Cruises & Sailing

(24 activities)
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    Sailing Excursion

    Set sail from San Diego on this small-group sailing tour! This three-hour adventure on a Catalina-style sailboat is limited to just six people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Your friendly and accommodating captain will ensure that you have the best possible time on the water sightseeing and spotting wildlife. Sit back, relax and enjoy the complimentary beer, wine, soft drinks and snacks as you soak in the warm sun with the shining harbor waters all around you or watch the sun drop into the horizon with the glistening city lights behind you. You can even bring your own music to plug into the boat's surround-sound system! Whether you're on vacation, celebrating a special occasion or just looking to take advantage of a beautiful Southern California day, this small-group sailing trip in San Diego is a great way to spend time on the water with your loved one or a group of friends. Choose from two sailings - either a daytime adventure in San Diego Harbor or a sunset cruise that takes you out on the Pacific to watch the sunset. Both tours are three hours long.

    No matter which sail you choose, your captain will ensure that you have the best possible time on the water. As you admire the views, enjoy the complimentary beer, wine, soft drinks and snacks. If you get chilly, grab one of the provided polar-fleece jackets, blankets, hats or wind-gear. If the sun is too bright, slather on the complimentary sunscreen or don a pair of provided sunglasses. And use the provided binoculars to admire the coastline or look for wildlife! You can even bring your own music to plug into the boat's surround-sound system.
    Sailing Excursion

    Point Loma, San Diego

    • Embark on a small group sailing excursion to take in the beauty of San Diego Harbor
    • Use a pair of provided binoculars to admire the coastline or look for wildlife
    • Enjoy complimentary beer, wine, soft drinks, and snacks on board
    • Bring your own music on the surround-sound speakers to set the mood
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    Dinner Cruise

    Enjoy a 2.5-hour cruise aboard one of San Diego's finest dining vessels. Spend the evening in luxury as you dine on a gourmet dinner, sip on a complimentary cocktail and enjoy lively entertainment throughout the night. Don't forget your camera - this cruise features 25 scenic miles of San Diego's magnificent skyline! Step aboard the Spirit of San Diego and be greeted with a glass of Champagne. You are in for an entertaining evening of dining, dancing and stargazing against the sparkling backdrop of the San Diego skyline. Enjoy the fresh sea air from the observation deck before and after dinner. Step aboard the Spirit of San Diego and be greeted with a glass of Champagne. You are in for an entertaining evening of dining, dancing and stargazing against the sparkling backdrop of the San Diego skyline. Enjoy the fresh sea air from the observation deck before and after dinner.

    Enclosed dinner seating will keep you comfortable in both warm and cool weather. With panoramic windows and breathtaking views of the skyline, the Spirit of San Diego will show you the best waterfront sights.
    Dinner Cruise

    1000 N Harbor Dr, San Diego

    • Relax and dine during a gourmet dinner aboard a luxury cruise in San Diego Harbor
    • Soak in panoramic views of the San Diego skyline and the beautiful California coastline
    • Listen to live entertainment while you cruise on the Spirit of San Diego
    • Enjoy a complimentary welcome drink as you immerse yourself in dancing and stargazing
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    Sunset Sail Tour

    (2)
    The Sunset Sail lets you enjoy the sunset from an incredible sailing vessel. Relax and enjoy alcoholic and nonalcoholic beverages that are chilled to perfection as your experienced crew steers your boat through the bay's beautiful waters. From snack bars to chips, there is something that will keep you satisfied as you explore San Diego from the water. You do not even have to worry about sunglasses or a jacket- this tour has thought of everything you might need while you are on a boat. You are encouraged to bring your own music to make this a true party.
    Sunset Sail Tour

    2646 Shelter Island Dr, San Diego

    • Enjoy a relaxing sunset sailing adventure around San Diego bay
    • See a different side of San Diego from a sailboat
    • Snacks, beer, wine and soda complimentary
    • Discover the fun of sailing with experienced pros
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    2 positive reviews
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    North Bay Harbor Cruise

    Take a relaxing harbor cruise through the North bay of San Diego, featuring unforgettable views of San Diego's skyline. This fully narrated tour will take you to all the places you want to see with time to spare! Enjoy live commentary that will give you background, history and highlights of this awesome bay. You'll see some of the largest watercraft in the world up close. Cruise through the San Diego North Bay as your friendly, informative narrators point out the sights. See North Island Naval Air Station, Harbor and Shelter islands, the Naval Sub Base and Cabrillo National Monument. On board, relax on the comfortable seating and pleasant sun decks, and head down to the galley below for food and beverages available for purchase. Cruise through the San Diego Bay as your friendly, informative narrators point out the sights. On board, relax on the comfortable seating and pleasant sun decks, and head down to the galley below for food and beverages available for purchase. On this cruise, see North Island Naval Air Station, Harbor and Shelter islands, the Naval Sub Base and Cabrillo National Monument.
    North Bay Harbor Cruise

    900 N Harbor Dr, San Diego

    • Enjoy a cruise to see the beautiful city skyline from San Diego's North Bay
    • Learn the history of the area with live commentary during the breathtaking cruise
    • Take in sights of seals and sea lions sunbathing on the rocks just off the shore
    • Relax with comfortable outdoor and indoor seating
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    Sunset Sail

    (6)
    Looking for the best things to do in San Diego? Set sail from Harbor Island to see the best parts of the San Diego Bay in all its natural beauty. You will have the opportunity to participate in the actual sailing, if you wish, and learn something new about the open water. If working the adventure is not your thing, everyone can still enjoy craft beer, chilled white wine and platters of cheese, salami, crackers and chocolates served by polite stewards. Each sailing cruise includes a captain, crew member, and a maximum of 6 total passengers -- a perfect support system for a truly unique nautical adventure. You'll all watch as the sun sets below the peninsula of Point Loma creating a spectacular array of light on the water. Additionally, the city lights of Downtown San Diego will come aglow just before you head in from the harbor. Whether you want to work the mast or work your jaw, this unique sunset yacht experience has something for everyone.
    Sunset Sail

    1450 Harbor Island Dr, San Diego

    • Sail on a beautiful sail boat through the San Diego Bay at sunset
    • Learn and participate in the sailing by gaining insight on techniques
    • Sip on craft beer or chilled wine as you enjoy the finer things
    • Escape the day with a picturesque view of the city lights of Downtown San Diego
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    6 positive reviews
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    South Bay Harbor Cruise

    Cruise through the San Diego South Bay as your friendly, informative narrators point out the sights. On board, relax on the comfortable seating and pleasant sun decks, and head down to the galley below for food and beverages available for purchase.

    Your fully narrated harbor cruise will take you to the US Naval fleet, the famous Coronado Bay Bridge, San Diego's bustling shipyards and theStar of India, the oldest iron-hulled sailing ship still afloat.
    South Bay Harbor Cruise

    900 N Harbor Dr, San Diego

    • Enjoy a cruise to see the beautiful city skyline from San Diego's South Bay
    • Learn the history of the area with live commentary during the breathtaking cruise
    • Take in sights of seals and sea lions sunbathing on the rocks just off the shore
    • Relax with comfortable outdoor and indoor seating
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    Signature Sailing Tour (2hr)

    (6)
    Looking for the best things to do in San Diego? Set sail from Harbor Island to see the best parts of the San Diego Bay in all its natural beauty. You will have the opportunity to participate in the actual sailing, if you wish, and learn something new about the open water. If working the adventure is not your thing, everyone can still enjoy craft beer, chilled white wine and platters of cheese, salami, crackers and chocolates served by polite stewards. Each sailing cruise includes a captain, crew member, and a maximum of 6 total passengers -- a perfect support system for a truly unique nautical adventure. Whether you want to work the mast or work your jaw, this unique yacht experience has something for everyone.
    Signature Sailing Tour (2hr)

    1450 Harbor Island Dr, San Diego

    • Sail on a beautiful sail boat through the San Diego Bay
    • Learn and participate in the sailing by gaining insight on techniques
    • Sip on craft beer or chilled wine as you enjoy the finer things
    • Escape the day with a picturesque view of the ocean
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    6 positive reviews
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    Adventure Daytime Sailing Tour

    (2)
    Explore San Diego and surrounding waters in this relaxing sailing adventure. You will not go hungry on this sail tour. From snack bars to chips, there is something that will keep you satisfied as you explore San Diego from the water. Enjoy alcoholic and nonalcoholic beverages that are chilled to perfection as your experienced crew steers your boat through the bay's beautiful waters. You do not even have to worry about sunglasses or a jacket- this tour has thought of everything you might need while you are on a boat. You are encouraged to bring your own music to make this a true party.
    Adventure Daytime Sailing Tour

    2646 Shelter Island Dr, San Diego

    • Enjoy a relaxing sailing adventure around San Diego bay
    • See a different side of San Diego from a sailboat
    • Snacks, beer, wine and soda complimentary
    • Discover the fun of sailing with experienced pros
    BOOK NOW ← Back
    2 positive reviews
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    Sunset Champagne Cruise

    Have you ever actually sailed off into the sunset? Leave your worries behind as you sail during a majestic sunset aboard a classic yacht. You'll be immediately struck by the uniquely smooth sail, beautiful teak interior, and traditional yacht lines illustrating the fine craftsmanship of this boat. Take some pictures of your surroundings or simply sit back and take it all in as you sail by seemingly endless coastal views. You may even get a glimpse of the "Green Flash" right as the sun sets. Sip on a glass of sparkling wine, beer, or soft drink or snack on some complimentary bites. You are also welcome to bring your own snacks along to enjoy on the ride. After you have spent the day sailing the waters, you'll feel relaxed and refreshed. It's time to reconnect with the sea and let the waves (and your captain) guide you.
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    Sunset Champagne Cruise

    1380 Harbor Island Dr, San Diego

    • Sail around the San Diego Bay guided by a skilled captain
    • Savor complimentary snacks and beverages
    • Take in the coastal views and natural beauty all around you
    • Relax and let your worries melt away
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    Couples Fondue Cruise

    Remember how you got too drunk at your in-laws' cocktail party last night? Remember when you threw up in your mother-in-law's sock drawer? No?!?! Well they do. Salvage your relationship by setting sail on a romantic evening with Ship 'N a Bottle. Climb aboard a sloop right out of a fairytale to take you and your special someone far away from all of your landlocked worries (and in-laws). Let the gentle hum of the motor (OK so a contemporary fairytale) and recline as your lover feeds you chocolate fondue and half-bottle of wine provided, compliments of the Captain. (You can upgrade to a full bottle for a small fee). Whether you're in a desperate attempt to save your relationship or you're just a regular casanova, this will be the perfect date night -- not one in-law in sight.
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    Couples Fondue Cruise

    1548 Quivira Way, San Diego

    • Step onto the deck of a '67 26-foot sloop sailboat and drift through calming blue waters
    • Indulge in chocolate fondue as you sail out in the the shimmering waters of the of the Pacific
    • Sip on a glass of wine and recline in the arms of your lover
    • Surprise your partner with an extravagant and affordable evening
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