Top San Diego Holidays in 2026

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.

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.

Celebrate the season with a holiday-themed Underground Donut Tour in San Diego’s Little Italy! Over two festive hours, you’ll visit four hand-picked stops featuring the city’s most delicious seasonal donuts and pastries. Stroll past twinkling lights, decorated lampposts, and the charming holiday market while soaking in the joyful neighborhood vibe. We kick things off at Devil’s Dozen Donuts with rooftop views and devilishly good flavors. Then, it’s off to a cozy local bakery known for its festive sweets, followed by The Donut Bar—famous for outrageous creations like peppermint, red velvet, and gingerbread. Finally, wind down at a local coffee roastery with a fresh brew to pair with your treats. This tour blends holiday cheer, waterfront charm, and sweet bites into a delightful winter experience. If you love donuts, lights, and holiday magic, this tour is your perfect seasonal outing. Book now and make some sweet memories!

Experience the ultimate party on the water with Paddle Pub San Diego! Our 26-passenger, pedal-powered pontoon boat is designed for endless fun and excitement. With a powerful sound system, 12 pedaling stations, a spacious sundeck, and vibrant party lighting, you and your friends are in for an unforgettable adventure. Mission Bay, just north of San Diego, offers stunning views and a lively atmosphere. Pack a cooler with your favorite snacks and drinks, and pedal your way around the beautiful lagoon. After the cruise, explore the iconic Mission Beach. Set sail with Paddle Pub and discover what sets us apart from other boat tours—a unique blend of fun, fitness, and scenic beauty!

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.

Private brewery tour for 2-4 people. Safe & Convenient: We’re your designated driver. For this private tour you can pick the start time and pickup location. This very small group tour is perfect for tourists, beer lovers, locals, or anyone looking for a fun and unique way to explore San Diego’s craft beer culture. We can choose the breweries according to your preferred beer styles, or you can let us know your 'must visit' breweries, and we will include them in the tour. We will visit 3-5 breweries and the tour will last about 4 hours.

Private Car’raoke experience for your group Professional driver/host to guide the experience Karaoke setup with microphones and music access LED/vibe lighting to enhance the atmosphere Custom music selection (choose your favorite songs) Pickup and drop-off within the San Diego area Interactive, high-energy group experience

Get into the Halloween spirit on Mission Bay with Fright Nights, a 90-minute Halloween cruise aboard the Ohana! The cruise begins with 30 minutes of creepy atmosphere featuring Captain Diablo and his cursed crew, costumed characters, fog, eerie lighting, themed décor, and atmospheric music. Then the haunting ends and the party begins! Enjoy an hour of music, dancing, and Halloween fun led by Captain Diablo and his crew. Costumes are strongly encouraged, and specialty Halloween cocktails are available for purchase onboard. The 5 PM cruise welcomes all ages, though the spooky atmosphere may frighten young or sensitive children. The 7:30 PM and 9 PM cruises are 21+ only. - 90-minute Halloween cruise on Mission Bay - Including a 30-minute haunting followed by an hour-long Halloween party - Creepy characters, fog, eerie lighting, and themed décor - Costumes strongly encouraged - Halloween cocktails available for purchase

Get ready for a bar-hopping adventure like no other as we celebrate in the heart of downtown San Diego! This is your chance to experience the best nightlife the city has to offer, with a curated lineup of vibrant venues and unforgettable experiences. Gather your friends and get ready to kick off the long weekend in style. We've handpicked the hottest bars in town, each offering unique vibes, signature drinks, and a lively atmosphere that will keep the party going all night long. Sip on creative cocktails and dance to the beats of top DJs as we begin the crawl at our first stop. Experience the electric energy and indulge in the incredible drink specials that will set the tone for an epic night of celebration. The fun continues as we hop from one buzzing venue to another, each offering its own distinct flavor and charm. Discover hidden gems, make new friends, and create memories that will last a lifetime.

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.

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.

Bring the magic of the season to life with a dinner cruise departing from San Diego. With cruises featuring festive décor and a delicious meal, celebrating Christmas on the San Diego Bay with your friends and family will keep your holiday merry and bright!

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.

Bring the magic of the season to life with a dinner cruise departing from San Diego. With cruises featuring festive décor and a delicious meal, celebrating Christmas on the San Diego Bay with your friends and family will keep your holiday merry and bright!

Enjoy a day in wine country outside San Diego in Temecula. Your small group is chauffeured to Old Town from San Diego to start the day exploring the quaint town and its shops and galleries. From there, enjoy lunch and a tasting at a winery. After your picnic, tour more wineries, enjoying tastings, and learn about the wines as you go.

Celebrate the magic of the season on the water with a Christmas Day Premier Brunch Cruise in San Diego. You and your guests will enjoy a holiday brunch buffet freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of San Diego’s iconic skyline and waterfront, entertainment, and festive décor. Our team will happily take care of the details, leaving you to celebrate the holidays on the San Diego Bay with your friends and family. Happy Holidays!

Have a ton of fun at San Diego’s Gaslamp quarter where you can meet new friends, have some drinks, and sing some karaoke. You’ll be taken to four bars tonight, all pre arranged for you so you don’t have to worry about that. You’ll have discounts on drinks at each venue, and check out some of the local favorites on this night tour.

This beginner-friendly sushi class at a local brewery offers a unique blend of hands-on learning and laid-back fun. You'll kick things off by prepping perfectly seasoned sushi rice, then dive into rolling a classic California roll with crab, avocado, cucumber, rice, and scallions. After mastering your roll, you’ll switch things up with a refreshing cucumber and ginger Oriental salad dressed in tangy ponzu — the perfect light and zesty side. Guided by a professional chef, you'll learn sushi-making techniques in a relaxed setting surrounded by the casual buzz of a brewery. Expect plenty of laughs, opportunities to get creative with your plating, and the chance to sip a local craft brew while you work. Whether you're flying solo, coming with friends, or planning a date night, this class delivers a memorable experience full of flavor, connection, and culinary inspiration.

Explore the diverse and colorful sites of Hillcrest, home of San Diego’s largest LGBTQ community, on a hosted walking bar hopping experience. Unlock the ultimate Hillcrest experience with a bar crawl. Join the only bar crawl in town and enjoy free entrance and discounts to bars and clubs, VIP experiences, and shots. Meet new people and make the most of your time in San Diego. Start your night with an exclusive pre-party at our local bar. Meet your queens and get ready for a night of fun. Enjoy 5 venues, shots, and VIP entrances, and a pre-drink ticketed event. Head to 1010 University Ave, San Diego, CA 92103 (University Ave & 10th Ave). You will find us in the courtyard area between Ike´s Place and Nishiki Ramen. Get free entrance all night long and enjoy a free shots start your night. Get access to the biggest club in town and party until the early hours of the morning.

Your dumpling era starts with a mixing bowl and a stack of wrappers. At a casual San Diego brewery, you’ll combine ground pork, shrimp paste and fresh chives to create a savory filling, then learn how to fold and shape Chinese dumplings without stressing over perfect pleats. You’ll get hands-on practice with each step, making the process approachable even if you’ve never folded a dumpling before. While your dumplings cook, you’ll whip up a sweet-savory dipping sauce using soy sauce, honey, sesame oil and rice vinegar. Then you’ll work with the remaining pork-and-shrimp filling to create shumai-style dumplings, learning a second shape and technique. Once everything is cooked, enjoy your freshly made meal. It’s hands-on, social and just messy enough to be fun — especially when that first dumpling actually holds together.

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.

With a Captain at the helm, you and your friends will enjoy a 2 hours Harbor Tour for up to 8 guests on the amazing Pink Boat in San Diego Bay. Our "Pink Panther" and "Flamingo" are new electric Duffy 2023 boats. Enjoy the view of Downtown San Diego, Coronado Island, and Bridge, Maritime, and Midway museums on the Barbie boat cruise. Best of all, you can bring your drinks on board! Whether you want to toast to the bride-to-be or enjoy a fun day with the girls. And the last one: Everything is better in Pink! The Pink Boat Harbor tour is a fantastic way to: - celebrate a Birthday party on the water - surprise the Bride with the best Bachelorette party idea - comfortable family cruise with kids - Barbie theme teenager Birthday celebration

Explore the connection between San Diego, California and Tijuana, Mexico on an afternoon craft beer tour. Your guide eliminates the stress of navigating through each city on your own: Head straight to popular watering holes and hidden gems for complimentary beer tastings. A small group size ensures a tailored experience and the full attention of your guide.