Deluxe private Sunset & Day Sail
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 3 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Deluxe private Sunset & Day Sail worth booking?
Deluxe private Sunset & Day Sail is a 2.5-hour experience in San Diego, United States, from $714 per person. It scores 49 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 3 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 49 / 100
- Rating
- 5/5 (3)
- Duration
- 2.5 hours
- From
- $714 per person
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wi
What you get
About this experience
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your hair, the sun on your skin, and the pure exhilaration of sailing. Explore hidden gems, soak in panoramic skyline views, and hear incredible stories from our expert guides. Whether you’re seeking excitement, relaxation, or unforgettable memories, this journey delivers it all. Don’t miss your chance to experience the magic of the ocean—book your adventure today!
What's included
Included
- Carbonated beverages
- Bottled water
- Alcoholic beverages
What you'll see and do
San Diego
Embark on a breathtaking private sailing excursion in the captivating waters of San Diego. Set sail aboard a luxurious yacht, where you and your companions can enjoy the ultimate seafaring experience. With a skilled and experienced captain at the helm, you'll navigate the sparkling Pacific Ocean, taking in panoramic views of San Diego's stunning coastline. Feel the refreshing ocean breeze against your face as you glide through the water, indulging in moments of tranquility and serenity. Whether you're seeking a romantic sunset sail, a memorable family adventure, or a unique way to celebrate a special occasion, this private sailing excursion promises an unforgettable journey on the shimmering seas of San Diego.
Pass by without stopping
Maritime Museum of San Diego
The Maritime Museum of San Diego, located along the waterfront, is home to one of the world’s finest collections of historic ships. As you sail past, you’ll see iconic vessels like the Star of India, the world’s oldest active sailing ship, along with a replica of the 16th-century San Salvador and the impressive HMS Surprise, known from Master and Commander. The museum offers a glimpse into maritime history, making it a striking sight from the water.
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San Diego Convention Center
The San Diego Convention Center is a striking waterfront venue known for its modern architecture and iconic sail-like rooftop. Located in the heart of downtown along San Diego Bay, it hosts major events like Comic-Con International, trade shows, and conventions. Spanning over 2.6 million square feet, it features expansive exhibit halls, meeting rooms, and a scenic outdoor terrace with panoramic bay views. Its prime location offers easy access to the Gaslamp Quarter, making it a vibrant hub for both business and entertainment.
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San Diego Bay Walk
The San Diego Baywalk along North Harbor Drive is a scenic waterfront promenade perfect for a relaxing stroll after your sailing excursion. Lined with palm trees, public art, and stunning bay views, it offers a lively atmosphere with street performers, waterfront dining, and landmarks like the USS Midway Museum and the Maritime Museum of San Diego. Visitors can unwind at outdoor cafés, watch boats glide by, or simply take in the beautiful coastal sunset.
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Cabrillo National Monument
The Cabrillo National Monument offers breathtaking panoramic views of San Diego Bay, the Pacific Ocean, and downtown San Diego. Located at the southern tip of the Point Loma Peninsula, this historic site commemorates Juan Rodríguez Cabrillo, the first European to explore the West Coast in 1542. Visitors can explore scenic coastal trails, tide pools, and the iconic Old Point Loma Lighthouse, making it a perfect post-sailing adventure for history and nature lovers alike.
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Coronado
Coronado Island offers a perfect mix of relaxation and adventure after your sailing excursion. Visitors can stroll along the famous Coronado Beach, known for its sparkling sand, explore the historic Hotel del Coronado, or browse charming shops and cafés in Coronado Village. Outdoor enthusiasts can bike along scenic paths, kayak in the bay, or take in stunning skyline views from Centennial Park. Whether you’re looking to unwind or explore, Coronado provides a picturesque coastal escape.
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Coronado Island
Coronado Island offers a perfect mix of relaxation and adventure after your sailing excursion. Visitors can stroll along the famous Coronado Beach, known for its sparkling sand, explore the historic Hotel del Coronado, or browse charming shops and cafés in Coronado Village. Outdoor enthusiasts can bike along scenic paths, kayak in the bay, or take in stunning skyline views from Centennial Park. Whether you’re looking to unwind or explore, Coronado provides a picturesque coastal escape.
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Shelter Island
Shelter Island is a peaceful waterfront retreat known for its marinas, parks, and stunning views of San Diego Bay and the city skyline. Visitors can enjoy a relaxing walk along the Shoreline Park promenade, dine at waterfront restaurants, or watch boats sail by from scenic picnic spots. The island is also a popular spot for fishing, kayaking, and stand-up paddleboarding. With its laid-back atmosphere and picturesque setting, Shelter Island is a great place to unwind after a day on the water.
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USS Midway Museum
The USS Midway Museum offers an unforgettable experience after your sailing excursion. This historic aircraft carrier-turned-museum lets visitors explore over 60 exhibits, including the flight deck with restored aircraft, the captain’s bridge, and interactive flight simulators. Guided by former sailors, you’ll hear firsthand stories of naval aviation and life at sea. Located along the waterfront, it’s a perfect way to dive into San Diego’s rich maritime and military history.
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Coronado Bridge
The Coronado Bridge is an iconic 2.1-mile-long curved bridge connecting downtown San Diego to Coronado Island. Rising 200 feet above the bay, it offers breathtaking panoramic views of the San Diego skyline, bay, and naval ships. A striking architectural landmark, it provides a scenic drive and serves as the gateway to Coronado’s beautiful beaches, charming shops, and the historic Hotel del Coronado.
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Where it starts and ends
Meeting point
San Diego
955 Harbor Island Dr, San Diego, CA 92101, USA Arrive at least 20 min. early. Turn into Sunroad Safe Harbor Marina Parking lot just before the flag pole. Park on the Left side of the parking lot or street parking is availble, and wait for your Captain at Gate 1. Says Docks A thru D above the gate
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
955 Harbor Island Dr, San Diego, CA 92101, USA Arrive at least 20 min. early. Turn into Sunroad Safe Harbor Marina Parking lot just before the flag pole. Park on the Left side of the parking lot or street parking is availble, and wait for your Captain at Gate 1. Says Docks A thru D above the gate
Options you can book
Private Sailing Yacht up to 8
Drinks complementary San Diego Bay Sailing yacht
Private Sailing Yacht up to 6
drinks included San Diego Bay Sailing Yacht
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- San Diego Sailing Excursions
Know before you go
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
Photos
What travelers are saying
Outty’s summary of the themes that recur across 3 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
1 mentionTravelers single out the guide as the reason the experience works.
Photo opportunities
1 mentionThe views and photo stops come up again and again.
Organization
1 mentionPickup, timing, and logistics are described as running smoothly.
Traveler reviews
3 verified traveler reviews for Deluxe private Sunset & Day Sail. Ratings and reviews provided by Viator and Tripadvisor.
Great cruise
Wonderful time. Very relaxing. Got to see all the sights in the harbor. Colin was a great captain. Very attentive and knowledgeable. We left a personal item on board and the company was extremely helpful in getting it back to us. Highly recommend!!!
Response from the operator: We are glad to hear that you had a wonderful and relaxing time sailing with us here in San Diego as you know there is other companies to choose from. We strive to keep our product a little bit more authentic than others and we hope we get the chance to sail with you again here on your next visit to San Diego. We appreciate the review and we hope that you had an absolute amazing vacation and visit to San Diego.
via Tripadvisor
You will definitely want to go again !
Captain Calhoun, was great his boat was clean and he had everything we needed. I would definitely recommend him to everyone and I would go again !
Response from the operator: We definitely want you back again! Thank you for choosing us here in San Diego!
via Viator
A Sunset Sailing Symphony: Magical Moments with Captain John and San Diego Sailing Excursions
Our sunset sailing excursion with Captain John and San Diego Sailing Excursions was an unforgettable experience that exceeded all expectations. Celebrating our 30th anniversary, we were delighted to find a bottle of champagne provided by Captain John as the sun began to set, adding a special touch to our celebration. The breathtaking views and peaceful ambiance created the perfect setting for our milestone moment. Captain John's expertise and friendliness made the journey even more enjoyable, as he guided us through the waters with passion and knowledge. The boat itself was stunning, providing a comfortable and luxurious experience as we cruised along the tranquil waters. What made the evening all the more memorable was the unique and special experience of getting to witness the Harry Connick Jr. concert happening in an outdoor amphitheater near the water. This unexpected delight added an extra layer of magic to our sunset sail. Captain John's promptness in communication before the excursion was timely and valuable, ensuring a smooth and stress-free experience from start to finish. We are grateful for the unforgettable sunset sail and the opportunity to experience such a special evening on the water. Thank you, Captain John, for a truly memorable and magical excursion. We look forward to returning for another sail with San Diego Sailing Excursions in the future.
Response from the operator: Thank you for your kind words. Captain John truly is a wonderful captain, and we strive to ensure every guest has an exceptional experience on board. We're thrilled that your time with us turned out to be amazing. It means a lot to us!
via Viator
Good to know
- Duration
- 2.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $714 to $900
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 1
- Verdict
- Worth a Look
Why this scores 49
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Deluxe private Sunset & Day Sail: questions travelers ask
Practical detail on this experience, plus the wider planning questions for San Diego.
How much does Deluxe private Sunset & Day Sail cost?
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Prices start at $714 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in San Diego usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Deluxe private Sunset & Day Sail take?
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Plan for about 2.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in San Diego is not rushed.
Is Deluxe private Sunset & Day Sail worth it?
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It holds an Outty Ranking of 49 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 3 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in San Diego, and how flexible the cancellation terms are.
Can I cancel or reschedule Deluxe private Sunset & Day Sail?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Deluxe private Sunset & Day Sail suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Deluxe private Sunset & Day Sail?
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Around 1 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in San Diego can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in San Diego and add a light layer if any part of the 2.5-hour experience runs outdoors or after sunset.
Where does Deluxe private Sunset & Day Sail start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central San Diego within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in San Diego?
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San Diego is an outdoor-first city: whale watching from December through April, La Jolla kayak and snorkel runs year round, harbour cruises and the USS Midway, plus Balboa Park museums when the marine layer sits low. We rank water operators on group ratios and gear quality, which is where the cheap La Jolla trips fall down. On Outty we rank every San Diego experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include USS Midway Museum Admission: Valid Any Date, Taste of Little Italy in San Diego, San Diego Whale Watching Cruise. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit San Diego?
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March to May and September to November, either side of the June overcast. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in San Diego?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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