San Diego waterfront itinerary

Cap'n Keller sails the much loved vintage boat, Interlude, a classic gaff rigged cat ketch, at Mission Bay Aquatic Center.

Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So cast off the dock lines and set sails from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." - Mark Twain

Variety, adventure, scenic ocean views, surfing and sailing -- fun options for all

STORY By CHRISTENE MEYERS

PHOTOS By BRUCE KELLER

--Photos by Bruce Keller

"The Carpe Diem Kids"

Editor's note: This piece was reviewed and updated July 20, 2026

If you're looking for the best San Diego waterfront activities, you'll find an amazing variety of experiences along the city's scenic bays and coastline. Explore the historic Cabrillo National Monument for sweeping ocean views, tour the fascinating USS Midway Museum, or set sail on a relaxing Hornblower harbor cruise. Every stop offers a different perspective on one of California's most beautiful waterfronts, our home base for several months each year.

Bruce Keller and Christene "Cookie" Meyers post by "The Pacific Portal," a sculptural gazebo on Shelter Island.

Golden sunshine, ocean breezes, and a laid-back coastal vibe make San Diego one of the most irresistible destinations in the United States. Whether you’re strolling along the vibrant harbor of Embarcadero, exploring the historic decks of the USS Midway Museum, or soaking in panoramic views from Coronado Beach, this San Diego waterfront itinerary is designed to capture the very best of the city. From sunrise walks to sunset sails, get ready to experience the perfect mix of coastal beauty, outdoor adventure, and Southern California sunshine best enjoyed from a sailboat.

Mark Twain's name was what Samuel Langhorne Clemens picked for his pseudonym

Speaking of which, I can't believe I got this old without understanding the nautical connection of Samuel Langhorn Clemmens' pseudonym, Mark Twain.

The popular Paradise Point Resort & Spa Boat Rentals on Mission Bay.

Good old Keller, who is by his own admission half amphibian, explained it to me. Joy! For a day without learning is a lost day. This reporter has never had one yet and doesn't plan to. It has to do with fathoms and the amount of depth needed in the water for a boat to pass safely over.

WHO KNEW?

The river boatman's cry was "mark twain" or, more fully, "by the mark twain......"  If the depth were around 12 feet or about two fathoms it was safe to pass over.

Torrey Pines sunset near Scripps Research Pier.

Sunny San Diego coastal activities:

Our favorite way to enjoy Mission Bay is from Paradise Point Resort & Spa, where we charter a boat, throw in a picnic lunch and leave our worries behind. We sail as often as time and money allow.  Sometimes it's just the two of us; other times, we treat friends and family.   Sailing is a time-honored cure for the blues, an antidote for almost anything that ails you! You can sail into the past, be in the now and contemplate the future all at the same time.  Last weekend, we took my sister Misha and her husband David out of Paradise Point. If you're lucky enough to have a sailor in the family as I do, you're on your own.  Lessons and skippers are available for the less experienced, along with motorboats, jet skiis, paddleboats and kayaks. (www.actionsportrentals.com)

IT WAS GLORIOUS.  On this peaceful saltwater lagoon, I've been introduced to Keller's past.  He lived in several places on Mission Bay as a college kid and employee of the beloved Aquatic Center where he is now involved in a cause to preserve and restore Interlude, a boat with a place in the hearts of several generations -- Baby Boomers and "Befores and Beyonds."

San Diego waterfront itinerary

Include a visit to Shelter Island and Mission Bay, where you'll enjoy waterfront parks, boating, cycling, and spectacular sunsets. Finish your day with dinner at Sea Level Restaurant on Harbor Island, where fresh seafood, harbor views, and the San Diego skyline create an unforgettable dining experience. It's a favorite of ours for fabulous sunsets.

San Diego has dozens of welcoming parks, with cooling breezes, palm trees and lovely bay and ocean views.

To our astonishment -- by complete kismet -- we recently found ourselves seated on a plane next to a woman (our contemporary in age and inclination) who grew up sailing on Interlude.  She got misty-eyed recalling her childhood -- eating tuna sandwiches and sailing with her family.  Kristen's 90-plus father remembers the boat well.

LISTENING TO Keller and Kristen reminisce prompted my wondering about the two bays.  Here's an excerpt from Cap'n Keller's explanation, transcribed by first-mate Cookie:

San Diego's beautiful Mission Bay is a sought after cooling spot when other places see high temperatures.

"Mission Bay and San Diego Bay are formed by several meandering rivers which deliver rain and snow melt from the coastal mountains forming the Baja Peninsula. Water is delivered via the San Diego River which runs through Mission Valley.  While Mission Bay is fed by San Diego River and Rose Creek, several other rivers feed San Diego Bay.

WHILE SAN Diego Bay is much larger than Mission Bay, both are treasures. Mission Bay is unusual, as one of the largest waterparks of its kind in the world. It is 4,200 acres of land and water, surrounded by 27 miles of shoreline of sandy beaches, attractive people and abundant bird life.

Smiling Cookie and Keller on Mission Bay, taking a break from bike riding on the wide trails.

Interconnected by a network of waterways, inlets and islets, the bay is best explored by boat...." (with Keller as cap'n) or by the progressively developed bike paths.

FROM MISSION Bay and Paradise Point, we've watched families barbecuing right next to the water, sharing a picnic, strolling, kayaking, jogging and taking in the internationally known spectacle of SeaWorld.

San Diego Bay from C-Level, our favorite restaurant in that area.

    San Diego Bay, also known as "the big bay" offers many options of entertainment and adventure, from whale watching to sport fishing. We've sampled it all.

   On the water, we've sailed off Shelter and Harbor Islands, along the Embarcadero, across the Bay to Coronado, and south to the shores of National City, Chula Vista and Imperial Beach.

   I had no idea San Diego Bay offered so many spectacular places to view the sky and the city lights.  Many are  attracted to the beautiful shops and first-rate dining. We're C-Level regulars.  Our favorite "big bay" restaurant offers gorgeous views,  fabulous appetizers, attentive service and a terrific wine list.

Cookie and her sister Misha board Hornblower on San Diego Bay.  We're regulars on the Hornblower fleet with array of cruises featuring narration and fine food.

  ANOTHER OPTION is a trip and meal on Hornblower Cruises which offers great value and a place to celebrate being alive and on the sea.  We are Hornblower devotees and have cruised the Hornblower fleet all year round, morning to evening, on Christmas, Thanksgiving, Easter and birthdays. Hornblower has it all -- robust coffee, tasty champagne and the delights of sea lions, whales, dolphins, sunshine, moonlight and a romantic dance as we pass under Coronado Bridge.  www.hornblower.com                                                                                     

If I could afford it, I'd be boarding Hornblower once a week for the baked spinach and artichoke appetizer, shrimp and crab, tenderloin and a stellar sea view of most of the city's 50-plus landmarks:  Point Loma and its beautiful light house, the fabled Star of India ship, the Midway Aircraft Carrier and Museum, the Naval Air Station, Cabrillo National Monument and other nautical accomplishments.  Hornblower's varied and many cruises offer a relaxing way to see and hear the history of our gorgeous city, set against the Bay's spectacular views.

The Maritime Museum on San Diego Bay features many historic ships.

NATIVE PEOPLE have long settled here but Juan Rodriguez Cabrillo was the first European to arrive in 1542.  He named it San Miguel.

I'm going to find out more about the green sea turtles who live here -- perhaps the only place on the West Coast. I've been introduced to a wonderful, myriad world in these two bays, both loved by Keller, my cap'n of the waterways.

I know how lucky I am.

"If we are always arriving and departing, it is also true that we are eternally anchored. One's destination is never a place but rather a new way of looking at things." - Henry Miller

Next up: Come with Cookie and Keller to the Oregon Shakespeare Festival, Ashland, Oregon, with theater treasures, the Yorkie-friendly Ashland Springs Hotel and a chocolate festival! Check us out weekly for more adventures around the globe, with money saving pointers and tips on making the most of precious time aboard.

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