Dear Reader ~
One of our favorite ways to end the day is sitting on the patio at sunset, watching the cruise ships sail out of San Diego Harbor. We have a wonderful view of the port, and there's always something interesting coming or going.
Recently, we watched Virgin Voyages' Brilliant Lady in the harbor. With Royal Caribbean arriving and Disney expanding its sailings, it got me thinking about just how much is happening on our waterfront.
So I took a closer look at what's actually sailing from San Diego in 2027—and found a few itineraries worth sharing.
Our Port expects its busiest cruise season in more than 15 years, with 183 voyages during the 2026–27 season. For those of us who live here, that's welcome news. But there are some interesting options even if San Diego isn't your hometown.
What's Sailing From San Diego in 2027?
Royal Caribbean is coming to town.
Serenade of the Seas will offer three-night cruises to Ensenada and four-night itineraries that include Catalina Island. For Southern California residents who usually drive to Los Angeles for a short cruise, having these departures in San Diego is a welcome addition.
Disney is expanding its San Diego sailings.
Disney Wonder and Disney Magic are part of the expanded program, with Baja and Mexican Riviera itineraries. More departure choices are especially useful for families and multigenerational groups trying to coordinate schedules.
Norwegian is sailing from San Diego, too.
Norwegian Star offers Mexican Riviera and longer Panama Canal itineraries. But if you're considering Norwegian for its luxury accommodations, there's an important distinction.
You may have heard of The Haven, Norwegian's luxury ship-within-a-ship experience, with enhanced service and private amenities on select ships.
Norwegian Star offers suites, but it doesn't have the dedicated Haven complex.
If The Haven is what interests you, we'd look at a different Norwegian ship. It's a good example of why I compare individual ships rather than recommending a cruise based on the cruise line alone.
Holland America has some particularly interesting itineraries.
If you've already visited Cabo, Mazatlán and Puerto Vallarta, consider Holland America's seven-night Baja Peninsula itinerary aboard Koningsdam.
It visits Loreto, Pichilingue (for La Paz) and Cabo San Lucas. Loreto and La Paz offer a different perspective on Baja and the Sea of Cortez. Two cruises to Mexico can be quite different depending on the ports.
And for travelers with more time, one departure that caught my attention is Holland America's 35-day Hawaii, Tahiti and Marquesas roundtrip from San Diego aboard Zaandam, departing October 14, 2027.
Five weeks isn't for everyone, but it's an appealing way to explore the Pacific without having to fly to your embarkation port.
We recently watched Virgin Voyages' Brilliant Lady in San Diego Harbor, but seeing a ship here doesn't necessarily mean you can board it here. Virgin's published 2027 West Coast itineraries depart from Los Angeles.
Virgin also has a limited-time promotion offering up to $1,000 in instant savings plus 70% off the second guest, with bookings due by November 2. If you've been curious about Virgin's adults-only cruises, this could be a good time to compare itineraries and fares.
Don't Live in San Diego?
San Diego is a wonderful place to spend a few days before or after a cruise. Depending on the itinerary, it may be worth comparing with departures from Los Angeles or other West Coast ports.
Wherever you're sailing, I recommend looking at the ship, itinerary, accommodations and overall value—not simply the departure port.
Before You Book Directly, There's Something Worth Knowing
As a Virtuoso-affiliated travel advisor, I have access to exclusive cruise benefits that you may not receive when booking directly with the cruise line.
On eligible sailings, these can include additional onboard credit, complimentary amenities or other preferred benefits—often on top of the cruise line's current promotions and your existing loyalty perks.
That means you may be able to book the same cruise, in the same cabin category, with something extra included.
And there's more to my role than finding a promotion. I'll help you choose the right ship, compare cabin locations and fare options, and understand exactly what's included before you commit.
Already found a cruise you like? Send it to me before you book directly. I'll check the available Virtuoso benefits, compare your options and let you know what I can offer.
Whether you're sailing from San Diego, Miami, Barcelona or somewhere else, I'm happy to take a look.
Thoughtful Travel. Beautifully Designed.
P.S. If you enjoy talking about travel almost as much as actually traveling, come join us in The Curated Voyage. It’s my small Facebook group where we share advice, cruise and destination ideas, travel photos, and the occasional excuse to spend far too long scrolling through old vacation pictures. Come join us ➡️
All itineraries, departure dates, promotions, pricing, and amenities are subject to availability and change without notice. No reservations have been made or confirmed. Additional benefits, including Virtuoso amenities, vary by sailing and eligibility. Promotional terms and restrictions apply.
