San Diego is a fantastic place for sailing, thanks to its calm waters, scenic coastline, and the chance to see iconic sights like the USS Midway and Coronado Bridge from a different perspective. Whether you’re celebrating a special occasion or simply want a relaxing day on the water, San Diego offers a wide variety of sailing tours. We particularly love Small-Group San Diego Sunset Sailing Excursion for its intimacy and stunning sunset views, and the Luxury Catamaran Sailing Charter for those seeking a private, upscale experience. Each offers a different way to enjoy San Diego’s waters, making the choice depends on your interests and budget.
Quick Overview
This list covers a range of sailing adventures including small-group sunset and daytime sails, private yacht charters, vintage yacht cruises, and luxury boat rentals. Whether you want a romantic sunset cruise, a fun family outing, or a private celebration, there’s something for all. We’ve included options with small-group experiences, private charters, and luxurious yacht trips. Keep reading to find the perfect match for your San Diego trip.
1. Small-Group San Diego Sunset Sailing Excursion
This 3-hour intimate cruise takes you out on a Catalina-style sailboat with a maximum of 6 guests, making it ideal for a personal experience. During this sunset sail, you’ll enjoy included beer, soft drinks, snacks, and the chance to plug in your own music on surround-sound speakers. The small group size ensures plenty of room to relax and take in the views, from the Point Loma lighthouse to the distant city skyline, all while watching the sun dip into the Pacific. Many past guests mention that the captain was friendly and knowledgeable, making the trip both fun and informative.
What makes this tour stand out is the personal touch—you can cozy up under blankets if it’s chilly, and the limited group ensures personalized attention. Perfect for couples or small groups celebrating a special moment, this cruise offers a balance of scenic beauty, comfort, and fun at a reasonable price of $127 per person.
Bottom Line: An ideal choice for those wanting a quiet, romantic sunset in a small, friendly setting.
2. Small-Group Sunset Sailing Experience on San Diego Bay
For around $112.50, this 2-hour sunset cruise on a comfortable sailing yacht offers a relaxed look at San Diego’s coast. It’s perfect if you prefer a shorter, more focused experience. The tour passes by notable sights like the USS Midway Aircraft Carrier Museum and the San Diego Maritime Museum, offering unobstructed views of the skyline and waterfront. The small group of six makes it easy to ask questions and take plenty of photos, especially as the sunset transforms the bay into a glowing scene.
Guests consistently describe the trip as “amazing,” with one highlighting the captain’s flexibility and friendliness. It’s a great option for couples celebrating a special evening or visitors wanting a quiet, personal cruise.
Bottom Line: A concise, intimate experience with fantastic photo opportunities and a relaxed atmosphere.
3. Small-Group San Diego Afternoon Sailing Excursion
This 3-hour daytime sailing trip offers a similar small-group experience, this time in the light of day. At $116 per person, it’s a great way to enjoy water views in full sun, and includes complimentary beer, soft drinks, and snacks. The itinerary takes you around San Diego Harbor, passing the Point Loma lighthouses and the Coronado Bridge, with plenty of opportunities to relax, take photos, or even play your own music on the surround-sound system. Many reviews praise the friendly captain and the relaxing pace.
Ideal for families or groups celebrating birthdays or just seeking a fun day on the water, this tour provides a semi-private, comfortable environment.
Bottom Line: A perfect daytime outing that balances scenery, comfort, and a laid-back vibe.
4. Sunset Sail On A Charming Vintage Yacht – Beer & Wine Included
This 2.5-hour cruise features a beautifully restored 1904-style vintage sailboat, offering a nostalgic sailing experience. The tour includes wine, beer, and light snacks, making it a classy way to enjoy San Diego’s sunset. As you pass landmarks like the Coronado Bridge and Maritime Museum, you might also see dolphins, sea lions, or other wildlife. The boat’s vintage charm, combined with the all-inclusive drinks, makes this a special, relaxed outing.
Guests love the picturesque views and the informative commentary from the captain, plus the historic boat adds a unique flavor. The ticket price is $125 per person, which offers good value considering the ambiance and included drinks.
Bottom Line: A romantic, vintage-inspired cruise suited for those wanting a cozy, wine-and-wildlife experience.
5. Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways
Starting at $119 per person, this private 34-foot Catalina sailboat offers a luxurious, personalized experience. Led by a local captain, the tour can be scheduled in the morning, afternoon, or evening, giving you flexibility. Passengers are encouraged to bring their own drinks, and snacks and water are provided. The tour includes learning about San Diego from your captain, making it both relaxing and educational.
Perfect for couples celebrating a romantic getaway or small groups seeking an upscale experience, this tour emphasizes comfort and intimacy. Many reviews mention the beautiful views of the skyline and bay, along with the personalized service.
Bottom Line: An excellent choice if you want a luxury, private sail tailored to your schedule and preferences.
6. San Diego: San Diego Bay Sunset & Daytime Sailing Experience
This 2-hour cruise at $89 offers a more affordable option for enjoying San Diego’s highlights on a sailing yacht. It’s suitable for travelers who want a short but scenic experience, with views of the USS Midway, downtown skyline, and North Island. The relaxed pace allows for wildlife spotting and taking photos of the iconic sights from the water.
Many travelers appreciate the easy, relaxing experience and the chance to see the city from a different angle without spending too much time or money. It’s a solid choice for those on a budget or with limited time.
Bottom Line: A straightforward, scenic cruise perfect for a quick, relaxing escape on the water.
7. 2.5 Hours of Fun: Catamaran Sunset Sail
This small-group catamaran cruise at $119 per person is all about comfort and fun. With bean bag seating and a lively atmosphere, it’s designed for a relaxed, social experience. The sunset views over San Diego’s skyline are stunning, especially as you enjoy white wine, beer, and soft drinks onboard. Past guests rave about the friendly captain and the dolphins and sea lions often spotted during the trip.
It’s well suited for couples, friends, or even a casual family outing that wants a fun, laid-back vibe. The tour prioritizes comfort and entertainment over technical sailing details, making it accessible to all.
Bottom Line: A lively, social sunset cruise with great views and drinks in a comfortable setting.
8. 2-Hour Private Sailing Experience in San Diego Bay
For just $35 per person, this private yacht experience offers the chance to customize your itinerary and enjoy up to six passengers in total. The private nature makes it perfect for special occasions or intimate outings. The captain handles navigation, so you can relax and enjoy sights like the Midway, Seaport Village, and the harbor seals.
Past reviews commend the friendly, knowledgeable captain and the excellent views. If you want an exclusive, flexible experience without breaking the bank, this is an excellent option.
Bottom Line: A flexible, private cruise ideal for small groups and special celebrations.
9. Small-Group Yacht Sailing Experience on San Diego Bay
At $90 per person, this luxury yacht outing allows you to enjoy a private, comfortable ride on a 40-foot yacht. With an included glass of wine and opportunities to spot dolphins, sea lions, and naval ships, it’s suited for those wanting a bit of luxury. The friendly crew and seating on deck cushions and bean bags help create a relaxed atmosphere.
Guests often mention the great views of the Midway and the informative, friendly captain. This tour is a good fit if you seek a more upscale experience with a small group.
Bottom Line: Perfect for those who want a luxury, intimate sailing experience with wildlife sightings.
10. Luxury Catamaran Sailing Charter of San Diego
This private charter can accommodate up to 12 people and offers customized itineraries. Starting from $1173.34 per group, it’s suited for celebrations, larger families, or small groups wanting exclusivity. The itinerary may include passing Sunset Cliffs, La Jolla, and Ocean Beach Pier, with room for music and refreshments.
Reviewers highlight the personalized service, dolphin sightings, and the ability to bring your own drinks. It’s ideal for special events or those seeking a luxurious, private day on the water.
Bottom Line: The top of the line for private, customizable sailing adventures in San Diego.
11. Afternoon Sail On A Charming Vintage Yacht Beer & Wine Included
This affordable vintage-yacht cruise at $115 offers a unique 1904-style vessel with snacks and soft drinks included. The itinerary takes you around the Star of India and under the Midway, with views of Seaport Village and other attractions. The reproduction vintage vessel adds character and charm, making it perfect for travelers wanting a historic touch.
Many reviews mention the interesting commentary and the comfortable, relaxed atmosphere. The tour is ideal for those seeking a less conventional, more historic sailing experience.
Bottom Line: A charming, vintage cruise that combines history with scenic views at a reasonable price.
12. 2.5 Hour Private Sunset Sailing Tour in San Diego
With up to 12 guests for $90 per person, this family-friendly private tour is perfect for groups wanting an exclusive, laid-back experience. The itinerary can include sailing near the US Midway, passing Seaport Village, or under the Coronado Bridge. The handcrafted cushions make it comfortable for all ages, and the private nature allows for tailored experiences.
Reviewers note the friendly captain and the opportunity to bring children or grandparents. It’s a flexible, fun way to enjoy San Diego’s waters with loved ones.
Bottom Line: Best suited for families or groups wanting a personalized, private sunset sail.
13. San Diego: Sunset and Day Sailing Excursion with Drinks
For $119, this 2.5-hour tour combines day and sunset sailing, with drinks included. It’s designed for those who want a relaxed, scenic ride and the chance to spot playful sea lions and dolphins. The tour emphasizes learning about San Diego’s landmarks and offers inside tips from the captain.
Ideal for travelers seeking a flexible, leisurely experience that combines views, wildlife, and a bit of local insight.
Bottom Line: A versatile choice for those wanting both daytime and sunset sailing with drinks.
14. Private Day Sailing Experience in San Diego up to 12 guests
This 2.5-hour private day tour costs $80 per person and offers a more active sailing experience. It’s perfect for those who want to help sail or see San Diego’s landmarks like the USS Midway and Seaport Village. You can choose to sail around downtown or to see sea lions, and hauling sails is an option if you’re feeling adventurous.
Guests mention the friendly crew, and the opportunity to customize the route makes this a flexible option. It’s best for small groups or families looking for an interactive experience.
Bottom Line: An active, private day on the water suitable for those who want to learn and participate.
15. 2.5 Hour Catamaran Sail Adventure
This casual, fun catamaran cruise at $119 offers comfortable seating, drinks, and the chance to see San Diego’s skyline while relaxing. The small group of six ensures a friendly atmosphere, and the possibility of spotting dolphins and sea lions adds excitement.
Ideal for family outings or friends celebrating a birthday or just wanting to chill out on the water, this tour emphasizes relaxation and socializing.
Bottom Line: A lively, social cruise with great views and the opportunity for wildlife sightings.
16. San Diego: Classic Yacht Sailing Experience
This $109, all-inclusive tour by Captain Phil features a restored 1914 replica sailboat, offering unlimited craft beer, wine, sodas, snacks, and scenic views of the Midway and other landmarks. Passengers can enjoy learning to sail, see wildlife like dolphins and sea lions, and choose between shared or private options.
Guests praise the personalized service and the historic vessel’s charm, making it ideal for history buffs or those wanting a classic sailing experience with modern comforts.
Bottom Line: A unique, authentic sailing adventure blending history, wildlife, and comfort.
How to Choose the Right Sailing Experience in San Diego
Picking the perfect sailing tour depends on your budget, interests, and the kind of experience you desire. If you want an intimate, romantic sunset, the Small-Group Sunset Sailing Excursion offers a cozy setting. For a luxurious private boat, the Luxury Catamaran provides exclusivity and customization. Budget travelers might prefer the Private Yacht, which offers a private but affordable outing.
Consider your group size and activity level—active sailors may enjoy the Private Day Sailing, while those seeking a classic, vintage vibe will love the Vintage Yacht Sunset Sail. Booking early, especially for popular sunset and private tours, is recommended to secure your preferred date.
San Diego offers a diverse array of sailing options. Whether you prefer a relaxed sunset or a custom private cruise, the city’s waters promise memorable moments. For a truly special experience, consider a luxury private yacht or a vintage-style sail. For those on a budget or with limited time, short and scenic day sails still capture the magic of San Diego’s coast.
No matter your choice, each tour provides a different way to see San Diego’s best sights from the water. Book early, pack your camera, and get ready for a fantastic day—or evening—on the bay.