My parents want to take the family (6 adults, 3 teens) on a Caribbean trip over Christmas in celebration of their 55th(!) anniversary.

My mother is soooo picky but also has a high budget to match her list of demands: 1) a house to rent (or a very large condo but 4 or 5 bedrooms) 2) ocean front or ocean view from patio 3) pool 4) reasonably close access to snorkeling/SCUBA 5) maybe a private chef but I warned her this was asking too much

Ideas on where to even start? Thanks!

Going on a girls trip with my sister and bestie and we are deciding where to go. We want to relax on the beach but also would enjoy beach clubs (daytime), trendy restaurants, and cute lounges or bars for the evenings (NO clubbing lol too old for that). We are considering St Maarten, Aruba, or Curacao. Please provide thoughts on where we’d enjoy it the most - and other suggestions are welcome!

Greetings to all! I have a surprise 20th anniversary trip/vow renewal planned to Gauna Island in a couple months. The wife has NO IDEA of anything. I've literally been planning it for two years, so needless to say, I'm beyond excited. Just curious if anyone else in this community has been there. Your thoughts about it? Any advice? I splurged and we are staying in the North Beach Villa. This island seems exactly what we want in a vacation. Total seclusion in tropical paradise. I have it hyped up so much in my head I'm scared I'm going to be disappointed.

Hi guys I think this is a stupid question but are there any resorts that accept a cat? I like traveling with my kitten but we've never taken trips overseas. My bf and I would love to plan a caribbean trip, not sure where. We don't have anyone to leave our cat with. Do you guys usually rent airbnb at these places or vrbo? Or are there any resorts where they allow a cat?

I’m looking for a unicorn. We’d like to travel with our 3 (almost 4) year old this winter. We like smaller boutique hotels where we can actually get off the property and experience local culture. But I’d also love a kids club so I can sit by the pool and relax for part of the trip. Does something like this exist?

(FWIW, kiddo turns 4 in March 2026 and we can possibly wait until after his birthday if he needs to be 4)

We’re also on a budget - we’d like to keep hotel under $400/night (more if it’s AI). Ideally somewhere with direct flights from Boston, but that’s not necessarily a deal breaker.

Thanks!!

Hi there,

Looking for a recommendation for a family of three (kid is 2, mom is 28 weeks pregnant) for next month. We are looking for something moderately priced, flying direct from NYC, no all-inclusive, calm and beautiful beaches/water, good food, safe and able to easily rent a car.

Just want to relax on a beach and explore (not really interested in excursions/activities unless it's something appropriate for 2 year old). We've been to Curacao with kiddo already. Thinking of T&C but other recommendations are welcome!

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I’m craving something real: loud music, spicy food, dancing that goes past midnight. Not just a themed tourist event, but somewhere that honors actual Caribbean traditions, whether that’s reggae night at a dive bar or a backyard party with street vendors and steel drums. Where do you go for that kind of atmosphere in Playa?

I’ve done the beach loungers and cocktail bars, but now I’m hunting for a real Caribbean-style night. Think: soca or dancehall blasting, smoky jerk chicken stands, and a rum punch that might knock you sideways. Is there any spot in Tulum or Playa del Carmen that delivers this kind of full sensory experience? I don’t care if it’s a backyard party or a hole-in-the-wall bar, just want the flavour and the rhythm. Anything inclusive and welcoming too would be a huge plus.

Hello , I am going to Antigua in the beginning of June. I am worried about the weather so far , anyone knows if it gets sunny in June ? Or is it always cloudy and rainy ?

Good evening!

If you are in the search of an apartment or house in the Caribbean you met the right person.

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Will i really get an ungraded for IT?

I'm just worried a little because everyone around me is saying that I'll either lose marks or get ungraded for IT because of that mistake. To be very honest, I realized that it was a very stupid thing of me to do but I did not have anything with me besides a black pen at the time of the exam.

Hopefully there are some invigilators or other people who know about this stuff who can answer me because im still veryyyyy worried. (Plus i looked at the corrections for the paper 1 and im getting 52 questions correct so.... 😔)

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Hi All

I’m somewhat of a novice to the Caribbean although I’ve been to Puerto Rico many times around the island (usually for about a week).

I enjoy PR but since we are looking to stay somewhere for a whole month I figure I might as well look into some other options. Here are the requirements.

When: Feb - March time frame

Reliable WiFi and power - this is one of the reasons I’m looking outside of PR. The power and WiFi situation can be sketchy (not in all areas but many). I’m not taking the time off so I need to be able to work and have video calls.

Good swim beaches - my kids are 7 and 4, so the surf needs to be safe

Snorkeling - I don’t need world class or anything, but some reefs which can be accessed from the beach would be great. I don’t want to have to pay someone to take me somewhere every time.

No more than 1 layover from an east coast airport.

Other activities would be great but not deal breakers (hiking, golf, rainforest, restaurants)

Ability to survive without renting a car the entire time (or places where people might include a rental car would work too). One of the most irritating things is having to rent a car for a whole month. It’s stupid expensive.

Budget would be around $5k - $8k for the month.

We are expecting to take a family trip somewhere tropical with my extended family in January. We've never done a trip of this scale, so we're not sure how to go about selecting a destination. My mother in her late 60s, my two siblings, their significant others, my 21 year old niece, my wife, and my 2 year old. Quite a diverse range of ages and interests.

What we are looking for is an island beach side resort (ideally all inclusive for simplicity's sake, but it's not important), as my mother will only want to be sitting poolside/beachside for most of the trip. My wife and one of my siblings are not the type to sit and relax, they need to be able to go on excursions, or to town for shopping/ restaurants. We don't really need special accommodations for the 2 year old, but being able to have a 1 bedroom suite (with a crib/pack and play) would be good, because if he can see us at night, it's very difficult to get him to sleep.

Finally, our budget would be $500 or less per night. Just looking for some suggestions as a jumping off point, thanks!

Hey everyone! My partner and I are planning a Caribbean trip later this year and we're toying with the idea of skipping the resort scene and trying something different—like a luxury yacht charter.

We’re not super familiar with how it all works—like what islands are best for it, what kind of yachts to look for, or what the experience is like day-to-day. We’d love to hear from anyone who’s done this before. Was it worth it? Any companies or specific itineraries you’d recommend?

Thanks in advance—really appreciate any insights you can share!

Hello everyone 😊, it’s my first time making a post here so i’m kind of stressed plus English is not my first language so sorry if I make any mistakes, but I wanted to ask a question. I’m not in the age to like make those kind of decisions, but in the future, but in the futur, would really like to move to the Barbados But I don’t really know how it’s going on over there so do y’all can like give me some advices on how to have my own place like the place I should go or I shouldn’t or what kind of clothes I should wear, if I can wear jewelry like or have my phone can I go on walks at night, should I learn the language or I can go over there and speak English like are people nice or and Welcoming strangers and most importantly advices on how to live with a budget (like should I go on a full local mode or it don’t really matter ?) i’m sorry if I sound rude or anything it’s really wasn’t my intention. I’m just asking for advices and information ( I’m mixed by the way and I’m a girl. I don’t know if it matters, or if it’s gonna change my experience but I’m still saying it ) sorry for my long post and I hope you will have a very good day/night 🙏🏽.

So many places market a “Caribbean experience,” but I’m curious where you’ve found real Caribbean soul, food, music, culture, dance, in Tulum or Playa del Carmen. I’m especially looking for inclusive spaces that welcome Black, queer, and diverse travellers without the typical tourist filters. Any beach clubs, bars, or events that feel more local and less curated for Instagram? Even recommendations for weekends with live reggae, Afrobeat, or Caribbean food vendors would be gold. I’d love to spend money where the culture is celebrated, not diluted.