San Diego Bay rewards sailors at every level and every pace. The protected inner waters make it forgiving and accessible; the coastal run out past Point Loma opens things up for those who want more.
Each itinerary here is a starting point. Your Waypoints Yacht Charters Specialist and the local Seaforth crew will help shape the actual plan around your group’s interests, the forecast, and the conditions on the day. Both routes depart from Safe Harbor Sunroad Marina on Harbor Island unless you’ve arranged an alternative departure location with the team at booking.
WEEKEND GETAWAY — 3-DAY ITINERARY
Saturday – Monday | Departing from Safe Harbor Sunroad Marina, Harbor Island
The ideal introduction to San Diego Bay — two days that cover the iconic, the scenic, and the genuinely surprising, all within easy reach of the dock.
DAY 1 | San Diego Bay Exploration
Sail Time: Half day | Distance: Bay sailing
Cast off from Harbor Island and head into the heart of San Diego Bay. Stop at Parkside Pier for lunch and a close-up look at the downtown skyline, then sail past the USS Midway Museum — the scale of the aircraft carrier is genuinely impressive from water level.
Continue south toward the Coronado peninsula and tie up for the evening at the Loews Coronado Bay Resort, where a slip is included in your charter. The resort’s heated pools, bike rentals, and waterfront restaurant make for an outstanding first night — the kind of arrival that sets expectations for the days ahead.
PLACES TO GO / THINGS TO DO
- Stop at Parkside Pier for lunch and sightseeing along the downtown skyline
- Sail past the USS Midway Museum — one of the Bay’s most striking landmarks from the water
- Tie up for the evening at Loews Coronado Bay Resort (slip included in charter)
- Heated pools, bike rentals, and outdoor waterfront restaurant at the resort
- Overnight at Loews Coronado Bay Resort
DAY 2 | Coronado & The Bay
Sail Time: Half day | Distance: Bay sailing
Sail back north toward Harbor Island with a stop at Glorietta Bay — the calm, sheltered cove just south of the Coronado Bridge, framed by the Victorian towers of the Hotel del Coronado. Dinghy ashore to explore Coronado Island on foot, grab lunch at the Hotel Del or Peohe’s, or simply stay aboard and let the afternoon find its own pace.
As the sun drops toward Point Loma, the west side of the bay delivers some of the finest sunset views in San Diego. Round out the evening with dinner at Bali Hai on Shelter Island or Brigantine at Point Loma — two of the Bay’s most established waterfront tables.
PLACES TO GO / THINGS TO DO
- Anchor in Glorietta Bay — calm, protected, and framed by the Hotel del Coronado
- Dinghy ashore to explore Coronado Island on foot
- Lunch at the Hotel del Coronado or Peohe’s on the waterfront
- Exceptional sunset views from the west side of the bay
- Dinner at Bali Hai (Shelter Island) or Brigantine (Point Loma)
DAY 3 | Coastal Sail
Sail Time: Full day | Distance: Bay and coastal
Depart early and head out through the harbor entrance past Point Loma into the open Pacific. The city falls away, the coastline stretches in both directions, and dolphins and sea lions are a regular presence on this stretch. Sail north toward La Jolla or Mission Bay depending on conditions, then drop anchor off Mariner’s Basin for lunch and a swim in the calm inner bay.
If the afternoon wind builds, a downwind run back into San Diego Bay makes for a perfect close to the weekend. Return to the marina, clean up, and choose your final evening from the waterfront restaurants along Harbor Island or the independent dining scene at nearby Liberty Station.
PLACES TO GO / THINGS TO DO
- Sail out past Point Loma into the open Pacific — a dramatic shift from bay to ocean
- Watch for dolphins and sea lions on the coastal stretch — sightings are common year-round
- Sail north toward La Jolla or Mission Bay depending on conditions
- Anchor in Mariner’s Basin, Mission Bay — calm water, good swimming, easy lunch stop
- Downwind sail back to San Diego Bay in the afternoon
- Dinner at Harbor Island waterfront restaurants or Liberty Station
LONG WEEKEND — 4-DAY ITINERARY
Friday – Monday | Departing from Safe Harbor Sunroad Marina, Harbor Island
DAY 1 | Settle In & Sunset Sail
Sail Time: ~2 hrs | Distance: Bay sailing
Arrive mid-day, provision the boat, and ease into the charter with a short afternoon sail around the bay. This first day is deliberately unhurried. It’s meant to orient the crew, introduce the landmarks, and deliver a view of the city from the water that sets the tone for everything that follows.
Watch the sun go down from the cockpit. Overnight at your marina or anchor in Glorietta Bay for the first evening at anchor.
PLACES TO GO / THINGS TO DO
- Arrive mid-day and provision — your Waypoints Yacht Charters Specialist can assist with advance provisioning
- Short afternoon orientation sail — skyline, bridge, bay entrance
- Sunset from the cockpit — San Diego does this particularly well
- Overnight at marina or Glorietta Bay anchorage
DAY 2 | Offshore Adventure
Sail Time: Full day | Distance: Bay and coastal
The day that earns the early start. Head out past Point Loma and sail north toward La Jolla or south toward Imperial Beach. Your crew will read the wind and pick the better direction. La Jolla’s sandstone cliffs and marine life reward the northern run, while the quieter southern stretch runs past the Silver Strand with the Coronado Islands occasionally visible on the horizon.
If conditions allow, anchor off Mission Bay for snorkeling or paddleboarding before making your way back by sunset. Dinner ashore at Bluewater Boathouse Grill on Coronado, a crew recommendation that hasn’t let anyone down.
PLACES TO GO / THINGS TO DO
- arly departure past Point Loma — the best offshore sailing starts before the bay fills up
- North to La Jolla (cliffs, marine life) or south toward Imperial Beach based on wind
- Coronado Islands visible on the southern route on clear days
- Anchor off Mission Bay for snorkeling or paddleboarding (conditions permitting)
- Return to Coronado or Harbor Island by sunset
- Dinner at Bluewater Boathouse Grill, Coronado
DAY 3 | Relaxed Bay Day
Sail Time: Half day | Distance: Bay sailing
Sleep in. Today the Bay rewards a slower pace. Head south to explore the Chula Vista Marina area and the South Bay wildlife refuge — a quieter, more natural corner of the bay where the character of the water changes entirely and the birdlife is extraordinary. A possible lunch stop at Pier 32 Marina before heading back north to Glorietta Bay for another afternoon at anchor — paddleboarding, swimming, or simply floating with a cold drink and an unimprovable view of the Hotel del Coronado.
PLACES TO GO / THINGS TO DO
- Relaxed morning departure — no rush
- Sail south to Chula Vista Marina and the South Bay wildlife refuge
- Lunch at Pier 32 Marina
- Return to Glorietta Bay — swimming, paddleboarding, or pure relaxation
- Second evening at anchor under the Hotel del Coronado’s towers
DAYS 4 | Leisure Cruise & Return
Sail Time: ~2 hrs | Distance: Bay sailing
A gentle final morning on the water — a bay loop or a short run past Point Loma for one last look at the Pacific before heading in. Return to the dock by early afternoon. Before the drive home, brunch at Tom Ham’s Lighthouse on Harbor Island is the right call, a converted lighthouse sitting right on the water with views back over the bay you’ve spent four days on. Order well and take your time.
ON YOUR FINAL DAY
- Short final sail — bay loop or a quick run past Point Loma
- Return to dock by early afternoon
- Brunch at Tom Ham’s Lighthouse, Harbor Island — the view and the food are both worth it
- Tag #WaypointsWanderer — four days of San Diego from the water deserves its moment
REWARDS PROGRAM
BECOME A WAYPOINTS WANDERER
Explore the world’s best cruising destinations as a Waypoints Wanderer and earn amazing benefits for your loyalty! Simply book and complete your first charter vacation with Waypoints Yacht Charters and you’ll be automatically enrolled.
STAY IN THE KNOW
Join Our Newsletter
Receive exclusive offers, the latest chartering information, and news from our Waypoints destinations directly to your inbox.