Looking for a win-win this month? How about a weekend getaway to take advantage of the discounted winter rates offered at many driveable destinations, while taking care of some holiday shopping? We’ve selected a few options starting in San Francisco and heading north to Healdsburg. Please enjoy our curated list of holi-ways (holiday getaways — let’s see if it catches on!)
San Francisco

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After some uncertainty regarding the status of Macy’s flagship store, it’s been recently confimred that they will be open for the immediate future. Luxury retail stores like Neiman Marcus dot the square’s perimeter, and more boutiques line the charming Maiden Lane, a narrow street with hanging lights, flowers and international shops a la Maison Margiela and Hermes. For more gifts, check out the many jewelry stores, or maybe the Williams-Sonoma (stock up on that peppermint bark), Apple store or Nike store (Warriors jerseys, anyone?)
Or, check out watch seller Breitling, which opened a boutique on Post Street last year, with Rolex right next door. Over on Market Street at the old Westfield Mall (redubbed the San Francisco Centre), familiar stores like Aritzia have been joined by spots for “kawaii” knick-knacks like MINISO.
And don’t forget the classics. Now’s a great time to visit the world famous SF destinations like Exploratorium with its “Glow” exhibit starting Nov. 20, the California Academy of Sciences (holiday festivities starting Nov. 22) and PIER 39 — gift opportunities galore in their various gift shops.
The 131-room San Francisco Proper lies a few blocks from Westfield San Francisco Centre, home to Bloomingdales, Nordstrom and many other stores. “However, some of our favorite local treasures include the wonderful Arsicault Bakery and a lovely chocolate shop, Littlejohn’s Candies, which have truly special holiday selections for gifts or gatherings,” said Robyn Montes, general manager of the hotel’s Villon restaurant.
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If you’re looking to be near Union Square, the Westin St. Francis is perfectly perched for enjoying the 30,000 lights on the square’s 83-foot Christmas tree and skating on the seasonal Union Square Holiday Ice Rink. Or, opt for the classic Beacon Grande, steps from Union Square, and check out their 21st-floor cocktail lounge Starlite. Starting Nov. 21, Fairmont San Francisco’s holiday-themed Santa Suite offer returns. Intercontinental Mark Hopkins also makes for a festive stay in comfort.
Sausalito

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Staycation with the option of a ferry ride (the most beautiful in the world) to San Francisco’s gourmet-themed Ferry Building. If you go, check the Book Passage’s event calendar to tie your trip in with one of their author events (weekends often feature cookbook authors with a Farmer’s Market tie-in), and try to plan for a sunset return trip — yes, they serve alcohol. There are plenty of viable shopportunities in Sausalito as well, including Sausalito Books By the Bay with its well-curated collection of unique books and gifts. And if you still haven’t found the perfect gift, Soxalito offers a whimsical sock collection sure to bring a smile on the grumpiest of scrooges. Head to Caledonia Street for whimsy, mermaid Waterfront Wonders, or Nordic-California lifestyle at SALT, offering unique home goods and fashion accessories.
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For those looking for a true staycation, now’s your chance to get into the iconic 33-room Inn Above Tide in Sausalito, which is also ideal for viewing Sausalito’s Lighted Boat Parade & Fireworks (Dec. 13–14) and browsing various stores and businesses’ entries in the town’s annual Gingerbread House Competition & Tour (Dec. 8–31). Casa Madrona is also an excellent option for the parade and sweeping bay views. Plus, room service is by Poggio, a frequent Best of the County winner for Italian food, including pizza, pasta and their famous negroni.
Napa

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Perishables are a very thoughtful gift — no awkward pause as the recipient wonders where the new pink eagle statue will go. For the artistically inclined oenophile, check out Orin Swift Cellars on St. Helena’s Main Street. During an expansion from a couple of years ago that tripled the square footage, they uncovered the original 1955 Art Deco facade that’s now the exterior of the building. In concert with the playfulness and intrigue of OSC labels and wines, their tasting room experience is not your average cheese-nibbling, sit-and-sip experience. Rock, Paper, Scissors and Vault (the names of the tasting experiences) pay homage to the old classic game and suggest that wine tasting should be playful not pretentious. With the holidays approaching, a perfect marriage of art and wine can be found in their distinctive gift sets, whether you want a duo, three-pack or large format bottle to dazzle anyone on your list.
Another option is Napa’s Oxbow Public Market to create your own gift basket, including shops like Whole Spice and The Olive Press, just to name a couple. Non-edible perishables can be found at Makers Market in the First Street Napa complex. Boho Lifestyle, at the corner of First and Main, is run by a 10-woman team. And while “no live gifts” are solid words to live by, a unique potted Monstera from Riza Plants is an exception.
Just up Highway 29 in St. Helena, don’t miss Napa Valley Olive Oil Manufacturing Company. Founded in 1931, the family-owned company produces delicious olive oil (available by the jug).
Jenny Toomer, general manager of the nearby River Terrace Inn, also recommends checking out the spirits for sale at Napa Valley Distillery inside the market. Milo and Friends Pet Boutique, is another one of her recommendations, and it’s named for owner Chandler Manasse’s Cavalier King Charles spaniel.
Scarlett Accurso, manager of the renovated, 11-room Milliken Creek Inn near the Silverado Trail, similarly guides guests to downtown Napa for wine tasting and shopping. “I like Walt Wines — known for their Pinot — and Krupp Brothers, very near Oxbow Market, who do nightly wine tastings for us about once per week,” she said. Another of her favorites: Vintner’s Collective, which features, “20-plus boutique wines in a historic building right of Main Street, with walk-ins welcome,” Accurso said.
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From Carneros Inn (yes, this is officially in Napa) to Calistoga, Napa can offer a holi-way for any budget. At the top of the valley and near holiday shopping, Roman Spa Hot Springs Resort, a tranquil 2-acre resort, won’t break the bank. For downtown Napa, Andaz Napa by Hyatt and The Westin Verasa Napa are great options for walkable shopping.
Healdsburg

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The picturesque Healdsburg Plaza oozes traditional holiday charm. The opposite of perishables can be found at the plethora of antique shops in town, however. It’s a world-class destination for cool salvage, antique items — giant Pepsi sign, anyone? On the square you’ll find something for everyone: ereloom for the fashion-forward man in your life; Mr. Moon’s Gifts, a one-stop gift shop selling carefully curated cards, toys, handbags and more; and Copperfield’s Books, which first opened in Sebastopol in 1981 and has a light and airy shopping experience that offers more than books.
And back to the perishables, this town is overflowing with tasting rooms and artisan foods. Journeyman Meat Co., a salumeria (handcrafted salami shop) sells boxed packs of salami, beef snack sticks, spices and other gift possibilities.
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With Marin-based founders, it’s no wonder both Hotel Healdsburg and h2hotel are dog friendly, so no worries about finding canine coverage for this getaway. If you want something a little more intimate, consider the 12-room Healdsburg Inn on the Plaza.
Mendocino

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While Mendocino’s rugged coastal landscape and picturesque Victorian architecture are justly renowned, its merchants also deserve attention. Those shopping for kids and teens should gravitate to Out of This World, founded in 1988. Gallery Bookshop is said to be one of the oldest and best independent bookstores in the nation, founded in 1962 and sharing a site (and ownership) with Bookwinkle’s Children’s Books since 1993. Just around the corner from Main Street, the store also boasts a spectacular view of the coastline, which can be enjoyed from cushioned window seats. Don’t miss Astoria Home Decor & Gifts of Mendocino on Main Street, where locally handcrafted items include charcuterie boards. And, save time for the quirky inventory of Tangents, a couple blocks north on Lansing Street.
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Within walking distance of all of the above are the Inns of Mendocino, three intimate inns that are part of the Four Sisters Collection. Check-in for all three is at the five-room Blue Door Inn on Howard Street, the most chic of the properties, while the six-room Packard House on Little Lake Street is the most affordable. Rates at the JD House on Ukiah Street, whose eight rooms include a converted water tower, tend to lie in between.
Carmel-by-the-Sea

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Carmel also hosts more than a dozen wine tasting rooms, which can serve as a source of locally produced gifts or as liquid revival for the shopper. Natrass recommends three in particular: Scheid Vineyards, which creates small-lot, sustainable wines from its 10 estate vineyards in Monterey County; De Tierra Vineyards, which offers live acoustic music from 3-5 p.m. Sundays; and Silvestri Vineyards, which produces seven varietals from its Carmel Valley vineyard. Luckily, guests at the 30-room Coachman’s Inn are within walking distance of all three.
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Artist Christian Jorgensen built the mansion that became La Playa Carmel, now a 75-room hotel, as a gift for his wife, Angela Ghirardelli, in 1905. Beautifully restored in 2012, the hotel now aids modern givers by offering free holiday gift-wrapping for their finds from the many intriguing shops uphill.
Palo Alto

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Downtown Palo Alto’s eclectic wares includes quirky home decor at Five Ten Gifts and artisanal greeting cards at Letter Perfect. The Palo Alto Caltrain station lies nearby, while open-air Stanford Shopping Center is mile away on foot, a little longer by bike or car.
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In recent years, design firm Nicolehollis revamped the Spanish-themed El Prado (formerly the Garden Court Hotel), including the library, rooms and public spaces and a solarium with breakfast cafe.
Sutter Creek

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Some 40 independent stores can be found in and around historic Main Street, home to the quaint Hotel Sutter. Vintage and contemporary fashion are abundant, with boutiques like The Clothes Mine, cowboy-themed Romancin’ the Range and Unique Boutique for U. Sierra Mountain Outdoors offers adventure-oriented gear, while the espresso drinks and pastries at Choc-o-Latte can help fuel shopping forays.
At Sutter Creek Cheese Shoppe, look for gifts among the locally crafted Miller Wine Work wines, jams and honey. Browsing the aisles at a half-dozen antique and collectibles stores such as Tigby Hill Vintage and the Antique Gardener can also yield more treasures.