Most people pick one island and stay at the resort. That’s a fine week. But the DR and Puerto Rico are ninety minutes apart and nothing alike. The DR is where you go if the pleasure isn’t only the place, it’s the people. Puerto Rico is the American neighborhood we wish we had — food, beaches and rhythm. Ten days gets you both: two very different takes on life and landscape, some of the best Latin American cooking anywhere, and two cultures thick with music and history. I’ve been going to the DR my whole life and to Puerto Rico a handful of times. Here’s how I’d build it for you.

[One line. Where this is, and what you’d be doing there.]

How the ten days break up

Days 1–4 · Dominican Republic

Santo Domingo

Central, close to the airport, and the version of the DR that has history, food and actual life in it. If you want the pool and a piña colada, that’s Punta Cana — I’ll plan that too, but it’s a different trip.

[What this is, and where you’d eat it.]

What most people missSlow down. Walk into the store you weren’t planning to walk into and ask what’s good — you’ll get an answer, and usually an opinion. And don’t leave having eaten plantains one way. We make them a hundred.

Day 5 · Transition

Island to island

You fly — it’s under ninety minutes, and you’ll need your passport. I book the flight, arrange your ride to the airport in Santo Domingo, and have a driver waiting when you land in San Juan.

What most people missBooking the cheapest morning flight and losing the whole day to it. Santo Domingo’s airport is a real drive from the city and the traffic is not theoretical. I put you on a flight that lands in time for lunch, with your bags somewhere safe if the room isn’t ready — so day five is still a day, not a travel day.

Days 6–10 · Puerto Rico

San Juan, and out of it

Roughly half in San Juan and half beyond it. San Juan has all the seasoning — but the island is bigger than the city, and the parts people skip are the parts they talk about afterwards.

[Where this is, and one line about it.]

What most people missThere’s a phrase you’ll hear in San Juan — lo vas a pasar muy cabrón. It doesn’t translate politely, and that’s the point. It means you’re going to have an outrageously good time. That’s the register of the whole island: warmer and louder than you’re braced for. Go with it.

• Full custom itinerary, day by day
• All hotel research, with direct booking links
• Your agent discount applied where available
• Inter-island flight coordination
• Ground transport and transfers
• Reservations you can book in two clicks
• Two rounds of revisions
• A destination brief before you fly

$450 for the full ten-day build

Flat fee for the whole trip, not per person. No markup on anything you book.