Episode 38

Curated Group Trips: Why We Love This Travel Trend

Published on: 13th June, 2024

One travel trend we've seen is the rise of group travel. These specially curated, itinerary focused trips allow you to explore a topic or area that you're passionate about. Bonus- you come away with new friends.

On this week's episode of Time to Talk Travel, podcast hosts Ciaran Blumenfeld, Desiree Miller, Maureen Dennis, and Nasreen Stump cover itinerary driven small group travel. What starts out as an exploration of the trend dives deep into why this type of travel is proving to be so impactful and what led folks to the point of craving community and connection.


Des Miller Travel Media

Nadia Carriere - Yoga Retreats

Kim-Marie Galloway- Embark Beyond, Luxury Travel Mom

Whale Camp

Intrepid Travel

Silent Retreats

Sleep Retreats

Ciara Blume - Rome for the Holidays

Chica Brava Surf Retreat

Meagan Wristen- Sri Lanka trip

Sri Lanka Tourism

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[00:00:16] Nasreen: Hi, and welcome back to another episode of Time to Talk Travel. We're here talking about group travel today, but more specifically, the type of group travel that has a very curated itinerary, where someone who is an Expert or very familiar with the topic or location has done a lot of thoughtful planning around a trip that you can join.

We've been seeing this as a trend specifically with women. You get to a certain age, you're like, I want to see the world and maybe someone else doesn't want to go with me. It's just time.

We are very lucky because Des has actually just launched something that ties directly into this topic. So I'm going to let her lead with why you got into this and what inspired it.


I saw your pictures. I want to stay where you stayed. I love traveling the world and I really enjoy sharing it with other people. So if I can bring people along with me and create a company where it actually becomes my next chapter in life, where I can make a living doing what I love by all means.

I was nudged along by a company layoff in my career. And I just said, okay, if not now, when? I jumped in and found a friend who wanted to invest and help me create a company. It's called Des Miller travel media. It's my jam.

My daughter says, mom, nobody says that anymore, but my passion, I love it. And I could go on and on and talk the whole hour about why and what have you, but Naz, you were the one who talked me off the cliff one day when I was like, what am I even thinking? This is a lot. And you said you just follow your heart.

If money had nothing to do with it, what would you be doing? And so every trip I plan is really okay. If I were going, where would I want to go? What would I want to do? I'm now putting those together for people who are at their next point in life that are hitting where we are, the kids are out of the house, they're no longer having to work and can go, can afford to go and just don't have people to go. I'm a connector.

I like that.


[00:02:42] Desiree: It is. Thank you. And I want to work with every one of you. Part of my business plan is partnering up with my travel writing friends who've gone to amazing places. That's part of the fun.

I haven't been everywhere, but I know people who have,


It's somebody running it, who's been to Italy a ton of times and loves the food and the experiences and has these go to spots and wants people to really feel immersed and fall in love. It's someone like Kim Marie doing Paris with an art expert where there's a very specific itinerary.

I guess I have to ask, I haven't done a specific tour like this myself. I've looked at some, I've been interested, specifically any World Heritage, UNESCO type ones in countries that are harder to travel in yourself. Ciaran or Mo, have you guys looked at any of these tours or ever done a trip that was focused on a specific kind of interest?


[00:04:40] Nasreen: Definitely.


I don't quite have all my kids out of the nest yet. So I still have a 12 year old who can't drive, obviously, and a 15 year old. I'm this close to being able to have a little bit more freedom to do those things. And that's when I see a lot of my friends who, you know, whose kids are in high school, even like they're not out of the house.

But they have more freedom to be able to do those things and can take a long weekend and go with some friends. A friend of mine just actually went on a retreat. It sounded pretty cool. Literally 12 strangers who all followed The Bachelor. One of the contestants that used to be on The Bachelor organizes these women's retreats and this one was to the BBI's and she applied.

And I found that interesting that you have to apply for it. Got in. And so she just got back. I just got back. Cause here's why I look like this. I just got back from traveling and I'm exhausted. It's funny that you need a vacation after a trip sometimes, right? I haven't really talked to her about it, but the pictures along the way look like she had a ton of fun and she didn't know a soul going in.

It's just looking at what's your jam as Des would say. Figuring out, do you have the cojones to basically go and see if you can hang with these kinds of people that have the same interest. I think we'll probably get into this, but I think you've really got to be an adaptable personality to do this sort of trip because you don't know who you're going in with. You're going to have to find your way and you're going to have to find your tribe within a tribe. Just because you like the same thing, you might like yoga or you might like the bachelor doesn't mean that everybody there is going to be exactly the same as you.

You've got one thing in common. That's a good start.


There were 10 of us, people who worked together 30 years ago. And there are always personalities. , in fact, someone backed out on that trip, literally flew in from California, landed in Norfolk, Virginia to go to the Outer Banks. And. Had an issue with somebody the night before we were all supposed to go. She got right back on a plane and went to California. And it was heartbreaking because it was someone I was really eager to see, but sometimes there are personalities and that's one of the things that a retreat leader or a Group Getaway Leader has to allow for and everybody comes together, but you still have your own space. And so that's part of it. You have this great opportunity to connect, but even on the trip we were on did you do the Costa Rica one?


[00:07:55] Nasreen: This was gonna be my question. I remember this coming up in conversation at one point about there being one person or someone who was a little off from the rest of the group. And I think that's why these trips are so unique when there's that good group leader who can set the vibe, who can set the expectations. I'd almost rather go with a bunch of people I don't know who are at least interested in the same thing with some ground rules and a good group leader than sometimes go with a group of people I do know.

Do know who I know. It's going to get interesting either way.


[00:08:31] Maureen: That's probably why I'm a little gun shy.

The details I remember on that one trip. We got there and we were introduced to our bed buddy. At no point did I realize we were sharing beds with strangers. Was really cool with that, but my bed buddy and I are still friends on Facebook, but I, you know me, I don't really read all the details sometimes.

I just, I'm excited to go, and I want to be there, and it was still great and fun but if that wasn't your jam, you'd be in trouble right off the bat, right?


I, that's. It was my bed buddy


[00:09:10] Desiree: adore Jill. I didn't know her before the trip and I had talked to another friend Sarah Sporthart, who does trips around the world now. And she was my roommate in Costa Rica and she said, we definitely did not sleep in the same bed.

That would have been a deal breaker for me. And I was like, so that is one

of the


[00:09:29] Desiree: As a retreat organizer, you deal with, cause a lot of these really beautiful places to stay only have rooms with one king size bed. If you really want to make it affordable for more people, like I rented a house in Portugal where we're going to stay, it's a beautiful home. It has six bedrooms with a king size bed, one bedroom with two twins. I put it as, it's a single occupancy, a double occupancy with twins or a shared bed with a really close friend. There are different prices based on what you do, but it's a dance. And I don't know that if it hadn't been a friend organizing that retreat, I would have said I'm cool sharing a room with somebody I had never met before, but I'm go with the flow, whatever, tell me where you need me, what you want me to do.


And it was about getting together and working on skills building and really kicking ass. And there were some amazing people going, but again, it was a rented house. So there were opportunities where it said. Book early if you want your own bed and room because this is what we've got.

You're going to need to make a friend. If you're not comfortable staying in the house, we'll have a couple of day passes available and you can stay nearby.


But then from getting from the airport to where she booked her own accommodations. They run the gamut. You do have to do your research and look at where you're going, what is included, what's not included. But I feel like it has become so common now. I have friends who are doing writing retreats, who are doing yoga retreats, who are doing meditation and wellness retreats. There really is a niche for everything. I will tell you, I've fallen in with a group of retreat planners. so interesting.

The one that is doing the very best is making a killing. She plans Outlander. Where the people all follow the Scottish, all the kind of countries for Outlander, she is making bank and having a blast. Like she just does the same trip twice a year and recycles. And I love it because you're following the movie and the fun of it.

We talked about set jetting on our very first podcast. I love it. And Ciaran talked about doing it with books, book settings, Naz. I think every time we talk about books, you talk about Anna Green Gables. And that's a great, that's a great niche there. Again, we're hitting that, or maybe it's just my. community, the people I know and people I connect with most are just hitting this age where we're looking for our next, our, what are we going to do with ourselves? We're either done working, retiring or the kids are out or we all need purpose, we all need. Fun. This is a really good way to go fill that bucket.

l bookings since the start of:

Proof of life still here today. I'm in Romania. Yeah. Whatever it is, because now my daughter's on a cruise this week with her dad. I asked her in advance, where are you even going? I don't know, mom. I'm just getting on a boat. She called me last night from the cruise. Where are you kiddo?

Oh, we're in Puerto Rico today. Do you know where you're going tomorrow? Nope, but

I have 360.


[00:14:11] Desiree: Said, oh, that's funny. I'm going to Puerto Rico in July. It's just this big world has shrunk down to this level. I know where she is because I have 360. She knows where I am because I have 360.

We talked about this last year when I was on my travel bender. I didn't really have an itinerary beyond the first two weeks. After that, it was like what country do I want to see this weekend? Even now it's just so easy to say, I want to go here and find a group of people who are doing exactly that.



That was the biggest age range of growth. And they were talking about how they were trying to either reconnect with old friends or make new ones. And It tipped me off to thinking about it. My grandmother had friends who were her lifelong friends, but she also didn't move anywhere. She stayed very close to where she grew up, and so she always had a ton of friends around and also had eight brothers and sisters, which helped.

And I was always like, how come I don't have friends around like she does? I don't have that. They had that. How come I don't have that? And I think this is filling that void that maybe some of us have if we've moved around a lot and not hung on to those friends to be able to go out and find like minded people, or instead of it being all like, Hey, person I haven't talked to in, 30 years, or we only talk occasionally, let's go to, Estonia together.

Instead, it's Hey, there's this really cool tour. I thought you might like it. I'm planning on signing up for it. It's a little low bar for entry.


[00:16:01] Desiree: Yeah. Nas, our friends are all over the world. It started with blogging. It really did. I would tell people all that they're like, someone everywhere. And I'm like, I truly do. Because I can't, we had this. Online community of people where if I went to Nova Scotia, I knew someone there. I could stay with them.

If I went to Barcelona, I knew someone there. I could stay with them or get together with them. Not, maybe not crash at their house, Hey, I'm that kind of gal. You can crash with me. If you come to Atlanta, but also you're right saying to that friend you went to high school with, Hey, time for us to get back together again.

Let's do it. Let's figure out where to go, throw a dart on the map and then find people who can take you there. If you'd like.


[00:17:22] Nasreen: Well, seriously, and then also, how many of us were told, Oh, you got to figure out what you want to do. You got to go to college. You got to get a job. How many of us - I came out of college in a recession and it was all make sure whatever you do is sensible and you can get a job in it.

And so that steered where I went. And then also how many people had late diagnosed ADHD or something, and they wonder why there are all these trips where you can study photography or learn to make stained glass or explore archeological sites is because all of us probably wanted to do something like that.

And then we did something sensible.


[00:17:57] Maureen: This is our gap year.


We want to be very conscious and conscientious about who the characters are and what the action is and what the plot is and what any plot twists are. So this is something you can control, where you're going and who you're going with and what you're interested in. It really is very empowering to do something that is something for yourself that you love. And that you have some control over, and that it's a chapter you can write, and write well.


[00:18:39] Maureen: It makes you more interesting at dinner parties. You

have a big, big piece of it. Is that even if you have your solid crew, or your regular people you hang out with it's nice to go through the exercise of meeting new people and you're not always given that in your day to day life.

It can be a little monotonous that way. I love meeting new people. I was at a club trip with my husband, his company. It was the top performers from all over the world. And I was like, this is my new friend from Singapore. This is my new friend from Australia. I sat next to a woman who's a Ukrainian who lives in Dubai. I was like, how could this be my job to just go around and meet people? Because they didn't even know each other. They all work for the same company, but they all knew me by the end. And I was the common denominator, but I , that just recharges my battery like nothing else.


I do have a time limit on how long I can be with a group like that though. I know even with my family, I start getting a little like. Not the nicest person after seven days. So know yourself, if you're good for two, three days, or you're a lot of my friends, we call them day on day offers.

Like they're good to be on for a day, but then they need a day off. They could not do every day, even have a weekend with people. They know, let alone. Have the energy to talk to new people. So at least know yourself and go, okay, you know what? This is even a day trip that might be an exciting sort of fun thing to warm up with. Or I know don't go beyond seven or you will come home with no friends.


day. Yeah.

If it's family, it's more like three or four days. Extended family. Sorry.


[00:21:01] Maureen: And that's it. I think, especially with my family, I put a lot of pressure on me, or actually, I'll take that back. I have done a lot of ladies trips where , I guess they are official if we've planned them, but not through someone else just with my own friends, I take it upon myself to make sure everyone is having a good time at all times. And it exhausts me. I don't even realize I'm doing it. It's taken me 47 years to realize that is something I need to let go of because I can't make everybody happy all the time.


[00:21:45] Maureen: you do need some

downtime. And I think as we get a little older, we do need a little more recovery time.

This is the aftermath of six days on, right? Even my voice is bad.


And when you go with people who know you and see you and tell you, no, you're this person. It's very hard to shed that skin. And I think for many of us too, as we look at what's next, like the nice thing about going with strangers is that, we're not going with our best friend who knows every detail about our agonizing divorce and, like we've shared our therapy sessions with, and as much as we love our friends and our friends are there to support us and they're awesome. They see us a certain way and that might not be the way that we want to be or that we want to move forward in. So it is very liberating to go on these trips alone and meet new people and try something new.


We are extroverts but some of my best friends are introverts and we are the yin and the yang where, they walk in a room and it's anxiety


[00:23:20] Desiree: I'm like, no, let's head here. And I will give you this tip. I learned from somewhere.

If you are one of those people and you're going into an environment or a meeting room or something like that, say it's a conference and you're really filled with anxiety. I was told the best place for you to stand is. At the end of the drink line, because that's when people have walked in the door.

Because some people are like, I'll get them as they're walking in the door. No, that's when they're sizing up the room and figuring out what they're doing. And they've got to walk in the door. They've got to let them go get a drink. And then as they're leaving, they're a little more relaxed and open to forming new friendships and that sort of thing. As a retreat planner or a group getaway guide, that would be that person's job to make sure other people do meet each other and that no one's left in a corner sitting by themselves that doesn't want to be there. Now, some people, that's exactly what they want. They're looking for solace and quiet.

There are actually no joke sleep retreats. There are silent retreats; these all exist. And I know people going to them right now. I have a friend whose mother died four months ago. She's going to a silent retreat because she just wants the world to just quiet down and let her sit with her thoughts.

Right now she's surrounded by people. Her mom was super popular in the community and everybody is just always, how are you doing? You can't heal when it's all being brought back up. So she's doing that. A sleep retreat. Dude I,

Five years ago when I was in the thick of it, I would have loved a sleep retreat.

We talked about this for Mother's Day. Just let me go away and please catch up. There really is something for everyone. I'm organizing one. Turtles on the treasure coast retreat. I grew up on the treasure coast of Florida where there are shipwrecks. Every July when I'm there, every night I would see a turtle nest hatch and people would say, Oh my God, I would give anything to see it. Okay, I'm setting it up. Come on down. And that's one I'm not going to make a whole lot of money on. Cause I do try and pick really nice hotels and places to stay. I just really want people to see and experience the things I've seen and experienced. And again, bringing like minded people together. You can't promise you're going to see a turtle nest hatch. You can't. The turtles control that, but the likelihood is very high.

If nothing else, you're gonna have a good time on the beach. We'll do a boat tour and great restaurants with seafood. It's just planning a couple of days of fun for you time. Because for so long, we didn't put ourselves first. We were the people taking care of everybody else, the house, the job, the kids, the parents, the husband, whatever.

Now it's our turn. It's our turn.


And there is a certain budget aspect to that. If you can budget to go on a trip by yourself in an interest area and then go on a trip with your family that you'll know they'll enjoy and then everyone's happy.


[00:26:40] Desiree: turtles on the treasure coasts.

We'll go see the

treasure ship museum. And it's, but it's again, this is home to me. So I love the idea of sharing where I'm from.


[00:26:57] Desiree: Yeah, 100%. I can tell you exactly what to order when you go to Riverside Cafe.

Tuna nachos are better than any other place in the world. Anyway, you get my point. But it's, I really love it. I love that I've launched this. A year from now I'm doing all the things I've got, lobsters and lighthouses.

That was a tour I did with my daughter for two summers straight. I would love to repeat that with friends where we just ride up the coast, and get Toyota or Ford to sponsor us. They gave me cars for this years ago. Why not make it a whole retreat? I love Ted Lasso. I want to put together a Ted Lasso retreat.

That's Outlander where I fly people. We go to England, watch a soccer game. Then we go over to Amsterdam. Find a boat like Rebecca did,


What should I do? Rent a car everywhere or something? I want someone to do a group travel, like train, see the highlights, cities and they arrange all that and I don't have to do any of it. That would be lovely.


[00:28:25] Ciaran: It's coming.


I can't even remember the books, but you get my


[00:28:54] Desiree: Mo could take us anywhere on earth, but I know it's going to be fun and I just love the idea of it. Now that I've got the whole business side set up where we've got taxes taken care of and the liability and the insurance and all of that.

Now I can do it with anybody. I love the idea of it. I love, again, My Jam is connecting people and destinations and showing everybody the world.


[00:29:20] Nasreen: We can't argue with that. That's like a dream job, honestly, except for I'll let you do the logistics and I'll just come along for the


[00:29:29] Maureen: Great job. Except for the logistics and the people.


And then, I could go and learn to surf without looking like a fool. Like I'm, I might be a late bloomer in some things. I grew up in New England and never learned to ski. I'd like to go somewhere and try it away from other people where no one I know can see me.


[00:30:03] Maureen: Yep, La Jolla Surf Divas are awesome for that.


[00:30:09] Desiree: Portugal is my retreat in October and it's the finding your next. We're staying on the silver coast and we're taking a day trip up to Nazar and seeing the 80 foot waves. We will not be surfing in these 80 foot waves, but we will be watching from the lighthouse that’s in all of the epic videos.


[00:30:30] Ciaran: I need more time to think about that. . I have so many. things that I would love to do more archeological trips. My daughter is an archeologist and she is constantly telling me about all these phenomenal things that I've never even heard of and. Some of my favorite things when I have traveled have been archaeological ruins I've stumbled on, so I'd love to do more of that. But then there's lots of nature stuff, and there's city stuff, and there's knitting and yarn. I love looking at yarn for that. I could come up with theme trips all day long.


[00:31:07] Maureen: can't say I ever would have come up with a yarn trip. But I'd do it. I would do anything. I just love to go places. I love the ocean and anything towards the beach and whatnot, but I have started watching Outlander again. I'd probably, although I don't know that I'd want to do it with a group.

I'd have to see who the group was because I don't do necessarily well in a group situation because I'm a bit of a heckler as so it'd have to be like a really fun group who's like drinking wine along the way or trying scotch or something loosen everybody up because if everyone's like dead serious about it and that and they're like think these people are real that then I would probably get kicked off the tour.

I like the idea of it. I want to go to Scotland and I want to see the places. So there you go.


[00:31:58] Maureen: I do like couples getaways, and we didn't touch on that. We could talk about that time for sure, because I think that I do that more often now than I ever have. We like our husbands, and we like to go places with them, and we find other people we like, and we go places. We can talk


and reconnecting. Once the kids are out of the house, a lot of people don't even know each other anymore and rekindling the spark kind of thing. That is not in the case with you. I know that. You guys are


[00:32:47] Nasreen: I think that would be something I'd be interested in down the road a little bit. Our kids are still pretty young, so it's a matter of kind of trading off and taking turns and going away occasionally when we can fit it in. But Don't know. For me, I think I was trying to think about what my bucket list trip would be.

I think I loved Sri Lanka. I'd love to go back and see more of the island with people, and I know Megan Riston did a trip there or has it coming up maybe, and timing wasn't good for me. The other one is I just like weird sites or like ancient things, seeing any UNESCO, anything with a lot of history and if there's a place to see a lot of different things at once.

That, for me, would be it and preferably not somewhere where I'm gonna have to worry about a bunch of people in the water getting stung by jellyfish or eaten by gators or whatever, I don't wanna, I like the New England ocean where you just look at it, it's pretty, you dip your feet in, it's cold, whoo, nothing eats you,


[00:33:48] Nasreen: Oh, not my thing.


[00:33:53] Maureen: Exactly. I want a trip to Dubai that I don't get arrested on.


steer you around


[00:34:00] Nasreen: a little bit.


hook it



And we could do a whole nother episode on how to choose the right trip and vet it out ahead of time, but you know what, we'll save that one for when Des has done a couple of them and she's ready to give, like, all the insider tips and pull in the other people who have all the nuggets that we don't see behind the scenes.

Anyone have any last pearls of wisdom to share?


Like Mo,


[00:34:47] Maureen: I still have


[00:34:48] Maureen: I have friends that I met on planes that I'm still Instagram friends with, 45 minute flight. Still friends 10 years later.


[00:35:00] Nasreen: We meet

people in the most random ways sometimes. You're talking about communities and things like this. I met a friend who was in a mom's group when I was in San Antonio, who was like, I want to learn how to coupon. And we jumped on this weird couponing trip with a bunch of people. And then we just That was what we did.

We were both trying to save money so we just used to go and roam the stores at night with drinks or coffee or whatever and hang out and it was awesome. So yeah, find your people.


[00:35:30] Nasreen: I know, right?


[00:35:33] Desiree: Yeah.


out of it and I got a good friend. So it all worked out.

Until next time, this was a great topic and we really would love to hear if you've gone on one of these curated trips or heard about a super cool one. Tell us, we want to know. Meanwhile, I'm going to be on the editing floor here, clipping up some of Ciaran's giant life revelations of the whole drowning in online communities, but starving for real connections.

I'm just gonna leave you with that again, because that was good. Until next time, happy travels..

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Time to Talk Travel
Do you love to travel? Whether you have your next trip planned, are looking for inspiration, or just want to live vicariously through others Time to Talk Travel is here for you! Let’s explore the world together. We’ll dive into themed trips, must-do’s, things that weren’t worth it, and getting the most out of every trip. Tune in as we talk about the adventures out there!
Time to Talk Travel, a podcast for travel enthusiasts, was born out of a need for community. The voices and faces behind TTTT met over a decade ago while navigating online content creation. Their kids grew up together on press trips, they were online cheerleaders for each others successes, and there to provide support to online friends when times were tough. Life got busy. Something was missing - that supportive community they craved. Now they're back- a little older, much wiser, and with a wealth of travel knowledge to drop.
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