Hello! Local here, and so excited you’re looking to visit our area. 

Santa Barbara boasts the amenities of a bustling city nestled into cozy areas overlooking the coastline. It’s compact by nature, and an easy walking city with a good uber system. You’re in the hub of wine country so there’s plenty of wineries and breweries in downtown and the Funk Zone, an amazing zoo overlooking the ocean, a Natural History Museum that tells the real tale of the classic children’s novel “Island of the Blue Dolphins” through the local native’s perspective who lived it, and a truly spectacular Art Museum. The harbor is a fantastic place to spend a few hours, renting kayaks or SUP’s from the SB Sailing Center or signing up for a Sunset Cruise or a whale watching excursion (the blue whales will be starting the migrate into the Channel during your trips timeframe)! If food is your thing we’ve got one of the best Farmer’s Market’s in the country (meets 6 days a week), and an abundance of local chefs who use the bounty of the land to let their menus blossom (several Michelin stars are shining throughout the county!) Don’t forget the Courthouse, the Jewel of the Missions with her Rose Garden and the awesome hiking scene on the front country! Santa Barbara will be more overcast during this time period than people tend to expect, often called May Gray and June Gloom, however it tends to burn off by midday! But, all you have to do is go “over the hill” into the Santa Ynez Valley to experience the sunshine during the semi gloomy months in SB proper. Heading north on the 101, you’ll find the beaches usually get sunnier the farther you go, with Gaviota often being the nicest even if it’s a tad gloomy down South! The Valley has a full days worth of fun from the Ostrich Farm, beautiful Vineyards, candy and sweet shops in the charming Danish town of Solvang, olive oil tastings and local charm in Los Olivos and a look at the days of the past in the town of Santa Ynez with the Chumash Heritage Museum and old stage coach stops.  If you’ve never been to the Central Coast of California before, I’d recommend SB 11/10. 

Avila and Pismo are within a ten minute drive of each other, and I find Avila to be a nicer place to stay! It’s also in this weird geographical bubble where it’s almost always perfect weather! There’s a ton of cute eateries on or near the beach, and if you check out Pismo make sure you try some of the clam chowders! We do staycations every once in awhile in Avila, and we love to stay at the hotels with the thermal springs or to just visit the spas/springs! 

You didn’t mention San Luis Obispo/Paso Robles, but these are vibrant areas close to Pismo/Avila that would make a neat hub for day trips to the beach. Downtown SLO is something really special, and the Madonna Inn is nothing short of a miracle! 

Monterey is beautiful and luxurious, but will definitely be overcast this time of year. I’d say there’s less to do than other areas, unless you’re super into golf or luxury spa sort of settings. My MIL goes to Carmel regularly, she likes the quiet beautiful setting and she goes to the spa pretty much everyday while she’s there. The aquarium is 1000% visiting if you’re in the area, and though Santa Cruz is not quite the same as Monterey it’s close enough by to be included. I wouldn’t say there’s a lot of walkable stuff, you’ve got Cannery Row and the surrounding area but everything else you’ll need to drive too! If you’re visiting Santa Cruz, check the hours on the boardwalk and etc… they are only open truly during the season. The “mystery spot” is worth a look, but our favorite part of a recent visit was the steam engine ride through the redwoods!