See San Diego’s historic waterfront on a private daytime sail
3 hrs
Up to 12 people
Beer, drinks, snacks
Set out on a private midday sail and take in historic San Diego from the water. Look for local sea life as you relax aboard your sailboat.
Cancel more than 72 hours before departure for a full refund. If Sail San Diego cancels the trip, receive a full refund.
Product ID: UPYHW6
Follow Coast Guard bareboat charter rules: your charter does not include a captain. Licensed captains are paid directly by you after the trip. The information provided lists captains at $75 per hour plus tips, and also mentions a $150 captain fee due after the trip—confirm the exact captain charges before booking so you know what to expect.
Check in 20–30 minutes before departure. You need a physical boarding pass to board; you receive it at the Sail San Diego office before heading to the marina.
Yes. Have every guest sign the digital sailing waiver before arrival, or sign when you check in at the office.
Sail San Diego Office, 2720 Shelter Island Drive, San Diego, CA 92106
Sail San Diego delivers consistently exceptional experiences on the water, earning praise from virtually everyone who steps aboard. The company runs intimate sails with a maximum of six guests, creating a personalized atmosphere that feels more like sailing with a knowledgeable friend than a commercial tour. Multiple experienced captains rotate through the fleet—including Greg, Dave, Stu, Rich, and Frank—and guests rave about their sailing expertise, local knowledge, and genuine personalities. The booking process is refreshingly smooth from start to finish. Staff make thoughtful touches like calling ahead with details, coordinating food pickups from nearby restaurants, and greeting guests warmly at the dock. On the water, captains skillfully handle everything from gusty conditions to relaxed sunset cruises while pointing out landmarks and answering questions. Many reviewers highlight spotting dolphins and enjoying spectacular skyline views. The boats themselves are clean and well-equipped, with some captains providing music, snacks, and drinks. Whether you choose a midday harbor sail or sunset cruise, expect a relaxing yet engaging experience that consistently ranks as a trip highlight.
Sail on a stable 138-foot yacht to spot migrating whales off San Diego
Smash breakables and blow off steam in a secluded rage room
Rent a beach cruiser with hourly, daily, or weekly options
Rent a pedal-assist e-bike and ride San Diego at your own pace
Release stress in a secluded rage room with tools and breakables
Ride the water with included fuel and a life jacket