My boyfriend and I (both in our late 20s) are planning a caribbean vacation for february 2010. We are having a hard time picking out "the best" island or two to visit. We might stop in Key West and/or Puerto Rico. Flights are not an issue (he's a pilot, so we go standby). We like to snorkel, do some hiking, enjoy good seafood, and want to see the best/most beautiful beaches. Relaxation is the name of the game this trip. Beachfront accomodations are always nice, but might be cost prohibitive for us.

I appreciate any and all insight. Happy Holidays!!

If you want to island hop consider going to either the US or British Virgin Islands. They are all in close proximity to one another and it's very easy to travel between islands on regularly scheduled ferries. These islands, by and large, have excellent beaches, lots of terrific dining options, access to very good snorkeling and plent of places to hike. You'll also find accomodations in all price ranges. In short, they offer everything on your list of desires.

I love Key West, but it really isn't a beach destination. In February, I'd head much further south.

Great hiking on both Grenada and St. Kitts/Nevis. Grand Anse beach on Grenada is beautiful.

Although, your phrase 'best/most beautiful beaches' might means Anguilla for you, although I've never been.

True, Anguilla has some of the "best/most beautiful beaches" in the Caribbean if by that definition you mean sugar white sand beaches lapped by torquoise waters but the island is relatively flat, scrubby and featureless and the beaches lack any significant natrual vegetation. The island also ack any meaningful hiking opportunities.

For hiking OP really should be looking at mountainous islands rather than the flat coral/limestone based islands such as Anguilla. The trade off is mountainous islands usually have smaller cove-like beaches with darker colored sand ranging from gold to brown to even black rather than the longer strands of white sand found on the flat coral/limestone based islands. Quite honestly, the beaches on the hilly lusher mountainous islands are often much more picturesque because of the abundance of natural vegetation along the edges of the beach.

Thanks for the helpful suggestions! We were considering St. Lucia, but no one has thrown that out there... thoughts?

Also -- what's your favorite island and why?

I agree with RoamsAround on the USVI and BVI. We just got back from them and really enjoyed it. Virgin Gorda has a peak you can hike and Tortola seemed like it might offer some hiking opportunities.

agree with us/bvi. i'd suggest st. john usvi. try the westin. if you're budget is really tight you might be able to get campsites at: http://www.cinnamonbay.com/home.html or http://www.maho.org/
or rent a one bedroom villa. great snorkeling from any one of dozens of gorgeous beaches. good hiking in national park. fairly laid back island and not hard to get to.
no one is mentioning st. lucia because the snorkeling is not that good.

also you can day trip to any of bvi or st. thomas. island hopping from st. lucia involves flights instead of relaxing ferries.

Agree with Virginia - St. Lucia doesn't lend itself to "island hopping".

On the contrary, it's particularly easy to hop from St. Lucia to Barbados. It's a short, easy flight, and if you stay near the Rodney Bay area of St. Lucia and the Gap area of Barbados, you can easily do this with a minimum of travel time.

Having said that, I'm not sure that either island would work for you in terms of budget, but there are some smaller hotels in Rodney Bay from which you can walk to the beach, and the Gap is one of the cheaper parts of Barbados.

But clearly, island hopping is much easier if you base yourself on Antigua (where Liat flies everywhere), the Grenadines, St. Maarten, or the USBVI.

So many good ideas - I really appreciate it! I will definitely do a little more looking at the VIs.

We fly American/American Eagle for the standby deal.

Another thought is that we don't really love super touristy spots, but still want to feel safe.

We're not really campers (although of all places to do it, the caribbean is probably pretty great). Thinking we'd like to stay under $200/night. Less than $150 would be even better

Keep in mind, Feb. is the height of peak season, the most expensive time to go. For that budget, you may want to consider Mexico, and maybe add Belize and/or Costa Rica.

For Feb., Anguilla, Virgin Islands and Barbados are probably out of your price range.