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Reasons Why Organized Tours Are Highly Underrated.

“My husband thinks organized tours are for geriatrics,” commented my friend Stephanie. She’s not one to mince words. She read that I’d be experiencing some tours while I traveled through Italy, and her reaction wasn’t far removed from anyone else learning that a fairly active, non-geriatric, semi-organized, outgoing, and capable thirty-something woman like me might depend on paid guides to show me a good time.


And the scoffing didn’t stop there.

I read quite a few travel blogs. And food blogs. And travel-slash-food blogs. And one thing many of them have in common is a palatable intolerance for organized tours. It’s especially prevalent among the budget backpacker crowd to sprout little seedlings of hate in their cultivated “cool way to travel” gardens about the decidedly lack of hipness associated with organized tour companies.

And I get it.

I do.

It’s uncool to traipse around a culturally/historically/architecturally significant city/monument/landmark amongst a huge crowd of strangers touting a dangling radio transmitter connected to ear buds. And most humans, as far as I know, don’t particularly enjoy being crowded onto a humongous bus-beast monstrosity with 49 other clueless tourists in order to get shipped, like freight, from one place to the next — no matter how plush the seat cushions. And the worst are those companies whose representatives descend upon you in the form of a middle-aged, pot-bellied ticket peddler as you step weary from the train, touting their pamphlets while they reach for your wallet.

But also —

As someone who’s not particularly adept at planning — as someone whose guide book arrived just one day before her departure and for whom the idea of renting a car or buying museum passes or standing in line or figuring out how to book a wine tasting are tasks she might rank just above visiting the gynecologist — a well-executed tour can be the stuff of dreams. And particularly to me, a person who becomes practically paralyzed when faced with even the smallest decision, a small-scale, carefully curated, well-varied tour with an enthusiastic guide is not only entertaining, but the ultimate solution for overcoming research and decision overload that often accompanies planning a trip.

Bonus points if there’s food involved.

...and awkwardly pose in a totally non-sexual way.
My sister enjoying her first-ever culinary tour in Chicago’s Chinatown

In order to fully research the gamut of tours available that fit my criteria for enjoyability (small scale, organized, food/adventure bonus), I reviewed tours from several different companies in order to share with you some of Italy’s most intriguing offerings.

Company Tour Name What’s Included
The International Kitchen Women Only Week Mediterranean Cooking Experience 7 nights lodging, cooking classes, most meals, drinks, day tours, guides, drivers, airport transport
MyTours San Gimignano, Chianti & Montalcino Entire day tour (10+ hours) van chauffeured food and wine tour of Tuscan countryside
MyTours Vespa Tour Day-long (7+ hours) Tuscany Vespa ride and wine tasting
Walkabout Florence Wine & Dine in the Tuscan Countryside + Florence By Night Evening tour (5+ hours) dinner and wine tasting at a Tuscan farm, plus nighttime Florence van tour
Walks of Italy Best of Florence Tour Educational morning walking tour (4-5 hours) of some of Florence’s must-see sights, including skipping the long line to see the original David

Yep. I was really roughing it.


Of course, before you run off and book the first tour with a pretty, English website, keep a few things in mind:

  • What type of tour are you interested in? Culinary? Adventure? Strictly educational? If you want it to involve food, does that entail cooking, or eating, or both? If you’re looking for something adventurous, what are the risks? Legal requirements? The MyTours Vespa Tour was an absolute blast, but I’m pretty sure I signed away any and all liability on their end had I ended up a smear on the windshield of some giant tour bus. If you’re just looking to get information about a place, what are the guides like? Funny? Enthusiastic? Understandable English skills?
  • How physically active do you want to get? To me, the best tours are a mix of walking and arranged transportation. But often it’s all-or-nothing. My Walks of Italy Best of Florence tour, for example, entailed a lot of walking throughout the city. But my Walkabout Florence tour, ironically, was conducted entirely by van. So be prepared ahead of time with the right amount of energy and of course the right shoes!
  • What level of hand-holding are you comfortable with? The MyTours San Gimignano, Chianti, & Montalcino tour did a fantastic job of filling my head with information while we cruised along in the van from one village to the next, then offered unguided free time to wander through medieval towns. I enjoyed exploring on my own, but some people might prefer a guided tour to see a village’s top attractions in a limited amount of time.
  • How long can you handle? While it’s always good to feel like you got your money’s worth, the simple truth is that sometimes tours can get a little long. Whether you get tired of walking, tired of listening, or are just plain too full and tipsy to deal with the world after that last shot of grappa, consider the length of a tour before you accidentally sign away an entire day you didn’t intend to spend. I wanted to make sure I saw some of Florence’s major sights with an informative guide, but I also know I have a relatively short attention span when it comes to the absorption of educational materials, so I signed up for Walks of Italy’s half-day Best of Florence Tour over their day-long tour, and that was the perfect length. That said, my week-long International Kitchen tour was so varied and carefree, it could’ve gone on forever and I wouldn’t have complained. It’s all about knowing your limits.

Getting lessons on how to taste our wine.

So. If you’re anything like me, there are actually several reasons why signing up for an organized tour (or seven) on your next trip is a really good idea.



3 Reasons Organized Tours Are Highly Underrated:

1. Efficiency — Organized tours are a really great way to become acquainted with an area in a short amount of time. Not a big planner? Tours can help ensure you don’t miss an area’s must-see attractions and allow you to access places you might not be able to access on your own. For example, since I wasn’t renting a car in Tuscany, I would never have seen the iconic cyprus tree-lined drives if I hadn’t taken any tours.


Also, tour guides are smart. You’re more likely to learn tidbits you might otherwise have never known. Like, if I hadn’t taken that bus tour of Seattle back when I was 20, I never would’ve realized that a suburban home we were passing was a place where Kurt Cobain once lived. And that would be a shame.

2. Socialization — The tours I attended during the second half of my trip saved me from becoming a hermit. No joke. As a married, female solo traveler who was staying in hotels and apartments as opposed to a more social hostel atmosphere, it’s quite possible I might not have spoken to anyone besides innkeepers for an entire week had I not gone on tours. And I met some of the best people on tours! They really helped keep the trip interesting.


This vintner was a riot!

3. Tours are maturing — While the days of sardine-packed busses and guides carrying tall flags so you can spot them among the crowd are not entirely over, it’s a simple fact that the variety of tour options out there is rapidly expanding — the choices extending far beyond drone-like mass groups. From learning how to make the silkiest mozzarella to zipping around the Tuscan countryside on a little red Vespa, there’s a plethora of choices to fit almost any style.


I was also very cognizant of spacing my tours out, so I didn’t become too exhausted from organized activities. With plenty of time to wander the towns on my own in-between, the tours I chose were an excellent way to break up the trip and learn more about the region.

What kind of tours have you experienced that you actually enjoyed?


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Great post and great tips! I’d also add to look carefully at the website before signing up to see how large of a group they have. Large, sardine-packed tours still aren’t much fun but there are so many tour groups out there with highly educated guides that specialize in small group tours of 6-12 people. In those groups you feel like you are out with friends and can interact with the guide and ask questions while learning so, so much. I don’t think every location requires a tour but there are so many places where you are just simply missing out if you don’t go with a guide. We did some great tours while in Rome with Walks of Italy and Overome but my favorite was our food tour with Eating Italy. We wouldn’t have ventured into the Trastevere neighborhood on our own because it is so hard to navigate, and we definitely wouldn’t have stopped into some of the small store fronts that we did with our guide and we would have been missing out not just on amazing food but learning about the history and cultural of the people and the food.


Great tip! You’re right — those huge tours are awful, and for me anything less than 10 is idea. My Vespa tour just had me and one other person plus the guide! So much fun. Culinary tours are my favorite — they’re such a great way to get to know a city and get you into places you might otherwise have been too nervous to try yourself!


I always want to go my own way only to wish later I’d done the organized tour.


It’s easy to do — you think you don’t want to be encumbered by a schedule, but then realize it actually takes a lot more precious trip time to figure stuff out for yourself. ;)


I actually don’t mind going on organized tours. I know it’s not the best way to really get to know a new city, but there is a time and place for it.. and nothing is beneath me! :) we actually went on a tour with contiki in new zealand and it was perfect. i wish we could go back and explore on our own more.. but it was a great intro and let us see everything we needed to see on a one week trip.. and best of all… i’m with you on the no planning! :)


They might not be the best way to get to know a city, but they’re definitely one of the best ways to get oriented and make sure you hit all of the “big ticket” sights. But nowadays they even have great tours for getting to know a city more intimately — I find culinary tours are one of the best ways to get into the nooks and crannies of a place and try things you might otherwise not have tried. :)


I’ve only been on cruises, but the cruise line organized excursions are the only way to go. When we were taken out on a catamaran for a snorkeling outing, they were over 1/2 hour late getting us back. Because we had booked the tour through the cruise line, the ship had to wait for us. Had we taken a tour from one of the people standing at the bottom of the gang plank, we’d have had to find our own transportation to the next port.


Great point! And I know it’s terrible to say, but I wouldn’t be shocked if some scammy companies actually stalled cruise passengers intentionally with the purpose of then making money getting them to the next port. So if people aren’t booking through the cruise line, they’d be best served doing some research and booking a reputable company rather than just going with someone who sells them a package at the bottom of the gang plank.

Amanda @ MoveLoveEat

Great post! I always thought that organised tours were for geriatrics as well! Just last weekend I won tickets to a local food tour and I was a bit nervous because I thought it was all going to be oldies! I was pleasantly surprised when we turned up and everyone was of a very similar age to us! Organised tours just make sense sometimes because you see and discover so much more than you would have if you were just by yourself, although I really do enjoy just wandering around by myself sometimes.


I loooove food tours! They’re so much fun. I’m glad you had a good time! And I like wandering around too — that’s why it’s good to have a balance between tours and alone time. :)


It is all about the people. You need to find the right tour company and one that hires local passionate people. I have done more than 20 organized tours, they were all small (6 people of less) with locals and every one of them has been exceptional! We always do them on the first day or two we are someplace so we know the cool places to go the rest of the trip – we totally pick the guides brains on everything.


You are absolutely right — I’ve gone on one where the guide wasn’t enthusiastic, and it just wasn’t as good. They have to be into it — almost cheesily so. :)

Saturday Six #135 - Misadventures with Andi

[…] [1] These days nearly all our trips include some kind of organized tour.  Many, many of them are with Context Travel, who I find to be top-notch when it comes to small curated tours with local experts.  I lot of travel bloggers knock them, but I think they just haven’t found the right ones.  Turns out my pal Katie of Domestiphobia agrees (I knew I liked her for a reason!) and she wrote about her feelings on this subject in her blog post this week, “reasons why organized tours are highly underrated.” […]

Colleen Brynn

I completely agree with you. I did an organized tour when I was in India, and it also went through Nepal, and I by no means hid that on my blog. Travel is travel, and that was how I chose to go about it. The only thing I didn’t do was mention the company because I didn’t want to seem to promote, or to make it look like I was compensated, because I wasn’t. Traveling somewhere like India was with a group was the best decision. I did WAY more with them than I ever would have on my own, and I saved a lot of hassle, time, and money by going that route. Not getting ripped off or having to worry about it 24/7 was nice too.


SAFETY! I can’t believe I didn’t think of that as a reason. As much as it pains me to say it, sometimes organized tours are just the safer option when traveling solo. It’s less hassle, and there’s someone looking out for you — making sure you got to your hotel at night. Sometimes that added security might not be necessary, but it’s comforting. :)

Britany Robinson

I totally agree. I did a two week tour during my time in Southeast Asia (so NOT cool by budget backpacker standards) and I really enjoyed it. It was so nice to not have to worry about finding hostels, and getting lost, and ripped off, and all of those “challenges” that apparently make travel so rewarding. And it’s true. Those challenges do make travel rewarding. But it doesn’t always have to be about that! Sometimes, you just want to see as much of a place and learn as much about a place as possible in the amount of time you have available, and my tour did just that. Looks like yours did as well!


Exactly! Rewards can come in the way of knowledge about a culture/locale that you probably wouldn’t have picked up had you just been wandering around. I think a good mix of both — guided tours and individual exploration — has the most potential for learning both from and about a place.

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