Islands + Identity, Damesly goes to Hawaii.

When I was younger, I dreamed of big worlds. I wanted open fields, majestic scenery—I wanted to own a car and be able to drive it, for as long as I wanted, in any direction.


Fast-forward 20 years of traffic: what was I thinking?


Isn’t it funny how we focus on the things we think we want, while ignoring the things we have in front of us?


I was lucky enough to grow up on Oahu, Hawaii but I’m not sure I started to really truly appreciate it until a year before I left home for college. But I’ve had a lot of time to reflect, and to recognize with new eyes, just how blessed I was to grow up in what was a small, friendly town called Kailua.


Damesly is heading to Hawaii!


In two weeks, I’ll be taking some lovely, creative, talented women back to the island with me, to show them the sights and secrets I grew up finding.  


We’re going to surf. We’re going to hike. We’re going to connect with the earth and each other and work on our #powergoals for the year. It’s going to be equal parts inspiring and relaxing. I’m going to show you some things that will blow your mind, historically. And if you’re lucky, you’ll also get to meet some people who have been incredibly influential in my life.


We still have a couple of spots left—join us!


Here’s a breakdown of what I’m most excited about:



  • Surfing: No surprise there! I have been out of the water for too long and I can’t wait to get back in and play. For those on this trip who have never surfed before, never fear! We have some really incredible women on hand to fascilitate that part.
  • Hiking: There are incredible trails all over the island, and I’m going to bring you on some of my favorite hikes. Some of these may, or may not, end in waterfalls. 😉
  • Snorkeling: Under-the-sea, under-the-sea: we can’t bring you to this magical paradise and not give you the chance to glimpse the amazing world that’s taking place just below the surface of the water.
  • Connecting: I love getting to know the dreams and ambitions of my fellow travel sisters. This journey is exactly what the doctor ordered and I know we will gain confidence and clarity by the end of the week. We all need a little reminder that we are on the right track sometimes. This is the week to seek that!
  • Exploring: Though we have a day-by-day itinerary planned, I also welcome the chance to get off the road and just explore. I’ll be bringing you to some of my favorite hole-in-the-wall poke and haupia joints, and I’ll pull the car over ANY time you want. Let’s feel that wonderful salt water in our hair, ladies! It’s TIME.
Yoga in Hawaii
Yoga in Hawaii

We have a few spaces left on this epic journey. Come with us!  

Damesly + Inspiration: What This Whole Thing is About

Hey Damesly babes, Kelly here. I wanted to take a minute to introduce myself and the team behind Damesly and tell you a pretty interesting story for our FIRST EVER BLOG POST! Exciting, huh?

Almost seven years ago, I was traveling solo through South America, when I started to subconsciously notice the differences in solo female travel, and all of the things that no one had told me before (hello, where are all the tampons here?).

After four months of traveling the continent by bus, I came home inspired and in love with the world – but I had no idea what to do with that. So naturally, I got three jobs and started working full time again, as an editor, a freelance writer, and a bartender on the weekends, hustling for no other reason than to watch my bank account breathe a little again.

Three months later, I had a dream in the middle of the night that I was looking at a travel guidebook for women and a voice said “this is totally your calling!” The next morning I called Alyson Kilday at the creative design agency Hop & Jaunt, who I knew from designing my original travel blog (Travel Bug Juice) to tell her about this premonition. And she didn’t laugh in my face!

That premonition went on to become Go! Girl Guides, the world’s first and only series of travel guidebooks for women. And that company went on to grow to include the Women’s Travel Fest, the world’s first consumer travel conference for women.

So it’s only natural that we should be here today, talking about actual real-life travel again.

Throughout this career journey I have met some truly amazing, entrepreneurial, creative women who inspire me to work as hard as I can to really reach my full potential and live my dream life. They remind me that anything is possible. These women are mentors to me. Many of them have spoken to sold-out crowds at the annual Women’s Travel Fest, where they have brought me to tears.

With Damesly, I hope to introduce you to them. The idea here is combine the workshop + informational components of the Women’s Travel Fest, with actual travel.

I am a big believer in travel as an integral route to personal growth, and it’s my goal that Damesly will fill in some of the gaps that come from typical group tours.

I want to see a community full of inspirational women, supporting one another in their careers and lives. I want to be a part of a new travel experience, that goes way beyond boring bus travel and stuffy hotels. I want to take you to places that I love, places that push me to do more.

Come with me. It’ll be amazing, I promise.


Kelly Lewis

CEO, Damesly