Listen to the Podcast About The Gypsea Traveller

Podcast for The Gypsea Traveller

Podcast Summary

Libbi Roed, known as The Gypsea Traveller, sat down with host Jake Carter from Felix and Fingers to discuss her passion for planning vacations and exploring the world. Originally from Canada, Libbi fell in love with Hawaii after visiting and decided to make it her home. With extensive travel experience to 29 countries and 16 cruises, her expertise in creating unforgettable experiences shines through.

In the interview, Libbi highlighted current trends in travel and events, noting a slight slowdown in visitors to Hawaii post-COVID. Despite this, Hawaii remains a top destination due to its tropical allure and relative ease of travel compared to other international locations. Libbi emphasized the lower visitor numbers resulting in a more pleasant experience for those exploring Hawaii, albeit with slightly higher pricing due to the high demand.

When it comes to events and travel, Libbi expressed her distaste for the mindset of seeking the cheapest deals possible, particularly in Hawaii. She stressed the importance of investing in quality accommodations to truly enjoy the beauty and comfort the destination has to offer, rather than compromising on essential amenities like air conditioning.

With a keen eye for ensuring travelers have an unforgettable and stress-free experience, Libbi’s dedication to curating exceptional vacations shines through in her insights and approach to travel planning.

This interview was provided by Felix and Fingers Dueling Pianos.

Podcast Transcript

Jake (00:25)
Hello, I’m Jake Carter with Felix and Fingers and I am here with Libbi Roed, The Gypsea Traveller. And you plan vacations and all kinds of beautiful things across Maui and all over the world, I think. Looking at your bio, it says you’ve been to 29 different countries and 16 cruises and you live on Oahu. So do you wanna tell me anything more about yourself and your background?

Libbi with The Gypsea Traveller (00:48)
Yeah, I mean, that’s a lot of it. I mean, being from Canada, I was cold my whole life and fell in love with Hawaii the first time I came here. My parents actually got married in Hawaii. I got married in Hawaii. And so it just kind of became, I think, a place that was near and dear to our heart and decided to move out here and kind of make it home.

Jake (01:09)
Yeah, yeah, I think it is a very beautiful home to have. Okay, so let’s dive right into this. So what are some current trends that you’re seeing in travel and events and all of those things? What’s new?

Libbi with The Gypsea Traveller (01:12)
Thank you.

Yeah, I guess, I mean, I am seeing a little bit of a slowdown in visitors coming to Hawaii just because kind of we in travel industry, we talked about pre and post COVID, everything seems to still be related around that. But post-COVID, everybody wanted to come to Hawaii. One, because it was really difficult to go to other countries. It was a lot easier to come to Hawaii, but you were still somewhere tropical, had the beach, it wasn’t continental US, it was amazing. But now as more places are opening up, you know,

Travel is slowing down a little bit, but I think that’s also amazing for people that are visiting Hawaii because it’s not as crazy when you come and visit. There’s not, you know, millions of people on the island at some of the different spots. Pricing is still a little bit high because they are seeing that Hawaii is really popular and everybody wants to come here, but I think as less people start to, you know, go to Europe and they’re going to Italy and they’re, you know, just going different places.

Hopefully the pricing’s gonna come down just a little bit back to, I would say pre-COVID. It’s still post-COVID pricing right now.

Jake (02:28)
Yeah, yeah, I think that’s super true. I think it is definitely different to like look at the occupancy rates of the hotels. And I know that like, what I’ve heard is a lot of the hotels kind of adjusted to this new post-COVID thing where instead of booking 1000 rooms at $300, they booked 50 rooms at, you know, $1 So it is very different, but it does make a difference in how many people are around and like how many people are in the pool and the beach and everywhere else. So it’s kind of like you have very personalized.

nice, like, calm service for yourself. So I totally understand that, that makes sense. So when you’re talking and thinking about events, you’re thinking about travel and coming out to Hawaii, what are the most cringe -worthy things that you hate seeing that you’ve seen at events or just people out coming out here?

Libbi with The Gypsea Traveller (03:22)
I mean, I think in the travel industry, honestly, some of the cringe -worthy things I think of are some words that relate to it, like deals and come as cheap as possible. And I just don’t think that’s what Hawaii really is. And if you’re going to spend all the time and money to get here, I do think it is a destination where you don’t try to do it as cheap as possible because…

you kind of are gonna get what you are gonna pay for. And in Hawaii, we know that includes cockroaches and maybe no air conditioning. This is life. You and I live here. We know that that is the thing. And so sometimes, cheap as possible, we want to spend just a little bit more so that you do get a nicer accommodation that’s gonna work for you and be clean and have air conditioning, which is something that we all, I think, appreciate when you live here. And especially if you’re traveling, you’re not used to some of the warmer weather.

Jake (04:01)
Mm -hmm.

Libbi with The Gypsea Traveller (04:20)
So I think just kind of that verbiage around it to me is more cringe -worthy when I see it, just because I hope when people are using those words and maybe looking at weddings, events, vacations around cheap and discount and that kind of thing, I hope in the end they really do get what they want and aren’t disappointed in the end. To me, I just think, oh no, no, just make it exactly what you want it to be so that…

Jake (04:42)

Libbi with The Gypsea Traveller (04:47)
It’s a once in a lifetime experience to come out here for a lot of people. So just do it, enjoy it. Even the same, I know some people are trying to save on parking, resort fees. Unfortunately, that’s just what Hawaii is right now. And I think it’s, again, you’re only coming out here once. You might as well just pay that parking fee for a week to have a car, to be able to experience and go everywhere you wanna go and not come home and wish that you didn’t do something that you could have done because…

you didn’t spend $50 extra for a night of parking. It is hard when you look at it and the pricing, but I think thinking about you don’t want to come home and not think, oh, I really want to go back. And you might never come back just because of pricing and because it’s so far away from a lot of places where people are coming to visit us from.

Jake (05:34)
Yeah, for sure. I mean, there’s, I totally agree. I’ve seen that quite a bit. And just people that come out and well, oh, well, you know, we don’t want to spend the extra little bit on this or the extra little bit on that. And it’s like, if everyone can come to Hawaii, I’m not trying to be like, don’t come. Like, we don’t want you here. We do want you here. We really do. But at the same time, it’s just, it’s not a place that I feel like is intended for you to come and try to like cut corners and like penny pinch, you know?

Libbi with The Gypsea Traveller (05:51)

Jake (06:04)
It’s not cheap. And I don’t think that like anyone really generally is trying to be like Hawaii is really cheap. You should come have a budget vacation here. It’s like, no, go to Vegas. Like Vegas is cheap. You can go have a budget vacation in Vegas, but Hawaii, not so much, you know. And so I think that you’re totally right. A lot of those situations, it’s like, you’re kind of going to make a bad experience for yourself and then not like it, but you chose to do like you, you can’t do that kind of stuff, you know, and I’ve seen the same thing with parking and people, oh, I don’t want to get a rental car. And it’s like, well,

You should, because it’s not going to be very fun if you don’t. If you’re just going to stay at a resort, go to Mexico. Go to an all -inclusive in Mexico, all those things. So yeah, I totally agree. That totally makes sense. Is there anything that is cringe -worthy that you’ve seen at events or weddings or anything like that that you’ve been to, that you’ve worked on, that you’ve planned? Anything that you were like, ooh, you know.

Libbi with The Gypsea Traveller (06:59)
Um, not really. I think, again, relating to literally the last thing I just kind of said, the only thing I can think of, again, is just…

what you spend and what you get, I have seen that relate to kind of like services in a wedding. An example would be photography. Sometimes I see people saying, oh, I can only spend this much. And then I see the photos afterwards and the background is white and it’s blown out. And you can’t even tell that there’s a beautiful, gorgeous green mountain behind you, where when you look at a photographer that has studied and has the knowledge and is charging for what they’re worth, you see these beautiful photos.

where the person is clear and the background is gorgeous and you can see, oh my gosh, they got married in Hawaii or you know the exact location or you can just tell that they’re married in Hawaii versus like a blown out white background because somebody spent less money for that. So I think again to me that’s again more cringe worthy because you’re spending this money to get married in Hawaii and just making sure that the people you’re using, you value them and their pricing because they’re working hard and

Jake (08:00)

Libbi with The Gypsea Traveller (08:09)
that pricing that you pay is going to get you the most amazing experience so that you can take it home and show people I got married on this random beach, you can’t even tell where I am, versus I got married and here’s this gorgeous background in Hawaii. And I know even my wedding photos, you can just see the background in the mountains and they look beautiful and it wasn’t even because of me or my dress or my, you know, us as a couple, it was the background that really made it absolutely amazing.

Jake (08:22)


That’s so true and such a good testament to good photographers where it’s someone that is a professional in what they’re doing, doing a good job at what they should be doing. Cool, so what is a unique or really fun idea that you’ve seen at a wedding event, something that someone’s booked, something that you’re like, wow, this was really amazing and everyone should do this, something cool?

Libbi with The Gypsea Traveller (08:42)

I mean, I think personally being in Hawaii, if you’re gonna do a reception and you’re gonna pay for a private reception, something fun that you could possibly think about is bringing a luau to your reception site. So it’s not just a regular reception, but you’re either buying out the whole luau site because there are some that are smaller, you know, that have like 75 to 150 people at it versus 500 or a thousand. Like on Oahu where I’m at, there’s some really large luaus, but you could buy out the whole,

Luau for a hundred, you know under 150 people if that’s your wedding size and Be able to do that as your reception where the dancers are there and the food is there and you know It is almost a reception, but it’s more of that Hawaii Luau the culture I think that’s kind of a unique experience that you could do another one is even first really small groups being able to charter a catamaran as a Reception or something, you know go out and do a sunset sail for your catamaran where they’ll have drinks and appetizers

Jake (09:49)

Libbi with The Gypsea Traveller (10:00)
and it’s just your group on the catamaran and I think that could be a unique experience if you’re looking for what do we do after the wedding for our guests and as a reception.

Jake (10:11)
Yeah. Awesome. Yeah, that’s fun. One of my other guests on the podcast was when I asked him this question, he was like, oh, the coolest thing is we’ve had people go and do these helicopter weddings and like get married, like they take them up and get married on cliffs. And then he’s like, and then we make them jump out of the helicopter and go swim in the ocean. I’m like, that’s insane. And so I was like, we, I was like, you and I, we need to do this where you guys bring us up to the top of a mountain. We’ll play at the top of the mountain. Like that’d be so cool. And now you’re talking about boats. I think 2024, the idea.

is we need someone to book a catamaran with dueling pianos on the catamaran. That would be so much fun. That’d be so cool.

Libbi with The Gypsea Traveller (10:44)
Oh, yeah. And I have seen the helicopter when you’re talking about that looks amazing. Yeah, they went right up to the and got off of there and got married at the top of the mountain, just the two of them. And yeah, it’s definitely a huge experience.

Jake (10:51)
Mm -hmm, yeah, yeah.


Yeah, so anyone that wants dueling pianos on the top of a mountain with a helicopter or out on a boat, let me know. It’d be super fun, I love those ideas. Okay, so this one’s a good question. Any advice that you can offer someone that’s just getting started on planning?

Libbi with The Gypsea Traveller (11:06)
Thank you.

I’m sorry.

I think definitely find your person, reach out to somebody that you’re seeing. I know a lot of ways to find somebody that you can trust are on Facebook groups, Google My Business, find that whether it’s a planner.

or even like me as a travel advisor, my clients will reach out to me once we plan their trip and they say, oh, I want to get married or we’re going to do a vow renewal. How do we find a officiant or a photographer or somebody to make lay pose and lays for us to wear? And I’m able to connect them with all the different parts. And I think a wedding coordinator can do that as well, pull all the pieces together. So just find that trusted person, look for

at reviews, look at pictures. Also make sure that they’re registered. Sometimes a lot of businesses, I notice, are not registered with the state and are kind of operating illegally. So make sure that they’re registered, trusted, and use that person to help you connect all the pieces. Because like I said, there’s so many from planning your trip out here, booking the hotel, if you’re bringing guests, you know, all of them need somewhere to stay. Again, the laze, the music, what you do, the venue, or

maybe a good beach photographer, music, there’s just so much involved.

Jake (12:38)
Yeah, yeah. And I know we were kind of chatting before the interview about how it’s important to start this process early, get people, get planners, get the people that do this professionally, work with them, work with someone like you, because I know I asked you, I was like, well, what is kind of your involvement in different things? And you were like, well, I can find all of the people and like you organize all of those different people and get them all together instead of like.

Couple or someone coming on vacation or someone booking an event instead of you have to be like I need to find all of these different people that do all of those things and bet all of them that’s kind of what you do right is so Makes it a lot easier if you can just be like here is the package of all of the options Here’s someone that does lays and travel and hotels and like yeah so

Libbi with The Gypsea Traveller (13:23)
Yeah, and it’s so nice living here and being on Instagram or some of the Facebook groups and seeing a photographer post pictures and I’m pulling that information and making my own list of like, oh, I really like this photographer on Maui. I love this photographer on Big Island. I have an amazing Leipo lady on Oahu and a ton of my clients have used them for photography and for photo sessions and vow renewals. And so just having those people that I’m seeing that they’re good and

or that person you’re working with, trust them to be able to refer them to you.

Jake (13:58)
Yeah. Okay, so my next question, it’s gonna be a two part question, is one, I wanted to ask this in the beginning. Your name, The Gypsea Traveller, is super cool and it’s spelled Gypsea with like, ocean sea, which is super cool. And so that, I feel like, is gonna pair into what makes your service unique.

Libbi with The Gypsea Traveller (14:19)
Yeah. Um.

I mean, again, because I changed it to Gypsea S .E .A. because I have a love for the ocean and kind of tropical destinations. I personally call myself a Gypsea because I’m always traveling. I’m never in one place very long. I’ve lived in a lot of different places. I’m from Canada. I’ve been to Hawaii, then left to California, back to Hawaii, and then I travel all in between. So I am. I am a Gypsea traveler. I’m all over the place. And I think a lot of my clients are too. They want to travel. And so one of my biggest specialties, I would say,

of course is Hawaii because I live here. I probably book about 90, 95 % of Hawaii and people all over the mainland find me because they’re looking for somebody that knows Hawaii. I guess it’s just really overwhelming for somebody. Even say from like, I get a lot of East Coast clients because it’s a 13, 11 to 13 hour flight out here from New York, Boston. It’s five hours for them to go to Europe. So they love Europe and the Caribbean and they know that, but Hawaii is just like, they have no idea.

which island to go to and where to stay and what to do. And that’s kind of where I come in of being that expert to be able to know. You literally can list five things that you want to see and do in Hawaii and I can tell you right away which island you should go to and then which activities you can do and I can put that all together for you just because I’ve been to the islands and I know which one’s good for each person. So that’s definitely kind of my main specialty for sure.

Jake (15:42)

Yeah, it helps to someone that’s out here, someone that knows, someone that’s seen it all, because it’s hard to like, it is hard, especially even just like you’re saying, like looking at the internet and being like, I wanna go to Hawaii, oh, there’s a bunch of different islands. And then people are like, oh, can I just go to all of them? Like in the same day, can I, you know, it’s like, no, not really. Like you kinda sort of can island hop it, like you do pick an island and you should go to that island, you know. So you start traveling in between them, it takes up big chunks of your day, so yeah.

Libbi with The Gypsea Traveller (16:10)

Jake (16:14)
Makes a lot of sense to help pick, and they are all very different. Like, Oahu is not the same as Kauai. Yeah.

Libbi with The Gypsea Traveller (16:22)
No, not at all. And even the resorts too. I mean, you can Google, you know, where should I stay? And you’re going to get…

thousands of options. I’ve personally been to probably over a hundred resorts on all of the five main islands. I go and I see them and I take pictures and I have my list of ones I like, ones I will never put anybody in because they’re terrible. Ones that are, and ones that fit all different budgets, whether you’re a budget traveler, kind of moderate, more luxury. I have options that I would recommend for kind of all those categories, which I think is helpful.

Jake (17:01)
Awesome. Okay, so the next part of this, these are gonna be just like shorter questions that you can answer as thoroughly or as short as you want. What is the current availability for you to book things for people? How far in advance do you want to book?

Libbi with The Gypsea Traveller (17:15)
I do recommend at least two months in advance. That’s like the absolute minimum. I mean, it only takes me a week to meet with somebody, book their vacation, and be ready for them to kind of go. But there’s a lot of pieces within that. And I say two months.

at minimum because with Hawaii, the resorts are selling out, the luau’s are selling out, amazing catamarans are selling out. So if you’re, you know, what is it, February, if you’re wanting to go in April, I can’t guarantee that anything great is going to be available for you then. So really four months is ideal and the furthest out we can book is 11 months. So sometimes I get a lot of families that are booking with me in the summertime for next summer, which is perfect timing. Or right now you’re booking for next Christmas, next December.

which is perfect timing. Giving it, yeah, I would say a minimum of four months is good for Hawaii just because of the, I wanna make sure that everything you want to do is available and not have to say, oh, sorry, this is sold out. Oh, this resort doesn’t have this room. I wanna make it the best available, best, you know, experience that you’re gonna have and not put you in, well, this is all that was available.

Jake (18:01)
Mm. Yeah.

Yeah, for sure. What about do you book small groups and big groups or just small groups or just big groups?

Libbi with The Gypsea Traveller (18:32)
Yeah, I can do everything. I do a lot of couples, especially on going on honeymoons or coming out here to get married or celebrating anniversaries. I do a lot of families, multi -generation, where grandparents are coming, cousins are coming. But then I can do lots of groups too, such as weddings. If somebody wants me to book the wedding package for all of their guests, where if their guest is going to join them, they don’t have to worry about where do I fly and where am I going to go.

to stay. I can put all that together for like each individual guest.

Jake (19:07)
Okay, so what about deposit and cancellation for your services? What are your policies there?

Libbi with The Gypsea Traveller (19:13)
Yeah, so I work with suppliers and we’re working off of their…

Deposits and cancellation policies. So what I love about this the deposits is the deposit is due when you are ready to book So once you’re you’re super excited about the package that I found you you would do a deposit It’s always the flights up front just like anywhere when you book a flight you have to pay it right away right away and it’s $200 per person to towards the resort that you’re gonna stay at and then after that nothing is due until 45 days before you leave that’s

That’s when the final payment is due. And I’m super flexible with, if you want to message me at any time and say, I want to pay towards my vacation, we can do it in small chunks until you get to that final payment amount, or some people forget about it. And then I just text them two weeks before we’re ready to go, or two weeks before they’re 45 days out and they know their final payments due and they get it all paid. And cancellation policies too. I always add in insurance. I think trip insurance, especially pre-COVID. You being on Maui, you know how important it was.

was for the Maui fires, I had so many clients that we had to adjust and move them off of Maui to other islands. And I was able to do that because they all had insurance. And anybody that did want to cancel, we had to cancel for any reason. They got future travel credit or they got a full refund. And so post-COVID, I think insurance is so important to make sure that you’re not having to really stick to those cancellation policies. Otherwise, cancellation policies usually, you know,

within 45 days, 30 to 60 days out, you’re gonna lose all your money if you had to cancel and you didn’t have insurance for a lot of, you know, resorts and car rentals and wedding venues, even photographers that are taking deposits, they’re not going to return that money because that’s how they survive too. Insurance is huge, even if you’re not booking a vacation package, adding it for your venue and your wedding to make sure everything’s safe in case anything happens.

Jake (21:16)

Libbi with The Gypsea Traveller (21:18)
because we all went through it for the Maui fires and there was so many stories, I can’t even go into all of them, about cancellations, whether it was people needing to cancel, whether it was photographers or people who lived on island who were losing business, it was just, it was not a good scenario for anybody.

Jake (21:36)

Yeah, and for everyone listening, Maui is open. Please come. We need you. So don’t take this as it’s still closed. It’s not still closed. We do need you. It’s okay. Everything’s fine. It was only a very short amount of time. So yes, everything’s okay. We need you. Do not come because of this. Cancellation insurance is always great regardless.

Libbi with The Gypsea Traveller (21:43)

Not close.

Yes, I’ve had many clients. Always get the insurance just in case. I mean, that is a good scenario just because nobody expected that to happen. And insurance is there in that case. But otherwise, since then, everybody has been visiting all the islands and going back to Maui and Kanapali. And they’ve been having really great experiences.

Jake (22:21)
So I know that you mentioned you have lists of different vendors that you like to use and preferred vendors for hotels and all the different things. Do you require that your people that are booking with you use those or are you open to anything that they also find and suggest?

Libbi with The Gypsea Traveller (22:36)
Yeah, I’m totally open. Like I said, I’m kind of that middle person where if they need some ideas, I’m able to say, here’s a few that I recommend. But a lot of the times, they’re finding their own. And that’s totally fine.

Jake (22:49)
Awesome. So when you are having a trip or event or whatever it is that you’re having, you’re booking with people, are you the main point of contact or is there someone else that they reach out to while things are going on?

Libbi with The Gypsea Traveller (23:06)
For their vacation package, I am definitely the main contact for them. If they’re booking their package with me and then also doing the wedding or a venue, they’re going to want to reach out to that person if they have a photography question or if they have the venue question. But I can always be that middle person if they have questions or aren’t sure who to ask in certain scenarios. Yeah.

Jake (23:21)
Mm -hmm.

for sure. So you’re kind of like the first step of the team of doing all the things and then they can specialize and talk to the different. Awesome. But you kind of help.

Libbi with The Gypsea Traveller (23:36)
For sure. Yeah. I’m kind of, you ask and then I can let you know who you ask next or if I can answer it for you. Yeah, for sure.

Jake (23:46)
Yeah. So what about, I know that we talked about different islands are better for different people. And you had some things that you wanted to say about which resort to stay on on certain islands and what islands best to visit and better times to visit different places. Do you want to tell me more about that?

Libbi with The Gypsea Traveller (24:06)
Yeah, so all of those scenarios are so individualized. I think if you guys listen and watch the last episode that Jake filmed with Iris, she’s the concierge on the island. I loved her responses. I was like, oh, I don’t even have to say anything. She said it all for me. Pretty much what she said was everything is super individualized, just because it’s.

Somebody you might have a cousin that came back from Maui and said oh you have to go to Maui and stay at this resort It was amazing that does not mean that you’re going to love it because everybody has different styles how my parents travel and how I travel are Totally different how my best friend travels and how I travel are totally different We’re not going to like the same resorts or maybe even the same island Even out here. I know a ton of people who love a certain island I’m not gonna say which one and it’s my least favorite and I have a different favorite island


And so what I do is kind of sit down with each person or couple or family group and I ask them a few questions. We call it qualifying. So I’m going to ask you, what do you want to see and experience and do? And from this information, I’m easily able to say, oh, this is the island you need to go to. And if you have multiple days, maybe you’ll even get two islands out of that because we don’t want to send you to too many islands in a limited time. But if you have over a week, sometimes I like to get you to see another island as well. And that goes with resorts too.

Every resort’s gonna be different, and so it’s good to sit down with you and figure out exactly what you wanna see and do. And do you wanna be on the beach or across the street from the beach or up in the mountains? There’s so many scenarios. So it’s important to ask all those questions so I can get you at the best place for you. And it might not be the best place that somebody else has recommended, but it’s gonna be exactly for what you want based on what you’ve said.

Jake (25:56)
So it’s highly personalized and you take everyone’s dreams and make them a reality, right? Awesome Well, thank you so much for joining I so appreciate you answering these questions and talking about your service and for everyone listening You’ll be able to see her website and all of the different things for you to book your events and your travels and everything as part of this podcast But thank you so much. Have a good day

Libbi with The Gypsea Traveller (26:02)
For sure, yeah.

Thank you.

This interview was made possible by Felix & Fingers Dueling Pianos

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