Valentine’s Day: it tends to happen this time of year.
We strongly advise against ignoring it. Instead, play the hero. But even heroes need a blueprint.
Thusly: three step-by-step St. Valentine's Day itineraries for the stumped but willing lothario.
Where to take her. What to buy her (besides fancy underpants). What to do.
One in the home, one in the city and one long weekend nearby. Mix and match, or follow one in its entirety.
THE HOUSE CALL
Step 1: The Massage
With Soothe, booking a two-hour couples massage is as easy as hailing an Uber — only without the surcharges for . We'd suggest deep tissue. After the professionals get you both sufficiently loose, try out any skills you've picked up on your lady, preferably with the help of this lavender massage oil from Good Eggs.
Step 2: The Dinner
Pizzeria Delfina delivers via Caviar now, so there’s no reason to go outside. We recommend sharing the Belfiore Burrata and a Broccoli Rabe pie, even if we accept that in many corners the Clam pie with cherrystones, tomato and hot pecorino is the more popular choice.
Step 3: The Presents
Plan on two presents. For the first, get her exactly what she really wants: a necklace, a photograph and a book (we recommend A Little Life, the current talk of the literary town). It won’t hurt to include a little something for you — like a chantilly lace and tulle bra-and-panty set from Agent Provocateur — you can see how it looks on the model here. Pick it up at the Union Square Shop.
THE GETAWAY: SONOMA
Step 1: Friday
Hotel Healdsburg is our favorite residence in Sonoma County. You want a Plaza Suite, which will come with a soaking tub and glass-walled showers. Chef Charlie Palmer co-owns the hotel; make sure your first meal is spent at Dry Creek Kitchen. The seven-course Valentine’s Day menu is offered from Friday night and includes fennel-crusted ahi tataki and truffle parmesan risotto.
Step 2: Saturday
Pick up supplies from Oakville Grocery, pack a picnic and plan to summit Mount Helena, the highest point in Wine Country. It’s a full-day, and one well-deserving of some time in that soaking tub on return. If you’re looking for something ever-so-slightly less active, head for Healdsburg Ridge preserve, conveniently located right near Simi Winery. Do dinner at Baci.
Step 3: Sunday
Wander around Healdsburg. Most important: Book your lady a spa day — staff will custom direct a series of treatments at your bidding. A couples room is available if you’re interested, but honestly, she probably doesn’t care if you’re there or not. Take the time to stop by Oakville for flowers, and prepare the presents you brought with: something from Eres, selected in consultation with the knowledgeable staff at Alla Prima, and, again, something she’ll love — like this Lucy Lippard first edition.
THE NIGHT OUT ON THE TOWN
Step 1: Check-in
Just because you’re staying in town doesn’t mean you’re staying at home: Drop your bags at The St. Regis in SoMa just below Market Street, which will include flowers and a bottle of Champagne with its special V-Day booking (obviously, plan on going in late — or not at all — on Monday).
Step 2: Lunch with a View
From the St. Regis, it’s a short walk to the Ferry Building. From here, catch the noon boat to Sausalito. You’ll want to get a leisurely lunch at the Barrel House — make sure you have seats on the patio, which offer spectacular views back to the city. If she likes history, tell her that the restaurant is on the premises of the town’s former ferry building. If she likes design, be sure to follow lunch with a tour through nearby Heath Ceramics. If she hates ferries, lunch and design, start at the St. Regis and instead of taking this ferry, get yourself to Pier 41 and spend the day hiking around Angel Island, which has equally spectacular views from the summit of Mount Livermore.
Step 3: Bourbon + Spa (+ Dinner)
Back at the hotel, shuttle your date off to a pre-dinner massage at Remède Spa; wait for her at the hotel’s restaurant, Ame. Order the Diplomat with Four Roses Bourbon, Cocchi Barolo Chinato, R. Jelinek Fernet and orange bitters. If you want to keep it local, get seats at Ame. If you don’t mind heading out, grab an Uber and make your way to Petit Crenn, the intensely intimate French restaurant from the Michelin-starred mind of Dominique Crenn.
Nota bene: Gifts? You need more gifts, you say? Right this way to our Valentine's Day Gift Guide, courtesy of our National bureau.