Anonymous
02/12/2026 10:32
Subject: Anguilla vs Cayman
Anonymous wrote:Anonymous wrote:Anonymous wrote:Anonymous wrote:Has anyone been to both? We love Cayman because of the beautiful beaches, great snorkeling, upscale hotels, safety, and convenience of nonstop flight. How does Anguilla compare? Seems like it would be fun to do a couple of nights in St Maarten and then a few in Anguilla though logistics are more complicated.
There is 0 reason to do St Maarten. You will want to get right to Anguilla once you land in St Maarten. It is a complete dump with mostly bad areas.
100%!
Interesting, I was intrigued by there being a French side. And Maho beach seemed worth a stop. A friend did both last summer and thought that Anguilla did not have much beauty other than the luxury hotels.
I'm mostly wondering if Anguilla is worth the effort since Cayman is more convenient and definitely has the upscale vibe.
It's worth the effort.
Anonymous
02/12/2026 10:26
Subject: Anguilla vs Cayman
Anonymous wrote:Anonymous wrote:Anonymous wrote:Anonymous wrote:Has anyone been to both? We love Cayman because of the beautiful beaches, great snorkeling, upscale hotels, safety, and convenience of nonstop flight. How does Anguilla compare? Seems like it would be fun to do a couple of nights in St Maarten and then a few in Anguilla though logistics are more complicated.
There is 0 reason to do St Maarten. You will want to get right to Anguilla once you land in St Maarten. It is a complete dump with mostly bad areas.
100%!
Interesting, I was intrigued by there being a French side. And Maho beach seemed worth a stop. A friend did both last summer and thought that Anguilla did not have much beauty other than the luxury hotels.
I'm mostly wondering if Anguilla is worth the effort since Cayman is more convenient and definitely has the upscale vibe.
That is utterly bizarre. Anguilla is like heaven on earth. And FWIW, there are only a handful of luxury hotels. Most who frequent Anguilla stay in villas. We've been all over the world and Anguilla is in our top 5.
Shoal Bay is incredible and peaceful
We love Meads Bay
And a trip to Sandy Island!
BTW- Maho Beach sits at the end of the airport runway. If you enjoy the aroma of fuel with the sound of airtraffic, sounds like its your place.
Anonymous
02/12/2026 06:12
Subject: Anguilla vs Cayman
I loved the French side of St Maarten, St. Martin. The food was delicious.
Anonymous
02/12/2026 05:22
Subject: Anguilla vs Cayman
Anonymous wrote:Anonymous wrote:Anonymous wrote:Has anyone been to both? We love Cayman because of the beautiful beaches, great snorkeling, upscale hotels, safety, and convenience of nonstop flight. How does Anguilla compare? Seems like it would be fun to do a couple of nights in St Maarten and then a few in Anguilla though logistics are more complicated.
There is 0 reason to do St Maarten. You will want to get right to Anguilla once you land in St Maarten. It is a complete dump with mostly bad areas.
100%!
Interesting, I was intrigued by there being a French side. And Maho beach seemed worth a stop. A friend did both last summer and thought that Anguilla did not have much beauty other than the luxury hotels.
I'm mostly wondering if Anguilla is worth the effort since Cayman is more convenient and definitely has the upscale vibe.
Anonymous
02/11/2026 08:09
Subject: Anguilla vs Cayman
Anonymous wrote:Anonymous wrote:Has anyone been to both? We love Cayman because of the beautiful beaches, great snorkeling, upscale hotels, safety, and convenience of nonstop flight. How does Anguilla compare? Seems like it would be fun to do a couple of nights in St Maarten and then a few in Anguilla though logistics are more complicated.
There is 0 reason to do St Maarten. You will want to get right to Anguilla once you land in St Maarten. It is a complete dump with mostly bad areas.
100%!
Anonymous
02/11/2026 07:59
Subject: Anguilla vs Cayman
Anonymous wrote:Has anyone been to both? We love Cayman because of the beautiful beaches, great snorkeling, upscale hotels, safety, and convenience of nonstop flight. How does Anguilla compare? Seems like it would be fun to do a couple of nights in St Maarten and then a few in Anguilla though logistics are more complicated.
There is 0 reason to do St Maarten. You will want to get right to Anguilla once you land in St Maarten. It is a complete dump with mostly bad areas.
Anonymous
02/09/2026 14:29
Subject: Anguilla vs Cayman
Anonymous wrote:We have been to both. Grand Cayman was busy, with a lot to do but had no cultural vibe. Did not have that "island feel" like many other Caribbean nations. The food was so-so and very Americanized.
Anguilla is beautiful, safe and had a distinct culture. The people are very kind hearted. The food is amazing. However, if you are a go go go type, this may not be the place for you. It’s very laid back, you won't find dance clubs, casinos, etc. You beach, explore, eat and listen to music.
Grand Cayman is beautiful, but I agree with PP that is has less distinct culture than other islands. The last time DH and I went we kept saying that it felt like we were in FL. We also lose on the exchange rate between USD-KYD so factor that into your planning once on the island.
Anonymous
02/07/2026 13:30
Subject: Anguilla vs Cayman
We have been to both. Grand Cayman was busy, with a lot to do but had no cultural vibe. Did not have that "island feel" like many other Caribbean nations. The food was so-so and very Americanized.
Anguilla is beautiful, safe and had a distinct culture. The people are very kind hearted. The food is amazing. However, if you are a go go go type, this may not be the place for you. Its very laid back, you won't find dance clubs, casinos, etc. You beach, explore, eat and listen to music.
Anguilla is beautiful, safe and had a distinct culture. The people are very kind hearted. The food is amazing. However, if you are a go go go type, this may not be the place for you. Its very laid back, you won't find dance clubs, casinos, etc. You beach, explore, eat and listen to music.
Anonymous
02/07/2026 13:28
Subject: Anguilla vs Cayman
Anonymous wrote:I’ve been to both. We took the kids to GC every year when they were young because it’s easy to get there and get settled, and there are tons of great condos to choose from. We did not stay at the big resorts there because they are crowded and not relaxing.
Anguilla is more rustic and less Americanized. Because you need an extra plane or boat ride to get there, it tends to be quieter. It has fantastic beaches (as does Cayman) and a surprisingly vibrant restaurant scene.
If your kids are older or you’re going as a couple, go to Anguilla. If your kids are very young, go to GC. If you’re foodies, go to Anguilla. If you want to scuba dive, go to GC.
You can fly direct to Anguilla now from East Coast.
Anonymous
02/07/2026 13:27
Subject: Anguilla vs Cayman
I agree completely with what the previous poster said. There are pros and cons to both. You drive on the left side of the road in both places, but the roads in Grand Cayman are much busier so it can take some getting used to.
Grand Cayman has everything you will find in the U.S. in terms of food, groceries, etc. Anguilla is less developed, but you can find some great food. Eat at Sharky’s if you go!
Cap Juluca in Anguilla is gorgeous. Kimpton Seafire Ain Grabd Cayman is great. Can’t go wrong with either island.
Grand Cayman has everything you will find in the U.S. in terms of food, groceries, etc. Anguilla is less developed, but you can find some great food. Eat at Sharky’s if you go!
Cap Juluca in Anguilla is gorgeous. Kimpton Seafire Ain Grabd Cayman is great. Can’t go wrong with either island.
Anonymous
02/07/2026 12:26
Subject: Anguilla vs Cayman
I’ve been to both. We took the kids to GC every year when they were young because it’s easy to get there and get settled, and there are tons of great condos to choose from. We did not stay at the big resorts there because they are crowded and not relaxing.
Anguilla is more rustic and less Americanized. Because you need an extra plane or boat ride to get there, it tends to be quieter. It has fantastic beaches (as does Cayman) and a surprisingly vibrant restaurant scene.
If your kids are older or you’re going as a couple, go to Anguilla. If your kids are very young, go to GC. If you’re foodies, go to Anguilla. If you want to scuba dive, go to GC.
Anguilla is more rustic and less Americanized. Because you need an extra plane or boat ride to get there, it tends to be quieter. It has fantastic beaches (as does Cayman) and a surprisingly vibrant restaurant scene.
If your kids are older or you’re going as a couple, go to Anguilla. If your kids are very young, go to GC. If you’re foodies, go to Anguilla. If you want to scuba dive, go to GC.
Anonymous
02/07/2026 11:54
Subject: Anguilla vs Cayman
Has anyone been to both? We love Cayman because of the beautiful beaches, great snorkeling, upscale hotels, safety, and convenience of nonstop flight. How does Anguilla compare? Seems like it would be fun to do a couple of nights in St Maarten and then a few in Anguilla though logistics are more complicated.