San Diego
The private bookings: sails, city loops and cross-border wine days in the Guadalupe Valley. The region spreads from beaches to borders; a private driver stitches it together.
Discover the best of Guadalupe Valley with this private wine tour from San Diego. Enjoy guided tastings, farm-to-table lunch, and scenic views—all in one day.
Most Popular“Mario was awesome. He picked us up right on time and was so helpful. He pointed out spots along the way and knew a lot of history! This was the best tour I have ever been on. Great wineries, and the food was amazing. He…”
Enjoy a 2-hour private sailing tour in San Diego Bay for up to six people. Relax, see iconic sights, wildlife, and enjoy personalized commentary from Captain Liz.
“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.”
Discover San Diego’s Balboa Park on a private Segway tour. Enjoy expert guides, scenic views, and a fun, eco-friendly way to explore this iconic destination.
“Bridgette was a very good tour guide. It was fun and easy to learn how to ride a Segway. We really enjoyed hearing some new information about Balboa Park.”
Discover San Diego on a private sunset sailing tour with stunning bay views, friendly crew, snacks, and the chance to see iconic landmarks up close.
“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!”
Experience San Diego from the water with a private sailing tour, passing iconic landmarks like the USS Midway and Coronado Bridge for unforgettable views.
“Fantastic cruise!!! Captain was so friendly and welcoming, sailboat was lovely (and handy that it had a bathroom!) views were spectacularloved the wind and ocean spray in your face feel when sitting up on the bow!! Cant wait to book again!”
Experience San Diego from the water with a private boat tour, visiting historic ships, scenic landmarks, and enjoying personalized service on a breathtaking sail.
“We had the BEST experience with Lucky Sol Sailing! I planned this outing for my best friend's bachelorette party, and it was the perfect way to relax and celebrate. We were able to bring our own drinks and music/speaker, and there was plenty of room…”
Experience a private morning sail in San Diego with stunning bay views, seals, and personalized service—perfect for families and groups.
“Such a great time with friends ! The captain was great and the boat was clean. We would bring a speaker next time and some snacks.”
Discover San Diego’s highlights in a private Lexus ES300 Hybrid tour, from historic sites to scenic coastlines, with personalized insights and flexibility.
“Looked at various tours. Could have paid over 400 dollars to take a bus tour with 4 adults. Got a private tour for significantly less. Very flexible could stay longer at stops that we liked and less time at stops that we weren’t as interested…”
Discover Baja California on a private tour from San Diego, enjoying lobster, margaritas, Mariachi music, and scenic border crossings—all with guided ease.
Experience San Diego in style with a 2.5-hour private sidecar tour, combining scenic rides and exclusive wine tastings at hidden local vineyards.
“We had such a wonderful experience. Such a unique way so see San Diego. Thank you for a memorable time!”
Discover San Diego's Balboa Park in style with a private 2-hour tour in a luxury vehicle. Explore gardens, museums, and iconic landmarks with expert guides.
“Excellent walking tour. Guide was very knowledgable and friendly, and he came prepared with water and snacks! Thank you for a full education on Balboa Park!”
Simplify your San Diego arrival with a private transfer for up to 3 people. Fast, private, and hassle-free transport from the airport to your hotel or residence.
“Excellent service! My flight was delayed several times and they kept on top of it. When flight landed the driver kept in touch with me as I got my bags, and found me easily. He was extremely helpful, considerate and friendly.”
Discover San Diego’s diverse flavors on a private 3.5-hour food tour, exploring Gaslamp Quarter’s best eateries with expert guides and authentic dishes.
“This is well worth it! The food is great and, the stories about the city makes this experience worth your time! Our guide knew his staff and made our tour enjoyable! Do this!”
Discover San Diego's beginner-friendly surf scene with a semi-private lesson. Personalized, fun, and perfect for families or friends seeking waves.
“Tanner was an awesome instructor. Took 2 first time surfers and got us up on some gnarly waves. Was a very fun experience.”
Experience San Diego’s waters with a private half-day fishing trip for up to 4 people. All gear, fish cleaning, and expert guidance included for a memorable outing.
“Captain Bobby was awesome. EXTREMELY helpful and knowledgeable. This was definitely worth it. It was a private trip— so it felt less like a tour and more like just being out on a friend’s boat. I would certainly recommend Pelican Sportfishing to anyone.”
Sea caves, sails and a zoo that set the standard, all in shirtsleeve weather.