San Diego · WINE TOURS
Every trip runs one free day short. These 15 wine tastings are the ones that earn the slot, priced and timed so you can decide over breakfast.
Board Flagship Cruises’ luxury yacht at Broadway Pier for a two-hour Sunday brunch on San Diego Bay. Expect bottomless mimosas, chef-attended omelets, seafood, sirloin, desserts, live music or a DJ, and views of the USS Midway, Coronado Bridge, and downtown skyline.
“Wait staff was attentive and friendly. Food was just ok. Overall, a nice 2 hours to spend on a ship seeing San Diego”
Join Captain Phillip aboard Liberty, a hand-restored yacht modeled on a 1904 sailboat, for a 2.5-hour San Diego Bay cruise. With space for six passengers, beer, white wine, soft drinks, snacks, and views of Navy ships, the Coronado Bridge, sea lions, and the skyline, this is a calm, personal evening on the water.
“Captain Phillip’s sailing tour was beautiful! My husband and I went out along the bay with our two other friends and it was an incredible experience! The views, the sailboat, everything was top tier. Will definitely be doing this again in the future and I recommend if you want an intimate personal experience, this is the tour to do! Thank you again!”
Travel from San Diego into Mexico’s Valle de Guadalupe with a private guide such as Mario or Rene handling the driving, border crossings, winery visits, and timing. The day includes three tastings, a winery production visit, a five-course BajaMed lunch at Finca Altozano, and hotel pickup in eligible areas.
“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 sat with us at lunch, helped order and helped us with any and all questions. He was so intelligent, welcoming, friendly and kind. Crossing back from Mexico was super easy! I felt entirely safe and taken care of. I would recommend this tour and plan to do it again myself. So fun and so worth it! Don’t miss out!”
Travel from San Diego to Mexico’s Valle de Guadalupe for three boutique winery visits, 10 to 12 tastings, Rosarito fish or shrimp tacos, and a tapas lunch at Adobe Guadalupe. Guides such as Oscar and Priscilla bring local color, while a stocked van keeps the long day comfortable.
“Fantastic experience! Great food, wine, and people! Highly recommend! If you have global entry, makes getting back across the border when you return back easier.”
Travel from San Diego to Temecula with a guide such as Dave, Vicki, or Sonia, stopping in Old Town and three contrasting wineries. Expect wine tastings, lunch, valley views, hotel pickup from selected locations, and a relaxed day in a group of no more than 15.
“Tour was ok lunch was served late but other than that is was ok I thought Wilson creek was the best winery we visited”
Spend about three hours walking through San Diego’s Little Italy with a guide such as Magda, Scott, or Angela. Taste wine at three local venues, enjoy Italian food at two, and hear neighborhood stories in a group capped at 12 people.
“It was a great experience, highly recommend. Our guide, Kirk, was very knowledgeable and super friendly. Food and wine was amazing!”
Ray and the Baja Wine and Dine team take you from San Diego, Tijuana, Rosarito, Ensenada, or Valle de Guadalupe to three wineries, a cheese tasting, and lunch among the vines. Expect an English-speaking private tour, a clean vehicle, and a full day of wine, food, and wide Baja views.
“They are one hour late to pick us up for our wine tour and are not responding to messages or phone calls. Terrible company. Do not use”
You’ll ride in a private motorcycle sidecar with a guide such as Steve, Ron, or Cesar, stopping at Legacy Resort Hotel & Spa and Pali Wine Co. for tastings. Expect city views, local stories, open-air riding, and a flexible pace. Tastings, lunch, and alcohol are extra.
“Our guide Ron was fantastic! He took us to lots of hidden treasure around San Diego that we would have never know about. The wine tasting was a lovely spot with very nice local wines. Seeing the city in a sidecar was a great way to get a feel of different areas! Thank you Ron for your friendly and helpful manner! We would do it again.”
Meet your English-speaking guide at Vino Carta for a three-hour walk through Little Italy. You’ll visit three tasting stops, sample California, Italian, and other wines, and pair them with cheeses, pasta, and other Italian foods. Guides Bleu and Raul have both led this experience.
“It was a nice walk, and we enjoyed the tastings but wished they explained the different wines a little more. Overall, it was a nice outing but a little pricey.”
You’ll ride in an open sidecar with an English-speaking guide, pass Downtown San Diego sights, and stop at three wine-tasting rooms. Tastings are included, groups are capped at eight, and possible stops include Pali Wine Co, Bottlecraft Liberty Station, and M Wine House.
Cross from San Diego into Valle de Guadalupe for three winery visits, local tastings, a production tour, a food stop, and a hacienda-style lunch. Guide Marco has earned praise for his care and local know-how. The small group, capped at 15, keeps the day manageable.
“Marco was a great driver and guide. The countryside was beautiful, and the wines were good. The wineries were stunning.”
Meet your English or Spanish-speaking local guide at San Ysidro for a private trip into Valle de Guadalupe. You’ll spend over seven hours among wineries, with three tastings, two Mexican meals and drinks, round transportation, and groups capped at 12. Bring your passport, ID, and comfortable shoes.
“The excellent tour guide . His attention to detail and knowledge made out wine tour a great one. Humberto was a true professional guide top block”
Spend about five hours with Darren Manson on a private San Diego County wine tour. Visit Bernardo Winery, Mia Marie Vineyards, and Hungry Hawk Vineyards & Winery, with hotel, Airbnb, cruise terminal, or airport pickup available by arrangement.
“The Private San Diego County Wine Tour with host Darren Manson was fabulous. The tour was absolutely one of the best tours that can be had.”
You and your party get a private 90-minute Mission Bay cruise with a licensed USCG captain, a raised observation tower, and 360-degree views toward the Pacific. Cheese, crackers, and water are included. Bring your own wine with no corkage fee. Captain Rich may also share local landmarks, history, and wildlife facts.
“We had a wonderful time!!! Captin so good at giving us information as were sailing. His did a wonderful job with the cheep spread jalapeño cauliflower dip. Thank you both for making our anniversary trip extra amazing.”
Join Remy Sternbach for a private, all-inclusive wine day from San Diego to Baja’s Valle de Guadalupe. You’ll stop at La Fonda for coastal brunch, visit two hand-picked vineyards, and enjoy dinner in the valley when traveling with three or more people.
“Everything was perfect! The scenery was magnificent, and the sunset was breathtaking! Remy was awesome!”
Water, streets, neighborhoods, or a run out of town.
