Welcome Aboard
Your Voyage Begins on the Bay
Intimate yachts. Fewer than 350 guests. Sail from San Francisco to hidden coves from California to Alaska — cared for like you're the only one aboard.
Intimate yachts. Fewer than 350 guests. Sail from San Francisco to hidden coves from California to Alaska — cared for like you're the only one aboard.
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.
Save $1,100
San Francisco • Bodega Bay • San Francisco
Save $900
San Francisco • Half Moon Bay • Monterey • Big Sur (cruise-by) • San Francisco
Low Price
San Francisco • Victoria • Ketchikan • Juneau • Skagway • Glacier Bay • Vancouver
Save $800
San Francisco • Astoria • Seattle • Victoria • San Francisco
Island Getaway
San Francisco • Avalon • Two Harbors • San Francisco
Round-trip island sailing — two full days at Catalina, snorkeling the Casino Point reserve, and sea kayaking the coves of Two Harbors.
New Route
San Francisco • Lahaina, Maui • Honolulu, Oahu • Nawiliwili, Kauai • Hilo
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.
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.
Visit secluded harbors and private coves that large cruise ships cannot reach. Anchor right in the heart of the destination.
World-class culinary experiences crafted by award-winning chefs using locally sourced Pacific Coast ingredients.
Complimentary kayaking, paddleboarding, sailing, and waterskiing from our onboard marina at the stern.
With nearly one crew member per guest, enjoy warm, genuine hospitality where the staff knows your name by day two.
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.
Read authentic reviews from our community of passionate cruisers who have experienced the Cypress Bay difference firsthand.
"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."
"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."
"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."
"Incredible little itinerary. Two full days at Catalina meant we could do Avalon one day and the quiet side at Two Harbors the next, which almost nobody bothers with. The only reason for 4 stars is we wanted a third day on the island!"
"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."
"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."
"Loved being able to drive to the pier instead of dealing with airports. Bodega Bay was a highlight — the crew set up a private oyster tasting on the beach that never felt rushed."
"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."
"Booked Catalina on a whim for our anniversary and it exceeded every expectation. Watching the island come up over the bow from the open-air deck with a glass of wine was worth every penny."
⚓ Cypress Wind • 3 Days
San Francisco → Bodega Bay → San Francisco
Please read the terms below in full. You must accept them before continuing with your booking.
These Booking Terms form the contract between you and Cypress Bay Voyages ("the Company"). The lead guest confirms they are authorised to accept these terms on behalf of every guest named on the reservation. A booking is confirmed only once payment has been received and a reservation number has been issued.
The fare quoted is the total price for the guests shown and includes taxes, port charges, and government fees unless stated otherwise. Full payment is due at the time of booking. Optional extras reserved through the Voyage Planner are charged to your onboard account and are not included in the fare.
If you need to cancel, written notice must be received by the Company by email at info@cypressbayvoyages.com. Refunds are calculated from the date that written notice is received, not the date it was sent, according to the following schedule:
| Notice Before Departure | Refund |
|---|---|
| 30 days or more | Full refund of all monies paid, including taxes and fees. |
| 8 to 29 days | 50% refund of the total fare paid. |
| 7 days or fewer | No refund. The full amount paid is forfeited, including all taxes and fees. |
Refunds are issued to the original method of payment and are normally processed within 14 business days of the cancellation being acknowledged.
The ship sails at the published departure time and cannot be held for late guests. Any guest not aboard before departure will be recorded as a no-show. A missed departure is treated as a cancellation with fewer than 7 days' notice: the entire fare is forfeited and no refund, credit, or rebooking will be issued under any circumstances, including delayed or cancelled flights, traffic, weather, illness, or missing or invalid travel documents. Guests are strongly advised to arrive in the port city the day before departure.
We strongly recommend that every guest purchase comprehensive travel insurance at the time of booking, from an independent third-party insurance provider of their choosing.
Cypress Bay Voyages does not sell, underwrite, arrange, or endorse travel insurance, and receives no commission from any insurer. Appropriate cover typically includes trip cancellation and interruption, emergency medical and evacuation expenses, and baggage protection. Because the refund schedule above applies regardless of the reason for cancellation, insurance is the only way to protect your investment against illness, injury, bereavement, delayed transport, or other unforeseen events. It is your responsibility to review any policy's terms, exclusions, and deadlines, as many policies must be purchased within a set period after the initial booking date.
Requests to change guest names, sailing dates, or cabin category are subject to availability and must be made in writing. An administration fee of $150 per change applies, plus any difference in fare. Changes requested within 30 days of departure are treated as a cancellation and rebooking, and the schedule in section 3 applies.
The published itinerary is an expression of intent, not a guarantee. The Master of the vessel may alter or omit any port of call, or vary the itinerary, where necessary for the safety of the ship, her guests, or her crew, or due to weather, sea conditions, or port restrictions. Such changes do not entitle guests to a refund. In the rare event the Company cancels a voyage in its entirety, you will be offered a full refund or an alternative sailing of comparable value.
Each guest is solely responsible for holding valid identification and any travel documents required for the itinerary booked. Guests who present without the correct documentation will be denied boarding, and no refund of any kind will be due.
Guests must be fit to travel and must disclose any condition requiring medical attention or special assistance at the time of booking. The Company reserves the right to refuse or revoke passage where, in the reasonable judgement of the Master or ship's physician, a guest's condition may endanger the guest or others.
Nothing in these terms excludes liability that cannot be excluded by law. The Company is not liable for loss or expense arising from circumstances beyond its reasonable control. These terms are governed by the laws of the State of California, and any dispute is subject to the exclusive jurisdiction of its courts.
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Our flagship sailing yacht, built for the California coast — billowing sails, a marina deck, and a warm, intimate feel.
Sister ship to Cypress Wind, specializing in short Wine Country and Big Sur getaways along the Central Coast.
An all-suite ship purpose-built for Alaska's Inside Passage, with reinforced hull and heated observation decks.
Our Pacific Northwest specialist, with expanded lounge space for scenic cruising through misty fjords.
Built for California coastal cruising to Catalina, with an open-air viewing deck and a tender platform for the island coves.
Our largest ship, equipped for the long Pacific crossing to Hawaii with extra pools and dining venues.