St Barth is our favorite place in the Caribbean. Beautiful island, beautiful beaches, very upscale shopping, and fabulous restaurants. You could stay at a nice hotel or rent a private villa. You definitely do not need to go all-inclusive.

We have vacationed there four or five times and have never been hassled in the way you describe in your OP. Everyone is friendly and low key. It's a great place to vacation.

Belize

I agree with Bermuda; we enjoyed the Raddison in Aruba. They will approach you every now and again to braid your hair on the beach but they aren't pushy or obnoxious about it....

Bermuda, my husband is from there and its so calm and relaxed. No one tries to hustle you and panhandlers are unheard of. The standard of living is really high and the people are very polite. Bermuda is expensive and most of the tourist I have seen there looked older. If your a college student and you want to get the most bang for your buck your not going to Bermuda.

Go to a smaller island where scuba divers go. It's very relaxing and nobody bothers you. Or a more upscale island. We like a self-catering type place (with a kitchen in your unit) so you can eat out or eat in when you want and keep picnic supplies and store-bought beer cold. We were "higgled" i.e. hassled on the beach, in parking lots etc. to buy things in St. Lucia, St. Martin and San Pedro, Belize. But not in Bonaire, Cayman Brac, St. Bart, Saba. St. Bart has over-the-top shopping (Dior, Gucci etc.) and great restaurants and lots of beautiful young people from France. Bonaire and the Sister Caymans have excellent diving. Saba is a trip - no beaches, one road, incredible flowers and scenic hiking, the diving was a bit too deep for me, they go to these underwater seamounts that start at 90 feet.

Recommendations of places to stay in Puerto Rico?

Go somewhere upscale and all-inclusive and don't leave the resort. Don't begrudge people desperate to make enough money to put food on the table. They know you spent thousands on your holiday.

My favorite place is the W on Vieques. It's not an all-inclusive, but it has a spa and is quiet and private and lovely.

Puerto Rico is awesome

No, you just have to go someplace a little more upscale than Freeport, the Newark of the Caribbean.

You'll have to go all-inclusive to avoid this.

I think it would be helpful to have more info about what sort of vacation you like, but I will say that I never thought I was an all inclusive person, but I have found that I have found that there are some decent ones in Punta Cana, DR and on the Mayan Riviera (if you are ok with Mexico). There's no need to leave the resort and no need to use cash at all.

We have only been to the Caribbean once, 20 years ago. It was a cheap newlywed package deal to Freeport, Grand Bahama Island. Everywhere we turned, locals were confronting us (even following) to get hair braided, carry our luggage 3 feet (then holding out hand for a tip, and then another person wants to carry it another 3 feet), selling us souvenirs, etc. I get that they are just trying to make a living. But it really felt like we were being stalked, and it was not relaxing. Are all Caribbean destinations like this? We would love to get away for a few days to warm beaches, beautiful views, and, frankly, to be left alone for the most part. Actually, I do like spas and shopping on vacation, but I prefer it on my own schedule vs. being confronted. I also expect that we need to tip hotel staff. But the way it was set up at our Freeport hotel, 10 different people handled our luggage from the time we got out of the airport shuttle until we reach our hotel room 200 yards away. It was non-stop nickel and diming. Same thing walking to dinner - confronted at every turn to buy something. Where do you like to go in the Caribbean? Thanks!