Please Help Me Out - Carrlibbean Family Trip

Agreed. Hiking Gros Piton will give him all the off beach excitement he can want.

It's like a 2000ft elevation gain over a 2 mile trail.

What golfer said and if you bring your passports you can ferry over to or do a day charter to the BVI.

ETA: You can rent at Grande Bay right in Cruz Bay on St. John and walk or stagger anywhere in town.

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I would prefer not to drive at all.

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Driving on St. John is in an open-top Jeep at 10-15mph between beaches.

They have (or used to have) a "bus" system...someone who's been recently can confirm.

You could also stay at the Westin...I think they're back open now...

You said on property so I stayed away as I’m not an all-inclusive lover or person. I’ll make some suggestions for you to check out.

Grace Bay, Providenciales, Turks and Caicos - the beach is about nine miles long. There’s plenty of walking obviously and there are some very good restaurants on the beach. Taxis are easy and there are some great restaurants on the island. You will not find a prettier beach or prettier water which goes on and on anywhere.

Roatan - West End Beach - pretty. Compact with a ton of restaurants on about a half mile long moon shaped beach. Inexpensive to boot. We rent a three bedroom condo there for about $3k for a week that is right on the water.

Isla Mujeres- stay in Playa Norte. Beautiful beach. Stay at Ixchel. A short walk to Hidalgo Street which is loaded with restaurants which are cheap and good. A taxi ride anywhere on the island is $5. You can rent golf carts to explore for a day if you wish. The island is only four miles long.

St. John, USVI - stay in Cruz Bay. Take the local bus to the beaches. Plenty of restaurants and shopping in Cruz Bay. You can take the ferry or do a day charter to the BVI if you have passports. Ferry to Jost Van Dyke and go to the Soggy Dollar Bar on White Bay. It’s a gorgeous bay and Soggy may be the most famous island bar in the world. Idyllic setting.

That should get you started. If you want all-inclusive Providenciales, Turks and Caicos is the most likely out of what I’ve listed.

Great info, thanks!! Can you give me the names of some properties?

Some great advice here but when I look for places, I don't know what to do...

Grand Cayman

Your budget will obviously influence things. I can imagine the pressure you're feeling. "Don't F this one up"!

With that kind of crew, the worries will be "how much flight time". You don't want to have multiple layovers and long flight times. Safety. Which island is "safe"? (Multiple threads on that one). Cost ("What's the freight going to be for this bunch?) Another point (and I dealt with this one): avoid places that offer "distractions" to "late teens". You know what I mean. Mixing the crew in with a location that's big at Spring Break, for example, would be recipe for disaster. Boring is good with this crew!

I've always wanted to go to St. John. Trunk Bay is supposedly one of the most beautiful beaches in the world. I don't know the current conditions after the hurricane, so you'd want to research that. But renting a villa type location (an "AirBnB") might be most cost effective.

There might be some good family type AI's in the Dominican Republic. I've been to the island, but not to an AI and they aren't all "party central".

I like Cheap Carribbean for researching deals.

I'd say just bite the bullet and go to Turk & Caicos and stay at Beaches. You can find some off-season deals. Atlantis in the Bahamas would be second.

Yeah, I know it's expensive. But you have to minimize the variable here!