balance when you make a reservation. Hotels and other suppliers typically pay commissions to advisors, so the cost of our services is often no greater than the cost of making your own reservations.
However, if you’re looking for the cheapest option, or are hoping to find someone with access to “secret” hotel rates, you’ll likely be disappointed. Some agents will cut their commission to put money back in clients' pockets, but be forewarned: you get what you pay for.
Is it worth using an advisor if you’ve already traveled a lot on your own?
It depends. For an easy beach vacation, you may not need an advisor, although an advisor may be able to arrange some benefits for you that you can't arrange yourself, like a free breakfast, room upgrade, or other resort perks. An advisor is most helpful for more complex trips involving multiple countries, a milestone trip (like a honeymoon), group trips, or trips to more remote destinations where logistics matter.
What is the difference between a travel agent and a travel advisor?
Not much – the terms are used interchangeably.
Choose an advisor who understands how you want to experience the world, rather than one who can find you a good deal. If you'd like to talk through your plans, reach out to us at Osaviva. We'll always tell you straight whether we're the right fit.