Featured Date Ideas

Palo Alto Holiday Date

Estimated Spend: $70 Estimated Time: 2.5 hours

  • Ice Skate at Winter Lodge

    Average Cost : $ 50
    Rating : 4.7
    Take your date to Winter Lodge for some ice skating. It's the oldest standing ice skating rink west of the Sierras. They do an awesome job during the holidays with the lit up Christmas tree in the middle of the rink and lights hanging from above. They have 2 hr sessions typically from 8am-10am, 3pm-5pm, and 8pm-10pm. We highly recommend to buy tickets in advance, especially during the holidays.
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  • Enjoy Bubbly & Chocolate or Sipping Chocolates from Timothy Adams

    Average Cost : $ 20
    Rating : 5.0
    Timothy Adams Chocolates is MAGICAL. This immaculate chocolate shop makes beautifully crafted chocolates with innovative fillings. The fun doesn't stop at their chocolate candies. They have sipping chocolates (hot chocolate) where you choose the chocolate and milk, and they whip up one of the best, if not the best, hot chocolate around with a marshmallow on top. Lastly, they serve bubbles and chocolates where you can drink a little bubbly with the chocolate delights. No better way to your date's heart than with chocolate.
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Itinerary

SF Holiday Date

Estimated Spend: $100 Estimated Time: 4 hours

  • Christmas Adventure Around Union Square

    Average Cost : $ 100
    Rating : 4.9
    Explore SF's Christmas Capital. While you're out, grab food, sweets, drinks, and hot chocolates. Maiden Lane is right outside of the hustle and bustle of the festivities, and has a few great options. -Check out the Giant Ginger Bread House in Fairmont: An engineering team that spends 520 hours each year building, lighting, and outfitting a life-sized Victorian gingerbread house in the lobby of Fairmont San Francisco. More than 8,000 baked bricks cover the two-story structure, which stands at 25 feet high, 35 feet wide, and nearly 11 feet deep. -See the sugar castle in The Westin St. Francis: Another marvel that takes endless hours to construct. -Shop or just experience the decked out Macy's and Nieman Marcus. Macy's has wreaths in every window facing the park and puppies and kittens in the windows by the street. Nieman Marcus has an 86-ft tall Christmas tree and if you can get in, try going for a meal or drinks at The Rotunda (by the star of the tree). -Ice Skate in the park There are many other spectacles around this area, and it's worth the adventure.
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HMB Christmas Date

Estimated Spend: $150 Estimated Time: 3 hours

  • Cut Down Christmas Trees near HMB

    Average Cost : $ 100
    Rating : 4.7
    Pick out that winning tree from one of the many Christmas tree farms along HWY 92. Here are a few favs: -Half Moon Bay Nursery -Cozzolino's Christmas Trees -Ski Lane Tree Farm (a little north of HMB)
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  • Take a Stroll through Main Street

    Average Cost : $ 50
    Rating : 4.5
    Take a walk through downtown Half Moon Bay on Main Street. It's a little downtown, but you'll find plenty of places to eat, shops to explore, and coffee and dessert to enjoy. Gem spots: -Jupiter & Main: Fun store to explore with the well-crafted knickknacks -Half Moon Bay Wine & Cheese: Grab samples and check out the wide selection of cheeses and wines -Abode: Find treasures for the house. -San Benito House: Food and drinks -Half Moon Bay Bakery: Coffee and Goodies
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Itinerary