Hello! Myself (30m) and my girlfriend (29f) are looking for a new destination this year. Typically we spend a few weeks of our winters on the west coast of Florida, but due to the bad hurricanes, our typical destination is still a bit underwater.

We live in Boston so the warm weather is a must during the short dark days of January and February. We are not backpackers. We like to go out for a nice meal, love the beach, love to golf, and don't mind an adventure on the side. Girlfriend also does enjoy some shopping.

I've been to Puerto Rico in the Caribbean which I really loved, I also speak good Spanish so wouldn't mind dusting that off in another Spanish speaking country. But I think my girlfriend wants a bit more of a "destination" if you know what I mean. Let me know what you think!

Hi,

Plenty of choice. It will all depend on choices:
rural v urban
resort feel v local
All inclusive v boutique
adventure v beach peace
luxury v shoestring (or in between)
one island v island hopping
departure spot (some prefer direct flights)

Enlighten!

Sorry, no, I’m not clear what you, or rather she means by destination.

To add to the good list above I would add

hotel vs self catering
spa on premises or not
what type of activities - and is that on premises or somewhere on the island
rent a car, or rely on public transport, or taxi, or walkability
exclusivity vs open to the public (such as beaches)
humid (green/jungle) or arid
water sports? Motorized, or not?
Flights - connection or. On-stop?

A hotel on the 7 mile beach or on the Cliffs in Negril Jamaica
https://www.tensingpen.com/ is pretty wonderful

Budget would be most important.

And what does "adventure" mean?

Budget - $4-5k total for two people, thinking 3-4 days.

rural v urban - Urban
resort feel v local - Resort
All inclusive v boutique - Boutique
adventure v beach peace - Beach peace
luxury v shoestring (or in between) - slight lean to luxury
one island v island hopping - one island
departure spot (some prefer direct flights) direct fo sho, from Boston

hotel vs self catering - self
spa on premises or not - a +
what type of activities - and is that on premises or somewhere on the island - on premise - really just golf, beach, and somewhere fun to go out. nothing crazy, just bars / restaurants
rent a car, or rely on public transport, or taxi, or walkability - rely
exclusivity vs open to the public (such as beaches) - exclusive
humid (green/jungle) or arid - arid
water sports? Motorized, or not? - wtf is a motorized water sport
Flights - connection or. On-stop? - non stop!

thank you for all your help!!!!!!!!!!

For me, the island that comes to mind is Aruba. Most other islands in the Caribbean are more jungle & humid. For self-catering I really like the Oceania residences - you can find units for rent on many different sites - here's one example on VRBO. https://www.vrbo.com/172892ha but there are many other sites. I've used this one https://www.bocobay.com/

For any self catering I find it convenient to have a rental car to be able to get to the supermarket to buy food. It's about a mile if you want to walk.

Motorized water sports are jet skis & parasailing. Some people love them, others want a more peaceful surroundings.... Non-motorized includes SUP & kayaks. All beaches in Aruba are public/not exclusive. Facilities on an individual property like pools, etc are not open to the public.

Personally, the Grand Cayman would be my top choice—it offers a little bit of everything. We always stay at the Kimpton Seafire (I prefer it to the Ritz), but the Ritz does have a golf course you can enjoy while she relaxes on the beach or shops. The island also has fantastic restaurants and plenty of activities. Let me know if you have any specific questions! Another great option is the Fairmont Mayakoba (or any hotel in the Mayakoba area). It features an excellent golf course, delicious food, stunning hotels, and a beautiful beach.

Aruba sounds like it’d be perfect for what you're after! It has the sunny, dry weather, and a good mix of resorts with a laid-back vibe. You’ll find beaches, golf, and plenty of places to eat and drink, plus it’s easy to get around. Great spot to relax without feeling too crazy.

As soon as you said "arid", I thought of Aruba. It fits all your requirements.

If you don't have a passport, the US Virgin Islands is the place to go. It is part of the US and it is easy to get to. There is also a direct flight from Boston on Jet Blue. No lay overs.