Top San Diego Wine Tasting Tours

Combine history with wine tasting on this guided walking tour around San Diego’s Little Italy. Discover the area’s history in a fun way, with stops at three locations to sample unique wines from California and Italy. Enjoy Italian food samples, such as pizza, calamari and meatballs, at two of the three locations.

California is where some of the US’s best wines are grown. Avoid the hassle of self-driving and set out on a guided tour to several San Diego vineyards that includes comfortable transportation by an expert driver. Enjoy a behind-the-scenes tour of several establishments and sample some of the region’s most popular vintages before stopping for an included dinner at a local winery.

Travel like a local through Valle de Guadalupe, Mexico's celebrated wine country. Start off with some tasty local tacos in Rosarito before we travel down the Baja coast in a private van with cold beers and water at the ready. Sample delicious reds, whites, and rosé wines at three renowned boutique vineyards, as well as farm-to-table dishes at a premier Valle restaurant. Note: At least eight passengers are needed to run the tour.

Private wine tour to Temecula stopping off at a lovely winery in Fallbrook. Monserate Winery began with a desire to preserve the beauty and integrity of Gird Valley. For 56 years, the beautiful 116-acre property was a public golf course, dotted with 100-year-old oaks and towering sycamore trees. After falling on hard times, the golf course closed. We had a vision to revitalize the land and create something incredible that would also enrich the lives of the surrounding community, and thus, Monserate Winery was born. We have been hard at work to bring this vision to life since 2016 and have made a lot of progress. Today, Monserate’s San Diego county wineries boast breathtaking vineyards, tranquil lakes, and spectacular scenery. Akash Winery & Vineyards is a family-owned boutique winery in Temecula, CA, producing 100% estate-grown wines alongside their Dreamville label the modern 20-acre estate is celebrated for its lively, approachable vibe, great vineyard views, and food and music.

San Diego has a great wine scene, and a fun way to explore it is to get there by riding in a motorcycle towncar. This is a private tour, great for family members, partners, and more. Wine tastings will be provided at each venue, and you can also choose to order food if you like (own expense). After this half day tour, the rest of the day is yours to do as you please.

Spend a few hours relaxing and sightseeing in the waters just off San Diego during this 1- or 2-hour San Diego Harbor cruise. Sit back and relax as you take in a fully narrated tour, offering top-notch sight lines of the San Diego skyline, a cruise under Coronado Bridge, a look at the bustling US Naval fleet, and a chance to spot some of the harbor’s resident sea lions.

5 hour private wine tasting tour of the wineries in North County San Diego. This is a very unique tour as most people head to Temecula. North County wineries are very good and produce some lovely wines. The tour itself will be approximately 3 hours the other 2 hours will be the drive time from downtown to Escondido and back to downtown and also the drive time between wineries. You will see some very picturesque scenery of the Mountains in North County and all the beautiful wineries along the way. It’s a very enjoyable tour.

Spend an evening gourmet wining and dining aboard the ‘Spirit of San Diego,’ enjoying top-notch food and drink while you soak up skyline views. During this San Diego dinner cruise, you sip a complimentary cocktail and enjoy live on-board entertainment as you cruise 25 miles of California’s coastline and gaze at the stars above.

Experience a luxury private wine tour in Valle de Guadalupe, Mexico’s premier wine region, with a fully customized itinerary featuring three to four amazing wineries, stunning vineyard views, and authentic Baja charm. Guests travel in style by BMW X1 (up to 4 people), XL SUV (5-8 people), or passenger van (up to 12 people) while enjoying curated tastings, boutique wineries, and the option to visit just wineries or pair their day with a Michelin-recognized lunch at Deckman’s en el Mogor, Finca Altozano, or Envero en el Valle. Perfect for romantic getaways, group celebrations, and serious food and wine lovers, this owner-curated Valle de Guadalupe wine tour delivers a personalized, seamless, and unforgettable Baja wine country experience.

Explore some of the top highlights of San Diego with your or or two day trolley pass (depending on option selected) for the city’s Hop-on, Hop-off Trolley Tour. Choose your own adventure as you get on and off the trolley at any of the 11 included stops, covering famous sights including the Gaslamp Quarter, the San Diego Zoo, USS Midway and the Cruise Ship Terminal, Little Italy, and many more. This San Diego trolley tour also features live commentary from the on-board guide during your ride.

Sip, Savor, and Explore Temecula Wine Country Departing from Pacific Beach, this full-day private wine tour offers a relaxing escape to Temecula Valley. With tiered pricing, the more in your group, the lower the per-person rate—ideal for couples, friends, or small groups. Pickup is available from your hotel or rental in Pacific Beach, or meet us at Capehart (Soledad) Dog Park: Soledad Mountain Rd & Felspar St, San Diego, CA 92109. This is a public lot we don’t manage—parking may be limited; rideshare is recommended. Begin with free time in Old Town Temecula for coffee or shopping. Then enjoy tastings and a guided production tour at Somerset Vineyard & Winery, followed by tastings, charcuterie, and a wine cave tour at Oak Mountain Winery. Lunch is at Cougar Winery (Mon–Fri) or Bel Vino Winery (Sat). Meals and tastings not included. End with a final tasting at Callaway Winery, a sleek hilltop estate with panoramic views Let us handle the details for a smooth, scenic wine country day

Experience the best wines of the San Diego area without worrying about a designated driver on this tour through Temecula Wine Country. Visit three local wineries to taste their finest vintages while learning how the region’s unique microclimates influence flavor and tasting notes. At one winery, enjoy a behind-the-scenes tour to deepen your understanding of winemaking and enhance your tasting experience.

Delight in Mexico’s fine wine and food on an intimate wine country tour that takes you across the border from San Diego. Travel to Baja California and visit the wine country hub of Valle de Guadalupe escorted by a local guide. Visit various local vineyards and experience exquisite wine tasting, gourmet cheese tasting, and a Mexican buffet all included. Discover why this area has long been renowned for its locally grown wine and produce. Round off your day gazing out from a terrace with stunning views over the Pacific Ocean.

Hit the bars in Pacific Beach with a fun loving group when you book this group bar tour in San Diego. You’ll have plenty of friends ready to party with you. Your guide will take you to some of the best bars in the area, and you’ll get exclusive discounts on drinks at each location. Have a great night out with a group of fun adults.

Taste your way through the Guadalupe Valley wine country with this tour from San Diego. You'll meet three different wine producers, learn about how wine is produced, and sit down for an included lunch at Finca Altozano, and sample plenty of locally produced wine, all with a private driver/guide so that you can drink responsibly.

Step into the shadowy underbelly of San Diego’s Gaslamp District, where the city’s rowdy frontier and hushed prohibition days of the past collides with its glittering modern nightlife, and where more than a few restless spirits linger long after last call. On this 21+ Haunted Pub Crawl, you’ll raise a glass in some of the district’s most storied and spirited locations. Stop by the Montijo Building, once home to a furniture store with a chilling sideline in coffins and embalming. Pause outside The Fluxx Nightclub, where the music and lights conceal one of the Gaslamp’s darkest histories. Then, uncover the eerie legends of the Horton Grand Hotel, a Victorian masterpiece said to still host a guest who never truly checked out. This isn’t your average stroll through the Gaslamp - it’s an adults-only journey into the eerie, intoxicating history that shaped the district and the ghosts that refuse to be forgotten. Valid U.S. ID or passport required. Drinks not included.

See San Diego from a marine vantage point on this 90min harbor cruise, including a look at the marina, seabirds and potential sea lion sightings. Listen to live narration from your captain and enjoy for-purchase snacks from the onboard snack bar.

Go sightseeing on the waters of San Diego Bay during this cruise that provides a delicious seated brunch of seasonal dishes accompanied by unlimited Champagne, mimosas, and sparkling cider. After enjoying a lavish plated brunch dish, stay at your private table or head outside to the open air for sunshine and sightseeing.

Experience the hidden gems of Southern California’s wine country with an exclusive four-stop journey through the rolling hills of San Diego County. From crisp, coastal breezes to sun-drenched inland valleys, you’ll enjoy curated tastings at lovely estates known for their award-winning varietals and stunning vineyard views.

Go whale watching from San Diego aboard a replica of a historic sailing schooner that won the world’s first America’s Cup sailing competition in 1851. Throughout your cruise, your expert guide shares informative commentary about gray whales, dolphins, and other marine animals, along with details about the US Navy sites you pass as you head out on the Pacific Ocean.

This relaxed tour offers an intimate alternative to Temecula tasting rooms and shuttle operators inundated by guests on Saturdays. Our informative guide engages with guests sharing nuances of Temecula’s culture of wine, microclimate, Pechanga Band of Indians intriguing lore, and the area’s historic significance in Southern California's development the past two centuries. Each winery promises a distinct style and fabulous view. Baily Family Winery sits high above Valle De Los Caballos. With sample in hand, a vineyard and production area walk, often conducted by owner Phil Baily, finishes with a seated tasting and charcuterie items. Frangipani Estate Winery guests enjoy table service, savoring wine and a delicious lunch while seated on the patio above a beautiful valley with Mount Palomar on the horizon. Bella Vista Winery, previously Cilurzo Winery founded by Vince and Audrey Cilurzo, boasts sweeping valley views and the original 5 acres of Petite Syrah grapes planted in 1968.

Explore some of the best eats in the Gaslamp Quarter of San Diego—and learn insider facts and stories about its sordid past—on this two-in-one, small-group walking tour. Join an expert guide who has the inside scoop on the district's hopping restaurant and bar scene. Sample delicious dishes at several eateries, sip drinks, and learn about the neighborhood's past as a notorious red-light district.

In just four hours, experience the scenic highlights of San Diego and its neighboring areas. Watch sea lions and pelicans on the beaches of La Jolla and capture fantastic views from the top of Mt Soledad. Soak up the Old World elegance of the mansions and Hotel Del on Coronado Island, and find peace in the urban oasis of Balboa Park. Wind through downtown and Old Town San Diego, learning about the city’s history along the way. Enjoy personalized attention on this small-group tour limited to just 14 people.