The Caribbean Is Not One Kind of Vacation.
Aruba, Jamaica, St. Lucia, Punta Cana, Turks & Caicos and the other Caribbean destinations may look similar in vacation photos. Once you start planning, the differences matter.
Some destinations are built around large all-inclusive resorts. Others are better when you get out and explore. Some have calm beaches and easy resort areas. Others stand out for scenery, golf, restaurants, snorkeling, nightlife or a quieter place to relax.
You do not need to know which island is right for you before you start looking. This page is here to give you a starting point, show you the destinations I already have guides for, and help you dig deeper into the places that catch your attention.
The goal isn't to find the Caribbean destination everybody says is “the best.” It's to find the one that makes sense for the vacation you actually want.
Start with the destinations below. If two or three sound good, that's fine. You can explore each one or use my Caribbean comparison guide to help narrow them down.
Start With the Kind of Caribbean Vacation You Want
There are a lot of Caribbean islands and resort areas, and reading a giant list doesn't necessarily make choosing one any easier. A better starting point is thinking about what you actually want to do once you get there.
The Dominican Republic deserves a little extra explanation. Punta Cana and Casa de Campo / La Romana can create very different vacations, so you'll find separate guides for both below.
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Don't worry about narrowing it down to one destination yet. If Aruba sounds good for the beaches and restaurants, Jamaica catches your attention for an all-inclusive, and St. Lucia looks interesting because of the scenery, open all three guides. The differences become much easier to see once you look beyond the beach photo.
Explore the Caribbean Destinations
These aren't meant to be quick sales pitches for an island. Each guide is there to help you understand what the vacation is actually like — the beaches, resort areas, things to do, advantages, drawbacks and the details that can make one destination work better for you than another.
Aruba
A good place to look if you want an easy beach vacation but still like having restaurants, shopping and places to walk outside the resort.
Jamaica
One island with several very different resort areas, a huge all-inclusive selection and plenty to do when you want to leave the beach.
Dominican Republic
Don't stop at “Dominican Republic” when you're comparing vacations. Punta Cana and the La Romana / Casa de Campo area can give you two very different trips.
Punta Cana
One of the Caribbean's biggest resort areas, with a very large range of all-inclusive choices and plenty of options at different price points.
Casa de Campo
A very different Dominican Republic vacation built around a large resort experience, golf, villas, the marina and more room to spread out.
St. Lucia
A strong choice when the scenery and experience beyond the resort matter just as much as having a beach and a nice place to stay.
Turks & Caicos
Best known for beautiful water and beaches, with a vacation style that can be quieter and more beach-focused than some larger Caribbean destinations.
The Bahamas
Close to the U.S. and useful for everything from shorter resort stays to bigger island vacations — depending on which part of the Bahamas you choose.
Curaçao
Worth a look if you want good water activities but also like the idea of getting out, exploring and seeing more than a resort area.
Barbados
A Caribbean vacation with a strong sense of place, plenty of restaurants and more reasons to explore beyond your hotel or resort.
Cancún
A large resort market with lots of choices and relatively easy access, but where picking the right resort area can make a big difference.
Have another Caribbean destination in mind? That's fine too. Antigua, Grenada, St. Martin and plenty of other islands may be worth looking at even though I don't have a full destination guide for every one of them yet.
Like More Than One Caribbean Destination?
Good. You don't need to force yourself to pick one yet.
I built a separate Help Me Choose a Caribbean Island or Resort guide for exactly this part of the process. Instead of giving you another list of resorts, it helps you compare destinations based on the kind of vacation you're trying to have.
Sometimes Comparing Two Is Easier
The Help Me Choose guide also has my Caribbean destination comparisons. So if you get down to something like Aruba vs. Jamaica, St. Lucia vs. Aruba, or Turks & Caicos vs. St. Lucia, you can look at those vacations side by side instead of bouncing between a bunch of resort websites.
What If the Caribbean Island You Want Isn't Listed?
That's not a problem. The destinations above are the ones I currently have full guides for — they aren't a list of the only places I can look at for your vacation.
Maybe you've already heard about Antigua. Maybe somebody recommended Grenada. Maybe you've stayed in St. Martin before and want to go back. Or maybe you found a resort somewhere else in the Caribbean and want to know if it makes sense for your trip.
You don't need to fit your vacation into one of the destinations on this page. When we get into the planning, tell me what has your attention and I'll work from there.
Not having a full guide on the website doesn't mean a destination is off the table.
And if you don't have an island in mind at all, that's fine too. Sometimes it's easier to start with your dates, who's traveling, what you want the vacation to feel like and what you realistically want to spend — then figure out which Caribbean destinations make sense.
Ready to Start Planning Your Caribbean Vacation?
You don't need to have the island, resort or every detail figured out first.
Start with what you know. Tell me who's going, what kind of vacation sounds good, what part of the Caribbean has your attention, your dates if you have them and the things that matter most to you.
If you're deciding between a few destinations, tell me that too. Narrowing down the destination can be part of the planning instead of something you have to solve before we start.
The Trip Starter gives me the basics I need to understand the vacation before we get into resorts, flights and all the smaller details. It saves us from starting with a long string of back-and-forth emails.
Still Trying to Figure Out Where to Go?
That's exactly what the Help Me Choose a Caribbean Island or Resort guide is for. Use it to compare vacation styles, islands and resort areas before you start planning.
Help Me Choose a Caribbean Island or Resort →One last thing: don't pick a Caribbean destination just because somebody else loved it. Their favorite resort, island or beach may be perfect for them and completely wrong for the vacation you're trying to take. That's why I start with the people going and the kind of trip they actually want.