Martha's Vineyard! I grew up going to edgartown and loved it. Oak bluffs will have fun stuff for your son....arcade, ice cream, fun shops, etc.

OP here, thank you for your replies!

Are there heated pools in MV and Cape Cod in June, since you say the ocean will be cold?

For the poster that mentioned St Croix, is that better for kids over St John or Provo?

Any thoughts on a Southern Caribbean cruise in June?

St. John's is super hot and humid in the summer, even June. Don't be tempted by the off-season rates.

I vote for MV.

We used to go to St John as kids and I would definitely take my kids there if they like beach, swimming, snorkeling hiking and adventures like riding in open backed keeps to hidden beaches.

But then my family enjoys camping and hiking, so it depends what is fn for you. Cinnamon Bay campground has communal type dinners where you can hang out with the kids you met during the day.

Not much internet though.

Anonymous wrote:St. John. Too cold up north. No to the cruise.

There is literally nothing to do on St. John aside from the beach. DH and I have been there, but we would never bring our kids.

St. John. Too cold up north. No to the cruise.

Disney cruise or Beaches on Turks and Caicos. The Buccaneer on St. Croix is nice. If there is only one parent to handle arrangements, cooking, driving, navigating, I would do an easy vacation like the cruise or an all inclusive resort so that I could relax also and maximize time with the kid.

If you can afford it, Oceans Edge Resort on the Cape may be nice. Seems like it would be a good place for your kid to connect with other kids.

I imagine you need to entertain your one kid unless he will just amuse himself with screens?

Honestly, I would do a nice cruise. How do you entertain one kid at a fancy resort or beach house? Who will he play with? What will he do?

A cruise with daily ports of call will give you plenty of options and keep you busy. Disney cruises are fun. Kid friendly Broadway style shows every night.

What about Europe? London, the Cotswolds, Paris, Versailles? Prague looks amazing. Does he like Harry Potter or castles?

Cruise as its easy.

Of these options, I've only been to St. John, but would definitely take my 10 y.o. there as a single parent - rent a jeep and hit a different beach for snorkeling each day, go out on a boat excursion, hike some of the ruins - that's exactly our type of trip.

Sounds like you need to decide whether you want nature, relaxation and/or being catered to. A cruise would be the most relaxing that sense, because there's little planning and no cooking, but you need to decide if you're in the mood for that. Also, does your DC need to be around kids? Mine does, so I look for trips where we can go on group tours or stay at campgrounds or cabins where there are likely to be other kids to play with.

Martha's Vineyard would be nice but the water will be cold. A week flies by on MV- plenty to do and see but also a great place for putting the feet up and chilling out. If you are looking for a beach vacation where you can swim, go further south (Hilton Head would be fun and the water warm).

Anonymous wrote:Sounds like you have money to spend. Therefore, any of these, other than the cruise, would be good choices. I would pick the Cape, where there would be lots of kids for yours to play with.

Although June is early for the Cape. I like June there because it's quieter. Late June is pretty lively, early June won't have many kids because most will still be in school. Early June can also be cool, although with the weather this year all bets are off.

Sounds like you have money to spend. Therefore, any of these, other than the cruise, would be good choices. I would pick the Cape, where there would be lots of kids for yours to play with.

I am stuck in analysis paralysis. My son will be 10 yrs old, and we're traveling in June. Out of those spots, which would you choose?

I haven't been to any except a cruise, but that was with adults only. I worry I'll get bored or feel claustrophobic on a cruise as a single mom. We like to explore, but also like to relax. Would love to hear any advice or input, TIA!