Need a Holiday Getaway (Holi-Way?) Curated Options for Your Next Weekend Trip

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 

Union Square
Photo: Courtesy of Ashish Tibrewal

Shop 

Despite recent dour news about the neighborhood, Union Square is still a destination for shopping. Macy’s flagship store will be open throughout the 2024 holiday season, likely offering some good deals. 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 (Hello Apple AI, the iPhone 16 has arrived) or Nike store (Warriors jerseys, anyone?)

Union Square’s retail closures are being met with new openings. Watch seller Breitling opened a boutique on Post Street just months ago, then Rolex moved in right next door. Over on Market Street at the old Westfield Mall (redubbed the San Francisco Centre), familiar stores like Zara and Aritzia have been joined by spots for “kawaii” knick-knacks like Miniso, Merkado and Hey Hi Toys. Of course, the newest big-box addition to the neighborhood was Ikea with its multi-restaurant food hall in 2023. 

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. 21, the California Academy of Sciences (holiday festivities starting Nov. 22) and PIER 39 — gift opportunities galore in their various gift shops. 

Stay

If you’re looking to be near Union Square, the 1,195-room 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, which just this year reopened its 21st-floor cocktail lounge Starlite. If you book a two-night stay right now through Jan. 12, you can receive 25% off. The Fairmont San Francisco also has its own deals, like 15% off a two-night stay, plus $50 food credit, and starting Nov. 22, its holiday-themed Santa Suite offer returns. Intercontinental Mark Hopkins also makes for a festive stay in comfort.

Sausalito

Sausalito Books by the Bay
Photo: Courtesy of Sausalito Books by the Bay

Shop

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. For those sustainability-minded ladies in your life, Amour Vert will have something to put in a box, and Sausalito Books By the Bay has a 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.

Stay

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. 14) and browsing various stores and businesses’ entries in the town’s annual Gingerbread House Competition & Tour (through Dec. 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

River Terrace Inn
Photo: Courtesy of River Terrace Inn

Shop

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. Last year, they expanded into the historic bank next door, tripling the square footage. Peeling back the stone, 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, 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).

Stay

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, River Terrace Inn and The Westin Verasa Napa are great options for walkable shopping.

Healdsburg

Healdsburg Shopping
Photo: Courtesy of Mariah Harkey

Shop

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.  Thumbprint Cellars’ tasting room on the plaza doubles as an art gallery, and Journeyman Meat Co., a salumeria (handcrafted salami shop) sells boxed packs of salami, beef snack sticks, spices and other gift possibilities.

Stay

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

Mendocino Coast
Photo: Courtesy of Four Sisters Inn

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. 

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.