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Welcome aboard Cypress Bay • Sailing from San Francisco

Cast Off From San Francisco Sailing Yacht Cruises

Intimate yachts for fewer than 350 guests, sailing round-trip and one-way from San Francisco. Wake up in secluded coves along the California coast, the Pacific Northwest, Alaska's Inside Passage, Baja, and beyond — all with the personalized service you deserve.

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Curated Itineraries • All Departing San Francisco

Featured Voyages & Prices

Limited-time savings on our most popular small-ship itineraries, every one sailing round-trip or one-way from San Francisco. Prices include complimentary Wi-Fi, all meals, and non-alcoholic beverages.

California Coast Save $1,200
⚓ Cypress Wind ⏱ 7 Days

California Coastal Discovery

San Francisco • Monterey • Santa Barbara • Catalina Island • San Diego

★★★★★ 4.9 (128)
One-Way Water Sports Ashore
was $9,099
$7,899 pp
Big Sur coastline Save $900
⚓ Pacific Mist ⏱ 5 Days

Wine Country & Big Sur Getaway

San Francisco • Half Moon Bay • Monterey • Big Sur (cruise-by) • San Francisco

★★★★★ 5.0 (214)
Roundtrip Wine Tasting Adults Only
was $10,699
$9,199 pp
Alaska Low Price
⚓ Bay Voyager ⏱ 14 Days

Alaska's Inside Passage

San Francisco • Victoria • Ketchikan • Juneau • Skagway • Glacier Bay • Vancouver

★★★★★ 4.8 (86)
Balcony Suite Excursions Expedition
was $10,499
$8,499 pp
Pacific Northwest coastline Save $800
⚓ Coastal Muse ⏱ 8 Days

Pacific Northwest Passage

San Francisco • Astoria • Seattle • Victoria • San Francisco

★★★★★ 4.9 (167)
Roundtrip Rainforest Hikes Wildlife
was $8,899
$8,099 pp
Baja California coastline Save $1,000
⚓ Golden Horizon ⏱ 10 Days

Baja & Sea of Cortez

San Francisco • Cabo San Lucas • La Paz • Loreto • Ensenada • San Francisco

★★★★★ 4.9 (93)
Roundtrip Whale Watching Snorkeling
was $11,099
$10,099 pp
Hawaiian Islands New Route
⚓ Redwood Star ⏱ 15 Days

Hawaiian Islands Crossing

San Francisco • Lahaina, Maui • Honolulu, Oahu • Nawiliwili, Kauai • Hilo

★★★★★ 5.0 (41)
One-Way Sea Days Snorkeling
was $11,499
$10,299 pp
Sailing From San Francisco

Explore Our Destinations

With access to secluded harbors and hidden coves, Cypress Bay takes you closer to the heart of every region we visit — all reachable from our San Francisco home port.

California Coast

California Coast

Monterey Bay, Santa Barbara's coastline, and Catalina Island, all within easy reach of home port.

Explore →
Pacific Northwest

Pacific Northwest

Misty rainforests, historic Astoria, and the vibrant harbors of Seattle and Victoria.

Explore →
Alaska

Alaska

Glaciers, wildlife, and untouched wilderness from an intimate vantage point.

Explore →
Baja and Mexican Riviera

Baja & Mexican Riviera

Whale watching, warm desert coastlines, and the turquoise waters of the Sea of Cortez.

Explore →
The Cypress Bay Difference

An Extraordinary Experience

With fewer than 350 guests, you'll never wait in lines or feel lost in a crowd. Every detail is tailored to create unforgettable moments.

⚓

Small Ship Access

Visit secluded harbors and private coves that large cruise ships cannot reach. Anchor right in the heart of the destination.

🍴

Farm-to-Table Dining

World-class culinary experiences crafted by award-winning chefs using locally sourced Pacific Coast ingredients.

🏄

Watersports Platform

Complimentary kayaking, paddleboarding, sailing, and waterskiing from our onboard marina at the stern.

🤝

Personalized Service

With nearly one crew member per guest, enjoy warm, genuine hospitality where the staff knows your name by day two.

Cypress Bay cruise ship at sea
Our Fleet, Homeported in San Francisco

Sailing Yachts & All-Suite Ships

Feel the ocean breeze aboard our classic sailing yachts with billowing white sails, or enjoy the spacious luxury of our newly transformed all-suite Horizon Class ships. Every vessel departs from San Francisco, designed for an intimate connection with the West Coast.

6

Elegant Ships

148-342

Guests Max

1:1.5

Crew-to-Guest
Meet the Fleet
Guest Stories

Trusted by World Travelers

Read authentic reviews from our community of passionate cruisers who have experienced the Cypress Bay difference firsthand.

4.9
★★★★★

1,286 verified reviews in the last 12 months

Sarah T.

Sarah T. Verified

Sailed on Cypress Wind • Oct 2025
★★★★★

"This was our seventh cruise but our first with Cypress Bay, and we are completely hooked. The crew knew our names by day two, the food was phenomenal, and waking up to the sails off the Big Sur coastline is something we'll never forget."

California Coast • 7 Days
Michael R.

Michael R. Verified

Sailed on Bay Voyager • Sep 2025
★★★★★

"The all-suite ship was immaculate, and the balcony views in Alaska were breathtaking. We saw whales from our veranda while sipping morning coffee. Worth every penny compared to the crowded mega-ships."

Alaska • 12 Days
Elena V.

Elena V. Verified

Sailed on Pacific Mist • Nov 2025
★★★★★

"Sailing out under the Golden Gate and waking up in Maui two weeks later still feels unreal. The watersports platform meant we could paddleboard straight off the ship into turquoise water. Unforgettable."

Hawaiian Islands • 15 Days
James & Linda K.

James & Linda K. Verified

Sailed on Coastal Muse • Dec 2025
★★★★☆

"Incredible itinerary through Baja. We visited small harbors we'd never heard of that turned out to be the highlight, and the whale watching in the Sea of Cortez was unreal. The only reason for 4 stars is we wanted an extra day in Loreto!"

Baja & Sea of Cortez • 10 Days
Robert Chen

Robert Chen Verified

Sailed on Golden Horizon • Aug 2025
★★★★★

"As a solo traveler, I was nervous, but the communal dining and small size meant making friends was effortless. Seeing Seattle's skyline from the water at sunset was a highlight. Already booked my next one."

Pacific Northwest • 8 Days
Amanda P.

Amanda P. Verified

Sailed on Redwood Star • Jan 2026
★★★★★

"Glacier Bay exceeded every expectation. The expedition guides were incredibly knowledgeable, and loved that we could sail out of San Francisco instead of flying to a port. Watching ice calve from the bow at sunrise with coffee in hand is a memory I'll cherish forever."

Alaska's Inside Passage • 14 Days
David L.

David L. Verified

Sailed on Cypress Wind • Aug 2025
★★★★★

"Loved being able to drive to the pier instead of dealing with airports. Catalina Island was a highlight — the crew set up a private beach landing that never felt rushed."

California Coastal Discovery • 7 Days
Priya N.

Priya N. Verified

Sailed on Coastal Muse • Jul 2025
★★★★★

"The Pacific Northwest scenery from the top deck was unbeatable, and the crew's local knowledge of Astoria made the shore day feel like we had our own private guide."

Pacific Northwest Passage • 8 Days
Tom & Julia W.

Tom & Julia W. Verified

Sailed on Golden Horizon • Feb 2026
★★★★★

"Booked Baja on a whim for our anniversary and it exceeded every expectation. Watching gray whales from the open-air deck with a glass of wine was worth every penny."

Baja & Sea of Cortez • 10 Days
Read All 1,286 Reviews
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California Coastal Discovery

⚓ Cypress Wind • 7 Days

San Francisco → Monterey → Santa Barbara

$7,899 per person
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Voyage (2 guests)$15,798
Taxes & port fees$412
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Meet the Fleet

Cypress Wind sailing yacht
Classic Sailing Yacht
Cypress Wind

Our flagship sailing yacht, built for the California coast — billowing sails, a marina deck, and a warm, intimate feel.

148 Guests Max
Pacific Mist sailing yacht
Classic Sailing Yacht
Pacific Mist

Sister ship to Cypress Wind, specializing in short Wine Country and Big Sur getaways along the Central Coast.

154 Guests Max
Bay Voyager cruise ship
Horizon Class
Bay Voyager

An all-suite ship purpose-built for Alaska's Inside Passage, with reinforced hull and heated observation decks.

210 Guests Max
Coastal Muse cruise ship
Horizon Class
Coastal Muse

Our Pacific Northwest specialist, with expanded lounge space for scenic cruising through misty fjords.

224 Guests Max
Golden Horizon cruise ship
Horizon Class
Golden Horizon

Built for warm-water cruising in Baja and the Sea of Cortez, with an open-air whale-watching deck.

298 Guests Max
Redwood Star cruise ship
Horizon Class
Redwood Star

Our largest ship, equipped for the long Pacific crossing to Hawaii with extra pools and dining venues.

342 Guests Max