Cayman and Jamaica in 9 days/8 nights!
 

My husband and I are planning a trip to the Carribean for the first week of December. I was thinking about spliting our vacation into two island stays. I wanted to be diverse about it. Don't want to visit two "identical" islands and don't want to waste too much time traveling from one island to another. So I looked at a map and saw that the Cayman Islands are not far from Jamaica. However, when I searched on Expedia, looks like we would have to travel back to Miami and then fly to Jamaica. Has anyone ever done this? Also, we will probably stay at Half Moon at Montego Bay,Jamaica. The Cayman's don't seem to have as good of luxury resorts as Jamaica. I wouldn't mind doing the "condo" thing, but I am not cooking on my vacation. Would like to have a refrigerator for "leftovers" and bottled water though. Any thoughts on this island combination and resorts or luxury condos in the Caymans. We plan to stay at each hotel for 4 nights each. I have never been to the Carribean so I am trying to educate myself on an itinerary that makes good travel sense. Also, my husband doesn't like the "secluded" feeling. He gets bored and will just sit in the room and watch TV, so I am looking for areas in the Cayman where activity is prevelant and close to proximity of where we stay. Please help.

Hi,
A lot of people on this board will tell you not to split your trip like that, but I am like you -- I like to see as much as I can!

I haven't been to either place, but I have done A LOT of research. My fiance and I were going to do this exact trip for our honeymoon, but ended up picking Hawaii instead. We wanted Cayman and Jamaica for the reasons you said -- two very different islands that were close to each other. I don't think you have to fly through Miami. CaymanAir flys between the two islands, and Air Jamaica offers a "Stopover Free In Jamaica" promotion where you can have layover in Jamaica for free (for several days) on your way to another island that they fly to. And they do fly to the Caymans.

If you want to be near activities on Cayman, stay on 7-Mile Beach. There is a Hyatt, a Westin, and you can find nice condos on www.caymanvactions.com. Hope this helps!

Oh boy.
This is a toughie.
I have tried to do this many times and just gave up in some cases because it was too much of a hassle.

There ARE many islands where you can do this though if you find some close enough together that have either:

1.) Ferry service that doesn't take too long
2.) Cheap regional airlines

Here are some possible choices.

Easy is the USVI's and the BVI's
Easy is Playa del Carmen and Cozumel
Easy is Anguilla and St Martin/St Maarten
Easy is St Kitts and Nevis

Then there's Grenada and Carriacou, some of the Bahamas islands, Cancun to Cozumel.

I'm sure you will get additional suggestions, but sometimes, the travel can be a real difficult part of the trip.

We normally do not split a trip between islands unless we have anywhere from 10 days to three weeks, and then we'll go to two or three. (We went to four on a 3 week trip, and that was tooo much ferry time for me!)

You can fly from MoBay (MBJ) to Cayman (GCM) on either Air Jamaica (daily flights) or Cayman Airways (about twice per week)... and it is only about a 40 minute flight... very close

Doing a twin island vacation to MoBay and Cayman is a great idea. Half Moon is also an awesome resort, I love it.

Half Moon is a huge resort and you could spend four days there just on that property.... although I would recommend a jeep safari inland.

Cayman is very different, you don't need to stick to the resort, you should feel free to rent a car and explore the island for yourself.

There are plenty of options in Cayman. Of course I would recommend an Oceanfront Studio at my place (The Reef), as we don't bother with nonsense like minibars, but instead have just what you are asking for, a fridge with microwave, coffee maker and a couple of place settings... but also a restaurant.

There are many options for luxury condos and hotels too in the Seven Mile Beach area, I am sure you will get further replies and recommendations on this thread.

One other thing. Does it make sense to stay in Jamaica first and end the trip in the Caymans or vice versa? I was leaning towards ending the trip at Half Moon in Jamaica since I can do the whole "spa" thing. I suppose it doesn't really matter. Any thoughts on which island I should stay at first?

Okay, more than just one more thing!

I don't want to stare at any cruiseliners while I am relaxing at the beach. Do cruise ships stop in the Caymans and Jamaica? If they do, where? I guess I don't mind crowds, but I don't want to see a big piece of metal floating in the ocean while I am sunbathing. Can't fantasize that I am living the "Corona" commerical or am like Tom Hanks in Castaway, when I stare out at the ocean and see a giant cruiseliner.

One thing to keep in mind - The Reef is somewhat isolated and it takes about 35to 45 minutes to drive into Georgetown and the 7 Mile Beach area. Not as many things to do on that part of the island for your husband.

I have done the same a few times, the AJ stopover deal is great. Usually not as much hassle as you may think.

There are cruise ships in Cayman almost every day, but not in front of Seven Mile Beach, so they won't interfere with your view.

As regards which order to do the trip, I would tend to go with JA first, then Cayman, as (spa or no spa), Cayman is probably more relaxing... certainly on your final departure from the airport it is less stressful than MoBay (although that airport is not too bad these days either)