Wine Tasting Tour in Little Italy, San Diego

Vino! Vino! Wine Tasting Tour in San Diego’s Little Italy

A guided tour

through the flavors and aromas of Little Italy

Planning a romantic date or your next friend’s night out? Our Little Italy wine tasting tour is the perfect way to elevate your outing and get to know one of San Diego’s most unique downtown neighborhoods.

As we stroll through this historic fishing town, you’ll learn all about the area’s rich history and, of course, sample the food and award winning wine that makes Little Italy one of the best culinary destinations in all of San Diego and, dare we say, Southern California.

What to expect:

  • Number of Stops: Visit 3 curated wine-focused venues in Little Italy, each selected for quality, atmosphere, and distinctive wine offerings.
  • Portion Size: Enjoy tasting-sized wine pours paired with small plates, including artisan cheeses and a pasta tasting. This tasting experience is designed to complement the wines with light bites rather than serve as a full meal. Guests are encouraged to enjoy lunch beforehand or plan dinner afterward.
  • Wine & Beverage Style: This is a wine-focused tour featuring premium wines from Southern California and international regions, including Italian favorites. Beer and cocktails are not part of this experience.
  • Walking Distance & Pace: A leisurely, easy-paced walk through Little Italy covering approximately 1 mile total with frequent seated stops. Comfortable shoes are recommended, but the tour is suitable for most fitness levels.
  • Educational Focus: Learn the basics of wine tasting, styles, and pairings, designed for both beginners and casual wine lovers (not a technical sommelier class). Relaxed, conversational atmosphere focused on wine, food, and discovery, not heavy drinking.

Important Information:

All guests must bring a valid ID with them for the wine tour. Some dietary needs may be accommodated with advance notice.

Rates:

Adults (Ages 21+): $125.00

Duration:

3 hours

Private Groups:

Do you have a group of 10 or more guests? We consider ourselves a boutique standout among destination management companies in San Diego, which means we have the capacity to coordinate memorable experiences for groups of up to 100 guests. Contact us to book a private wine tour.

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Vickie Walraven profile picture
Vickie Walraven
17 days ago
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Loved the tour. Wine was amazing and the food was excellent. Ben was the best tour guide ever!!! Highly recommend. We had such a lovely group of 6 they were all so much fun.
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Seth Crystall profile picture
Seth Crystall
40 days ago
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Had fabulous food tour of Little Italy with Ben. Food was off the charts and Ben’s knowledge of San Diego, as well as his personality made this tour very memorable. Highly recommend!
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Brad profile picture
Brad
51 days ago
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Ben was an exceptional guide. The wine was plentiful and was extremely high standard. Food was also included. I would recommend this to anyone
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William Cunningham profile picture
William Cunningham
69 days ago
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Bleu was an exceptional tour guide on the Pizza, Pasta, & Piazzas Food Tour through So Diego’s! From start to finish, Bleu made the experience memorable with a wonderful blend of local history, culture, and—of course—amazing food. Bleu did a fantastic job sharing the fascinating history of Little Italy while guiding us from one incredible food stop to the next. Every stop tantalized our taste buds and gave us an even greater appreciation and love for authentic Italian cuisine. What really stood out was Bleu’s knowledge, enthusiasm, and genuine passion for the area and the food. The tour was informative, relaxed, and a whole lot of fun. If you're visiting San Diego and want to experience Little Italy in a truly memorable way, I highly recommend this tour—and especially Bleu as your guide. Five stars all the way!!
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Jean Brittain profile picture
Jean Brittain
82 days ago
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We had an amazing time doing a food tour of Little Italy. The food and drinks were outstanding. Our guide Bleu was so knowledgeable and fun. She gave us fun facts and had a fantastic knowledge of the history of Little Italy. I highly recommend doing this food tour if in San Diego.
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Paige Hector profile picture
Paige Hector
85 days ago
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We had a wonderful adventure with the little Italy tour and Bleu as our guide! She was fun and took great care to create a memorable experience for us. Her knowledge of the area and passion made it so much fun. Thank you for this memory on our girls trip!
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Emily Gates profile picture
Emily Gates
110 days ago
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Our guide Ben was amazing! He was very personable and knowledgeable about San Diego history. We got to watch a great selection of food and got to see a lot of Little Italy.
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Kofi Bonsu profile picture
Kofi Bonsu
119 days ago
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My family and I did the Little Italy food tour with Magdalene! She was absolutely lovely! She was personable, kind, and extremely knowledgeable about the area—sharing so much interesting history that I didn’t know as a someone that has lived in San Diego for 15 years! She was very accommodating to the dietary restrictions for one of my family members, providing lovely alternatives. I would HIGHLY suggest this tour and more specifically Magdalene!
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Kyle Winnick profile picture
Kyle Winnick
205 days ago
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+0
Had a great time. The stops were lovely, the wine was tasty and Aparna was a delight as a tour guide!
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Rich DiBenedetto profile picture
Rich DiBenedetto
219 days ago
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We have been on many Walking Food Tours around the world, and this one (Little Italy Food and Drink Walking Tour: Pizza, Pasta & Piazzas) ranks right at the top. Our tour guide, Magda, was a sweetheart and took great care of our every need, while imparting some really great history of this area of San Diego. As a San Diegan, I have eaten in Little Italy many times, but this tour gave me a look at some really great options. The various stops, the quality, and quantity of the food were top-notch. My wife and I were amazed at the amount of food and drink we received, topped off with a scrumptious gelato. We highly recommend this tour and meeting Magda.
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J B profile picture
J B
259 days ago
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We booked a tour with So Diego Food Tours as a work team building. It was a fantastic mix of food and trivia/history, and the whole team enjoyed it a lot (much better than other 'forced fun' team buildings usually done). I was worried people would come away hungry but it was the opposite - maybe a little too much food and drink! All in all, a really great way to see San Diego's Little Italy especially for non-local team members, spend some time as a team and enjoy some food!
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Beth Caldwell profile picture
Beth Caldwell
266 days ago
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We had a great time on the Little Italy Food tour with Bleu as our guide. She explained the history of Little Italy in San Diego, the buildings, local color, and took us to 4 different places to try pasta, wines, pizza, beef sliders and topped it off with gelato. We were with a great group of people to share the experience and Bleu made it fun and informative. I’d go again in a heartbeat.
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Larry OConnor profile picture
Larry OConnor
266 days ago
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By far the best of our San Diego tours. Bleu was excellent with town and Little Italy history, so we had more than just fine food. We all loved the tour and the food!
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Brittany Hunley profile picture
Brittany Hunley
286 days ago
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We had an excellent experience booking three excursions with So Diego for Proof Summit 2026 ---- a Golf Scramble, a guided hike, and the Little Italy Coffee Tour. Bianca and Nicole were truly fantastic to work with: responsive, organized, and incredibly solutions-oriented from start to finish. They put in real effort to tailor each experience to our group, and it showed onsite. A special shoutout to the team for pulling off the Golf Scramble. This was their first of its kind, and they did a great job securing Coronado Golf Course and hosting the excursion smoothly and professionally. For the hike, we had to change locations twice due to unforeseen conflicts with the original options, but Bianca and Nicole handled the pivots with ease and ultimately delivered a great experience with the Cabrillo hike. The guides were also wonderful. Ben led an engaging, fun, and informative Little Italy coffee tour, and Magda was an excellent hike guide (friendly, knowledgeable, and great with the group). If you’re looking for a local partner who can execute memorable group outings and navigate last-minute changes with professionalism, I highly recommend So Diego. Thank you again to the So Diego team!
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Heidi Mabe profile picture
Heidi Mabe
302 days ago
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Vino! Vino! Little Italy Tour was excellent! My brother & I joined our guide, Magda, & other guests Sunday afternoon. My brother is local & I am from Arizona. We were intrigued by the 3-hour/3 stop tour in Little Italy with a history lesson. Magda is very knowledgeable & we learned a lot from her. We had fantastic conversations with her & other guests that made it all the more enjoyable. Each of the 3 stops showcased very nice wines & our last stop included a delicious pasta dish. The portions were generous & we were happy to use Uber. This tour was definitely a great value for all we experienced & consumed. I will be recommending this particular tour to all my family & friends that will be visiting San Diego. We look forward to returning to Little Italy to explore more businesses. We will also look into booking other tours through So Diego Tours.
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glasses of wine lined up on a table for the Little Italy wine tasting tour

WINE TASTING

From local San Diego wines to Italian classics, you’ll learn all about different premium wine varieties as you taste your way around this chic downtown area.

wine and pasta offered on a San Diego wine tour

SMALL BITES

Of course, it wouldn’t be a complete Little Italy tour without a delicious food tasting. We’ll indulge in Italian favorites, including a generous cheese board and a pasta dish.

HISTORY TOUR

Explore the town’s hidden gems and learn the history of the Italian immigrants who helped revive this area and transform it into the thriving community it is today.

Explore + Experience

Our Restaurant Partners

2161 India St
San Diego, CA 92101

Is a small, family-owned California wine retailer and tasting room that sources their wines globally from small, sustainable wineries and vineyards.

1643 India St, San Diego, 92101

(619) 255-7826

This restaurant is the epiphany of everything we love about Italian cuisine. From their hand made pasta, to their traditional pizza, house-baked breads and cookies, and house-made gelato. Enjoy the best of Italian cuisine in a relaxed environment. It is situated in the heart of Little Italy, next to the Piazza della Famiglia, a community gathering place that is home to the Little Italy food hall, farmers’ markets, concerts, and more.

Sogno di Vino

1607 India St.

San Diego, CA, 92101

An urban winery in the heart of Little Italy, they source grapes from the Santa Rita Hills area in California to create their acclaimed Pinot Noir and Chardonnays.  They offer a beautiful indoor/outdoor setting where they serve their wines and some delectable bites.

Little Italy

Ready to wine and dine with us in Little Italy?

Group tour walking across a cross walk

Book your tour

Our Little Italy walking tour is the perfect choice for your next date night or girl’s night out, and all it takes is a few easy steps to book your tour!

Learn something new

What makes sipping a glass of wine even more enjoyable? Learning all about the flavors and aromas you’re experiencing.

Group sitting at table with a tour guide holding wine glasses in Little Italy, San Diego
Group cheering glasses around table

Meet the locals

As we make our way through local wineries, you’ll meet some of the wine enthusiasts responsible for producing some of the best wines in the area.

Spoil your senses

From the sights of the historic buildings to the scents of fine wines, this winery tour is the ideal experience for satisfying all of your senses.

Red wine and italian food sitting on wooden table

Little Italy

Ready to wine and dine with us in Little Italy?

Group tour walking across a cross walk

Book your tour

Our Little Italy wine tour is the perfect choice for your next date night or girl’s night out, and all it takes is a few easy steps to book your tour!

Group sitting at table with a tour guide holding wine glasses in Little Italy, San Diego

Learn something new

What makes sipping a glass of wine even more enjoyable? Learning all about the flavors and aromas you’re experiencing.

Group cheering glasses around table

Meet the locals

As we make our way through local wineries, you’ll meet some of the wine enthusiasts responsible for producing some of the best wines in San Diego.

Red wine and italian food sitting on wooden table

Spoil your senses

From the sights of the historic buildings to the scents of fine wines, this wine tour is the ideal experience for satisfying all of your senses.

Tour guide holding up wine glasses

An elevated touring experience

If you’re looking for a more upscale approach to seeing San Diego, the Vino! Vino! Tour is for you. But don’t worry, we always maintain a down-to-earth feel with our fun and friendly tour guides and close partnerships with local wine and chefs.

Man cheering drink with group sitting at a table

Where history and modern luxury meet

Little Italy caters to all tastes. From luxury high rises and trendy bistros to historic buildings and quaint piazzas, this downtown neighborhood has so much to offer, and you’ll get to experience it all while tasting unique wines from San Diego and across the world.

Three women cheering wine glasses while sitting at table

A wine-lovers paradise

While we’ll certainly be dining on classic European dishes, this tour is all about the vino. As we make our way through three different establishments, you’ll get to sample and learn about unique wine varieties and meet with the local wine fanatics that produce them!

The perfect group outing!

Tour group sitting on red little italy chair

What better way to connect with others than over a glass of wine and delicious eats? When you book for groups of 10 or more, you can join us at any day and time. Plus, you can choose exclusive add-ons to make your custom tour even more memorable.

Vino! Vino! Tour FAQs

Wine sampling in Little Italy wouldn’t be complete without delicious bites to go with it. Indulge in wine pairing with a light Italian meal, where you’ll get to taste Artisan-style favorites including cheeses and a daily pasta dish from one of our restaurant partners. If you’re looking for a tour solely focused on culinary tasting inspired from Italy, check out our Little Italy food tour.

Instead of wine or beer, you have the option of selecting non-alcoholic beverages. Additionally, we will indulge in traditional European cuisine such as a cheese board and pasta. We will also embark on a historical walking tour of Little Italy, discovering lesser-known parts of the town and learning about the impact of Italian immigrants and their culture on the community’s development and growth.

There is no strict dress code, but we recommend smart-casual attire. Also consider the weather on the day of your wine tour, as we will be outside walking from restaurant to restaurant. You will be walking so wear comfortable shoes.

Yes! If you book custom San Diego wine tours for 10 or more people, you have the flexibility to schedule your visit to Little Italy on a day and time of your choice, and you can also add-on exclusive options to make the experience even more tailored to your liking.

We offer daily food tours in Little Italy, La Jolla, Old Town, and the Gaslamp Quarter. We recommend booking our daily Little Italy food tour if you want to explore this historic neighborhood, or book the Old Town food tour for a cultural experience. If you have a group of 10 or more, we suggest booking a private tour to ensure you and your group are well accommodated. Private tours can be booked on the day and time of your liking, as long as the local eateries are open. Whether you’re a local San Diegan or just visiting, we have something for everyone!

You may make modifications or cancel up to 48 hours before the start of your tour.  In the event that the tour does not meet the minimum guest count of 4 guests needed to operate, our team will reach out to you with options to switch your tour, or offer you a full refund.  We offer trip protection at checkout that protects you from unexpected changes to your booking within the cancellation window.

We recommend planning to eat both before and after the tour. The wine and food pairings are tasting-style portions and are not intended to replace a full meal.

Yes, all stops include reserved table seating for our group, so you’ll have a comfortable place to relax and enjoy each tasting.

This is a fun tasting experience rather than a party tour. While there is plenty of wine to enjoy and you may leave with a pleasant wine buzz, the focus is on flavor, storytelling, and neighborhood discovery.

All of our partner venues are carefully selected for their unique offerings. If a location needs to change, the replacement will always be aligned with the spirit and description of the tour, ensuring a comparable experience.

Our San Diego Tour Guides

Our San Diego Tour Guides

Kaylee Killebrew - Tour Guide

I’ve lived in San Diego for: 5 years, I quickly fell in love with this city. 

My favorite thing about being a tour guide is: Meeting people from all over the world, making them laugh, showing them some of my favorite spots and creating meaningful memories. 

My favorite San Diego neighborhood is:  Hillcrest or Old Town. Both are walkable and friendly places with endless restaurants, bars, coffee shops etc. You can find me in Old Town most weekends.

My favorite restaurant in San Diego is: This is a tough choice, for atmosphere and cocktails probably InsideOUT or Coasterra. For Breakfast…Morning Glory or Great Maple. For Dinner, Queenstown, Underbelly or Bronx Pizza. There are way too many options to choose from!

My favorite thing to do in San Diego is: To Read on the beach, host dinner parties with friends or scope out new happy hour spots.

headshot of tour guide kaylee killebrew

Kaylee Killebrew

Kaylee Killebrew - Tour Guide

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Magdalene Medofer - Tour Guide

I’ve lived in San Diego for: my whole life, I was born here.

My favorite thing about being a tour guide is: meeting new folks and sharing San Diego with them.

My favorite San Diego neighborhood is: Barrio Logan, I love the history of Chicano Park, the eclectic artisan shops, and extensive food scene.  The weekend is the best time to explore and watch the lowrider car clubs cruise the neighborhood and visit the shops.

My favorite restaurant in San Diego is: Artifact at the Mingei in Balboa Park.  Any dish off their international food menu will blow your mind.  They also host monthly themed dinners that highlight a particular cuisine and region.

My favorite thing to do in San Diego is: Go for a hike at Cuyamaca State Park and swim at Green Valley Falls.

headshot of tour guide magdalene medofer

Magdalene Medofer

Tour Guide

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Aparna Thakur - Tour Guide

I’ve lived in San Diego for: 1 ½ years!

My favorite thing about being a tour guide is: Meeting new people, showing them around and telling stories and history of the city.

My favorite San Diego neighborhood is: La Jolla because of its beautiful beaches, great restaurants and shopping as well as abundance of sea life.

My favorite restaurant in San Diego is: Brigantine

My favorite thing to do in San Diego is: Watching sunset in point loma Ocean Beach

headshot of tour guide aparna thakur

Aparna Thakur

Tour Guide

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Raul Torres Valadez - Tour Guide

I’ve lived in San Diego for: One year recently and also when I was a teenager.

My favorite thing about being a tour guide is: Meeting new people.

My favorite San Diego neighborhood is:  Pacific Beach and Coronado.

My favorite restaurant in San Diego is: Oscar’s Mexican seafood and Birrieria la Huasteca.

My favorite thing to do in San Diego is: Hike in the canyons.

headshot of tour guide raul torres valadez

Raul Torres Valadez

Tour Guide

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Ben Schorr - Tour Guide

I’ve lived in San Diego for: 5 years, I quickly fell in love with this city. 

My favorite thing about being a tour guide is: Meeting people from all over the world, making them laugh, showing them some of my favorite spots and creating meaningful memories. 

My favorite San Diego neighborhood is:  Hillcrest or Old Town. Both are walkable and friendly places with endless restaurants, bars, coffee shops etc. You can find me in Old Town most weekends.

My favorite restaurant in San Diego is: This is a tough choice, for atmosphere and cocktails probably InsideOUT or Coasterra. For Breakfast…Morning Glory or Great Maple. For Dinner, Queenstown, Underbelly or Bronx Pizza. There are way too many options to choose from!

My favorite thing to do in San Diego is: To Read on the beach, host dinner parties with friends or scope out new happy hour spots.

headshot of tour guide ben schorr

Ben Schorr

Tour Guide

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Bleu Ford - Tour Guide

I’ve lived in San Diego for: A long time!  I moved to San Diego in 1986 so I have lived here for most of my life.  I consider it my adopted home town.

My favorite thing about being a tour guide is:  I love both meeting new people and sharing knowledge about this beautiful city.  After retiring from USPS I wanted to do work that brings me joy and I have found that being a guide.  I love getting a laugh from a group or seeing the spark of excitement when I share a bit of San Diego’s colorful history.

My favorite San Diego neighborhood is:  I am partial to my own hood, North Park.  I love living here!  We lost so many great places due to Covid but it warms my heart to see that this neighborhood is returning to being a vibrant and fun place.  It always seems like there is something new or some fun event happening.

My favorite restaurant in San Diego is:  A few of my go-to favs are Buona Forchetta in South Park for relaxed patio dining with great food Jimmy Carter’s in Hillcrest for the comfortable and colorful ambiance and great Mexican comfort food and Shwarma Guys food truck (which parks regularly at 30th and Grape in South Park).  It is my go-to “I’m super hungry and too tired to cook” take home.  It always hits the spot.

My favorite thing to do in San Diego is: I recently got an e-bike and my new love is re-discovering the uptown area on two wheels.  It is pretty amazing how differently you see the city on a bike.  I love strolling through Balboa Park with my wife.  We are so lucky to have this awesome park with such a rich history so close to our home.  Finally, you can’t beat an early morning walk along the harbor.  The waterfront is beautiful in the morning quiet with a bit of fog hanging in the air.

headshot of tour guide bleu ford

Bleu Ford

Tour Guide

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