Hello William, congratulations on getting married. And with such a big family, too. You must be very excited. I can see that from the Midwest, it’s cheaper to fly to some Caribbean islands than other ones, so I’ll comment on those.
From what I can find, your family could fly cheaply to:
Grand Cayman (beautiful and expensive island, no all-inclusives but very nice condos on Grace Bay and it’s very safe),
Punta Cana (beautiful beaches in Dominican Republic, wonderful Club Med resort there and I was at a wedding at their Cancun resort where they did a great job… also lots of other great value all-inclusives)
St. Thomas (the USVI are part of the US, so you don’t need a passport which could save some money. Not my favorite island because it’s such a busy cruise port. However, the Buccaneer on sister island St. Croix is terrific, very romantic and traditional with great kids programs.)
Nassau (lots going on there and the Baha Mar hotel development just opened, so there are lots of good deals there now. Nassau has beautiful weather, great food and the nicest people. Very safe.)
Montego Bay (Our cousins got married at Beaches in Negril which was nice, it’s a small resort on a very nice beach. Jamaica has lots of family all-inclusive resorts at all prices. Maybe not as safe as some islands but tourists usually don’t have issues there.)
San Juan (Puerto Rico does not require a US passport either, and there are lots of values here while they recover from last year’s hurricanes. Not so many all-inclusives but many smaller and elegant hotels.)
In general, the Karisma all-inclusives in the Riviera Maya region do a great job with weddings, can’t go wrong at any of them.
