Turning your dream trip into reality can happen in a few different ways.
You might join a guided group trip with down-to-the-minute itineraries and a tour operator to follow every step of the way. Or, you might team up with a travel advisor who can take your travel wishlist and bring it to life without you having to lift a finger. Or, you might DIY every booking, activity, and transfer yourself for full control of each day.
Each approach has its pros and cons, and all three routes can get you to that long-awaited moment of gliding under the Ponte Vecchio on Florence's Arno River in a traditional wooden barchetto.
The difference is in the journey: who calls the shots, how much is planned, and how much work falls to you all shifts depending on the path you pick.
In this article
Booking a Group Tour
I’ve taken many group trips in my life, which gets you a ready-made trip from the get-go.
The group size is usually 14 to 16 people, and while you can bring friends, you'll also meet new faces along the way. All those little choices that make a trip run smoothly? Someone else has already handled them for you, and is there with you on the ground, should any trouble arise.
On a San Sebastián and Rioja journey I took with Roam by Tauck, I hiked 6 miles of the Camino del Norte, biked through Rioja vineyards, and easily hit 10,000 steps a day. There are lots of active tour options out there where the most exercise you get isn't just walking to the bus.
With this specific tour provider, you meet your tour leader before you even leave home and they stay your primary point of contact the entire time. About half of your day is planned and guided, and the rest is yours to explore. Most group tours do allow for some sort of similar free time, but not all do. Most of my meals were shared with the group, but I did have chances to eat on my own.
Another perk of tours? They have long-standing relationships can open doors that solo travelers usually can’t access. On my trip, that meant dinner at a Txoko, a private Basque cooking club where members must vouch for you just to get in.
That kind of access also means extra support when things don’t go as planned. Tour operators have strong relationships with hotels, restaurants, and local guides, and those connections matter most when a booking falls through or a flight is canceled.
Instead of negotiating as a single guest, you have a whole company backing you up. On the flip side, you can’t spontaneously pivot plans one morning (well, you can, but why would you when you paid for it?), you can’t help shape the itinerary, and solo time can be fewer and farther between.
Hiring a Travel Advisor
Working with a luxury travel advisor (which I do part-time) can be a nice middle ground for some travelers. Like a tour operator, an advisor can arrange every detail: hotels, flights, transfers, activities, meals, private guides.
The big difference is that your trip will be built around just you and not a large group. Every detail is customized: the right hotel for your style, a guide who knows how to avoid the crowds, a schedule as busy or as empty as you’d like, and reservations you probably couldn’t get on your own.
A travel advisor brings the same kind of influence as a tour company, because hotels value steady business from agencies more than one-off bookings. If your room isn’t what you expected, your advisor can step in and advocate for you, backed by the agency’s relationship.
And while you won’t have a director by your side, your advisor is always only a call away if you need help. Sometimes their connections can even yield a nice welcome gift or upgrade.
You could also combine both types of support: book your group trip through a travel advisor.
There are just a few things to consider. While a travel advisor can save time and offer a white glove approach, companies vary on whether they charge a fee to their customers for these services. You also might have less control over bookings and last-minute changes.
Planning Your Own Trip
Then there’s the do-it-yourself route. This is how I’ve planned my own trips and my family’s for 35 years.
It’s the most flexible option, but also the most demanding. When things go off track, there’s no director to help. You’re the one in charge, and on your own. That means you’ll be the one on hold with an airline after a canceled flight; no one will take that chore on for you.
There’s also no advisor’s black book or ready-made itinerary. You research and choose every hotel, transfer, meal, and activity. For people who love to travel, this can be the fun part. When you get it right, the reward is a trip that’s truly yours. You can linger where you want, change plans on the fly, or spend a day following your own curiosity.
The tradeoff is the time and know-how it takes, and if something goes wrong, you’re just one traveler with one reservation, not part of a relationship the hotel wants to protect.
I’ve learned this the hard way: like the time I trusted glowing TripAdvisor reviews for the “best meal ever” and ended up disappointed, with no one to turn to but the waiter. Or when I misread an Italian train schedule and bought a non-refundable ticket to the wrong city.
Some people who dislike planning logistics and pouring over small details will likely prefer a different approach. But for those who want to save money, hold full control, or enjoy the planning process, it can be the best route.
How to Choose
Once you know the pros and cons of each option, the answer to this question depends on what fits your trip best.
When I’m heading somewhere remote and unfamiliar and want to skip the guesswork, I turn to a tour operator. They’ve already found the standout hotels, lined up the guides, and mapped out the activities. Nearly everything is covered and paid for, right down to gratuities.
But for trips with lots of moving parts, think family groups with different arrival times, ages, and interests, a travel advisor can be a lifesaver. They handle all of the logistics, so you can focus on enjoying the experience instead of juggling details.
Most often, though, I still plan trips on my own. That’s a natural fit for me, though years of travel writing and helping others plan their journeys have given me a head start.
If you’re new to DIY travel, ask yourself whether you enjoy the process or would rather let someone else take the reins. I also find this is the best option for those on a super strict budget or who want to fly solo. There’s no single right answer, however. Just the one that feels right for you and the trip you’re planning.
The Shortcut
A tour operator or an advisor's longstanding relationships translate to real leverage when a hotel or restaurant falls short, which is something a solo traveler booking one room can't match.
Planning travel yourself means you’ll have no one to call when a reservation goes sideways, like a non-refundable ticket booked to the wrong city. But you also don’t have to travel alongside annoying tourists or give up spontaneity.
The best of both worlds? Book a tour operator trip through an advisor and stack both forms of backup: the operator's access plus your advisor's leverage, working for you at once. You might also bookend it with a few days you plan yourself to see which part you enjoy the most.
Dana Freeman was hosted by Tauck as part of their trip to San Sebastian and Rioja. Some expenses were covered. All opinions and recommendations in this article are their own.
