Try living on a sailboat for a week. 

Join our crew.





Have you ever wanted to try sailing?

Maybe experience living aboard for a bit?

Here’s your chance.


Join my crew for upcoming trips:

Mexican Riviera

I’ll take you out for 6 days/5 nights to one of these areas.


“Absolutely do it! I'm so happy that we did.
It was, 10 times better than I expected.
You're in for a treat.”
— Whitney Johnson (Sailing client & CEO of Disruption Advisors)



Here's how it works:


✅ I provide the boat, all the food and captain the boat.

✅ We’ll sail beautiful pristine water, swim and snorkel every day and basically enjoy life on the water and on shore.

✅ You’ll get a private cabin for 2 people, with your own 2-person bed and bathroom, complete with shower, toilet and sink.

There’ll be 8-10 of us total.

How’s that sound?

Here's what I ask: 

1. You help prepare a meal or two for the whole group. (Again, I’ll provide the food and meal plan.)

2. You help with some basic tasks around the boat like steering, raising/lowering sails, raising/lowering anchor.

No experience necessary.

I’ll teach as we go.

Again, I arrange the boat and all the food.

You arrange to get yourself there and back.

Sound fair?



Hammock on sailboat

Part Vacation

Part Sailing Lesson

Part Exploring

A bit about me:

My name is Erik Orton and I lived on a catamaran sailboat with my wife and five kids for a year, sailing from the Caribbean back to our home in Manhattan.

My wife and I wrote a book about our experience called Seven at Sea: Why a New York City Family Cast-Off Convention for a Life Changing Year on a Sailboat.

It became a New York Times Top 10 Travel Book.

If you’d like to try a miniature version of our experience, I’d love to help you with that.

(I’m also American Sailing Association certified.)

To join the crew, just sign up for a quick zoom conversation to make sure we’re both real, nice, and normal people.

If we both feel like it’s a good fit, you’ll get the rest of the details. If it’s not a match, no worries. I’ll be glad to have made a new friend.

Confirm your spot with as little as $250.
8 people max per trip.
Payment plans are available.


"Do it! Especially do it with your family!

This was incredible activity and adventure to do together as a family."

- Kathleen Peterson


“Sailing with Erik and Emily cracked something open for me. 

The sense of adventure, excitement and exhilaration woke me up to what is possible."

— York Young


Jump on it

“If you have any inclination to do something like this, just jump on it.
It is so much richer than simply going on a Caribbean vacation."


- Joel Wiest

Absolutely do it!

I'm just so happy that we did.

It's been, ten times better than I expected.

You're in for a treat!" 


- Whitney Johnson

You won't regret it.

"Sail with Emily and Erik.

You won’t regret it.

It will be one of the best things you ever do.”


- York Young

Life will never be the same.

"By the end of the trip I sat across from my husband and he said, 'Life’s never gonna be the same after this.' I said, “Yeah, I feel it. I know that’s true.”


- Jayne Young


"Magical. It was amazing! Better than I expected.”


- Karen Wiest

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"If you and your family or company want to do something that will really help you feel more connected and restored, which we all do, 100% yes!"

— Whitney Johnson

What's in it for me?


💙 I love sailing, exploring new places on the water and giving people a chance to experience life on a private sailing yacht.

💙 I get to enjoy sailing without incurring the cost of buying or maintaining a boat. (I charter a new boat for each trip.)

💙 Plus I enjoy introducing people to life on the water and giving them a peek into sailing life.


What's in it for you?


🌴 You get to experience a slice of sailing life without having to overcome all the hurdles of getting licensed and certified.

🌴 You get to enjoy learning a little about sailing without the pressure of captaining your own boat, or getting paired with a captain you don’t choose.

🌴 You don’t have to figure out the fairly complicated process of buying or chartering a boat.

🌴 You don’t have to arrange all the food, permits and logistics for snorkeling and diving.

🌴 You just have to show up and enjoy. Easy peasy.

📷 Plus you’ll probably get some sweet pictures to remember the trip and share with friends and family.

Who knows, maybe you’ll be inspired and start down the path like I did that ends with living on a boat.

Either way, it’ll be a wonderful week.



Trips start at $5,000/cabin (sleeps 2 people).

All inclusive except airfare.



These trips are alcohol, drug and smoke free.

If that’s really important, I’m happy to refer you to some other options.


Otherwise, sign up for a quick zoom call.

Again, signing up for a call is not a commitment. It’s just a chance to connect, answer any additional questions you have and see if it’s a good fit.


Thanks for reading this far! That tells me you’re interested, and have the right enthusiasm level to have a good time on one of these trips. I look forward to getting acquainted.