Date Nights and Couple Trips in Santa Cruz
The romance in Santa Cruz is low-key and mostly outdoors: redwood air in the morning, a walk along the cliffs, and an evening on the water or at a table with a view. Below is one way to string those together as a Saturday for two, followed by notes on booking and where to stay. Prices are in US dollars and operators change schedules by season.
A Saturday for Two
Morning, among the redwoods. Henry Cowell Redwoods State Park charges $10 per vehicle, and its Redwood Grove Loop is a flat 0.8 mile under coast redwoods. You can step inside the Fremont Tree if you carry a flashlight. The park is about 6 miles from downtown.
Lunch on the Wharf. The Municipal Wharf extends about half a mile into the bay and has seafood restaurants, with sea lions resting close by. The wharf was repaired after its December 2024 collapse and is open to the public.
Afternoon on West Cliff Drive. Walk the paved path toward Lighthouse Point. The Santa Cruz Surfing Museum, inside the Mark Abbott Memorial Lighthouse at 701 West Cliff Drive, is free and open noon to 4pm from Thursday to Monday, though it can close unexpectedly. The road reopened in August 2025, and the bluff is still eroding, so stay on the path and behind the barriers.
Evening, on the water or on a hillside. Choose between the two options below.
Sailing at Sunset
Chardonnay Sailing Charters leaves from the FF Dock at 790 Mariner Park Way in the Santa Cruz Harbor. Its two 70-foot yachts, Chardonnay II and Chardonnay III, run Sunset Sail, Coastal Sail, Winemaker Sail and specialty sails. The Winemaker Sail is paired with local wineries, and October 2026 dates name Sones Cellars and Bargetto Winery. Prices for public sails start from about $80 a person, so the booking calendar is the place to confirm the figure for your night. The bay gets cold quickly after dark, and a jacket is the one thing couples forget.
Dinner at Shadowbrook
Shadowbrook Restaurant in Capitola is reached by the Hillevator funicular from the Wharf Road lot, which turns the arrival into part of the evening. The restaurant is listed as open in 2026, but phone 831-475-1511 to check your date before you drive east from Santa Cruz.
Choosing Between the Two
The sail puts you out on the bay for the light going down, while Shadowbrook gives you a sit-down dinner after a short drive east. Both want advance planning, one through the booking calendar and the other through a phone call. A Winemaker Sail is the simplest way to taste Santa Cruz Mountains wine, since Bargetto appears on its schedule.
A Quieter Alternative
Big Basin Redwoods State Park takes limited day use with parking reservations at $8, and only a few trails are open. There is no cell service, and no drinking water, so pack your own.
Where to Stay
Book early for summer weekends and holidays. Parking near the Boardwalk and Wharf is paid, so ask a hotel whether a space comes with the room. In winter, Wharf parking costs $1 an hour for the first four hours, then $2, up to a $12 daily maximum.
The sailing line explains its trips on the Chardonnay Sailing Charters site . You can browse rooms through Booking.com results for Santa Cruz .
Read more: couple activities in Santa Cruz and multi-day trips from Santa Cruz . If you are driving down for the weekend, the San Francisco guide covers the northern end.