First Timers Guide

This is far and away the most common concern we hear — and we take it seriously. As a physician, Tim has a very clear-eyed view of what works and what doesn't. Catamarans are dramatically more stable than monohulls, our routes involve mostly protected waters, and we have an arsenal of prevention and treatment recommendations. We've dedicated an entire section to this below — but the short version is: it's manageable, and we'll make sure you're set up for success before we ever leave the dock.

Smaller than your house. More comfortable than you'd think. The catamarans we sail are generally 42–45 feet — which sounds tiny until you realize it means everyone has their own private cabin with an ensuite head (that's boat-speak for bathroom) and that there are multiple distinct "hang-out areas" where you can be social or find privacy depending on your mood. We typically dine together al fresco in the cockpit, swim off the back of the boat before breakfast, and fall asleep to the sound of water. By day three, most guests say it starts to feel remarkably natural. By day six, most guests don't want to go home.

Yes — and we mean that in the best possible way. This isn't a cruise. Tim and Donna are your hosts, not your staff. When the dinghy needs hauling, we haul it together. When something needs cooking, we cook together. When a line needs handling, whoever's closest handles it.

Most guests are surprised by how naturally this happens — and how much they end up loving it. There's something genuinely satisfying about being useful on a boat. By day three, you'll be eyeing the helm. We'll let you.

Typically one to three other couples total, including Tim and Donna as your hosts. We keep things intentionally small — this is not a party boat, it's not a flotilla, and it doesn't feel like a cruise. It feels more like a week away with close friends in a remarkable place.

We cut you adrift. NO!! Genuinely honest answer: in our experience, the people who worry most are often the ones who end up loving it most. But if you're truly uncertain, consider this — we're usually in beautiful places with excellent snorkeling, fresh food, warm water, and spectacular sunsets. Even on the rare day when the passage is bumpy or a passing squall has us confined to quarters for a few hours, the destination tends to make up for it. We've never had someone leave wishing they'd stayed home. That said, if you're deeply uncertain, let's talk before you book. We'd rather have the right conversation upfront.

There is no typical day — and that's somewhat the point. But roughly: coffee and breakfast before the sun gets serious, some sailing mid-morning (usually 2–4 hours, sometimes less), an anchorage by early afternoon, swimming and snorkeling, sundowners in the cockpit, dinner aboard or ashore. We plan each next day together as a group over drinks after dinner. Repeat, with variations, for seven of the best days you'll remember for years.

We eat extraordinarily well. Breakfasts, lunches, and dinners are planned in advance with your preferences in mind. We usually dine ashore most evenings, since there are amazing restaurants almost everywhere we stop. If you and the group like to cook, we've got all the kitchen appliances and gear, plus a BBQ aft. Nobody has ever gone hungry. Nobody has ever complained about the snacks. The open bar is always open.

It varies by destination. In the BVIs we have on-board WiFi (via cellular network) with generally very good service throughout most of the archipelago — we can stream movies at most anchorages. In the Med, you'll have cell service in most places. French Polynesia: less so. Most guests report that being mostly offline is better than they expected. You'll have plenty to do.