Ruby · Virgin Voyages

Three picks, each with a reason.

Travelers searched, then didn’t book. Ruby closes that gap: one conversation, from “somewhere warm” to Book now.

Relationship
One of six projects for a Google Cloud partner
Role
Lead designer
Outcome
Virgin funded the next phase; the MVP was demoed at Google Cloud Next

01 · The ask

Live screen · open a pick

I’ve narrowed it down to three warm-weather itineraries in April.

Eastern Caribbean & Bimini Beach Club 7 nightsScarlet Lady4 dates Starting at $1,490 / cabin Up to $250 in drinks Learn moreLearn less

Miami · San Juan, Puerto Rico · Puerto Plata · The Beach Club at Bimini

Ruby’s take

You asked for warm and relaxed. April is the sweet spot here: dry and easy, sea days stay slow, and the trip ends on the sand at Bimini. Nothing feels rushed.

Itinerary

Flows well, with a smart balance of port days and sea days. San Juan stays late, so you get the city at night.

Fire & Sunset Soirées 4 nightsResilient LadyApr 22, 2026 Starting at $890 / cabin 80% off second sailor Learn moreLearn less

Miami · Puerto Plata · The Beach Club at Bimini

Ruby’s take

The shortest of the three, and the most beach. If relaxed matters more than ports, this is the one.

Itinerary

Two sea days, one port, one long beach day. Nothing to plan.

Dominican Daze 5 nightsValiant LadyApr 18, 2026 Starting at $1,190 / cabin Up to $100 in drinks Learn moreLearn less

Miami · Puerto Plata · The Beach Club at Bimini

Ruby’s take

The stretch: one more port than you asked for, but the Dominican coast earns it. Still warm, still easy.

Itinerary

Three relaxed sea days, Puerto Plata, then Bimini to close.

02 · Three picks, each with a reason

03 · Or just say it

01 · The problem

Virgin asked for a radically simpler way to book: a few clear options instead of a catalog, personal enough to feel like a high-end travel concierge, automated enough to run for every sailor.

02 · The constraint

Ruby could recommend, but it could never price. Every number came from Virgin’s booking system.

03 · The decision

Three voyages, total.

Each one has to earn its place with a reason tied to something the sailor said.

What it cost

Browsing. A sailor who wants more leaves Ruby, and a voyage that fits but can’t be explained to this sailor never makes the three.

Ruby · The decision

Three, total.

Ruby says what it narrowed on, then shows three. Every price and offer on the cards comes from Virgin’s booking system. Open any card — it works.

I’ve narrowed it down to three warm-weather itineraries in April.

Eastern Caribbean & Bimini Beach Club 7 nightsScarlet Lady4 dates Starting at $1,490 / cabin Up to $250 in drinks Learn moreLearn less

Miami · San Juan, Puerto Rico · Puerto Plata · The Beach Club at Bimini

Ruby’s take

You asked for warm and relaxed. April is the sweet spot here: dry and easy, sea days stay slow, and the trip ends on the sand at Bimini. Nothing feels rushed.

Itinerary

Flows well, with a smart balance of port days and sea days. San Juan stays late, so you get the city at night.

Fire & Sunset Soirées 4 nightsResilient LadyApr 22, 2026 Starting at $890 / cabin 80% off second sailor Learn moreLearn less

Miami · Puerto Plata · The Beach Club at Bimini

Ruby’s take

The shortest of the three, and the most beach. If relaxed matters more than ports, this is the one.

Itinerary

Two sea days, one port, one long beach day. Nothing to plan.

Dominican Daze 5 nightsValiant LadyApr 18, 2026 Starting at $1,190 / cabin Up to $100 in drinks Learn moreLearn less

Miami · Puerto Plata · The Beach Club at Bimini

Ruby’s take

The stretch: one more port than you asked for, but the Dominican coast earns it. Still warm, still easy.

Itinerary

Three relaxed sea days, Puerto Plata, then Bimini to close.

1 / 1Decide Three, never a catalog. Ruby narrows to three and says what it narrowed on: warm weather, April. What it cost Browsing. A sailor who wants more has to leave Ruby.
Ruby · See why

See why.

Open any pick and Ruby says why it fits what you asked for, next to the itinerary and the price.

Eastern Caribbean & Bimini Beach Club 7 nightsScarlet Lady4 dates Starting at $1,490 / cabin Up to $250 in drinks Learn moreLearn less

Miami · San Juan, Puerto Rico · Puerto Plata · The Beach Club at Bimini

Ruby’s take

You asked for warm and relaxed. April is the sweet spot here: dry and easy, sea days stay slow, and the trip ends on the sand at Bimini. Nothing feels rushed.

Itinerary

Flows well, with a smart balance of port days and sea days. San Juan stays late, so you get the city at night.

1 / 1See why Ruby’s take, on every pick. The reason ties back to what the sailor said — warm and relaxed — in plain words. What it cost A voyage that fits but can’t be explained to this sailor never makes the three.
What changed

Virgin funded the next phase.

The MVP was demoed at Google Cloud Next.

Building something the model decides? Let’s talk about yours.

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