Hawaii: Islands + Identity

Calling all ladies unafraid to dream big—we’re going to Hawaii!

Is something keeping you from living your dream life? Have you got an idea for a business that you want to work towards? Do you just want to get some clarity on things? Join us in Hawaii for our “Islands + Identity” tour, where we get to the heart of what’s keeping you from actualizing the things you know you want to pursue and come together to help you get crystal clear about your heart’s calling.

Work with our fantastic life coach in group and private sessions in between snorkeling, surfing, hiking and exploring.

This is the perfect adventure for women unafraid to get a little dirty, do the work and reap the rewards.

Check dates and availability
Trip Dates Availability Price Payment
May 7-14th, 2021$2850 USD
Reserve this trip with a $500 deposit, or pay in full. The balance of your tour is due in full 60 days before departure.

Day 1: Arriving to Hawaii

Arrive to Honolulu and transfer to our beautiful island villa, rest for a while before we get ready for dinner.  Tonight over dinner we will get to know each other better while we toast to an incredible week.

Hawaii womens tour damesly

Day 2: North Shore + Surf Lessons

Enjoy breakfast as we get ready for a big day.

Today we’ll head up to the North Shore where we’ll have surf lessons and explore some of Hawaii’s most famous beaches and waterfalls.

First, we’ll have our surf lesson, as the waves are best in the morning. Afterwards, we’ll travel along the North Shore coastline, passing by and stopping at beaches like Waimea Bay, Pipeline and Sunset. We’ll have lunch at a famous North Shore shrimp truck, and will have the opportunity to snorkel if you would like.

After returning home in the evening, we’ll have a group discussion start our meetings with our life coach to start to de-clutter and align you with your dream life.

Meals included: B, D

women only tour damesly

Day 3: Snorkeling + East Coast

Today we’ll head over to the east side of the island for some breathtaking views and fun. We’ll start by snorkeling at world-renowned Haunama Bay, and then we’ll wind our way through Waimanalo, where we’ll stop for an authentic plate lunch.

After lunch, we’ll head back to our accommodation, where we can continue 1-on-1 sessions with our life coach.

Meals included: B, D

hawaii group tour

Day 4: Manoa Falls Hike + Iolani Palace

After breakfast this morning, we’ll go on a short 1-mile hike to famous Manoa Falls. The hike will take us about 1.5 hours, and will show you a side of the island you haven’t seen: jungle.

Take in the amazing trees, flora and fauna of this beautiful island. Afterwards, treat yourself to a shaved ice in the gift shop.

We’ll have lunch as a group. This afternoon, you’ll visit Iolani Palace — the only ruling palace on US soil —  to learn more about Hawaiian history and culture.

Afterwards, you’ll have downtime to relax or continue sessions with our life coach.

Meals included: B, D

hawaii womens tour

Day 5: Hula + Kailua

After breakfast this morning we’ll head towards Kailua, where we will have a hula lesson with an incredible woman who has been in Damesly owner Kelly Lewis’ family for decades.

Our lesson will take approximately 1.5 hours, and afterwards, we’ll have lunch together.

Following lunch, we’ll head to Kailua to visit some of the world’s most famous beaches.

You’ll have some downtime this afternoon, before we have dinner together as a group.

Meals included: B

women only private tour of kailua oahu

Day 6: Waikiki + Sunset Sail

After breakfast this morning, we’ll go on a hike of beautiful Diamond Head. If you’re not interested in hiking, we can schedule 1-on-1 time with our life coach.

When you return, we will head to Waikiki Beach, where you will have the option to rent a stand-up paddleboard or surf board, or to partake in a lesson.

Today is really all about you — if Waikiki doesn’t appeal to you, we are also happy to make adjustments and suggestions.

This evening for our farewell dinner, we’ll board a catamaran for a sunset dinner sail. With any luck, we’ll see dolphins and whales, the perfect way to end an incredible week together in Hawaii.

Meals included: B, D

oahu group tour womens tour

Day 7: Departures

Today is departure day, and we’re bummed!

It was an incredible week together, and we’ve loved getting to know you. We know you’re leaving us with a lifetime of memories and we know we’ll see you again.

After breakfast, we will begin airport transfers.

Meals included: B

View full itinerary

Cost includes:

  • Accommodation in a beautiful private home (all participants have own room)
  • Life coaching workshops
  • Surfing lessons
  • Hula lessons
  • Admission to all attractions
  • Snorkeling
  • Airport pickup and drop-off
  • Transportation
  • Private tour guide
  • Most meals (lunch not included)

Does not include:

  • Flights
  • Lunches
  • Travel insurance
  • Gratuity for Driver (optional)

What to pack:

  • Journal
  • Bathing suits
  • Cover up for easy transition beach-to-store
  • Camera
  • Small backpack for personal items

Additional Info:

Flights Where do I fly into?

You’ll fly into Honolulu airport (HNL).

If you would like for us to book your flights for you, please email us at

Differences What sets this tour apart?

We get it—there are plenty of ways to see Hawaii. But, Hawaii’s hotels are set up in touristy Waikiki, or way out in the North Shore, and those options aren’t the best if you want to see the place like a local. Our location in an island villa means we can navigate the island more freely and without the tourists.

Like the rest of our Damesly tours, the main bonus here is our incredible community. On this tour you will meet women who inspire you, who support you, and who are dedicated to helping you to reach your goals. Our leader on this tour will help you get past all the BS that distracts to make a plan you can follow towards living your dream life. We’ll be having incredible adventures on the island, and we guarantee you’ll leave feeling refreshed and inspired. If you’re coming with an idea you want to workshop in entrepreneurship, we will make sure you leave with a clear plan in place.

We're Locals Why Hawaii?

Damesly founder Kelly Lewis is from Oahu—she’s excited to show you the waterfalls and secret places she grew up visiting! Hawaii has an undeniable energy and makes for a perfect weeklong getaway.

What to Expect Is this tour for me?

This tour is for you if you: have been looking for a retreat that will leave you energized and inspired/want to combine vacation with actualizing things you’ve been putting off/want to learn how to surf or just play in the sun for a week/want to help other women get their dreams off the ground/want to see a side of Oahu you’ve never seen before.


  1. K

    Kim Tran

    I stumbled on Damesly and a NYT interview of Kelly as I was searching for Hawaii trips. I was so surprised to see that there was one spot left and booked it immediately.

    I was in a toxic job at the time and felt stuck. What attracted me to the trip was that I had never been to Hawaii before and wanted to meet other like-minded women while I figured out “what’s next” for me.

    The trip was just what I needed. We learned how to surf, we hiked, we did yoga and meditated. But what I loved most about the trip was the company of the attendees–we came to the trip as strangers from different backgrounds and life paths and throughout the trip we got to know each other and learn from each other. It was amazing!

    On one of the coaching sessions with Maya, we talked through the concept of “ikigai”, which is the alignment of what we are passionate about, what the world needs, and what others are willing to pay for. I came home with some great notes from that session and took it to heart and worked on it all last year.

    It’s been almost a full year since that trip and I’ve since quit my old job, started a new one that is much more aligned to my personal/professional values about 7 months ago, and I also launched a business/project that has been a passion/idea for SO long! I just needed the clarity and confidence to make it all happen and this trip and the women on this trip played a really integral role in that journey for me.

Add a review

Your email address will not be published. Required fields are marked *