Need advice for starting sailing life/location

[TMay]

Hello all, first post, long time lurker.

Quick background: I grew up racing Catalina 25's and a Capri 15 in the PNW in the 80's and 90's. Mostly in the Columbia river with excursions to surrounding lakes and the San Juan Islands. Now a couple decades later I'm ready to get back into it and eventually get a boat of my own. However... I remember enough to at least know that boats come in all different kinds and are suited for different things with various pros and cons. So before I buy something, I want to crew on a bunch of different boats for a couple of years to get my skills up and hopefully be able to make a good first purchase. I'm going to be looking to move in a few months and need to figure out a good location, which is what I come to you for advice on. Here's what I want to do:

- Participate in club racing, preferably at least on a weekly basis
- Be able to experience a few different locations within a day or two drive
- Have access to sailing communities who are open to taking on crew members and where there will a variety of boats
- Setup roots in an area with an active sailing community with lots of cruising options, from East Coast to Bahamas and Carribean

I'm not interested in doing the PNW again, been there done that. Here's some locations I was looking at:

1. Chesapeake Bay area
2. Tampa Bay FL
3. Fort Myers FL
4. Jacksonville FL

Any thoughts on those places? Any obvious choices I missed? I didn't include Miami because I think it would just be too big for me. Any advice would be appreciated. thanks

[BlackOak]

Annapolis Maryland is the mecca for sailing on the east coast. Sailing is a way of life for many on the Chesapeake Bay.

[MicHughV]

Most any place on the Florida coast...east or west....would be good.
Bahamas is a mere 50 miles away from south-east Florida....'jes sayin'...

[Chotu]

Tampa and Fort Myers.

I travel a lot. I’m a full time traveler. I’ve been and lived in countless places. Both of these cities have a lot to offer. Tampa (St Pete) probably wins with more sailing, but I love fort myers overall too.

I spent a fair amount of time in Gulfport, a small part of St Pete. Wonderful little neighborhood right on the water.

[OldManMirage]

I'm in Jacksonville and my boat is at the Rudder Club. Sailing in Jax is mostly river sailing on the St. Johns in the areas south of downtown. To get to the ocean is a several hour trip that's affected greatly by which way the tides are running.

That said, it's a nice area to sail, I've been boating here for 30 years now. The Rudder Club is also pretty active with a lot of stuff, and they have the yearly Mug Race.

[Chris Cringle]

Chesapeake Bay

[Auklet]

Originally Posted by TMay

Hello all, first post, long time lurker.

Quick background: I grew up racing Catalina 25's and a Capri 15 in the PNW in the 80's and 90's. Mostly in the Columbia river with excursions to surrounding lakes and the San Juan Islands. Now a couple decades later I'm ready to get back into it and eventually get a boat of my own. However... I remember enough to at least know that boats come in all different kinds and are suited for different things with various pros and cons. So before I buy something, I want to crew on a bunch of different boats for a couple of years to get my skills up and hopefully be able to make a good first purchase. I'm going to be looking to move in a few months and need to figure out a good location, which is what I come to you for advice on. Here's what I want to do:

- Participate in club racing, preferably at least on a weekly basis
- Be able to experience a few different locations within a day or two drive
- Have access to sailing communities who are open to taking on crew members and where there will a variety of boats
- Setup roots in an area with an active sailing community with lots of cruising options, from East Coast to Bahamas and Carribean

I'm not interested in doing the PNW again, been there done that. Here's some locations I was looking at:

1. Chesapeake Bay area
2. Tampa Bay FL
3. Fort Myers FL
4. Jacksonville FL

Any thoughts on those places? Any obvious choices I missed? I didn't include Miami because I think it would just be too big for me. Any advice would be appreciated. thanks

SW Florida (Clearwater to Key West) is probably the overall best sailing venue of FL; very active. Many yacht clubs, sailing clubs, marinas, and anchoring destinations. Tampa Bay is very large; so lots of sailing and anchoring there in sheltered waters. FL has become a very popular destination for a “new life” the past 10-15 yr, so some research/planning is well advised. Costs of anything/everything on or near the water are up of course.

Folks make trips from St Petersburg to Dry Tortugas, Key West, and Bahamas frequently. There is a proven route from there into the Caribbean Sea as well. Active racing in season, October to April. There may be crew opportunities.

[Old Bay]

Chesapeake Bay.

[thomm225]

The Chesapeake Bay is the perfect place to perfect your sailing skills especially the lower Bay.

You can sail North of Cape Charles and have smoother conditions or if you would like to see how your stomach can deal with ocean swell you can sail South of Cape Charles where on some days you have a mixture of bay waves riding on ocean swell.

Then for a test of you and your boat out in the Atlantic Ocean you can sail the 16 miles Offshore to Chesapeake Light and back.

Also down on the Southern Bay, you can find isolated places to anchor within 3-5 hours of Hampton Roads.

The Bay is nearly 30 miles wide in places like up near Tangier Island. Onancock, VA to Reedville, VA is close to the widest section.

Usually once passed the Thimble Shoal Ship Channel which is about 5 miles off, you pretty much have it to yourself.

You will see ships and other boats but many times can stay miles away

Chesapeake Bay Entrance

https://www.charts.noaa.gov/OnLineViewer/12221.shtml

Chesapeake Light

https://www.ndbc.noaa.gov/station_pa...?station=chlv2

[Auklet]

Originally Posted by thomm225

The Chesapeake Bay is the perfect place to perfect your sailing skills especially the lower Bay.

You can sail North of Cape Charles and have smoother conditions or if you would like to see how your stomach can deal with ocean swell you can sail South of Cape Charles where on some days you have a mixture of bay waves riding on ocean swell.

Then for a test of you and your boat out in the Atlantic Ocean you can sail the 16 miles Offshore to Chesapeake Light and back.

Also down on the Southern Bay, you can find isolated places to anchor within 3-5 hours of Hampton Roads.

The Bay is nearly 30 miles wide in places like up near Tangier Island. Onancock, VA to Reedville, VA is close to the widest section.

Usually once passed the Thimble Shoal Ship Channel which is about 5 miles off, you pretty much have it to yourself.

You will see ships and other boats but many times can stay miles away

Chesapeake Bay Entrance

https://www.charts.noaa.gov/OnLineViewer/12221.shtml

Chesapeake Light

https://www.ndbc.noaa.gov/station_pa...?station=chlv2

Sounds wonderful, but I’ve heard it can be uncomfortable at sheltered anchor b/c of biting insects. Along the SW coast of FL behind the barrier islands they generally are not a problem b/c the sailing season begins in the fall (October) with lots of wind around. Sail through the winter into May.

[dfelsent]

Don’t forget about New England. Long Island sound, Narragansett Bay, Buzzard’s Bay, Mass Bay, Boston Harbor, Marblehead/Salem/Beverly/Gloucester, Portsmouth and the Maine coast

Lots of active sailing racing and cruising communities

[thomm225]

Originally Posted by Auklet

Sounds wonderful, but I’ve heard it can be uncomfortable at sheltered anchor b/c of biting insects. Along the SW coast of FL behind the barrier islands they generally are not a problem b/c the sailing season begins in the fall (October) with lots of wind around. Sail through the winter into May.

I’ve never experienced an insect problem at anchor along the lower Bay.

[TMay]

Thanks all for the inputs.

I took a hard look at SW Florida. Would have been nice to be sailing out of St. Petersburg and be based in Lakeland. But as I looked into the housing/insurance/hurricane situation, I felt like it just wouldn't be sustainable to live there.

So now I'm looking at Chesapeake Bay. Annapolis would be cool of course, but is expensive. Looking hard at Virginia Beach - anyone have any experience with that area in particular?

Any racing club recommendations off the Virginia side of the Bay?
How bad are the crab pots and obstacles around there? Is it stressful trying to get around in the bay?

thanks

[TMay]

Originally Posted by dfelsent

Don’t forget about New England. Long Island sound, Narragansett Bay, Buzzard’s Bay, Mass Bay, Boston Harbor, Marblehead/Salem/Beverly/Gloucester, Portsmouth and the Maine coast

Lots of active sailing racing and cruising communities

I think New England would just get too cold for me. Maybe those could be summer cruising destinations?

[TMay]

Originally Posted by MicHughV

Most any place on the Florida coast...east or west....would be good.
Bahamas is a mere 50 miles away from south-east Florida....'jes sayin'...

That would be nice. One thought that's been sticking in my mind is how much easier it would be to have a trailerable sailboat that I could just drive down to Miami in a day or two, rather than sailing all the way down. Then I could just unpack, supply up, and cross the gulf stream when the weather window is right. The concept of trailering has me leaning towards corsair trimarans, but I'm trying to avoid fixating before I get the chance to try different boats.