Where to go for two weeks (need good Wifi)

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I think that the time difference is 4 hours.
It's just 3h in Sept-Oct. Curacao stays on AST (GMT-4), whereas most of the US is still on Daylight time.
 
I also look for wifi on dive trips as our small group always seems to need it. Curacao was fine - except not at our condo in Piscadera Bay - we had to go to a nearby resort bar (not the worst plan...lol)

Grand Cayman has excellent connectivity thru Cable & Wireless also. I'd guess island-wide as they have a highly developed infrastructure. It's extremely clean and pleasant there also as well as the extraordinary wall diving 10 min. from the dock.

Based on fairly recent experience, I'd pass on the Bay Islands - the internet went down a couple days - even at the internet provider store on Roatan and Utila was painfully slow even just to email.

I thought of Maui also when I read your first post. Not cheap but probably a non-stop flight. It could work the other way there since it's about a 4-5 hr. time difference - have the day free and catch up at night. Most people from the states get up early the first couple days also so that could be a work option. Or it's nice since the Kihei to Molokini boats all try to leave at 6am.

Since the Maui Supercomputing Center was there - (they did military image assessment) they have a "fat" pipe to the island so speeds are fast.

And the diving is great plus there's a lot of other stuff to do. With two weeks you could move over to Oahu or Kona for a week.

It will be pricey though..

How's the Internet access in Cozumel? IDK so asking...
 
Nice thing about Doc's other suggestion - USVI is that the BVI's are literally an hour or two by fast ferry from St. Thomas so you[d have all those islands to explore/dive as well. I'd guess Tortola has fast internet - possibly Virgin Gorda also. If you like nice, isolated sandy beaches - Gorda is the place. The BVI's did take a major hit in one of the recent hurricanes though.

Plus you can "drive (car ferry)" over to St. John for the day.

We've dove off many of the islands there - some good wrecks and lots of shallower reef diving. The Rhone off Salt Island is one of the best I've seen - they filmed parts of "The Deep" there.
 
I also look for wifi on dive trips as our small group always seems to need it. Curacao was fine - except not at our condo in Piscadera Bay - we had to go to a nearby resort bar (not the worst plan...lol)

Grand Cayman has excellent connectivity thru Cable & Wireless also. I'd guess island-wide as they have a highly developed infrastructure. It's extremely clean and pleasant there also as well as the extraordinary wall diving 10 min. from the dock.

Based on fairly recent experience, I'd pass on the Bay Islands - the internet went down a couple days - even at the internet provider store on Roatan and Utila was painfully slow even just to email.

I thought of Maui also when I read your first post. Not cheap but probably a non-stop flight. It could work the other way there since it's about a 4-5 hr. time difference - have the day free and catch up at night. Most people from the states get up early the first couple days also so that could be a work option. Or it's nice since the Kihei to Molokini boats all try to leave at 6am.

Since the Maui Supercomputing Center was there - (they did military image assessment) they have a "fat" pipe to the island so speeds are fast.

And the diving is great plus there's a lot of other stuff to do. With two weeks you could move over to Oahu or Kona for a week.

It will be pricey though..

How's the Internet access in Cozumel? IDK so asking...

Grand Cayman is my usual suggestion for someone that wants a variety of good topside activities, first world conveniences and communications, great Caribbean diving, and easy travel from the US. But the OP also asked for cheap and he wants to avoid the risk of bad weather - yet he suggested traveling to the Caribbean in Sept/Oct - so what he is looking for may not exist.

The Cayman Sister Islands of Brac and Little Cayman are not as reliable as GC in regards to WiFi - at least not in my experience. We have gotten better connectivity on Brac than on Little in the past, but it was okay on LC during our recent trip to LCBR. But since this trip is an experiment to prove his availability to his Boss, then I think he should look for someplace with consistently reliable WiFi.

We have traveled to the Caribbean many times in October/November and we have usually been lucky with the weather. We have had beautiful, calm, glorious weather many times but we have also experienced rainy, windy, and stormy weather. There's a reason why summer and fall are the low season in the Caribbean and the prices are cheaper.

Of course, there is no guarantee about the weather, wherever and whenever you travel, and just because one area of the Caribbean gets hit with bad weather doesn't always mean that it will also hit your location - it's a huge geographic region. The link below is for the graph that shows the monthly distribution of bad storms and hurricanes in the Caribbean and it may help the OP decide when and where to travel.

Hurricanes and Storms
 
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@diversteve

Cozumel WiFi is very reliable. At least, it was for me at Occidental. I worked a lot when I was there and I require VPN access to sign into SAP. SAP is extremely sensitive to any lapse in internet because it will immediately error out and if you’re in the middle of something, you could lose work. It didn’t happen and it was really good. :)
 
If you are looking for budget accommodations downtown, then I highly recommend Suites Colonial Cozumel -- They are part of the Casa Mexicana family of hotels, so your buffet breakfast is included at Casa Mexicana each morning. I have stayed in room 203 and the WIFI router/booster for this floor is right outside this unit and very reliable. Below is my trip advisor review of the hotel. Also happy to recommend dive operators within walking distance, if you decide to go this route. All the best!

Clean, comfortable and quiet
We stayed at Hotel Suites Colonial for 10 nights over Christmas. It is in the heart of downtown and surrounded by great restaurants. It is 2 blocks to the main plaza, 3 blocks to the Playa del Carmen ferry and a block to the waterfront. We booked a “suite” vs a “studio” room. The suite afforded a lot of additional square footage due to a separate living/dining room and a kitchenette enclave that had a sink, large mini-fridge, 2 burner electric stove and lots of cupboards full of eating and cooking utensils. The beds are very comfortable, the sheets and comforters are very nice quality for this price point and the AC and WIFI worked flawlessly. AC was also nice and quiet. The hotel is very quiet and impeccably clean, even though it is in the heart of downtown- this is due to the fact that the entrance has a long beautiful, bougainvillea lined corridor that leads from the street back to the main entrance. Also, no vehicle traffic is allowed on this street (foot traffic only). Suites Colonial is a sister hotel to the Casa Mexicana and the Suites Bahia. Breakfast is included in the room rate and the breakfast is provided at Casa Mexicana each day from 7am-11am. (a 4 block walk along the waterfront). It is arguably the best full buffet breakfast on the island. I will be staying here for all future visits to Cozumel. As a diver who dives each day and prefers to stay downtown, there is no place better in this price point- for me. The HD flat screen TV worked very well and had many english speaking cable channels. The room is also equipped with a safe and the hotel has an elevator.
Room Tip: We stayed in room 203 and were very happy. Getting a Suite vs Studio is worth the upgrade.
 
Nice thing about Doc's other suggestion - USVI is that the BVI's are literally an hour or two by fast ferry from St. Thomas so you[d have all those islands to explore/dive as well. I'd guess Tortola has fast internet - possibly Virgin Gorda also. If you like nice, isolated sandy beaches - Gorda is the place. The BVI's did take a major hit in one of the recent hurricanes though.

Plus you can "drive (car ferry)" over to St. John for the day.

We've dove off many of the islands there - some good wrecks and lots of shallower reef diving. The Rhone off Salt Island is one of the best I've seen - they filmed parts of "The Deep" there.

St. Croix is another good destination in the US Virgin Islands, not the cheapest but not the most expensive, either. Nice reefs and the Fredricksted Pier is a truly excellent and easy shore dive. But it was hit by a hurricane last year also, so I don't know the current situation - and like most other areas of the Caribbean, you run a greater risk of bad weather in the fall.
 

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