Sandals Barbados: The rooms that are in your budget at Sandals Barbados are the Caribbean Village Premium rooms .
Your rooms would be located in the Caribbean Village block. The level of service that you would receive in these rooms are luxury, which is a basic room.
The luxury rooms do not have a mini-bar or room service included. I estimate you will spend $6700 for this room once you add in airfare. This resort does have the swim-up suites. These rooms have club level service. Please refer to this link that explains Sandals Club Level Service: http://www.sandals.com/all-inclusive/sandals-club/
Your total budget would need to be increased to almost $8k for the Crystal Lagoon swim-up suites. During our meeting I mentioned the water at Barbados. It is a little rough in this area. It is good for boogie boarding and there is a surf school off-property right next door where you could take lessons. But, it is not a good property for stand up paddle boarding or snorkeling off-shore. The waters need to be calmer than that. The beach is a nice, powdery white sand though. There is a special right now if you stay 7 nights here you get a sunset snorkel cruise for free!
My main concern is that your room would not be located near the ocean even if you upgraded to a swim-up suite.
These rooms do come with a tranquility soaking tub on the balcony. These are also luxury rooms. I estimate that this room will already put you slightly over your budget once we had in airfare. Probably $7200-$7300 total. Grenada is way down south in the Caribbean almost to South America, so airfare can get expensive. However, if you wanted to increase to a Club Level room you would need to add another $2k to at least put you near the beach or in a swim-up room. For a reference, the sky pool suites will be about $15k for the week.
Grenada is a great island to go diving. The water here is smoother making it better for watersports. The sand is a nice golden/light brown sugar color. This resort is very laid-back. There is entertainment here every evening, but it's not as active/"lively" as the resorts in Jamaica.
Again my main concern is that you are going to be at least a 10 minute walk from the beach.
Sandals Montego Bay, Jamaica: This property has received a MAJOR overhaul in the past year. 80% of the property has been updated, room blocks have been gutted and modernized, the lobby and amphitheater area is new, and a couple of the restaurants decor have been softly touched up. Like I said in my email this resort is very close to the airport and you will hear airplane noise a few times a day when they pass overhead.
By staying in the Montego Bay area you do have access to visit Sandals Royal Caribbean 10 minutes away (transportation IS provided at no cost). You can pack up and head over to Sandals RC for a full day or a half day several times a week if you wish. You can use their pools, eat at their restaurants, and use everything there except for the rooms. It is a nice option to be able to change your scenery a couple times a week.
Jamaica is going to give you the most bang for your buck. There are two room categories that fit a lot of wish-list:
The Beachfront Honeymoon Walkout Club Level room has a soaking tub on your patio. And just like the name sounds you are located on the ground level. The room is in the center of the resort. I estimate that your total will be $7000-$7100.
Sandals has a Butler Level service. Follow this link to learn more about having a butler: http://www.sandals.com/all-inclusive/butler-service/ This room automatically comes with butler level service. Upon arrival you are given a phone and you can stay in contact with your two butlers (they rotate shifts) during your stay. I have had butler service twice and it does come in handy. They make your dinner reservations and excursion reservations, one of my butler's played tennis with me one day, they try to anticipate your needs and do a good job. They are not always underfoot and hanging around because they are assigned to other couples - 6 at most. If you like extra pampering, then you would probably enjoy this level of service. It is highly recommended that you tip your butler at the end of the week. Depending on how much you use your butlers, the average is $200-$300 total split between the two. If you run him or her ragged then you probably will want to tip more :) I estimate that this rooms will cost $6500-$6600. The walkout rooms (as pictured) are not available, so you would be on the 2nd or 3rd floor with a balcony and a soaking tub. This room is also located in the middle of the resort.
If you stay 7 nights here you do get a free catamaran cruise!
The resort has a very nice walking beach and several outdoor restaurants. They now have a Cafe de Paris, where you can order specialty coffees, ice creams, desserts, etc.
Jamaica is another great island for diving and several different tours: waterfalls, ziplining, river rafting, snorkeling, horseback riding, Bob Marley tour at Nine Mile, and many more.