Checked in, checked out: 3 Caribbean hotels I’ve actually stayed in
“What I loved most, what made me raise an eyebrow, and what I’d tell a friend before they book. Honest luxury hotel reviews from a travel advisor who doesn’t do generic.”
- Anna Fishman, founder of Olegana Travel Boutique
If you read my European “Checked In, Checked Out” where I reviewed six hotels from Lake Annecy to Rome and gently roasted a Barcelona room layout that required a PhD to navigate, you know the format. What I loved. What made me raise an eyebrow. And what I’d tell a friend before she books.
This is the Caribbean edition. Three islands. Three luxury hotels I’ve stayed in with my own family. Same honesty, warmer water.
Anna Fishman and her family enjoying a Caribbean family getaway, with turquoise waters, stunning coastlines, and some of the Caribbean’s finest luxury hotels.
Photo©: Anna Fishman / Olegana Travel Boutique
A note before we start. These were personal family trips. I booked and paid for all three stays, some at industry rates, and none of them were hosted.
My boys were also at different ages each time. Roughly two and a half and eight at The Landings, three and a half and nine at Calabash, and four and ten at Carlisle Bay. So I have seen all three of these hotels with a toddler in tow and with an older kid who wants something to do.
Amazing beach view at Carlisle Bay in Antigua, featuring soft white sand, calm turquoise Caribbean waters, and a tranquil tropical setting.
Photo©: Anna Fishman / Olegana Travel Boutique
These three tend to get lumped together as luxury Caribbean resorts, and having stayed at all of them, I do not think they are the same experience at all.
If a friend asked me which one to book, I would not start with which hotel is best. I would ask her five questions.
How important is the beach? How much space do you actually need? Do you want a small boutique hotel or a larger resort? How much do you care about design and updated rooms? And what does luxury mean to you?
Here is how I would break them down.
The Landings, St. Lucia
The Landings in Rodney Bay, Saint Lucia, is a luxury beachfront resort known for its calm turquoise waters, secluded beach, and scenic mountain views.
Photo©: Anna Fishman / Olegana Travel Boutique
Checked in
The Landings truly wowed me. The setting is stunning because of its secluded beach, calm turquoise water, and mountains framing both sides like a postcard. Even at 96% occupancy, it felt blissfully quiet. Most mornings and evenings, we had the beach completely to ourselves. If your dream vacation involves not having to reserve a beach lounger at 6 a.m., this is your spot.
The Landings in Saint Lucia features a beautiful resort pool surrounded by tropical landscaping and a luxurious beachfront setting.
Photo©: Anna Fishman / Olegana Travel Boutique
The beachfront suite with a private jacuzzi steps from the sand? Perfection. The butler service made everything seamless from beach snacks to mid-nap room lunches. The two beachfront restaurants served fresh, delicious food all day, and the weather in June was a dream: warm, breezy, and far less humid than New Jersey in July (sorry, NJ).
We had a true two-bedroom residence with a living room, a kitchen and a dining area. It felt less like fitting a family into a hotel room and more like having an apartment in the Caribbean, which is a different kind of vacation when you are traveling with a toddler and an eight-year-old who go to bed at different times.
And of these three, The Landings gets my vote for the best beach.
Checked out
The only real downside? Getting there. It is over 1.5 hours from the airport, and the roads are, let us just say, adventurous. But once you arrive, you will forget all about the journey.
The property is also large. Depending on where your unit sits, you may find yourself using golf carts to get around. I would take a beachfront unit if I could.
And here is the thing I would want a friend to know before she books. The residences are not all identical. There are timeshare units within the property, and decor and condition vary from one to the next. The exact unit you book matters more here than it would at a traditional hotel, and that is not something a booking site will tell you.
I also would not put The Landings in quite the same category as Calabash. To me it feels like an upscale Caribbean resort rather than a true luxury boutique hotel. That is not a criticism. If I were traveling with young children and I wanted two bedrooms, a kitchen, a living room, a fantastic beach and room to spread out, The Landings could easily make more sense than a smaller, higher-end property.
Best for
Families with younger children, anyone who needs a lot of space, and anyone who puts a beautiful beach high on the priority list. I have traveled here with my own boys and it is genuinely wonderful for families. The residences give you room to breathe, the beach is calm and safe, and the butler handles everything from beach snacks to mid-nap lunches. June is a lovely time to go, warm and breezy, with far fewer people around.
Carlisle Bay, Antigua
Carlisle Bay in Antigua is a luxury beachfront resort known for its secluded sandy beach, lush tropical surroundings, and calm Caribbean waters.
Photo©: Anna Fishman / Olegana Travel Boutique
Checked in
The beautiful beach at Carlisle Bay in Antigua, featuring soft white sand, calm turquoise Caribbean waters, and a peaceful tropical setting.
Photo©: Anna Fishman / Olegana Travel Boutique
Breakfast on the balcony overlooking that turquoise water, pure perfection. And here’s the thing about Carlisle Bay: every single room is beachfront. You step out and you’re on the sand. The service was wonderful, and you can feel the warmth in every detail. The rooms are spacious, though this is an older property, and I think that is worth knowing when you are comparing it with the other hotels in this conversation. Some of the common areas felt dated to me and were due for renovation when we stayed.
There is a big exception, and it matters. The renovated beachfront suites are gorgeous and they feel like a completely different hotel. One thing to know before you fall in love with them: those suites are adults-only, so they are not an option if you are traveling with children. Your impression of Carlisle Bay can be quite different depending on which room category you are in, which is exactly why I pay attention to that here.
The beach is beautiful, calm, and exactly where you want to lose track of time.
Checked out
The restaurants have delicious food but could use a menu remix. The same dishes for a week across two venues had me considering a side hustle as the chef’s consultant. We also had the resident cats, who took an intense professional interest in our lunch. My children found this considerably more entertaining than I did.
The moment I’ll never forget
One night, the hotel hosted a Jewish wedding on the beach. The music, the joy, the Hebrew songs floating across the bay it was emotional, powerful, and so full of life. After everything, hearing “We will dance again” in that setting hit differently. Some places remind you why travel matters and this was one of them.
Best for
A couple looking for a romantic Antigua stay, particularly if they can book one of the renovated beachfront suites. The room service breakfast, eaten on your balcony overlooking the water, is one of the best ways to start a day in the Caribbean. It works for families in the other room categories too, and I have brought my own boys here, but the newest and most beautiful rooms are adults-only, so a family will not be in them. Also ideal for honeymoons and milestone celebrations.
Calabash Hotel, Grenada
Calabash Hotel in Saint George’s, Grenada, is a luxury boutique beachfront resort on Lance Aux Epines Beach, known for its elegant setting and tranquil Caribbean atmospher.
Photo©: Anna Fishman / Olegana Travel Boutique
Checked in
Honestly? Everything. It is the smallest of the three and to me it felt the most genuinely luxurious, not because it was flashy but because everything felt personal.
It is about fifteen minutes from the airport, which is wonderful after a flight with children. Set that against the hour and a half to The Landings and you will understand why it matters on arrival day.
The beautiful beach at Calabash Hotel in Grenada, featuring soft white sand, calm turquoise Caribbean waters, and a tranquil tropical setting.
Photo©: Anna Fishman / Olegana Travel Boutique
The staff got to know my boys. One evening we had cocktails with the owners of the hotel. There is a feeling of being welcomed into someone’s home rather than checking into a resort.
And the food was outstanding. Not just good for a Caribbean resort. Some of the most memorable food I have had anywhere.
The beach was a completely different experience from a large resort too. At any given point there might have been seven people on it. There were moments when it honestly felt as though we had our own small private island.
The trade-off is space, and Calabash sits at the premium end of the three. Our rooms were smaller than what we had at The Landings, and this is the most intimate of these hotels by some distance. If all three were sitting in front of me tomorrow on equal terms, this is still the one I would choose for my own family.
Checked out
Word to the wise: do not leave your breakfast unattended on the porch. Grenada’s cats have refined taste and will absolutely steal your bacon. Yes, we met the cats at two of these three hotels. No, I do not know what that says about us.
Best for
Travelers who care more about exceptional food, personal service and a true boutique feeling than about having the largest room or the biggest resort. If I had to choose one Caribbean hotel for couples, this would be it. It is also wonderful for families. I have traveled here with my own boys, and the boutique feel, the beach and the warmth of the staff make it work beautifully for all ages. Grenada itself is underrated, and this hotel is one of the reasons it deserves more attention.
Dreaming of the Caribbean?
I design custom Caribbean trips for couples and families. The right island, the right hotel, the right room. Let’s find yours.
The verdict: which Caribbean hotel should you book?
Photo©: Anna Fishman / Olegana Travel Boutique
For couples, my #1 pick
Calabash Hotel, Grenada. The food, the intimacy, the ownership hospitality. This is the one I recommend first for couples who want something genuinely special.
Photo©: Anna Fishman / Olegana Travel Boutique
For the best beach
The Landings, St. Lucia. The most beautiful beach of the three, secluded, calm, and it feels like it’s yours alone. Plus private suites and butler service.
Photo©: Anna Fishman / Olegana Travel Boutique
For a romantic stay in a renovated beachfront suite
Carlisle Bay, Antigua. Every suite faces the ocean, and the room service breakfast on your balcony is one of the best ways to start a day in the Caribbean. The renovated beachfront suites are the ones to ask about, and they are adults-only.
Photo©: Anna Fishman / Olegana Travel Boutique
For families
The Landings first, for the space and the beach. Calabash next, for the food and the warmth. Carlisle Bay works too, with one caveat: its most beautiful rooms are the renovated beachfront suites, and those are adults-only, so a family will not be staying in them.
Photo©: Anna Fishman / Olegana Travel Boutique
For the best food
Calabash Hotel, Grenada. Not good for a Caribbean resort. Some of the most memorable food I have had anywhere.
The one I would go back to tomorrow
Calabash Hotel, Grenada. If all three were in front of me on equal terms, this is the one I would book for my own family.
Why these reviews matter (and why a travel advisor helps)
Photo©: Anna Fishman / Olegana Travel Boutique
This is why a question like what is the best luxury family resort in the Caribbean is so hard to answer without knowing the family. The Landings gave us far more space and my favorite beach of the three. Calabash gave us the most personal service, the best food and the strongest overall luxury experience. Carlisle Bay has a gorgeous setting and those beautiful renovated suites, though some of the older parts of the property felt dated when we visited. Three good hotels, and I would send three very different travelers to them.
I do not review hotels from press trips or comped stays. I stay at these properties, I pay attention to the details, and then I recommend them or I do not, based on what I actually experienced. That is the difference between a review and a recommendation.
As a luxury travel advisor, I know which room category to request, which season to visit, and which hotel matches your style. It is the difference between booking a resort and booking the right unit inside it. The Caribbean has hundreds of beautiful properties, and the right one for you depends on who is traveling, what matters most, and what kind of trip you are building. That is what I help with.
Anna Fishman is the visionary and soulful force behind Olegana Travel Boutique, orchestrating transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
Let’s plan your Caribbean escape!
Grab a time on Anna’s calendar here.
Frequently Asked Questions
-
Of the three hotels in this post, Calabash in Grenada is my top pick for couples. The intimacy, the food, and the warmth of the hospitality create something really special. Beyond these three, it depends on what you want: St. Lucia offers dramatic scenery and seclusion, Antigua has calm beaches and polished resorts, Barbados combines beaches with culture. I match the island and the hotel to the couple.
-
December through April is peak season, with the most reliable weather and the busiest hotels. June and early July are an excellent window: warm, less humid than you would think, and far quieter. June is when we went to St. Lucia and the weather was lovely.
-
You do not need one, but the right advisor knows which room category to book, which restaurants to reserve, and which properties live up to their photographs. At The Landings, for example, the residences are not identical and there are timeshare units in the mix, so the specific one you are given changes your week. That is the kind of thing a booking site will never tell you.
-
Yes, with one caveat. I have stayed at all three with my own boys. The Landings has the best beach and the most space, with two-bedroom residences that include a kitchen and a living room. Calabash has the best food and a boutique warmth that makes children feel welcome. Carlisle Bay works for families too, but its renovated beachfront suites are adults-only, so the newest rooms are not available to you if you are traveling with children. Ask about the age policy for any room category before you book.
-
Calabash in Grenada is about fifteen minutes, which is a gift after a long flight with children. Carlisle Bay in Antigua is about forty minutes from V.C. Bird International. The Landings in St. Lucia is over an hour and a half, on roads I would politely call adventurous. It is worth factoring into your arrival day, particularly with young children.
-
More than it would at most hotels. The residences are not all identical and there are timeshare units within the property, so decor and condition vary. I would request a beachfront unit and I would confirm exactly which one you are getting before you book.
-
The Landings was the easiest of the three with a very young child, because a two-bedroom residence with its own living room means the whole family is not going to bed at the same hour. Calabash is small enough that it feels manageable with little ones too, and the short airport transfer helps.