Where to find a romantic charter in Key West?

March 2, 2006 5:44 AM

Kayaking / picnic / romance suggestions in Key West. We're heading down in April, and I've promised her a day of activities in Key West for her birthday. Ideally, a chartered sailboat, a lot of kayaking, and a picnic lunch on some kind of small island. Having a naturalist on hand (or just an old salt) to explain what we're seeing would be nice, too.

I've googled a ton of charter sites, kayaking sites, etc. (and read past threads on AskMe) but can't figure out how to jigsaw this all together- plus I have no idea who's good and who's not good. Any Key West natives or frequent travellers who can point me in the right direction?

posted by bobot to Travel & Transportation around Key West, FL (5 answers total)

I don't know what kind of accommodations you have, but a lot of the small hotels/B&B's in Key West have referral agreements with a few sailing companies and can offer you discount coupons. In addition to whatever recs you get here, it's probably worth calling up your hotel and asking them who they would recommend; Key Wester's are an extremely helpful lot, especially when it comes to showing folks the best ways to enjoy their town.
posted by junkbox at 5:57 AM on March 2, 2006

I'm happy to shill for a schooner company I sold tickets for a few years ago, feel free to drop me an email, as I grew up down there and can answer a lot of these questions, but need to know more about what you specifically want/need.
posted by bilabial at 6:24 AM on March 2, 2006

It's not Key West proper but I can't help but mention Pennekamp State Park in Key Largo. I have great memories of kayaking through the mangroves there and good but slightly nauseous memories of the glass-bottom boat ride. The picnicking is pleasant, there's a little sandy strip, room to wander around in, and it's just a really nice place. (Both times I went we drove down from Miami specifically to go there. It's a lot of fun.)
posted by whatzit at 10:51 AM on March 2, 2006 [1 favorite]

Funny, I was just there two weeks ago. We stayed in the Center Court cottages run by Key West Vacation Rentals. That company has a pretty good concierge service to help set up these events.

The south side of the island has some pretty nice public beaches with picnic areas, but the "shelters" are usually taken by homeless/vagrants (from what I saw). The Dolphin Research Center on Marathon is a little touristy, but still pretty nice.

Simonton is a good street to stay on, in general. It's close to a lot of the neat things to see, but not as loud as some of the others. Bikes are a way better rental investment than a car. You can get to most of the island easily--many times faster than a car, and you don't have to fight for parking and pay $1.50/hr for parking. There are good big grocery stores not far from the airport end of the island, but there's a nice little one called Faustino's close to the touristy district, 1 block off Simonton.

Pretty much every restaurant is going to run at least $20 a head for even a light meal. We ate many of our dinners in (those cottages had functional kitchens), the cost of that was like $5 per meal with copious amounts of wine.

We talked to an officer for a little while and Spring Break is not the greatest time to be there.

We did not take boat trips, but there are a lot of options advertised widely that offer something along the lines of $45 a head for tours, usually throwing in free beer. Sunset tours abound as well.

There is a butterfly conservatory which is pretty nice--wish I could've spent more time there (fussy child). They have some fairly typical species for more butterfly farms, but they also have a few unusual ones, like Atlas moths, which are astounding to see in person.
posted by plinth at 6:06 PM on March 2, 2006

What about snorkling or diving? Key West is gorgeous with the strange critters and sea life.
posted by 45moore45 at 7:42 PM on March 11, 2006