REI's Under 35 Trips: Equal Parts Adventure and Legendary

There are a lot of ways to travel, domestic or international, solo or in a group, guided or unguided, organized or winging it, foot or donkey train – you’re smart, I’m sure you get it.

The past couple of years I’ve pigeonholed myself in a world of “Solo, no plans, I can do everything myself” travel – and things are going quite well in this regard. However, the fact this style has worked so well for me does not automatically exclude alternatives. Logically speaking (the only real way we should be evaluating things – unless we’re talking about the risk of being abducted by the boogieman when camping alone in the forest), enjoying solo travel does not equate to not enjoying group travel (you following?).

REI (the US-based outdoor gear co-op where I buy nearly all my backpacking gear) has just launched a new line of Under 35 trips to destinations all over the world – from Whistler to Vietnam – and I was lucky enough to head to Greece (one of the new destinations) on one of these trips. What? Mac on a guided, group tour in the homeland of his arch-nemesis, Zeus?

That’s right, friends. And guess what. It was glorious.

Greece Amorgos Hike View — Climb up into the mountains and get epic sweeping panoramas of the islands? Check.

Greek Isles Santorini — Explore the classic cliffside towns of Santorini? Check.

Our Greek Guides (aka Champions of Olympus)

I’ve always struggled with making the decision to hire a guide. On this trip, I didn’t have a choice, so this was not an issue; REI employs local guides on the Under 35 trips and our time in Greece was no exception.

So how did things go? Sure, it can sometimes be more an adventure discovering things for yourself and having absolute freedom to explore however you see fit. That said, this can equate to a lot of missed opportunities and wasted time as things don’t always work out for the best (damn you, tourist traps of the world). My hesitation to explore with a guide stems from the fear a guide will stifle my time in a new place and stop me from being able to feel as if I’m experiencing something authentic. What this attitude fails to acknowledge is that this is what a bad guide will do; a good guide will do just the opposite.

I tend to paint guides with a single brush – a mistake. Sure, there exist situations wherein you can pay a guide to accompany/lead you along a path that you may be completely capable of navigating on your own. These are the guides I would do anything to avoid. But then there are guides who show you things that you would never be able to experience on your own as a newcomer to a foreign land. I have zero problems blindly following a friend of mine around their hometown, so why should guides be any different? If anything guides have more incentive to ensure you have an incredible time because their livelihoods can literally depend on it.

Greece Santorini Guides — Learning all the things I never would have known if wandering on my own.

Greece Santorini Guides Mac — I know everyone always says their guides were awesome, but these two really were.

Greek Priest — Not our guide, but an awesome dude we never would have been able to communicate with if not for our guides.

But back to our guides.

As I said, REI employs local guides on all their Under 35 trips and in Greece, we had two of the best (I legitimately don’t know what more we could have asked of them). It felt like we were visiting two local and expertly-informed friends who were determined to show us awesome things and ensure we had a fantastic time; my fear that having guides would mean that we were being chaperoned along a well-worn tourist track was quickly put to rest.

As cliché as it sounds, our guides became as much as our friends as the rest of the group and saying goodbye to them was just as hard as saying goodbye to each other (miss you, Anna and Archelaos!).

Day by day in Greece

The trip spans seven days (five full days plus the arrival and departure days) and three of the Greek Isles: Paros, Amorgos, and Santorini.

The itinerary is full but also allows for some flexibility. One thing that differentiates the new Under 35 itineraries from those of the existing REI trips is the deliberate inclusion of more free time. This means that you can set off and explore on your own (or go back to the hotel and sit quietly in your room) or select one of a number of local activities to fill your afternoon (in Greece these include scuba diving, hiking, paddle boarding, canoeing, cultural tours, cooking classes, or dance lessons).

We land and meet up in the Greek capital of Athens. After a quick dose of history and ruin-aweing, we board a ferry and were off to our first of three Greek Isles (why does Greece get isles and not islands? Do they think they’re better than everyone else or something? I mean, they kind of are, but that doesn’t mean they need to rub it in – sorry, fellow archipelagan nations – I think I made that word up). Our first stop is Paros, where we check into our waterfront hotel, have our first group dinner, and meet the first of many local cats inhabiting the islands.

Athens Acropolis — Fun fact: the word “acropolis” means highest point or extremity.

Greece Flag on Boat — So long, city life!

Early the next morning, we hit the hotel’s (included) breakfast buffet before heading out to the dock where we find a boat waiting to take us out on our first adventure.

We sail to a small, uninhabited, and (apparently) for sale island where we dock for a bout of boat-jumping-off-of and swimming before being treated to an excellent lunch prepared by our crew. Normally, there is also cliff jumping as a part of this boat excursion, but sadly, the weather prevents us from throwing ourselves from places higher than the boat into the water (I just tried to jump extra high).

The water here is some of the clearest and bluest I’ve ever seen firsthand (like what I imagine the water is like in the Maldives or Barbados) which is awesome because one of the optional activities available one day is SCUBA diving. Unfortunately, it’s still too early in the season for this (when the trips officially commence later this year, all should be okay), but I would definitely suggest bringing a mask (or at least goggles) for any and all the swimming you’ll be doing out in the Isles (because no matter how clear the water is, it’s still salty and will sting your eyeballs).

Mac Swimming in Paros — A great start to a great trip. Photo by: Paulina Dao

Greece Paros Boat Lunch — One of the many meals included in the price of the trip.

The next day, our final on Paros, we hike a byzantine trail from the village of Lefkes to the village of Prodromos where we get our first glimpse of the iconic white buildings spotting the Greek Isles. Our afternoon is free (this is done intentionally to give us the option to explore on our own) and a group of us decide to take a taxi to a beach opposite the bay from the village where our hotel is located – excellent decision (it’s not a good day in the Isles unless you go swimming).

Speaking of hotels, I’m impressed with our accommodation. Our hotel is definitely nicer than somewhere I would stay when traveling on a budget (and is far nicer than my tent). That said, spending time in a hotel room is the last thing you should be doing when traveling to experience a new place (the local television programs will only entertain you for so long).

We reconvene in the village of Naoussa at our hotel before heading out to a group dinner – our last on Paros.

Greece Paros Hiking Trail — Exploring Paros on foot (it’s easy to forget you’re on an island out here).

Greece Paros Rocks — Free afternoon? Better spend it at the beach jumping off rocks into crystal-blue water.

The next morning we catch a ferry to the island of Amorgos (this was probably my favorite).

We’re greeted at the port by our transfer who drives us the short distance to our hotel (which I would argue is nicer than the first). We unload and get ready to embark on (what I think might be) my favorite hike of the trip. We climb from the ocean (where our hotel is) to a village overlooking the bay our ferry came into (and where we have views to the center of the island – where we’re going to be hiking tomorrow). The trail continues out of the village and follows a ridge with impressive views where we find our group completely alone (minus the occasional donkey, chicken, or goat).

The trail takes us into another village where we befriend some locals and relax watching the sunset on their porch before heading back down to our hotel for a free night. I end up at dinner tonight with most of our group at a small place with excellent food and friendly service – everything I’ve come to expect and love in my short time in Greece.

Best of all? The clowder of local cats who join us for dinner (yeah, a group of cats is called a clowder, you didn’t know that?).

Greece Amorgos Trail — Hiking from hilltop village to hilltop village alongside island ridges.

Greece Amorgos Mac Jump — You can also practice your parkour (optional activity). Photo by: Paulina Dao

Our last day in Amorgos and we head into the heart of the island where we hike around the back to some spectacular oceanside cliffs. We head for the Monastery of Hozoviotissa where we meet the coolest priest I’ve ever met before continuing up a climb to the island’s largest village (and still a small one at that), Chora for lunch.

Back at the hotel we change gears and make dinner by way of a Greek cooking class. After dinner? A dance class. After dance class? More dancing. After more dancing? Cats.

Greek Isles Amorgos Cliffs — I never expected the Greek Isles to look like this.

Greece Amorgos Monastery of Hozoviotissa — The Monastery of Hozoviotissa

We spend our final full day and night on the island of Santorini.

If you’ve ever seen a picture of Greece that isn’t the Acropolis or tzatziki, it’s probably of this place. Classic whitewashed buildings capped with blue domes, you know, Santorini. This place was a bit overwhelming at times due to the sheer popularity of the island and mass of humanity all searching for that perfect photo that nobody back home really wants to see but the stress of being surrounded by so many people in one of the country’s “must-sees” was helped greatly by the presence of our guides and by the rest of our group.

Leaving the craziness behind, we hiked around the Santorini caldera to the village of Fira where our guides led us to an intimate rooftop restaurant with a perfect view of the setting sun – the perfect setting to behead and eat some crustaceans.

Greece Santorini Buildings — The flat roofs make Santorini (and the rest of the Greek Isles) excellent parkour venues (but seriously).

Greece Santorini Dinner — Goodbye, dinner (but get it? No? The comma? It’s like…goodbye dinner but also goodbye, dinner – hahahaha – still no? It’s okay).

Traveling With A Group of Strangers

Traveling alone or traveling with a group of strangers – both can be intimidating options if you haven’t done a lot of traveling (or even if you have and you’ve gone too deep on either the solo or the group side). The REI Under 35 trips have a minimum of four people per trip and a maximum of sixteen (although some max out at ten).

And just in case you’re over 35 and wondering why you’ve been excluded, you haven’t been. The new Under 35 trips from REI are not exclusive to people under 35; you can be any age and participate in one of these trips (that said, they are specifically designed for a younger crowd and most participants will be in their 20s or 30s). In addition to being geared toward a younger crowd, these trips are also offered at lower price points and have more free time built in. Over 35? REI has over 250 other trips to choose from! Check them out here.

Just remember, you need to be at least eighteen to participate (sorry, minors).

Swimming Paros Boat — Everyone’s got something in common with everyone – in this case, swimming (a daily necessity).

Santorini Group Dinner — By the end of things, you’re basically a family.

Traveling in a group can provide a buffer between you and the craziness of a place – a small mental retreat (if not sometimes literal physical retreat) from the madness that can grip the world’s most Instagram-impacted sites.

All of my skepticism about group travel quickly melted away. I’ve been traveling alone for so long now that I’ve forgotten how rewarding it can be to experience a new place together with new people. Groupthink and a lack of decisiveness are two things that scare me away from traveling in a group, but when you have an awesome itinerary laid out for you by experienced guides, there’s no risk of this happening.

And one of the best things about traveling in a group of strangers? You’re almost guaranteed new friends.

The Conclusion

If you’ve made it this far, you may be wondering why I haven’t mentioned anything about the cost of all this yet (or maybe you’re just waiting for the cat pictures – don’t worry, they are coming). Another hallmark of REI’s new Under 35 Trips is that they’re offered at a lower price point. Huzzah! The total cost of this seven day Greece trip? $1,999 for REI members and $2,199 for non-members (if you’re not a member, you should definitely sign up).

Not included in this number? Your flight. However, I would argue that this is more advantageous than a wholly inclusive package. Want to include an Under 35 trip from REI as part of your larger itinerary or world travel? Do it. Can’t take a lot of time off and want to pack as much into seven days as possible? Do it. Want to fly out for the start of the trip and then continuing traveling with your new friends before heading home? Do it.

I’m not going to lie, I was skeptical about how much I would enjoy this trip before setting out. Being thrown into a group of strangers to follow an itinerary can be as intimidating as setting out all by yourself with zero planning whatsoever. Years of solo travel put me at risk of becoming something of an elitist cynic, but this guided group trip has reminded me that there is no “right” way to travel (that is, unless we’re talking about respecting local peoples, cultures, and customs, that’s definitely the right way).

Discover all of REI’s new Under 35 Trips here.

Oh yeah, and here are your cat pictures.

Disclosure: This post is sponsored by REI, but the content and opinions expressed here are my own.