Hi! Ok I think I can help - I actually just got back from the island and did lots of investigating! I am getting married on Seven Mile Beach - probably Governor's Beach - with my toes in the sand And then shuttling people over to Grand Old House for the reception. Desiree at GOH is great, but there is no beach there as you probably know. Governor's Beach is directly next to the Westin beach and it's GORGEOUS. It's very wide and the sand is perfect. My planner, Juliette Heath, recommended it and we are 99% sure that's where it will be. It's also a public beach and is FREE to use. The Westin beach is beautiful, but they will probably charge you site fees. We are also getting a room block at the Westin and Sunshine Suites (which is right across the street from the Westin, but cheaper). We didn't eat at any of the restaurants in walking distance from there, but there are a bunch. We ate at Tukka, which is prob a 30-minute drive, and it is AMAZING. I think we are doing our rehearsal dinner at Ristorante Pappagallo which is also beautiful, and about 10 minutes from 7 mile beach. We are also using Aaron for photos and Picture This for vidoegraphy! So many similarities! He said that most people do 4-6 hours of photography (I think we are doing 6). And for a Trash the Dress, he just charges you for 1 extra hour of photography (even though the shoots usually go longer than an hour), so it's a pretty good deal. Bottom line, if you do the wedding and reception all in one spot, you may be fine using the on-site planner. But if you have them in separate places I would recommend hiring a local planner. We are so happy with Juliette and her price is very reasonable compared to some of the other planners on the island. It was great meeting her in person and her local knowledge just makes me feel better about everything. Let me know if you have any more questions! Sounds like our plans might be very similar