I’m turning 50 in July, and while I’m not terribly oppressed by the aging process I really don’t like to spend my birthday at home. There’s just so much awkwardness. Do we throw a party? Do we pretend it’s not happening? And why does no one seem to understand that the best birthday cake is dark chocolate with vanilla buttercream (or gobs, gobs are always good)?

We thought we weren’t going to be able to leave town for this big milestone and it was getting me down. We started planning to go somewhere great a week or two later, or maybe have some sort of extra-special trip in November to make up for it. Here were the criteria:

1. Limpid blue water.
2. Lots of fun, sporty things to do: snorkeling, biking, kayaking.
3. If possible, outside the U.S. I feel like we’re wasting our passports if we don’t use them.

I started going through my huge library of bookmarked vacation properties. St. Bart’s? In the offseason it’s super cheap as long as you don’t start eating too many fancy meals, and you can go around pretending to be a movie star. A fat, 50 year old movie star. Whale sharks? But we were in Mexico just last year.

Narrowing it down based on snorkeling, I started looking at the Caymans, Roatan, Eleuthera, and St. John. Then I threw Jamaica in just for the hell of it because we stayed on the Negril cliffs for a long weekend a couple of years ago, absolutely loved the people and food, and are itching to go back.

Grand Cayman? Holy crap is it expensive, and beaches lined with high rises don’t really appeal. But Cayman Brac looks like our kind of place. It has great snorkeling, most places provide free bicycles and/or kayaks, and there are really cool caves and a parrot sanctuary. I could break my lodging for $100 or less per night rule to stay at Winta Cottage. It’s a house on stilts!

But they serve sea turtle on Grand Cayman (farmed, but still) and even the cheapest island is still a little pricey. Maybe spring break sometime?

And then Roatan. We’ve been thinking of going for years. It’s supposed to be one of the top two places for snorkeling in the Caribbean, right up there with Bonaire (which we’ve also been thinking of for years). There are plenty of reasonably priced places to stay, but it has a reputation as one of the buggiest places around. Google “roatan sand fleas” at your own peril. We’d still like to go, but not in the rainy season. No way.

Eleuthera…well, it’s just the prettiest word. And they know a thing or two about conch in the Bahamas. I’ve had my eye on a little complex of cottages in Gregory Town, five minutes walk from the Friday night fish fry, for years. But then I found Take Ya Time cottage.

A golf cart and two kayaks, that view, and $110 a night? I would love to barrel around the Bahamas in a golf cart. Unfortunately Rainbow Bay seems to be the equivalent of a newly built subdivision in the U.S.

So, Jamaica? My original idea was to fly into Kingston, rent a car, drive to the Great Huts and spend a few days, then gradually work our way back along the north coast and fly home from Montego Bay. But I’ll admit it: I’m afraid to drive in Jamaica. Those people are nuts.

So if we stayed in one place, Treasure Beach seemed like a good option and in the low season we could even afford to stay at Jake’s. The only problem is that I really don’t like to spend an entire week eating out for every meal, and we’d end up spending quite a bit on excursions and such: looking at crocodiles in the Great Morass, trying to make it to Little Ochie’s to eat in a boat on the beach, drinking at the Pelican Bar. I mean, look at the Pelican Bar. Just look at it.

I’d want to be there every day. But maybe Treasure Beach would be a better group vacation? Jamaica is a place I want to share.

Meanwhile, it turns out that Buck will be able to take my birthday week!

To be continued…