California: San Francisco to Point Reyes

Optional Barbary Coast Trail; 4 miles, easy, 100-ft. elevation gain and 300-ft. elevation loss

After settling into your boutique hotel near Fisherman’s Wharf, set out to discover San Francisco’s beautiful waterfront, museums, galleries, and neighborhoods—on foot, or aboard a historic cable car. Enjoy dinner tonight at one of the city’s world-class restaurants.

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Accommodation: Argonaut Hotel, San Francisco

A deluxe boutique hotel ideally located between Fisherman’s Wharf and Ghirardelli Square. The century-old renovated brick building blends authentic timber and brick with a theme reminiscent of the neighborhood’s seafaring past: a working astronomer’s clock, whimsical décor inspired by ocean liners, and nautical print fabrics. The hotel’s environmental program demonstrates a strong commitment to sustainable practices while guests enjoy spacious rooms, a fitness center, spa services, and complimentary bicycles.

8.5 miles, easy, 250-ft. elevation gain and loss

Savor a scenic morning walk along San Francisco Bay, passing the Ghirardelli chocolate factory, historic Fort Mason Park, and the Palace of Fine Arts. Linger over views of Alcatraz as you cross the majestic Golden Gate Bridge, then stroll along Sausalito’s charming waterfront promenade, lined with cafés and galleries.

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Accommodation: Casa Madrona, Sausalito

Built in 1885 as a private villa overlooking the Bay Area, and temporarily hosting military families during World War II, the mansion as well as 16 hillside cottages are now listed on the National Register of Historic Places. The elegant Casa Madrona offers spacious contemporary rooms with private balconies overlooking the harbor and heart of historical Sausalito. Amenities include a 3,000-square-foot spa and a fitness center. Dining options range from casual alfresco bistros to a Michelin-recognized restaurant (some requiring advance reservations).

5.5 miles, easy to moderate, 700-ft. elevation gain and loss

This morning’s route leads through the gorgeous Tennessee Valley to the Pacific Ocean, emerging onto a lovely wild beach nestled between steep bluffs. Protected within the Golden Gate National Recreation Area, this region shelters over 1,200 plant and animal species. This afternoon, enjoy spectacular views of the ocean (and, on a clear day, San Francisco’s skyline) as you meander up and down coastal headlands towards beautiful Muir Beach.

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Accommodation: Pelican Inn, Muir Beach

From a family of British innkeepers, Charles Felix drew his inspiration from Sir Francis Drake when creating this charming inn in 16th-century English West Country style in the quiet cove of Muir Beach. The seven-room hotel features antique furniture, a cozy salon with an inglenook fireplace, and covered garden patio. Typical English fare of locally sourced ingredients is served at a full country breakfast and for dinner, either alfresco or family-style at the dining room’s refectory table. Of course, fine ales are available at the lively pub.

5.5 miles, moderate, 700-ft. elevation gain and 1,100-ft. elevation loss

Stunning hilltop panoramas unfold as you enter Mt Tamalpais State Park and descend toward Muir Woods National Monument, a magical old-growth redwood forest with a cathedral-like setting. The trail snakes along streams through fern and redwood canyons, before climbing to your final destination, a magnificently situated mountaintop inn.

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Accommodation: Mountain Home Inn, Mill Valley

Perched atop Mount Tamalpais, this historical inn was founded by a Swiss couple, and was once a stop along the “Crookedest Railroad in the World.” Eco-friendly restorations were inspired by the 1930s-era Grand National Park Hotels, featuring hardwood floors and redwood columns. Ten guest rooms with French doors or large windows open to stunning views. In the evening, a dinner of organic California cuisine is served either on the expansive deck or in front of the fireplace in the cozy dining room.

8.5 miles, moderate, 1,300-ft. elevation gain and 1,100-ft. elevation loss

A scenic one-hour transfer takes you along the Mount Tamalpais ridgeline and up the coast to Point Reyes National Seashore. Set off along Limantour Beach, watching for tidal pools, bobbing harbor seals, and—in springtime—gray whales guiding their calves offshore. Traverse coastal scrub and lush forest to Bear Valley Visitor’s Center, where you can learn more about the park’s diverse ecosystems and cultural heritage before dinner at a favorite local restaurant.

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Accommodation: The Lodge at Point Reyes, Olema

In the charming town of Olema and set in five acres of landscaped grounds and flower beds along the Olema Creek, this comfortable lodge is adjacent to the Point Reyes National Seashore. Spacious suites feature fireplaces and private balconies. Adirondack chairs in the garden and a well-stocked library and game room offer plenty of opportunities to relax.

After breakfast, transfer back to San Francisco or Oakland.