San Diego’s blend of coastal beauty, diverse neighborhoods, and deep-rooted history makes it an ideal city for exploring through specialized tours. Whether you’re interested in tasting California wines, uncovering local legends in the Gaslamp Quarter, or getting spooked by paranormal stories, this city offers something for every kind of history lover. I personally enjoy how some tours, like the San Diego to Temecula Wine Country Tour, combine scenic drives, expert-led tastings, and storytelling—making history and culture accessible and fun. Other options, such as ghost tours, bring to life San Diego’s darker past with chilling tales and haunted locations.
San Diego isn’t just about beaches; it’s packed with fascinating neighborhoods, military history, and spooky stories. In this list, you’ll find walks through historic districts, boat cruises that highlight naval legacy, and pub crawls that reveal the city’s lively past. I’ve included tours with stellar reviews, unique themes, and detailed itineraries to help you find the best fit for your interests.
Quick Overview
This guide showcases a variety of historical tours that highlight San Diego’s past—from wine country adventures and historic walking tours to true crime and paranormal investigations. For example, the San Diego to Temecula Wine Country Tour ranks highly for its combo of scenic drives, tastings, and storytelling, perfect for wine lovers. Meanwhile, the Coronado History and Highlights Small Group Tour offers a relaxed walk through one of the most upscale islands, revealing its secrets. For those intrigued by San Diego’s darker side, the Gaslamp Quarter True Crime Tour takes you into the city’s criminal past, and the Paranormal Investigation Tour adds a hands-on ghost-hunting experience. Below, each tour is examined in detail.
1. San Diego to Temecula: Wine Country Tour & Historic Old Town
At number 1, this Wine Country Tour & Historic Old Town offers a full day outside the city exploring Temecula’s charming streets and lush vineyards. The tour includes exploring Old Town’s rustic shops and galleries, followed by visits to three different wineries along the scenic De Portola Wine Trail. You’ll enjoy learning wine tasting techniques from experts, sampling multiple wines, and sharing in an upscale picnic lunch. The small-group setting — with pick-up and drop-off from select San Diego hotels — makes for a personalized experience. Reviewers love how the guide shares stories of local history and cultural insights. Perfect for wine enthusiasts wanting a relaxed, educational day with plenty of tastings and scenic views.
Bottom line: An excellent choice if you’re into wine, scenic drives, and learning about California’s viticulture.
2. San Diego Coronado History and Highlights Small Group Tour
Number 2 on our list is the Coronado History and Highlights Small Group Tour. This 2 hour 45 minute walking tour takes you beyond the beaches, into Coronado’s Victorian architecture, historic mansions, and charming downtown. Your guide shares stories of early residents, aviators, and artists, giving you a sense of local lore. Stops include Coronado’s iconic Hotel del Coronado, the historic library, and a sweet treat at a beloved local shop. The tour is praised for insider tips on how to enjoy the island’s best spots and for its engaging storytelling. It’s a perfect fit if you want a relaxed, in-depth look at this upscale coastal enclave without the crowds.
Bottom line: Ideal for those wanting a personable, comprehensive exploration of Coronado’s history and culture.
3. San Diego’s Gaslamp Quarter Historic True Crime Tour
At number 3, this Gaslamp Quarter True Crime Tour offers a dark twist on San Diego’s history. In about 1.5 hours, you’ll explore Stingaree’s notorious past, including gruesome crimes, haunted hotels, and unsolved mysteries. The guide regales you with stories of murder, corruption, and scandal that once rocked the city. The tour has a lively, engaging tone and is highly rated for its storytelling and local insights. It’s great for anyone interested in darker history or ghosts of the city.
Bottom line: A fun, fast-paced way to discover San Diego’s gritty, lesser-known stories.
4. San Diego Small-Group Gaslamp History Tour Pub Crawl
Number 4 features the Gaslamp Small-Group Pub Crawl. Over just over two hours, you’ll visit four historic pubs with a guide who shares local stories of conquistadors, bootleggers, and aviation pioneers. The focus here is on San Diego’s lively drinking history, with tastings of local craft beers at each stop. The small group size ensures an intimate experience, and comments highlight the informative and humorous guides. It’s perfect for those who love history combined with socializing over good beer.
Bottom line: An entertaining way to combine San Diego’s boozy past with a relaxed, social atmosphere.
5. Historical Walking Tour of San Diego
The Historical Walking Tour at number 5 is a budget-friendly choice, costing just $10. It covers downtown San Diego’s key sites, including Old Town, the Gaslamp District, and Horton Plaza. The 1 hour 15-minute walk features stories about San Diego’s founding in 1542, the Mexican-American War, and the era of prosperity that shaped the city. Your guide, Josh, is praised for knowledgeable storytelling and recommendations for exploring further. It suits travelers wanting a quick, informative overview of San Diego’s evolution.
Bottom line: Great for budget travelers who want a focused introduction without sacrificing detail.
6. History Tour Pub Crawl of Famous Gaslamp Quarter
Next, the Gaslamp Quarter Pub Crawl is a more casual experience for those wanting to mix history with fun. Over two hours, you’ll hop between unique bars sharing unknown stories of San Diego’s past, from prohibition to conquistadors. The tour emphasizes local beers and lively storytelling, making it ideal for social travelers who want a relaxed evening with a historical twist.
Bottom line: Best suited for adults looking for a fun, low-key way to enjoy San Diego’s past.
7. PCF 816 Swift Boat Naval History Bay Tour
Number 7 features the Swift Boat Naval History Bay Tour, which offers a 1 hour 15-minute cruise from the Maritime Museum. It takes you under the Coronado Bridge, past Naval Base San Diego, and highlights naval and military history aboard the historic Swift Boat. This is a rare chance to experience a vessel on the National Register of Historic Places and feel the power of twin Detroit Diesels. Reviews mention the engaging narration and authenticity of the vessel. It’s perfect for military history fans or those curious about San Diego’s naval significance.
Bottom line: An immersive, active experience that combines history and a boat ride.
8. Pies & Pickaxes: A Historic Walking Tour of Julian, CA
Just over an hour from San Diego, Julian’s Pies & Pickaxes offers a self-guided audio tour through historic Main Street. Focused on gold rush roots, mining pioneers, and apple orchard transformation, you’ll explore the Bailey House, cemetery, and historic buildings, with stops at Julian Pie Company for a taste of the famous pies. The tour includes stories about early residents and scenic views from Cemetery Hill. Reviewers praise its informative narration and delicious pie stop. Best suited for those seeking a casual, scenic day trip with a touch of history and local flavor.
Bottom line: Ideal for leisurely explorers fond of small-town history and sweet treats.
9. Paranormal Investigation History & Ghost Tour Old Town San Diego
The Paranormal Investigation Tour combines history with ghost hunting in Old Town. With hands-on paranormal equipment, you’ll visit seven locations, including Heritage Park and El Campo Santo Cemetery. The tour features stories of ghost sightings, disturbed burial sites, and spectral activity. It’s a rare chance to participate in a true paranormal investigation, making it perfect for adventurous spirits and history buffs alike. Reviewers mention exciting stories and fun use of ghost-hunting gear.
Bottom line: A must for those wanting a thrilling, interactive way to explore Old Town’s haunted past.
10. San Diego: Food Tour of Historic Gaslamp District
The Gaslamp Food Tour offers a 3.5-hour walk through downtown, sampling international cuisine with Mexican, Asian, and Italian influences. Led by a passionate local guide, you’ll learn about San Diego’s culinary scene and cultural history while tasting delicious dishes. It’s a flavorful way to see the city’s historic district and learn about its diverse communities. Reviewers love how stories enhance the food experience, making it both tasty and educational.
Bottom line: Perfect for food lovers who want a tasty, cultural tour of San Diego’s historic neighborhoods.
11. Historic Bay Cruise Aboard 1914 Pilot boat with General Admission
Number 11 offers a 45-minute narrated cruise on a historic 1914 pilot boat. Departing from the Maritime Museum, you’ll cruise under the Coronado Bridge and see Naval Base San Diego, North Island, and the aircraft carriers. The boat is on the National Register of Historic Places, adding a special touch to your experience. Reviewers highlight how being on a vessel with such history makes this a memorable outing. It’s best suited for those interested in maritime and naval history or just wanting a short, scenic cruise.
Bottom line: A short, engaging way to explore San Diego’s maritime past.
12. Heritage Park & Old Town Walking Ghost Tour in San Diego
The Heritage Park & Old Town Ghost Tour offers an atmospheric walk through San Diego’s haunted spots. It includes Heritage Park, Graveyard, and the Whaley House grounds. The tour features stories of true crime, ghost sightings, and disturbed burial sites. It’s suitable for those who enjoy spooky tales combined with historic sites. Reviewers appreciate the entertaining storytelling and the chance to see San Diego’s darker side.
Bottom line: A fun, slightly creepy activity perfect for history and ghost enthusiasts.
13. San Diego: Gaslamp Quarter Frontier History Walking Tour
This Gaslamp Frontier History Tour explores the Old West roots of San Diego’s historic district. Walking in the footsteps of Wyatt Earp and Alonzo Horton, you’ll hear stories of prohibition, haunted sites, and pioneers. The hour-long tour offers a lively look at San Diego’s frontier days with a focus on adventures, scandals, and pioneers. It’s suited for travelers who enjoy history with a rugged, wild west flair.
Bottom line: Perfect for those interested in Western legends and frontier life.
$35 per person
14. Gaslamp’s Wild Past: Daytime History Tour
The Gaslamp’s Wild Past offers a 2-hour daytime exploration of Gaslamp’s scandalous and colorful past. Telling stories with humor, the tour covers prohibition, crime, and architecture, providing an entertaining look at San Diego’s lively history. It’s a good choice if you prefer lighthearted storytelling combined with historic sites.
Bottom line: Suitable for those who want a fun, lively introduction to Gaslamp Quarter’s risqué side.
$999 per person
15. Haunted History & Paranormal Tour Go: Old Town
This Paranormal Tour includes hands-on ghost hunting in Old Town’s most haunted locations. You’ll explore Heritage Park, cemeteries, and historic buildings while using paranormal equipment to capture spectral activity. It combines history with adventure for those interested in spectral phenomena and interactive experiences. Reviewers praise the excitement and stories of ghost sightings.
Bottom line: Ideal for adventurous spirits and those curious about spectral activity.
$999 per person
How to Choose Your Ideal San Diego Historical Tour
With such a wide array of options, selecting the right tour depends on your interests, budget, and available time. For wine lovers, the Temecula tour offers a relaxing day of tastings, while history buffs might prefer the Heritage Park Ghost Tour. If your goal is to explore San Diego’s naval legacy, the Bay Cruise or Swift Boat Tour are great options. Budget travelers will appreciate the Walking Tour at just $10, while those interested in unique stories might love the True Crime Tour. Booking early is recommended, especially for popular tours during peak season or weekends.
Final Thoughts
San Diego’s diverse historical tours offer something for every traveler—whether you’re drawn to wineries, haunted houses, or naval history. For a relaxed day with a splash of culture, the Coronado tour or Julian walk are excellent choices. For thrill-seekers, the Paranormal Investigation and True Crime tours add an extra layer of excitement. Whichever you pick, booking ahead ensures you won’t miss out on these engaging, authentic experiences.