My fiance and I are heading out to San Francisco for our destination wedding in early August. It will be us, my fiance's 13-year-old son, and 5 other couples - couples include our parents and friends. Two people in the group have been to SF a number of times, but it's the first time for everyone else. We're all flying out together and will arrive around lunchtime on a Thursday. We'll all be together until Sunday morning when some people fly back, some will stay in SF to explore some more, and my fiance and I will split off and start the honeymoon portion of our trip. I have included a rough outline of our itinerary below. I'm curious about finding kid-friendly options for vineyards in Napa, must-see or must-do activities in SF, and tips for the Monterey/Carmel/Big Sur part of the trip. We also love food and views, so any restaurant/rooftop bar recs would be appreciated. We'll be on a budget so please keep that in mind (not pinching pennies, but we also don't want to spend $100 for a wine tasting or $250 on a dinner).

Thursday:
Arrive at SFO at 11:30am
Get marriage license at City HallExplore if there is time, probably around 5pmStaying somewhere between Union Square and City Hall

Friday:Wedding early morning at City Hall (11am)
Wedding photos until 1pmGrab rental vans, head to American CanyonWith our budget and number of people, we found two rentals in American Canyon just a 3 minute walk from each other. I know it's not ideal, but it's what we were able to work out. Unload, refresh, etc.
Dinner at Brix in Napa

Saturday:

Vineyard tours, currently no set plansNeed recommendations for vineyards that allow visitors under 21 years old

Sunday:
Head back into SF early morningWe split off from everyone else Sunday morningSightsee in SF
We are staying near Union Square

Monday:
Sightsee in SFA few things we want to see/do while in SF:Alcatraz
Embarcadero
Ferry Building
Exploratorium
Crissy Field
Alamo Square
Cupid's Span (just seems fitting)
Cable cars (California Street?)

Tuesday:
Rent car, sightsee on drive to Monterey
Explore the Monterey/Pacific Grove areaStay in Pacific Grove

Wednesday:
Drive down to Big Sur, as far south as possible before construction
Nepenthe
17 Mile Drive
Back to Pacific Grove

Thursday:Drive North - see redwoods (Henry Cowell?)Red-eye flight out of San Jose

Just one quick comment right now . . .

>>Staying somewhere between Union Square and City Hall

I probably shouldn't have said "between". We just need to stay somewhere near City Hall and the Union Square area has been recommended numerous times. Budget-wise, definitely below $300/night. I know that limits us....

Both the Exploratorium and Alcatraz will take quite of bit of time. With just one day, I might skip them. If you do decide to go to Alcatraz, plan now, it will sell out. There is only one boat - everyone else is a reseller selling something else along with Alcatraz. https://www.nps.gov/alca/index.htm

Agree with Janis about hotel location. My nephew recently stayed at the Proper Hotel and said it was "okay". It's closer to city hall. I don't think he'd choose to stay there again.

The Embarcadero (a great walk - we did it just yesterday, 10 miles worth), Cupid's Span and the Ferry Building are all one walk. Be sure to walk on the water side of the Embarcadero, and also, go into the Ferry Building but also out the back - lots of people watching, restaurant tables, boats, etc. Crissy Field is another great walk, It would be great to do if you have time because it gets you close to the Golden Gate Bridge, but you don't really have to go that far. Instead, depending on time, after the Ferry Building, keep walking or take a streetcar toward Fisherman's Wharf. Eventually you will come to a great view of the bridge around Ghirardelli Square, and will not have gone nearly as far as Crissy Field. If you skip Crissy Field, you can take the cable car from Ghirardelli over the hill. It will be much more crowded than the California Street line, but you're nowhere near the California Street line. If you want to avoid the crowds, make your way back to the Hyatt Regency (Uber or Lyft, or streetcar), which is the end of the California Street cable car line. Take the cable car to Van Ness Avenue. Grab a Lyft from there to Alamo Square.

For your hotel, a Thursday night only in early August....
We seem to always stay in Marriotts when we're in San Francisco but their rates are pretty dang high these days. Wow.

I did a quick search. So on Travelocity--I saw that the Sir Francis Drake, has a nonrefundable $210/night rate. It's now a Kimpton property. I chose the first Thursday in August. That's a great price. It's a landmark hotel and would be a memorable place to stay before your wedding. It is about a block from Union Square.

We stayed at the Sir Francis Drake on our recent visit to San Francisco. It is a great location, and the Powell St. cable car runs right by the front door.

Unfortunately, we'll be staying August 9th and I can't find the Sir Francis Drake for anything less than $259 (plus the $30 resort fee). After taxes and fees, that might be stretching the budget for some of the folks with us. The more I look, it seems like we might just have to bite the bullet.

OK -- probably none of my business . . . But why are you planning a destination wedding to a place you've never been, with people on strict budgets, to a city with VERY high room rates? Seems you are causing yourselves a lot of grief.

Edit to add: I wrote all the following and then realized.... you really should just call the Drake directly, and see what they would do for you given that you're reserving 5 rooms. Mention you saw them on the search engines. See if for two of the rooms, they'd lower it a little more since you're taking 5?
______________

I am presuming you guys already bought plane tickets, so there's no backing out. If not--I do agree with Janis and rethink this plan. I didn't realize the Drake had a resort fee, yeah, that would put the night at $350 with tax. I didn't see many others for much less for your date. This one looked okay:

The Mystic Hotel is $233 on Travelocity. And it's about a block from the Drake. I don't know anything about it. First glance, decent but very small rooms. There's only 8 rooms left on Travelocity (might be more if you call hotel directly). But I wouldn't wait long.

Or... here's my risky idea. You could save quite a bit on Hotwire.com with their "Hot Rate" mystery properties. There are two methods of renting rooms on Hotwire. One is just like all the other search engines. But the Mystery Properties is like Priceline. Prepay. No cancellations. You can select the zones you want and this is really key, or you could end up with a hotel in a bad zone, or a long ways from your target location. You also can check star level. I tend to check 3-star and up. Recheck everything, date, details before hitting "buy."

The two zones I would advise you to pick:
Union Square East
Union Square West

I searched for your dates. I found a 4-star boutique Hotel in Union Square East for $220/night, for 5 rooms. Hotwire will sometimes give you a "teaser" as to which 4 or 5 hotels it is. This is what it showed: Galleria park, Hotel G, the Drake, or Hotel Nikko. All would be good. These rates are pre-tax and pre-resort fee.

In all honesty, one couple is on a budget and we're doing our best to work around that. At this point, everything (flights, Airbnbs, etc.) has been booked and everyone is comfortable with the accomodations. Thursday night will be the only night we have to book individual rooms and be conscientious of the one couple's budget. I tried getting a room block at a handful of other hotels and they all required a minimum of 10 rooms. The Hotwire recommendation below actually seems like a pretty good idea.

To answer the question about Henry Cowell to see the redwoods~YES. It's beautiful.

Re 5alive's hotwire suggestion - just one comment . . .
>>The two zones I would advise you to pick:
Union Square East
Union Square West

Janis is right - there are some hotels in the Union Square West area that would be fine, but if you're doing it "anonymously", you could get something anywhere in the USW area, much of which would not be terribly pleasant.

Most hotels around there are going to be $350+ -- it's a little farther away, but the Urban Hotel does have doubles for less than $200 that night and is just above Union Square
https://www.theurbansf.com/

The Mystic at least has rates below $300.
https://www.mystichotel.com/


As for wineries, I thought they all allowed kids on those tours, at least had some they did. I toured Beringer, not because I like their wine much (although I do like their Chenin Blanc, surprisingly), but they have a nice estate and good tour. It's only $30 also and they allow people under 21 on their "legacy cave tour", in fact, I think they are free as they don't get drinks. They have other tours with drinking, but you do have options. robert Mondavi has a tour that allows all ages, also
https://www.robertmondaviwinery.com/discovery-tour

The location of the Urban is fine - the communal bathrooms maybe not so much.

Okay, I am agreeing with Janis's assessment given that you don't really use Hotwire. The Union Square West Zone, you would really need to spend some time on Better Bidding.com and find out what hotels actually get chosen. It takes time and it's fussy and if you are getting ready for a wedding, that's probably not time you have right now.

So stick with the Union Square East and see what you can do.

I also had quoted the Mystic Hotel at $233 on Travelocity, and Christina also noticed it as well.

If it's really down to one couple, it's too bad you can't just take the Drake and be done with it all, and pay the difference for the one party.

>

I guess it depends what you are willing to pay for a hotel in one of the most expensive cities in the US, in one of the most expensive areas. I've stayed in hotels like that, back in the day, that wasn't that unusual in Europe for 1-2* hotels. And you can still find 1* hotels like that in Europe. It doesn't really matter that much for one night, or wouldn't to me, anyway. Many people stay in hostels or dorms under those conditions or B&Bs, I have for a month at a time, I guess I don't find it that outrageous, but if it's a dealbreaker for someone, they can pay $100-200 more a night to have their own private toilet. Those rooms do have a sink, I believe. I admit for women, it can be less convenient at certain times.

I was really just pointing out that it has communal bathrooms, obviously, this may or may not be important to the OP and guests. It would be important to me.

I think it's good you gave them all the options you saw, Christina. There's a time and place for everything, including communal bathrooms. They are getting ready for a wedding in the morning. It may or may not be a dealbreaker, but I think sf7307 was right to mention it.

I hope the OP comes back and posts what they decided to do because I'm curious.

We're still trying to sort it out - and probably caused more damage by waiting this long. We're going to be choosing between Warwick Hotel, Hotel Union Square, Hotel Diva, and Hotel G. One of the first two will probably be the final destination. Unfortunately, the communal bathrooms wouldn't be an option for us due to the fact that we'd be getting ready for a wedding, as you stated. We realized pretty quickly that we need to be prepared to spend in the neighborhood of $300 and probably a little more. We were able to smooth that over with the couple I mentioned earlier.