2027 Trips

Yes, you can come solo. We have all kinds of people on these trips—solo travelers, married couples, two friends that want to travel together. It might be a father-son or any combination of people. But yes, you can come solo.

We sometimes have married people coming solo just because this is the kind of activity their spouse isn't interested in.

Each trip has it own you unique mix. You can come as a solo traveler, as a couple, or with a travel buddy. If you come solo, you will make friends. If you come with somebody you know, you'll get to know them a lot better and likely get closer, while also making friends with people on the boat you may not know yet.

This is a very common concern. I myself am very prone to motion sickness, so I have a lot of sympathy for this. It is very manageable. I have yet to have somebody come on a trip and be miserable all week because they were seasick.

A couple of things: first, your body will acclimate. Secondly, there’s a lot you can do on a sailboat to stay comfortable. Cruise ships, dive boats, whale watching boats, and deep-sea fishing boats are usually the worst for seasickness because they don’t adjust for wind or swell—they’re going somewhere no matter what.

With a sailboat, we stay flexible and sail in harmony with the elements rather than against them. From the skipper standpoint, I do a lot to keep things comfortable. My pro tip: if you want to get seasick, go below deck while the boat is moving. If you don’t, stay on deck, get fresh air, stay hydrated, and don’t overheat.

The captain will also give you a heads-up before sailing so you can take care of anything below deck beforehand.

No. If you are a solo traveler, you do not have to share a cabin. You can pay for two spots and have a full cabin to yourself, including a private bathroom. If you choose to share, you’ll be paired with someone of the same gender.

We rarely have bunk beds—very rarely. Most cabins have a shared double bed. Think of it like camping—you’re sharing space but have your own linens. If that’s not your preference, booking a full cabin or bringing a buddy is a great option.

Only if you book a single spot. If you want your own space, book two spots. Otherwise, you’ll share with someone of the same gender. There are also alternative sleeping spots like the deck or salon if you prefer.

Yes, you can scuba dive. We’ll help you rent gear and have it delivered to the boat. What we don’t do is plan multiple tank refills, so you’ll likely get one to two dives in. The rest of the time you can snorkel.

If you want to dive a lot, we recommend booking a dive excursion before or after the sailing trip.

Our number one recommendation is to get travel insurance as soon as you make your deposit. That way, if you can’t make the trip, you can be reimbursed—even your deposit, depending on the policy.

We partner with Trawick Insurance and you'll have the option to purchase a policy from them during or after the booking process.

If the trip can’t happen due to something on our side, you’ll receive a full refund or full credit to another trip (your choice). If it’s due to outside factors, your travel insurance would cover you.

You’ll have opportunities to go on land every day—often multiple times a day. Sometimes it’s a quick swim to shore, other times it’s dinner, hiking, or exploring towns. You’ll definitely not be stuck on the boat the whole time.

I don’t have a favorite trip—just like I don’t have a favorite child. Each destination offers something unique. Italy has incredible food and scenery, French Polynesia has stunning turquoise water and marine life, and every place has its own magic. It depends on what you’re looking for.

Fins are provided. Masks and snorkels are sometimes available but can be hit or miss, so we recommend bringing your own.

I personally like full-face masks. They’re comfortable, easy to use, and offer a wider field of view. Many also collapse for easy packing. We provide a packing list with our recommended favorites.

You can bring a CPAP. We recommend bringing a battery if you have one. Boats have power, and we often run generators at night, so you’ll be able to use it comfortably.

Yes. You’ll fill out a form, and we build the menu around your preferences and needs. We’ve handled everything from vegan to keto on the same boat.

We plan and provision all meals ahead of time. Everyone pitches in—guests sign up to lead a meal, and others help prep and clean. Breakfast is on your own; lunch and dinner are shared efforts.

Meals are also a key part of the experience—time to connect and reflect on the day together.

That’s totally fine. You can participate as much or as little as you want. Some guests go all-in on learning, while others relax and enjoy the experience. Everyone finds their own balance.

Absolutely. Many guests return and even bring friends. Some people book multiple trips in a year.

As much as you want. We sail every day, and you can participate in real tasks like raising sails and anchoring. No forced lessons—just hands-on learning if you’re interested.

Trips range from about $4,000 to $5,000 per person depending on location and duration.

Currently 25%. An additional 25% is due 180 days before departure. The final balance is due 90 days before the trip.

The deposit is 25%. An additional 25% is due 180 days before departure. The final balance is due 90 days before the trip. Within that, you can make payments of any amount at any time.

Yes, USB ports are always available. Most cabins have standard outlets as well. It varies a bit by boat/location. We also bring adapters to share when needed.

Yes. Most boats have fans and air conditioning. AC is used at night if we decide as a crew that we want that.

Yes. All boats have engines, so we're never dependent solely on wind.

Yes. We bring plenty of bottled water and have freshwater systems onboard, including water makers.

It means conserving water—quick showers, turning water off when not in use, and being mindful while doing dishes.

You can stay connected via cell service in most places. We also have WiFi via Starlink as a backup.

All boats have basics like a stove, oven, fridge and freezer. They often a toaster, blender and microwave, though it can vary. If something is important, let us know and we’ll do our best to arrange it.

Yes. You can bring gear or rent it. Some areas require licenses, and we’ll help guide you through that.

Yes—if it’s safe to eat, we’ll help you prepare it.

Yes. We usually set up a WhatsApp group or shared Google folder so everyone can share photos and videos.

Yes. Many guests form lasting friendships and even travel together afterward.

No. Everything on board is included. If we go to a restaurant or rent scooters, everyone pays for their own.

If you have another question, sign up for a call or email us at hello@theawesomefactory.nyc.