How our sailing trips work

The Dream

Whether you're a complete beginner or a well weathered sailor, lots of people dream of living on a sail boat. No matter your skill level, that can feel intimidating. We want to give you a chance to try it out, hands-on, without all the headache.

So...

• We'll 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 vanity.
• We're looking for people willing to learn and ready to pitch in.

There’ll be 8-12 of us total.

How’s that sound?

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.

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

I'm 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. 

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?

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 vanity, 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.

Here are some example photos and layouts of the type of boats we use. Each boat is slightly different, but all our boats will be similar to this.

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.

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.

Note:

These trips are drug and smoke free.
No alcohol is permitted on board.
Any drinking on shore 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.