Cruises & Sailing

(45 activities)
Reset Filters
  • Book Now

    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
    BOOK NOW ← Back
  • Book Now

    Hot Tub Cruisin - 1 Hr Self-Captained Cruise

    Has life been stressing you out lately? Need a getaway but don’t have much time? A ride on Hot Tub Cruisin’s awesome hot-tube equipped boat is just the luxurious experience you need. You and up to 9 other friends will sail the Mission Bay, finally throwing that party you’ve been looking for an excuse to have. The hot tub water can be adjusted to your satisfaction. Connect your music-playing device to hear your favorite tunes through the cruise’s sound system. A propane grill, dry storage for personal items, deck seating, a 50 quart under seat cooler, and a 6 quart “in-hot tub” cooler are also available. Kick back and unwind with your friends on this beautiful nautical journey.
    Hot Tub Cruisin - 1 Hr Self-Captained Cruise

    1010 Santa Clara Pl, San Diego

    • Explore the waters of Mission Bay in a relaxing hot tub boat rental
    • Experience the luxury of hot tubbing on a boat in the middle of a gorgeous Bay
    • Feel luxurious during a scenic, nautical getaway
    • Give yourself some “me time” with the mini-vacation you’ve been searching for
    BOOK NOW ← Back
  • Book Now

    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
    BOOK NOW ← Back
  • Book Now

    Champagne Brunch Cruise

    There's no better way to relax and enjoy San Diego! Take in the sights, listen to relaxing music, linger in the sun and visit the captain. Indulge in a lavish brunch buffet featuring a savory selection of all your favorites and complimentary champagne. An astonishing range of sights awaits you in beautiful San Diego Bay! Take in the sights, listen to relaxing music, linger in the sun and visit the Captain on this San Diego Brunch Cruise. The lavish San Diego Champagne Brunch Cruise features a buffet selection of all your savory favorites, including complimentary champagne. An astonishing range of sights awaits you in beautiful San Diego Bay such as submarines and the Naval Air Station, San Diego's distinct skyline and the soaring Coronado Bay Bridge. There's no better way to relax and enjoy San Diego!
    Champagne Brunch Cruise

    1800 N Harbor Dr , San Diego

    • Take in the glorious sight of the San Diego Skyline on this lavish brunch cruise
    • Indulge in a gourmet brunch buffet featuring a savory food selection and complimentary champagne
    • Pass by iconic San Diego sights like the Naval Air Station and Coronado Bay Bridge
    • Linger in the sun as you listen to music while relaxing on deck
    BOOK NOW ← Back
  • Book Now

    Hot Tub Cruisin - 2 Hr Self-Captained Cruise

    Has life been stressing you out lately? Need a getaway but don’t have much time? A ride on Hot Tub Cruisin’s awesome hot tub-equipped boat is just the luxurious experience you need. You and up to 9 other friends will sail the Mission Bay, finally throwing that party you’ve been looking for an excuse to have. The hot tub water can be adjusted to your satisfaction. Connect your music-playing device to hear your favorite tunes through the cruise’s sound system. A propane grill, dry storage for personal items, deck seating, a 50 quart under-seat cooler, and a 6 quart “in-hot tub” cooler are also available. Kick back and unwind with your friends on this beautiful nautical journey.
    Hot Tub Cruisin - 2 Hr Self-Captained Cruise

    1010 Santa Clara Pl, San Diego

    • Explore the waters of Mission Bay in a relaxing hot tub boat rental
    • Experience the luxury of hot tubbing on a boat in the middle of an exquisite bay
    • Bask in luxury during a scenic, nautical getaway
    • Reward yourself some “me time” with the mini-vacation you’ve been searching for
    BOOK NOW ← Back
  • Book Now

    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
    BOOK NOW ← Back
  • Book Now

    3 Hour Small Group Sunset Sail

    (1)
    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
    BOOK NOW ← Back
    1 positive reviews
  • Book Now

    Private Sailing Excursion

    Set out on a private, relaxing sailing excursion from San Diego on a fully restored, 36-foot Cal Jensen yacht. The Lei Lani can host up to six passengers, creating the ultimate setting for an intimate get-together. Sail past the Maritime Museum and the surrounding San Diego Bay all while enjoying complimentary snacks and beverages served to you by your own personal crew member. This private sailing trip is perfect for celebrating a birthday, anniversary or just to have a good time with friends or family! Come aboard the Lei Lani, a 36-foot (11-meter) 1967 Cal Jensen yacht, for a 2-hour sailing excursion from San Diego. Sit back, relax and enjoy the spectacular scenery as you sail past the beautiful coastline of the surrounding San Diego Bay. Your own personal crew member will come around with assorted beverages such as beer, wine and soft drinks, while you indulge in chocolates, cookies and gourmet chips.

    Private Sailing Excursion:
    Gather your friends and family for a private sail around the San Diego harbor. The Lei Lani can host up to six passengers, creating the ultimate setting for an intimate get-together. If you're celebrating a special occasion, just let your captain or crew member know and they will ensure that you and your party have a fantastic time.

    Romantic Private Sail for Two:
    For a romantic private sailing experience, set sail from the Harbor Island area on a private yacht with your special someone. Sit back with a glass of wine and enjoy the scenery as your captain and crew member ensure your comfort and enjoyment. If you're looking for a romantic way to celebrate an engagement, anniversary or to even pop the question, don't miss your chance to take this romantic, relaxing and scenic private sailing trip -- a perfect way to say ‘I love you’!

    Please note: the price displayed is based on six passengers for the private sailing excursion; see the pricing calendar for more details.
    Private Sailing Excursion

    1450 Harbor Island Dr, San Diego

    • Experience a 2-hour private sailing trip from San Diego
    • See views of the Maritime Museum, the San Diego coastline and more
    • Sail on a 36-foot yacht with a captain and personal crew member
    • Enjoy complimentary snacks and beverages served on board
    BOOK NOW ← Back
  • Book Now

    Sunset Sail

    (1)
    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
    BOOK NOW ← Back
    1 positive reviews
  • Book Now

    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
    BOOK NOW ← Back

Page 1 of 5

Kind words from our customers