Cruises & Sailing

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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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    Gourmet Dinner Cruise

    Soak up the San Diego skyline in luxury and style on this relaxing dinner cruise, an exclusive that can't be booked anywhere else! As you travel along San Diego Bay aboard a deluxe yacht, take in views of the sparkling city lights and enjoy lively DJ entertainment. Pop open a bottle of Champagne and savor a gourmet 3-course meal at your guaranteed private window table. This is the perfect way to celebrate a birthday, anniversary, or any other special occasion. Board your cruise at the San Diego Grape Street Pier in the evening. You'll be welcomed aboard your luxury yacht with a glass of chilled Champagne or sparkling cider to set the mood for this luxurious 3-hour experience. Make your way to the open deck to soak up views of the San Diego skyline. Spot the Coronado Bay Bridge, the North Island Naval station, the USS Midway aircraft carrier and the Maritime Museum of San Diego with its Star of India, the world's oldest active sailing ship. Inside, head to your own private table with guaranteed window seating and pop open a bottle of Champagne to share with your sweetheart. You'll be served a gourmet 3-course meal freshly prepared by onboard chefs using local, seasonal ingredients (see below for a sample menu). After your lovely meal, hit the deck for a spin on the dance floor under the stars! Lively DJ entertainment will keep the party going all night long. As the sun sets and the city lights illuminate, you'll get breathtaking views of San Diego's most famous sights sparkling against the night sky. This magical evening is one you'll never forget!
    Gourmet Dinner Cruise

    1800 N Harbor Dr, San Diego

    • Enjoy a night of gourmet food, drinks, and dancing on this luxury dinner cruise
    • Be welcomed aboard the yacht with a glass of chilled Champagne or sparkling cider to set the mood
    • Savor a gourmet 3-course meal freshly prepared by onboard chefs using local, seasonal ingredients
    • Make your way up to the open deck to soak up views of the beautiful San Diego skyline
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    Sunset Sail Tour

    (1)
    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

    2051 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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    1 positive reviews
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    Couples Appetizer 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 the soft sea breeze caress you as you sample the appetizers 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.
    Couples Appetizer Cruise

    1548 Quivira Way, San Diego

    • Step onto the deck of a '67 26-foot sloop sailboat and drift through calming blue waters
    • Nibble tasty appetizers as you sail out past San Diego and into the beautiful Pacific Ocean
    • 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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    City Sunset Sailing Excursion

    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!). Sit back, relax and enjoy the complimentary beer, wine, soft drinks and snacks as you soak in the warm sun or watch it drop into the horizon with the glistening city lights behind you. 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.
    City Sunset Sailing Excursion

    Shelter Island, San Diego

    • Set sail from San Diego on this small group sailing tour on a sunset sail on the open ocean
    • Enjoy complimentary beer, wine and soft drinks and snacks
    • Witness breathtaking views of the San Diego skyline
    • Watch the sun disappear as you enjoy the open air and great company
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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

    1000 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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    3 Hour Small Group Sunset Sail

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    There's no feeling you love more than the spray of the surf on you face and a stiff wind at your back -- your first love is the sea. But you would never admit that to your partner, they don't like playing second fiddle to anybody. Combine the two great loves of your life into one romantic evening full of surf, sails and a stunning sunset.You'll set sail about an hour before sunset to give you plenty of time to catch the full range of hues painted on Mother Nature's canvas. Nestle under a few blankets with you lover and watch the beauty of San Diego Bay unfold before you. It's always nice when the two people you love get along. And it's even better when the two great loves of yours get interested in each other -- looks like you're going to be doing a lot more sailing.
    3 Hour Small Group Sunset Sail

    955 Harbor Island Dr, San Diego

    • Set sail on a 3-hour adventure through the San Diego Bay at dusk
    • Take in the sights, sounds and the incredible sunset on a relaxing cruise
    • See the unique sea-side architecture, military crafts, historical landmarks, natural sea life, and spectacular photo opportunities
    • Enjoy a day out on the water that is perfect for friends and family
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    1 positive reviews
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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

    (2)
    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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    2 positive reviews
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    Dinner Cruise with Beer Pairings

    A "booze cruise" might be fun, but we wouldn't call it classy. Instead, live like an upscale socialite and try champagne and beer pairings on a yacht. Float through San Diego Harbor on a sunset cruise aboard a luxury yacht, featuring a gourmet dinner paired with local craft beer. Start with a glass of Champagne as you board, and then enjoy your meal with two beer tasters. Food options include a pasta bar, barbecued pork, brisket and desserts; additional drinks are available for purchase from the full bar. While you glide across the harbor, watch the sunset and take twilight views of the San Diego skyline. The fun continues after dinner with live music and dancing on board! Stay classy, San Diego explorer!
    Dinner Cruise with Beer Pairings

    N Harbor Dr, San Diego

    • Hop on a yacht for a 2.5 hour cruise with gourmet dinner paired with craft beer
    • Sample 2 beer tastings from a rotating roster of craft breweries
    • Watch the sunset and twilight views of the San Diego harbor
    • Loosen up to some live music and get to dancin'
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