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“We had the BEST experience on this tour! We had Rene as our guide and he made the whole date incredibly smooth. He kept us on time, took us to some beautiful spots, and made us feel safe at all times. I couldn't believe how…”
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.
“Captain Liz was amazing. She allowed us to determine what we wanted to see, provided commentary on our surroundings. Would 10 out of 10 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.
“We had a great afternoon. Bridgette was a great teacher and guide. It was so much fun! Would highly recommend”
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.
“Jason was an amazing captain. We wanted a peaceful ride and the experience did not disappoint. It was a beautiful day with just enough wind, a beautiful boat, a knowledgeable captain, good friends, and good music made for an unforgettable experience. Would do it again!”
Experience a private morning sail in San Diego with stunning bay views, seals, and personalized service—perfect for families and groups.
“Fantastic morning out on the boat with Captain Paul! The boat was great, clean and modern with a sleek cabin. The cushions on the bow was great touch”
Discover San Diego’s highlights in a private Lexus ES300 Hybrid tour, from historic sites to scenic coastlines, with personalized insights and flexibility.
“Our tour guy Darren went out of his way to make sure our tour was excellent. We would have never seen as much as we did if we went with the cruise tour and the price for this private tour was very affordable Everything we…”
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.
“Steve was fantastic and waiting on us 30 minutes before time and ready to take us! We saw every part of San Diego that one could wish for. The sidecar was way cooler than we imagined. Zoom zooming all around SD in the open air…”
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.
“Perfect timely pick up at airport in a spotless Mercedes! Driver was friendly, helpful, and courteous”
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.