Destinations

Aside from KeyWest.

1. Exumas- Staniel Cay up to Highbourne- beautiful, a wide variety of things to do (but all nature related)
2. Charleston, SC.- Beautiful town, the ride up from GA to Charleston is Beautiful on the ICW. The town has many historic things to do as well as a wide variety of great food and great shopping.
3. Key West- For reasons you mentioned
4. St. Michaels, MD- beautiful, great food/sights.
5. Ocean City, MD, it's a fun city with good marina's, lots of stuff to do on the boardwalk......
St. Augustine- can also be nice with the fort, cobblestone streets, restaurants, shopping.

I second Ocean City MD. The boardwalk is right out of the 1960's and lot's of fun. Last time I was there was a week before Superstorm Sandy.

Fernandina Beach FL. Last year we pulled in during the Shrimp Festival and it was insane. The 70's soft rock band Firefall was playing a concert on the grass next to the marina and the town was in full party mode.

West coast of Mexico stay away from the big tourist ports and instead check out Barra de Navidad - and if you get that far don't miss Baja. Everyone knows about Cabo but what you really want to see is the Sea of Cortez - it is like no place else on earth. Start your trip out of La Paz.

Absolut favorite are the exumas... Nothing comes close to teh variety and number of anchorages and scenery along with the privacy and lack of crowds. If there is one such area where you make good use of being on a boat, this is it.

It is also easy to get to, safe and nicely sheltered so you dont have to worry about anyone getting sea sick

But i wouldnt restrict to the highborne - staniel stretch and include the southern exumas as well, especially rudder, lee stocking, rat, etc which have some spectacular anchorages and even fewer boats. 6 to 7' draft is the limit down there though.

Everybody ve taken there over the years has loved it, including those who ve travelled to the top vacationing spots in the world. Heck, i lived on st barths for 13 years and find the exuma much better cruising grounds than the NE carib.

As far as one town destinations, newport RI obviously, Nantucket, Annapolis, Savannah and charleston. There are many other great little towns along the east coast, all accessible by boat, incl fernandina beach and cumberland island with its wild horses.

Personally i find the keys to be nice in a small boat, under 50' and 5' draft, but way too limited in anything bigger. The tourist trap known as key west is best visited by car , really no point going there by boat.

We tried going a couple of years ago, 6' draft was a bit tight from what they said. I think it was $8 a foot but plans changed and we never made it. It is a very nice little island but probably best enjoyed staying at the resort.

Everybody has their own criteria when it comes to favorite place or cruising style so obviously we all going to come up with different places.

Mines are...

- water I can get in and enjoy. If it s too cold, murky, brown... I m not interested! So off the list goes most of the east coast, north of biscayne bay
- there has to be a variety of things to do, of places to explore. No just a one destination place like the Dry Tortugas or the Florida keys which with any decent size boats have little to offer.
- must be fairly sheltered so you don't get beat up between spots. I may be a little lazy but having to spend an hour securing everything is a pita. Give me some flat protected waters, will you?
- distances between places have to be pretty short. My time (or the guests') is precious so spending 3 or 4 hours underway is mostly a waste of time.

These last two basically eliminate most of the Caribbean and that s why the exumas are at the top of my list.

NOw don't get me wrong, there are some great spots in New England, if you can get there between August 10th and sept 5th so you can get in the water for 5 minutes at a time without going into hypothermia. I love Newport and Bristol.... mystic or fishers sound. Cuttyhunk is great to spend a couple of days. Woods hole is as scenic as it gets and a night or two in Hadley Harbor, if you can fit in, is a must. Nantucket is beautiful.. Love it. Martha s vineyard, well, first of all there are too many tourists as the ferries are easier to get on, including a well known family from Chicago . But again, New England is only enjoyable for a couple of weeks a year or you will freeze your behind...

Anchoring vs marina is an interesting question. Personally I prefer spending more time anchoring out than being in a marina. While on charter we usually combine both and almost all the guests we ve had on board end up preferring anchoring vs docked. More privacy, better views and a special feel are what guests come up with when I ask them which they preferred. Obviously it comes down to picking the right anchorage with good scenery, protection etc. Not just anchor anywhere.