What a week on the water with Captain Tim & Admiral Donna actually looks like.
Coffee before the sun gets serious. A short morning sail to somewhere beautiful. An afternoon at anchor — swimming, snorkeling, beachcombing. Sundowners in the cockpit as the sky does extraordinary things. Dinner aboard or at an unforgettable restaurant ashore.
Repeat, with variations, for seven of the best days you'll have in years.
Every evening we hold a crew meeting — usually informal, always with something cold in hand — to plan the next day. Where do we want to go? How much sailing do we feel like? Is there somewhere we've heard about that we want to find? The itinerary is open for everyone to plan.
A note on sailing time: On many days we sail 2–4 hours, sometimes less. If we find an exceptionally beautiful spot and the group wants to stay, we stay. This is not a race. If you want more sailing time, we'll find more. We'll work it out as a team.
The skipper is usually first up and has coffee going. Breakfast is aboard — whatever the crew has previously agreed on, from full cooked breakfasts to light pastries, yogurt and fruit. A pre-departure walk-around, and we cast off when everyone's ready.
We find an open stretch of water, hoist the mainsail, deploy the genoa, kill the engines, and sail. Anyone who wants the helm gets the helm. Anyone who wants to lie on the sun lounge and watch the islands drift by is equally welcome to do that.
Once we're moored or anchored, the pool opens. Swim ladder down. Adrenaline up. We snorkel, explore by dinghy, wander to shore, visit a beach bar, or simply float in a turquoise bay reading a book. By late afternoon, it's time to freshen up for sundowners.
The cockpit at golden hour, with something cold in hand and the sun doing something spectacular. This is the part of the day that makes people understand what all the fuss is about.
Usually ashore at a fantastic local restaurant — we've eaten extraordinarily well everywhere we've sailed. On some trips, the group prefers to cook aboard, in which case we fire up the BBQ and make something memorable. Either way, nobody goes hungry.
After dinner, a crew meeting to plan tomorrow. Sometimes music, sometimes trivia (Donna usually wins), sometimes star-gazing from the sun lounge. You will never have seen the Milky Way the way you'll see it from a mooring in the BVIs.
This is a guide to highlights, not a fixed schedule. We adapt based on weather, crew preference, and whatever spontaneous magic presents itself.
We cast off from the Moorings Base in the morning and motor out into the Sir Francis Drake Channel. First, a safety briefing including man-overboard procedures. Then practice under power for anyone who wants it: starting, stopping, figure-8s. Then we hoist the sails and head east toward Cooper Island, tacking across the channel. Great practice for a new crew. Once moored, the pool opens immediately. Cooper has fantastic snorkeling — a small rocky island teeming with fish, and grassy shallows full of sea turtles. Evening: the rum bar at Cooper Island Beach Hotel has one of the best sunsets in the Caribbean. Maybe the world! Trust us!
A big day. We arrive early at The Baths — an otherworldly maze of house-sized boulders forming cathedral-like rooms filled with knee-high sparkling water. We try to get there before the cruise ship excursions arrive. Then north along Virgin Gorda to Leverick Bay, buzzing past Necker Island. At the top of the bay: Saba Rock (tiny island resort, great bar with swings, fine dining, one-hole golf course) and the famous Bitter End Yacht Club (wood-fired pizza, great "sailor's vibe", regatta recovery area, huge knots on the wall). The Canadian kid on the Rum Runner will appear at our boat with frozen daiquiris in hand when we hail him on VHF 72.
Weather permitting, we head due north toward Anegada — the only non-mountainous island in the BVIs. It appears from the sea like something from another world. We navigate a tricky shallow entry and arrive by lunchtime. The most important task: order the lobster. The local guys will catch however many we need. While they're at it, we can rent scooters or buggies from the (very grumpy) local lady and explore the island, visit the flamingo observatory, and head to Loblolly Bay or Cow Wreck Beach for the afternoon. Lobster dinner at sunset.
The biggest sailing day and arguably the best. A long downwind run to Jost Van Dyke with Tortola and a parade of islands visible the whole way. We stop at Sandy Spit — a castaway island the size of a baseball infield with a cluster of palm trees — perfect for a swim and a Wilson-from-Cast-Away photo. Then the Bubbly Pool (warm Atlantic swell swirling in a natural rock bowl), then White Bay Beach — Tim's favorite beach in the world. The Soggy Dollar Bar serves the BVI's national drink, the Painkiller. At the end of the day we moor at Great Harbour and hit Foxy's for dinner.
A short crossing back to Tortola's north shore. Cane Garden Bay has a beautiful beach lined with restaurants and bars, lots of sea turtles in the shallows, and the last remaining rum distillery in the BVIs at the far end of the beach — a rustic family operation offering short tours and tastings. This tends to be a relaxing beach day. For the more ambitious, Sage Mountain (highest point in the BVIs) is nearby and hikeable.
We round Tortola's southwest corner past Soper's Hole marina, thread through the Narrows (a channel where the whole Caribbean tries to squeeze through to the Atlantic — it can get exciting), and sail upwind to the Indians. Extraordinary snorkeling: shallow coral arches teeming with fish on one side, a wall that drops into the abyss on the other. Then on to The Bight at Norman Island — supposedly the inspiration for Treasure Island. Sea caves explorable by kayak. A great beach restaurant. And Willy-T's — a permanently anchored battered old ship converted into a bar, with a jumping ledge upstairs from which everyone jumps, with steadily decreasing amounts of bathing attire as the evening goes on.
Last trim of the sails across the Drake Channel. We may stop at Peter Island Resort (newly reopened, day-pass program, pool with a killer view). Then back to the Moorings Base — with the greatest of ease. Disembarkation by 9 am.
Note: This itinerary is a guide to highlights, not a fixed schedule. There are many other islands, beaches, and restaurants we may visit — Marina Cay, Scrub Island, Guana Island, Trellis Bay, Fallen Jerusalem, the Dogs, Sandy Cay, and more — based on weather, crew preference, and the mood of the moment.
A month or so before each trip, we have a Zoom call that is about 95% focused on food. What do you love? What do you hate? Any restrictions, special diets, preferences? We plan around all of it.
Most breakfasts and lunches are aboard — anything from full cooked breakfasts (omelets, pancakes, bacon) to lighter continental fare with fresh pastries from the French bakery a half-block from the Moorings base. It depends entirely on what the crew wants.
For dinners, most of our crews prefer to eat out — and there are spectacular restaurants everywhere we sail. In the BVIs we've hit pretty much every good one and have strong opinions about all of them. In the Mediterranean and Croatia, the food is extraordinary — and we have high hopes for French Polynesia come October. But if your group wants to cook, we have a full galley and a BBQ aft, and we've had some memorable boat dinners too.
The boat is always stocked with snacks, fresh fruit, cheese, and an open bar. Nobody has ever gone hungry. Nobody has ever complained about the snacks.
The Irish Wake isn't a cruise ship and Tim and Donna aren't your stewards. When the dinghy needs to get up on the beach, everyone gets the dinghy up on the beach. When someone's making lunch, you might find yourself chopping. When the lines need winching, whoever's closest winches. Friends help friends.
This is precisely what makes a week with us feel different from a typical charter vacation — and it's what makes it stick in memory long after a resort week fades. Nobody who's sailed with us remembers being served. They remember being part of it.
The BVIs are our home base, but we've sailed extraordinary destinations — from the Caribbean to the Mediterranean and beyond. Each destination brings a different boat, a different culture, a different kind of magic.
Starting from Agana Marina (Split), sailing the island-studded Dalmatian coast. Ancient walled cities, fresh seafood, exceptional local wines, and some of the clearest water in Europe.
Raiatea, Taha'a, and Bora Bora — otherworldly turquoise lagoons, overwater bungalows in the distance, and sailing so beautiful it looks like a dream. We're headed there in October 2026. Stay tuned.
Athens and the Saronic Gulf for history, culture, and incredible food. The Abacos in the Bahamas for pristine sailing in a protected island chain close to home. Both on the 2027 calendar.
We have openings in 2026 and several excellent options in 2027. Cabins fill quickly — reach out early.