San Diego · SAILING TRIPS & YACHT CHARTERS
23 reviewed
A steady afternoon breeze and a protected bay make San Diego one of the easiest places in the country to get out under sail. These are the best sailing trips and yacht charters on the water: which run small-group and which go fully private, what the sunset excursions include, and how prices compare hour for hour, so you can pick the right boat for your evening.
San Diego Bay sunset sail in a small yacht group with bean bags, blankets, and big skyline views near USS Midway and the Maritime Museum.
“Not worth for money you pay. This is just a trip during sunset but not purely sunset viewing ride. Last 45 min we are close to sea shore.”
Small-group San Diego sunset sailing with skyline views, Point Loma lighthouses, USS Midway, and Coronado. Drinks, snacks, blankets included.
“Very much worth it! Loved our experience. The complimentary drinks and snacks were a great touch. Our guide was amazing and provided great music for our time on the boat. Would book this again with a group of friends!”
A 3-hour small-group sailing cruise in San Diego Harbor with snacks, beer, and your own music, passing Point Loma and Coronado views.
“Six of us went on the boat tour for a bachelorette party. We had a wonderful afternoon! There were assorted chips and snacks provided as well as drink options, such as beer and seltzers. We were able to connect our phone to the boat’s speaker to listen to our favorite music. Our captain had a great personality and was very informative. While on the boat, we were able to see seals and dolphins in the bay. It was a little chilly due to the wind, but the captain offered us blankets to use in order to stay warm.”
San Diego Bay sunset sail aboard Liberty, a hand-restored 1904 yacht. Beer, wine, snacks included on a small 6-person cruise.
“Lovely evening with Capt. Phillip and two other couples, sailing through the bay! The captain is a wealth of knowledge… just ask him questions!”
A small-group sunset sail in San Diego Bay with onboard drinks, marine-life spotting, and photo-ready views of Coronado and downtown.
“Book this!! Many reviews say this was the best thing they did in SD and that was true for us as well. Our captain, Ann was amazing, so fun to talk to and very accommodating for everything we needed. Definitely recommend the sunset timeframe, it was beautiful.”
Small-group San Diego sunset catamaran with drinks, blankets, and motor-off sailing past USS Midway, downtown views, and Point Loma.
“Very relaxing, private and friendly experienced captain Matt! We had a great time with perfect weather. Free wine was a bonus!”
Luxury small-group sailing on a 34-foot Catalina from Harbor Island, with skyline/coastal views, snacks, and BYO drinks.
“Capt. Mike was awesome! We had so much fun and his knowledge about the area was incredible. The best part was when we sailed back from the Coronado bridge. It was so peaceful and relaxing! I would absolutely do it again!!!!”
Sail San Diego Bay for 2 hours day or sunset, with white wine and skyline views plus USS Midway and Coronado Naval Station.
“Thank you so much Corinne for making this experience super memorable! ❤️”
Private 2-hour sail on San Diego Bay for up to 6. Customize your route with Captain Liz, enjoy snacks and champagne, spot sea lions.
“5 star experience. Liz was on time, friendly and helpful. The boat is clean, has a bathroom and is perfect for a sunset cruise. Highly recommend.”
Daytime sail on San Diego Bay: wine included, comfy bean bags and blankets, dolphins/sea lions, and a Midway aircraft carrier view from the water.
“It was our first experience sailing. Captain Bry was excellent! She was very informative and made us feel very comfortable. Definitely would do it again!”
Private luxury catamaran sailing from Mission Bay, cruising to La Jolla Cove or Sunset Cliffs with a friendly crew and included water.
“We had an amazing sunset cruise thru the bay with Maddie and Jake. Our family of 12 enjoyed the evening on the boat. Maddie and Jake were so accommodating and welcoming. Would highly recommend this tour!!”
A 2.5-hour small-group catamaran sail in San Diego with drinks, motor-off sailing, and big-harbor views of downtown to Coronado.
“Memories that will last a life time for my kids (10 &9). Captain Matt was knowledgeable on all sites around the bay.”
A small-group classic yacht sail past Star of India, USS Midway, Seaport Village, and Coronado. Snacks, drinks, and skyline views.
“Very relaxing ride through the SD harbor! Beautiful views, smooth sailing, and a peaceful atmosphere—highly recommend.”
A private 2.5-hour San Diego sunset sail for up to 12, with blankets, drinks, snacks, and a dramatic pass under the Coronado Bridge.
“Great experience to see the harbor and the San Diego Skyline! Beautiful views and lots of fun! We had a group of 13 girls on the sail for a bachelorette party and we were well taken care of!”
A 2-hour San Diego sunset sail from Harbor Island to Point Loma and Coronado, with onboard snacks and captain-led stories.
“I'll give you 3 1/2 stars. Captain Charlie was very good. Sailing duration was 1hr 35 minutes not 2 hours as advertised. I am not sure I would take this sailing again. Price versus value received requires a max rating of 3 1/2 stars. Good time, not a GREAT Time.”
