Santa Cruz Romance: Sunset Sails and Cliffs
Couples come to Santa Cruz for sunsets, redwoods and unhurried evenings by the water. Below are the experiences that suit two, with practical details. Prices are in US dollars and change with the season, so check before booking.
Sailing at Sunset
From the FF Dock at the Santa Cruz Harbor, Chardonnay Sailing Charters runs Sunset Sail, Coastal Sail, Winemaker Sail and Specialty Sails on Chardonnay II and Chardonnay III, 70-foot yachts. On the Winemaker Sail, local wineries are poured on board, and October 2026 dates name Sones Cellars and Bargetto Winery. Plan on fares from about $80 and look at the booking calendar for exact prices. Pack a warm layer for the return.
Golden Hour on West Cliff Drive
Walk toward Lighthouse Point as the sun drops. Surfers work the waves at Steamer Lane directly below the cliff. The road was repaired and reopened in August 2025, but the bluff is still wearing away, so keep behind the barriers and on the path.
Dinner at Shadowbrook
Capitola’s Shadowbrook Restaurant is approached by the Hillevator funicular from the Wharf Road lot, a memorable way to arrive. It is listed as open for 2026, and the number to call is 831-475-1511. Capitola Village lies a few miles east of Santa Cruz.
A Wharf Seafood Table
The Municipal Wharf, about half a mile long, has seafood restaurants, and sea lions gather around it. Winter parking costs $1 per hour for the first 4 hours, then $2, with a daily cap of $12. On Tuesdays two hours are free with a validation stamp from a wharf business.
Redwoods Together
At Henry Cowell Redwoods, the flat 0.8-mile Redwood Grove Loop is an easy shared walk, and the Fremont Tree can be entered with a flashlight. Day use is $10 per vehicle. Big Basin Redwoods State Park takes limited, reserved day use at $8 for parking. Only a few trails are open there, and there is no cell service.
A Day Out Together
Monterey is about 45 miles south, roughly an hour’s drive without traffic. Monterey Bay Aquarium tickets are $65 for adults, and buying in advance is recommended. Highway 1 moves slowly on summer weekends, so start early.
Stays
Book ahead for summer weekends and holidays. Parking at lots near the Boardwalk and Wharf is paid, so ask a hotel whether it includes a space.
Learn about the sails on the Chardonnay Sailing Charters site . To compare hotels, look at Booking.com .
Read more: Santa Cruz couple activities , plus multi-day trip plans .