The Voyage II

Virgin Islands  ·  Jan 23 – 30, 2027 (TBC)  ·  Invite Only
Hosted by Aram DiGennaro & Bryant Harrison
The catamaran at sea

Cabin Availability

Now Forming  —  All 5 Cabins Open
Cabin 1 — Open Cabin 2 — Open Cabin 3 — Open Cabin 4 — Open Cabin 5 — Open

What Is The Voyage?

It's a business leadership retreat unlike any other you've attended. If you invite your spouse or partner, they're included in all of it — not just the fun parts.

The answers to the questions that matter most are always with us. But they're like whispers among the shouts of daily demands. The Voyage puts you in a place where those whispers can be heard.

Sandy Cay

Who This Is For

This isn't defined by your title. It's defined by your seat — the one where decisions end with you. CEOs, Executive Directors, physician-owners, and the rare leaders who've earned the right to step back and think.

Every person on The Voyage was personally invited by Aram or Bryant. If you're reading this, someone thought you'd belong here.

6–10 leaders + optional spouses/partners. Small enough to know everyone by day two.

Onboard the catamaran Typical cabin

The Boat

"To reach a port we must set sail. Sail, not sit at anchor. Sail, not drift."

We sail on a charter catamaran — big enough for a small group to live comfortably, small enough that the boat itself becomes part of the experience. You'll learn to sail it. You'll feel the wind change. You'll watch the stars from the trampoline at anchor. The boat is not a backdrop. It's a key part of The Voyage.

Anegada

The Trip

"On a day when the wind is perfect, the sail just needs to open and the world is full of beauty."

January 23 – 30, 2027 (to be confirmed) in the Virgin Islands. Itinerary shaped by the group and the wind. Final dates and route will be locked in once the group is formed and the charter is booked.

Expect: open anchorages, legendary beach bars, world-class snorkeling, a night or two at marina, and at least one meal you'll still be talking about a year later.

Potential Stops

  • Trunk Bay, St. John — quiet anchorages
  • Charlotte Amalie, St. Thomas — marina night
  • The Bight, Norman Island — snorkeling, The Willy T
  • The Baths, Virgin Gorda — cathedral rock formations
  • Soper's Hole, Tortola — local restaurants, marina
  • Jost Van Dyke — Soggy Dollar Bar, White Bay, hiking
  • Anegada — reef, lobster, flamingos, serious remoteness
  • Cooper Island — quiet anchorage, beach bar, reef

Potential Restaurants

  • Ikigai Omakase — Virgin Gorda
  • Pirates Bight — Norman Island
  • Soggy Dollar Bar — Jost Van Dyke
  • Cooper Island Beach Club
  • Lobster Trap — Anegada
  • CocoMaya — Virgin Gorda

Stops and restaurants above are indicative — actual itinerary will be confirmed with the group.

Illustrative Route
Illustrative example route through the Virgin Islands — not a fixed itinerary
An example of how a week might flow — shown for shape and feel, not as a fixed itinerary. The actual route will be set with the group and the wind once the charter is booked.
Gorda Peak Virgin Gorda

What to Expect

"Pain is not the enemy. Pleasure is not the goal. Joy comes from learning to accept both as teachers."

What You Bring

  • An extraordinary attitude — the energy you carry is the energy we all live in
  • Openness to discuss what you want from life and business
  • Willingness to give things a try

What You'll Find

  • Time with nothing in it. Real nothing.
  • An invitation to take the helm and sail
  • No-stress movement — yoga, swimming, hiking, all optional
  • Early nights and late mornings. Or the reverse. The rhythm is yours.
Gorda Peak Guana Island

Practical Details

Indicative Pricing: From $5,500 per person, sharing ($11k/cabin) — final figure to be confirmed alongside the charter. Covers your trip — all nights aboard, experienced skipper, upscale dining on board and on land, gourmet provisioning and cocktails, moorings and marina fees, curated experience programming, and your first night at a hotel so you can arrive and board comfortably. 7 nights, 6 at sea. A 3.5% discount applies for payment by check or ACH.

Because we plan around a fixed group, payments are non-refundable once confirmed. We're happy to transfer your spot to someone you nominate, or issue a full refund if we cancel the trip.

Coming Soon

Recommended Flights — Tentative dates are January 23 – 30, 2027. Likely entry points are STT (St. Thomas) or EIS (Beef Island, Tortola) — to be confirmed with the itinerary. Guidance to follow once the charter is booked.

Coming Soon

Packing List — A detailed packing guide is on its way. For now: pack light, pack for heat and water, and leave most of your ambition for the conversations rather than the luggage.

Rhythm & Sands Restaurant, Anegada

Interested in Voyage II?

Tentatively January 23 – 30, 2027. Details are still coming together. If you want to be considered, reach out to Aram or Bryant directly.