Customs

There is no big problem this time of year just don't get carried away.  Bringing thousands of dollars if gifts will get you trouble.

https://www.aduanas.gob.do/faq

There are various limits as listed above, but the key one in relation to your question is that you are allowed gifts of 500 USD duty free plus 200 cigarettes/tabacco and 3 litres of liqour.

You are asked a simple question (21) on the customs declaration form - are you bringing in goods subject to tax?

I guess most expats don't bother much about this and they don't as a rule get checked over much but they do check Dominicans very thoroughly but again at this time of year there are big exemptions from Dominicans living abroad for the month of December. My experience is that Santo Domingo airports have tended to be straightforward dealing with customs with bags scanned and Punta Cana was also straightforward but more checks by opening bags. Puerto Plata was known for customs being awkward opening bags and looking for tax payments/bribes if new items were found. Santiago often involved being pulled aside for bag checks.

I guess my question would be is how do they value it? Say you bring a new watch as a gift. Will they just let it go if they do not feel it is above $500?

Does it have to be declared? And what is difference of you saying it is yours.

I bought a good Tag Hauer watch in San Juan duty free when returning to Santo Domingo from the islands a few years back. I put my decent older watch in my travel bag and wore the new watch. No packaging, personal item, no problems.

Bringing in a packaged new brand watch could...could....be a red flag. They know the brands here.

If it's a gift leave it unwrapped and carry the receipts with you.

The last time I brought gifts, wrapped in my suitcase, everything was stolen.  Just to be clear I traced it back to Canada baggage in Toronto (NOT in the Dominican Republic)!!!  It was confirmed by Police in Canada, I put in a police report and received my claim in full from the airline.

Moral of the story, don't put valuables in your suitcase.  Only in your carry-on.