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September 5, 2022 12:21 PM   Subscribe

What's the best Caribbean island(s?) for a mid-30s couple who are not really all-inclusive resort people?

We really like to travel, and we loved Puerto Rico (~eight or nine years ago -- we spent time in Vieques and San Juan, and drove out to Arecibo and El Yunque for a day each). We've also been to Key West a couple times and love the food and walkable streets and relaxed vibe. Where else in the Caribbean would be fun for us to visit?

For the purposes of this question, don't worry about flight times/connections or money.

Ideally we'd love a place with:
- a town/city that is interesting and safe to walk around, has restaurants, a street scene, etc. we are definitely city kids.
- historical/cultural sites to visit
- nice beaches for swimming/snorkeling
- easy-to-moderate hiking opportunities
- cool animals (birds, reptiles, others)
- day trips! like, maybe to other islands? or at least other parts of the same island?
- good transportation options (so, some place where we could rent a car, or that's mostly walkable/bikeable, or where cabs are easy to get and safe)

We don't really want/care about:
- nightlife (I have a hard 9:30 bedtime)
- being fancy
- all-inclusive resorts (I don't mind a resort to sleep at, but I'd like to have easy access to an actual town to go get dinner in, for example)
- places that are packed with cruise-ship folks

I know this info is out there but there are SO MANY islands and they all sound nice, so it's sort of hard to tell what would actually suit us. We are closer to the backpacker end of traveling, and a lot of the blogs we've seen are more geared toward honeymoon/family/extreme luxury types.
posted by goodbyewaffles to Travel & Transportation around United States (12 answers total) 48 users marked this as a favorite
 
Tobago has

- good beaches
- a lot of nature and birds (there's a rainforest!)
- some towns to walk around (Crown Point, Scarborough)
- car rentals, also if you just stand on the side of the road usually someone will offer to drive you wherever you're going and you can negotiate with them

If you stay in Crown Point you can walk to Crown Point / Pigeon Point beaches, also the airport is walking distance.
posted by oranger at 12:45 PM on September 5, 2022 [3 favorites]


Aruba absolutely fits everything you list. It also has very little poverty. It's owned by the Netherlands so people there can get free college / healthcare. South of hurricanes, day tips around aruba or to bonobos or Curacao. It's truly the best you could list.

The one thing it's missing is it's not suuuper walkable. Most people rent cars. The downtown is and the "high rise" area are walkable but most people that grocery shop use a car.
posted by bbqturtle at 12:50 PM on September 5, 2022


I think Grand Cayman would tick off most of those boxes. Plenty of lodging options from fancy hotels down to VRBOs.

The ecosystem and geography is a little more diverse than, say, the ABCs. Rent a car, it's easy to drive (although it's left-hand traffic) and explore. Skip the charter boat and drive to Starfish Point on your own. Visit downtown George Town on a day the cruise ships aren't around. There are a few nature reserves and parks worth hiking. Cayman Brac is more rugged and adventurous but you can only get there by air, no ferries are available.
posted by JoeZydeco at 12:56 PM on September 5, 2022


Seconding Tobago. Your travel style sounds very similar to mine and a friend and I had an incredible time in Castara on Tobago this March. We stayed at Castara Retreats, which was perfect. I wouldn't hardly describe it as "urban" but there's a little village to walk around with a few cafes and bars and there's some not too late island nightlife, which was very fun. Great beach right in front of the resort and tons of interesting day trips you could take to go birding, snorkeling, hiking, etc. Trinidad and Tobago are all the way down off the coast of Venezuela and getting there is a bit of an adventure, but it was pretty manageable from the east coast.
posted by fancypants at 2:23 PM on September 5, 2022


It's been forever since I've been, but I remember Dominica being very beautiful, both the coasts and the rainforest interior. I don't recall any big cities, but lots of good food regardless.

Alternatively, have you considered the Caribbean coast of Colombia? Besides not being an island, it ticks all of your boxes. And there are islands off the coast that you can catch a boat to, if the island part is really key
posted by coffeecat at 3:54 PM on September 5, 2022 [1 favorite]


I was in Trinidad almost 20 years ago but loved it. I stayed in a B&B in someone's house. Amazing beaches, delicious fruit and seafood and food in general, steel drum bands practicing all around, and lacking in the agregious post colonial dynamics very prominent elsewhere in the Caribbean. I don't know what's changed though.
posted by latkes at 4:25 PM on September 5, 2022


OK, not the Caribbean, but Panama City. Great walkable old town, easy-to-get-to hiking with great nature ($2‐20 Uber ride, depending on where you want to go), a day trip to beautiful San Blas islands in the Caribbean, a nice waterfront walkway/bike path that will keep you busy for 2 evenings, amazing food for ALL budgets, a few great historical museums, and, well, the canal locks lookout. Each neighborhood is pretty walkable but the city is so big you do need to Uber between neighborhoods if you want to get out of the touristy old town. $2-5 a ride to most places within the city. You do have to know spanish a little bit to get around.
posted by never.was.and.never.will.be. at 4:55 PM on September 5, 2022 [1 favorite]


I highly recommend Barbados. It has pretty much everything you're looking for. Beaches, nature, restaurants, historical sites, plus Bridgetown is decently sized. Also, it is less touristy than most islands because it doesn't really have mega-resorts/hotels.
posted by Conrad Cornelius o'Donald o'Dell at 8:31 PM on September 5, 2022 [1 favorite]


Also not an island, but the Yucatan peninsula checks all your requirements, although you'd have to split up the trip between beaches/towns/sights. You can fly into Cancun but probably don't want to stay there long, if at all.

-a town/city that is interesting and safe to walk around, has restaurants, a street scene, etc. we are definitely city kids.
Merida, and some smaller cities
- historical/cultural sites to visit
Mayan ruins, among others
- nice beaches for swimming/snorkeling
Self explanatory.
- easy-to-moderate hiking opportunities
It's flat, so no mountains, but still hiking
- cool animals (birds, reptiles, others)
yep
- day trips! like, maybe to other islands? or at least other parts of the same island?
Like I said, it would make most sense to travel around, but you could stay on the coast and do day trips inland if you wanted to sleep in the same place every night.
- good transportation options (so, some place where we could rent a car, or that's mostly walkable/bikeable, or where cabs are easy to get and safe)
When I was there many years ago, I just picked up a car at the Cancun airport and drove around.

Caveat: I have seem some reports of growing crime, but don't know if there's really anything to be concerned about. You should research it to make sure you'd be comfortable.
posted by Mr.Know-it-some at 6:38 AM on September 6, 2022


St Martin ticks your boxes. There are cruise ship days, but it's quite easy to avoid them since there are plenty of beaches that aren't on the cruise ship packages. I'd recommend staying in Grand Case on the the French side, but doing your grocery shopping on the Dutch side.
posted by Runes at 7:05 AM on September 6, 2022


A little to the side of your question - when I went in late 2021, each individual island had it's own covid requirements around both entering and exiting, because each is it's own independent nation.

I thought it would be super easy to simply take the ferry from one island to another. Luckily I realized the time and expense that would be before my trip, and simplified my plans. Leaving the french Dominica required setting an appointment to wait in line for 90 minutes for a test the day before I was scheduled to depart.

I don't know the requirements now.
posted by jander03 at 8:22 AM on September 6, 2022


St Martin isn't as nice or safe as the neighboring islands, Anguilla and St Barth, but it makes a decent base for excursions which are easy by ferry or inter-island plane. You'll have to take a rapid antigen Covid test to enter Anguilla, but it has incredible beaches and great restaurants – Meads Bay offers both. From the French side of St Martin you don't need a Covid test to enter St Barth since you're already "in France", and the main port town Gustavia has good restaurants and cafés and a world-class street scene – the restaurant at the Carl Gustaf hotel has terrific food and ambiance and an incredible view over the harbor. Gustavia has a very active nightlife but it starts after you're abed.

If you stay in Grand Case try the Grand Case Beach Club – it's on a promontory at one end of town and has its own beach and casual restaurant. The next bay over is Anse Marcel and has a nice hotel but no "town".

Or, depending on your budget and adventurousness, a crewed catamaran charter can be about the same per-night as a nice hotel room – and you can take it with you!
posted by nicwolff at 11:55 PM on September 6, 2022


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