Sunset Over Sonoma

It’s a common situation: You’re in wine country, finishing up some tastings, feeling pretty good—now you want to enjoy a sunset. Where to go? The answer is just north of Sonoma’s historic plaza. The Overlook Trail is a local favorite. The 1-mile (one-way) hike to reach the "overlook" is a gentle grade among meadows, grasslands, and oak trees. The viewpoint is marked by three rock-benches; we like the second and third best. You’ll feel like you slipped in on a secret as you bask in an unexpected vista spanning the town of Sonoma, its Valley, and—on clear evenings—Mount Tam and San Francisco. Arrive about 30 minutes before sunset to enjoy the full effects. And don’t be startled by deer; they like the view up here too. Enjoy the moment but don’t linger too long—you’ve still got a return trip. It’s a short jaunt down from this Sonoma sizzler.

To reach the trailhead from Sonoma Plaza, head north on First St. West. Find the staging area just beyond the Veterans Memorial Building on the right side of the street. Follow the signs for the Overlook Trail's Upper Loop Trail. Give yourself 30 minutes to reach the top. Bring a flashlight for the walk back down. No dogs.

Sunny Side SUP

Where can you combine a bay-mazing sunset and one of the fastest growing watersports in the world? The pros at Sausalito’s Sea Trek Kayak and Paddleboard Center lead a sublime stand-up paddleboarding sunset trip that’s available by request. Wriggle into your wetsuit and get briefed on the basics for this beginner-friendly, two-hour tour. Departing from Schoonmaker Beach, paddle into the protected cove of Richardson Bay, an estuary ecosystem teeming with eelgrass, cormorants, brown pelicans, and seals with a penchant for pop-up greetings so close that you can see their whiskers. The relaxing voyage passes Sausalito’s floating homes and harbors. As the magic hour gleams over the water, San Francisco, Alcatraz and the Golden Gate glow in the fiery light. Two thumbs-SUP!

BONUS: Afterward, swing by the recently opened Trident restaurant on the Sausalito waterfront. It’s been renovated to reflect its original culinary tenant—a 1960s restaurant legend that served up rock ‘n' roll after-parties, hosting guests like Janis Joplin and the Rolling Stones. It even employed a busboy named Robin Williams.

Sea Trek Kayak and Paddleboard Center is located at Schoonmaker Pt. Marina in Sausalito on Liberty Ship Way. Sunset SUP trips must be booked in advance by calling 415-332-8494. Trips are $60/person. The Trident, 415-331-3232, is located at 558 Bridgeway in Sausalito.

A Cool Grand

Looking for a stairway to heaven? You’ll get awfully close at San Francisco’s Grandview Park, also known as Turtle Hill. On clear days this one-acre gem tucked in Golden Gate Heights delivers big panoramas. The prime viewpoint is reached via a split-level stairway, the first of which comprises more than 150 mosaicked steps as illustrious as they are celestial, with specs of mirror reflecting sunbeams toward the ocean. When you reach a split-level road, cross it and take the wooden steps to the top of the dune where you’ll find slivers of random trails, along with a bench and ancient chert rock outcrops. Set the camera to "Panorama": This is the kingdom of the City by the Bay. Enjoy unobstructed views as the setting sun bathes Golden Gate Park, the Pacific, downtown San Francisco, and the Golden Gate Bridge in deep orange and popping pink hues. Just be sure to bring a windbreaker—things can get gusty while you’re gushing.

Street parking is located at the corner of 16th Ave. and Moraga St. in San Francisco. The mosaicked stairs begin at the junction of 16th and Moraga. Continue up the stairs until you hit a split-level road (15th Ave.), cross it and continue up another set of wooden stairs to reach the peak. Dog-friendly!

Your Year to Ride

It’s one of the most beautiful bike rides in the world: A seven-day journey from San Francisco to Los Angeles. AIDS/LifeCycle is an amazing tour through California, seeing the state's most beautiful landscapes, from forests to the sea, and country roads to rolling vineyards. Sign up now for AIDS/LifeCycle 2013 and you’ll get $20 off the registration fee using promo code SHERPA. Then get started with expert-led training sessions—from easy spins to intensive hill training, along with advice on fitness and proper nutrition—plus plenty of social gatherings. You’ll be supported from the time you sign up all the way through the main event: An amazing seven-day ride with hot meals, massages, gear transport, pit stops and lots of cheering from the community. It'll be a blast for a good cause: Helping the San Francisco AIDS Foundation and the L.A. Gay & Lesbian Center provide vital HIV prevention, treatment and support services to our communities. Meet new people and bond with friends and loved ones on this classic California adventure. You belong here! Check out this video to see what it's all about. Even better, join a training ride to learn more! It’s your year to ride.

TIP: Space for the 2013 AIDS/LifeCycle is filling up quickly—register online with promo code SHERPA and get $20 off your registration fee.

Join AIDS/LifeCycle for a reception at The Castro Theatre on December 1 to commemorate World AIDS Day. Space is limited, so an RSVP is required. Includes a complimentary ticket to the film screening "How to Survive a Plague."