Yan 

Northern Japan. Good roads, great scenery. Very comfortable tourism infrastructure, but not cheap. I liked it more than cycling in the Bay Area or in Colorado.

Here's a photo from the ride up Mt. Azuma in Fukushima.

Bob Ross

LOL! It seems like every time one (or several) of our cycling friends from NYC come to Tucson we say "Hey, you're welcome to stay with us!" and without fail they all say "Thanks, but we're staying with Cycling House!" And they all rave about the riding with that gang.

Steve B.

A significantly hillier endeavor. MANY more hills. And has some of the same issues of Nachez in that the locations for lodging and eating are sometimes a ways off the Parkway and in this case, down off the parkway.

merlinextraligh

I’ve done both and no doubt there is a lot more climbing on the BRP, and lodging choices can be limited. However, I think there are a number of more interesting lodging choices on, or near the BRP, than the Natchez Trace.

Pisgah Inn, Switzerland Inn, and Peaks of Otter are all directly on the BRP, and each are neat places to stay. Asheville is a pretty easy on and off and has many hotel restaurant options.

Floyd Virginia is a relatively easy on/off, has a nice hotel and is a great live music scene.

On the Skyline Drive, there are several neat lodges directly on the drive.

With a second home in Asheville, I’ll admit my bias, but I’d take the BRP/ Skyline Drive ten times over Natchez

Pantah

Born and raised Bay Area, been in the Northbay since 1990, most of it in Santa Rosa (and currently in Santa Rosa). I've been biking here my entire life. I have not found drinking and driving to be anything outside of what you would expect for any city. Maybe be aware on Highway 12 between Santa Rosa and Sonoma where there are vineyards and wineries the entire drive and the same for Dry Creek Road, but that's it and most of that doesn't make for interesting cycling. Once you get off the main roads and onto the back roads, that's where it's at. My favorite is up in the Coast Range between Santa Rosa and the coast, known locally as West County. That's where a good chunk of all the routes for Levi's Gran Fondo go through.
Go east of Santa Rosa and you'll be up in the Mayacama mountain range where there are excellent climbs and stellar views to go with it. Many of the roads that were in terrible condition have been repaved over the last 3 years so riding has improved greatly.

I did a 50 mile ride out of my front door in downtown Santa Rosa on Sunday up into the Mayacamas and my total elevation gain was 3700 feet. I can match that easily out in West County.

There's plenty of places to stay like hotels, bed and breakfast type places and Air BnB. You can fly in from anywhere to San Francisco or Oakland and take any combination of bus, ferry and train from there. Some airlines do fly straight into Santa Rosa, the municipal airport is quite large and can handle moderately big passenger jets, though you won't see any 747's flying in.

There's quite a few bike shops in the area, though I honestly don't know offhand which ones provide rental services since I own a bunch of bikes and always do my own service, but I'm sure most here do rentals.
The most well known names for shops in Santa Rosa are Bike Peddler, Norcal Bike Sport and the Trek Store while the two larger companies with a decent bike section are REI and Sports Basement. There are more, smaller shops that are dotted around but I don't know them well and some are service or sales only.
If you head out west into Sebastopol, there is Sebastopol Bike Center.

If you're into mountain biking, there are trails all over Annadel State Park and the basically attached Spring Lake Regional Park as well as Taylor Mountain Regional Park not far away. However, I will say that heading south to Marin County, home of Mount Tamalpais where mounting biking was born, has far superior mounting and gravel biking options. One could also rightfully argue that the road biking down there is better as well. San Rafael, Fairfax and Mill Valley are hotspots for cycling and deserves its own separate post.

Chandne

Colorado has some amazing alpine rides near Breckenridge/Vail and also near Aspen. Truly stunning and lots of food/lodging options. Additionally, Moab Utah has some killer scenery as well and low traffic.

terrymorse 

Yes, another of my favorite areas for cycling. Frisco or Breckenridge are decent base camp spots, and Aspen is good for a few days. Finish off the trip with an epic ride up Mt. Evans Blue Sky.

Chandne

Ah yes, Mt. Blue Sky is iconic, practically. I actually bought a little place in Breckenridge so we could spend most summer and autumn weekends there. I do lots of road and mountain biking around there. My little boy (he is almost 5) is addicted to Breckenridge. He packs his little backpack every Thursday and boy, do I hate disappointing him when it comes to that! The road biking there is so much nicer than around Denver though I do live close to the amphitheater so the traffic is good and I can access a lot of the climbs out west. Frisco is another great basecamp for sure! Aspen is just magical to me, though I am a bit of a John Denver fan too! Not all but maybe 4-5 songs make me dream of the mountains

aliasfox

Another vote for San Francisco Bay Area. From south to north, Carmel, Monterey, Santa Cruz, San Jose, San Francisco, Sausalito, and Sonoma/Napa wine country are all within 2hrs driving, so the family will have plenty to do - hiking, shopping, eating, amusement parks. Beaching, tourist spots, wine tasting. All available. As for riding:

On the peninsula (where I'm at), between San Francisco and San Jose
- The roads leading up to Skyline Dr. from Silicon Valley are all nice little climbs. Can start with the famed Old La Honda at 3mi @8%; or can tackle Kings Mountain, 4.4mi at ~7%. There are other options - Page Mill Rd, Big Basin Way, Montebello (gravel at the top). All will put a minimum of 3-400m in your legs just getting to the top.
- You can go down the other side to the coast and ride on the Pacific Coast Highway. If you do, you may want to stop in Half Moon Bay or San Gregorio for fluids and snacks, as there aren't that many places on that side. I've heard Duarte's in Pescadero has good pie.
- Coming back to the valley, Tunitas is a leg buster. La Honda (different from Old La Honda) is shallower, but longer
- If you stay along the ridge (Skyline Dr), you can catch a glimpse of both the the SF bay (eastward) and the Pacific (westward) at the same time, while you're barreling down towards Rt 92 at ~35mph. Careful though, M3s, Porsches, and Ferraris like playing up here, too.
- For a nice little warm up climb, consider taking one of the roads out of Redwood City up to Cañada Rd, which runs alongside the SF reservoirs. This time of year, it's lined in orange poppies. Jefferson, Farm Hill, Edgewood, and Crystal Springs (a little further north) are good options, and you get the reservoir view when you're up there

South Bay
- The aforementioned Montebello and Big Basin roads, as well as Hicks Rd, which leads to Mt. Umunhum. Haven't tried it yet, but I hear the views are spectacular at the top.
- If you want a long grind, the ride up to the Lick Observatory is 18mi at ~7%. Due to it being a construction access road for horses back in the day, it never gets above 8%, but it will get you about 1200m, IIRC
- The truly adventurous will start from the peninsula and make their way to Santa Cruz, which is about 50mi and 1300m in each direction, I believe (could be wrong on the elevation part).

East Bay
- Not as familiar, but I hear there are great rolling hills around Livermore
- Mt. Diablo

Marin, Sonoma
- Mt. Tam. An epic climb from Stinson Beach. You'll have hawks flying below you, with the Pacific Ocean in the distance.
- Sausalito is a bit touristy, but a good stop in the Marin Headlands for a coffee or lunch
- Sonoma State Park. Check out the routes for Levi's Gran Fondo for some good options. One of my favorite cycling memories is riding on the PCH here, as the early morning fog was lifting off the surf