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My mom and I did a trip together to Punta Cana. We also did a trip with my sister in law and her mother and went to St Thomas. St Thomas is easier because it's US territory and it's a safer place (you can freely move about the island on your own whereas in Punta Cana, it is unsafe to go outside the resort complex without a guide).
check out Homepage - Intrepid Travel and do one of those trips
they are great, I have done a few of them (Nepal, India, Thailand, Bali, Lombock, Morocco), the group leader arranges the hotel and transport for the next leg of the trip while your out seeing the sights
This is not a place to go when it is cold. But when my daughter was 13 she and I went to Mackinac Island in Michigan. It is a sweet little island that you take a ferry over and the island has no cars. So you get around my horse drawn carriages and bikes. It has lots of victorian homes, a fort, cute downtown area, walking and riding trails. There is a bike trail that goes all the way around the island. She and I stayed at a nice B&B and it was great walking/talking time for us.
When my daughter was 17 we went to Bermuda and that was wonderful also.
I think you must have a destination purpose when you travel. There are some wonderful places in the midwest that offer history, shopping, museums, outdoor activities, learning, awesome scenery, music shows, artist colony, and you can even sleep with wolves if you like adventure.
I highly recommend the Riviera Maya/Tulum area in Mexico (it is near Cancun). Beautiful beach, away from the rowdy college-age crowds in Cancun, and there are plenty of things to do if you don't want to just lay on the beach (cenote water caves, Siaan Kaan Biopreserve, various ruins, shopping in Playa). Depending on what you like, there are plenty of large all-inclusive resorts, but also many smaller hotels to choose from.
Or, if you have serious money and time to spend, you can't beat Ilha Grande in Brazil.
They specialize in traveling with families - and they do features on traveling with parents, traveling with grandparents, traveling with toddlers, etc.
I'm sure they've done stories on Mother/Daughter trips!
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