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 our crew for upcoming trips:

✅ Bahamas
✅ Caribbean
✅ Mexican Riviera
✅ French Polynesia
✅ Greece
✅ Italy
✅ Croatia

We’ll take you out for 6-8 days to one of these areas.

"It's the unicorn of sailing experiences."

— Mary Young (sailing guest)

SCHEDULE YOUR CALL

“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, complete with shower, toilet and sink.

There’ll be 8-12 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?

SCHEDULE YOUR CALL

What would my cabin be like?

Each cabin accommodates two people. Come with a friend, spouse, adult child, or meet someone new.

Your cabin includes a double wide "queen" size bed, private bathroom with shower, toilet and sink, as well as drawers, mini-closets and your own lighting and electrical outlets. (Depending on the size of the group, some cabins may include bunk beds.)

All sheets, pillows, linens and towels are provided.

What if I'm prone to motion sickness?

No worries. We've got you.

If you've ever gotten queasy on a cruise ship, whale watching, deep sea fishing or dive/snorkel trip, sailing is very different.

Sailing is a slower, gentler way to travel. We move with the water rather than trying to fight against it. All this makes it smoother and more comfortable.

Plus, after living aboard for a year with his own five kids, I have all the inside tips and techniques to make sure everyone has an amazing time.

We've never had a person not have a wonderful experience.

Featured

Part Vacation

Part Sailing Lesson

Part Exploring

Who will be your host?

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 a certified skipper with experience sailing in Tahiti, Bora Bora, Greece, Italy, the Bahamas, Virgin Islands, Puerto Rico, the Caribbean and Mexico.

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.

"Do it! Especially do it with your family!

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

- Kathleen Peterson

"What an incredible trip!

Adventurous, breathtaking, challenging, and relaxing all at the same time. And so great to meet such wonderful people. I really feel I came back a little different, a little better person. Ready to try new things, find more joy, and have adventures."

— Jean E.

“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.”

- Y.E. 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.

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

- Karen Wiest

Sailing retreat adventure French Polynesia South Pacific couples

Sailing in the Mediterranean sailing retreat adventure couples retreat leadership team building

Sailing retreat Caribbean adventure leadership team building couples retreat family retreat offsite

"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.

Cost:

Trips start at $2,950.

All inclusive except airfare.

Note:

These trips are drug and smoke free.
No alcohol is provided.
Any drinking must be done responsibly.
This is NOT a booze cruise.

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 from me or you. 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 have the right enthusiasm level to have a good time on one of these trips. I look forward to getting acquainted.

Best,

Here's what one of our recent crews had to say.

Please Note:

Once you book your time below:

you can immediately watch an 11 min video that will give you an overview of our trips.
You'll receive an emailed link so you can watch it later if that's better.
We'll cover more details when we chat in person.

The first half of 2025 is already SOLD OUT. The second half is filling fast.

Schedule a call soon for the best chance of going on the trip you like best.

Please note: all trips are by-invitation only. A quick "get acquainted" call is the first step.