Company Retreat - looking for suggestions

Hello Everyone!

I'm a partner at a small company, and most of our employees work remotely, so we like to plan a nice destination for a holiday party every year for people to get together in person. I typically plan the trips, so would love to get suggestions for places people would recommend for a great trip. Some details:

-2 nights, usually in early December (I know it's fairly late notice for some places, but that's not really something we can work around given our how business works)

-Usually about 20-25 rooms needed. Spouses are included, but no kids

-We cover all meals/drinks/transportation and try to plan at least one group activity, and 2 group dinners

-Budget: We try to stay around ~$800 per room per night for room rate. There's some flexibility here, especially if the destination includes more extras, but as a ballpark that's what we usually like to start with

-Employees will be flying from California (6), New York (4), Canada, Miami, Midwest, and Colorado, so we try to keep it somewhere fairly easily accessible from North America. International destinations are fine, but we try to keep it under a ~6 hr flight ballpark for most (though the East coast employees are usually willing to travel a bit farther if needed).

-Needs to be some sort of activity available that the group would enjoy. Ages range from 22-65, so nothing too physically taxing or extreme.

-No need for any conference or meeting room space, this is just an opportunity for people to socialize and enjoy.

We've done some great trips in the past, but try to come up with different fun destinations each year that people would enjoy visiting (in December), so would love to get some new ideas! Past trips include:

-Alisal Guest Ranch in Santa Ynez, California: This was all inclusive which made things really easy from a budgeting standpoint, we planned horseback riding and archery/axe throwing as a group, and then individually people could venture out and do their own activities, go hiking, etc. Everyone loved this, only downside was that it was a bit far from the nearest big airport.

-Four Seasons Cabo Del Sol: We did this last year and it was a huge hit. The resort was so nice and the group dinners were fantastic, and we rented a yacht for a few hours to go do some whale and bird watching as the activity.

-Pelican Hill Newport Beach: The resort is really nice, but at the time the activity was golf, and not as much of our group golfs anymore. It's also increased quite a bit in price.

-Manhattan: People stayed at different hotels and we planned group dinners/bowling at Chelsea Pier. This was fun, but I think people enjoy doing something a little different now that we've been going to more out of the way places.

Let me know if I left anything out or if there are any other questions, thanks in advance!

Posted May 12, 2026, 2:44 PM UTC

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