I donât think this lad won the lotto.Thatâs a lot of stuff for a Lad who backs horses for a living.San Diego is the nicest place Iâve been to in the states.La Jolla is some spot.
Money wonât be an object.
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Off ye go so.
Decent suggestions, esp from @maroonandwhite and @blake.
Are you flying into SF? If so spend a few nights there to unwind and get over jetlag. Nob Hill is a nice central location, not too touristy and Polk St has some of the finest bars in the city. Both the Intercontinental Mark Hopkins and Fairmont are nice hotels, you are a short walk to Chinatown, Union Sq etc. Need to be booking Alcatraz now, a boat trip around the bay is nice, Ocean beach, GG bridge, etc. If you want to see redwoods and a nice beach, Muir woods, about 10 miles north of the GG bridge, you could do that along with Sausalito in one day.
If youâre only going to do one long drive I would say rent a car in SF and drive down the coast to San Diego, you could so it in one day but better to plan for two and stay overnight somewhere, Santa Barbara is lovely or Morrow Bay for something more out of the ordinary. Drive down 101 to Monterey, do the 17 mile drive, have lunch in Carmel and then head down 1 through Big Sur. Plan your second day to avoid LA traffic, but a stop in Santa Monica is worth it. San Diego is a lovely city, stay downtown and go out to Coronado for an evening. I wouldnât advise Tijuana but if youâre young and brave, etc.
The Yosemite suggestion is a great one but wonder if you can fit it in. A half day to get there, two days min in the park, and a half day back, well worth it though. Vegas is Vegas, hopefully towards the end of the trip as 3 nights there could completely wreck you.
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We stayed in Venice Beach years ago,lovely during the day but dodgy as fuck at night.
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Dont bother with Vegas. If you have the time go to Page Arizona and take in Antelope Canyon and Horse shoe bend. From there go to Monument Valley.
We stayed in a dive motel in Hollywood, the corner of La Brea, the non English speaking desk boy responded to every query with a number, 661 or something, turned out it was the porn channel
Donât call it San Fran or Frisco. All the other advice about the Bridge and the Pier and Sausalito, Giants game (Go Giants!!), Ashbury etc etc all good. Castro on a Saturday is good for a gawk. The Mexican restaurants down the end of Mission are authentic and class. Stay away from Oakland unless the Aâs are playing.
Alright lads, he asked for a few suggestions not a 100 page guide and collection of memoirs⌠Dear oh dearâŚ
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The roasters whoâve been on one J1 canât help showing off.
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Fucking students.
That sounds exactly what an addictive gambler in his early 20s wants to see 
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He said heâs keeping powder dry until Cheltenham. Who knows, he might get some enlightenment.
I can stop gambling any moment I want
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I bet you that you canât.
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+1. Carmel on sea had Clint Eastwood as Mayor and you also have Pebble beach on the peninsula drive
Give it up when the fun stops.
Clint has a nice ranch and restaurant that you can stay in. You may not see Clint though.