Cruises & Sailing · This Weekend

(24 activities)
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    Sunset Sail Tour

    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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    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
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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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    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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    Hot Tub Anchored Cruise - 1Hr

    Hot tubs on a boat: why just get IN the water when you can get IN the water ON the water? Enjoy this one-of-a-kind rental with a killer sound system, 56 quarts of cooler space (including 6 attached to the hot tub), optional propane grill, and did we mention a hot tub? On a boat? Anchor up with 10 friends for one of the most entertaining ways to experience Mission Bay San Diego. Anyone can go boating, but only the lucky ones boat like this. Great for tourists and locals alike.
    Hot Tub Anchored Cruise - 1Hr

    1010 Santa Clara Pl, San Diego

    • Enjoy the unique experience of renting a hot tub boat for your next Mission Bay outing
    • Invite up to 10 friends and take advantage of onboard coolers and grill
    • Relax and let your cares slip away as you enjoy the beautiful weather and the warm water
    • Plug your musical device into the onboard sound system and get the party started!
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    Sunset Sail

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    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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    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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    Duffy Electric Boat Bay Cruise

    Climb aboard the Duffy of San Diego, a luxurious 22' Bay Island Duffy Electric Boat! Silent and eco-friendly, this boat will take you through the calm Mission Bay waters towards Sail Bay, Santa Barbara Cove, and Mariners Basin. You'll also cruise by the luxurious Paradise Point and Catamaran Resorts, as well as the Mission Bay Yacht Club and Bahia Resort -- which is further than where any other local charters will take you. As you enjoy your cruise, you'll encounter sea lions, local and migratory birds, and -- if you're lucky -- dolphins! You'll also be able to head to the spacious cabin of the boat, where there's a great sound system and a Surrey top with clear 360-degree views. The top can be open or closed depending on the weather. Plus, all captains are US Coast Guard licensed!
    Duffy Electric Boat Bay Cruise

    1548 Quivira Way, San Diego

    • Take a cruise tour of San Diego's Mission Bay waters in the 22' Bay Island Duffy Electric Boat with a spacious cabin
    • See the beautiful views of Sail Bay, Santa Barbara Cove, Mariners Basin, the Paradise Point and Catamaran Resorts, the Mission Bay Yacht Club, and the Bahia Resort
    • Enjoy a complimentary bottle of wine and an artisan cheese and meat board, or vegetarian snack of choice
    • Bring your camera and keep your eyes peeled for sea lions, local and migratory birds, and dolphins
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    Afternoon / Sunset Sail (Individual Ticket)

    Stuck in the doldrums? Put some wind behind your sails with a sailboat tour of San Diego Bay! You'll set out aboard a thirty-two-foot sailboat with up to seven other passengers. You're free to sit back and enjoy the view as you skim across the top of the water while the crew handles the tough stuff! Take in all the sights of the bay and beyond as you sail under the Coronado Bridge, and oggle the impressive Navy Fleet. Complimentary snacks and beverages, including beer and white wine, are also made available to enhance the experience. Things are a-boat to get ridiculous! Did we mention Sail Liberty won Charter Company of the Year for San Diego 2016 from Luxury Travel Guide? It doesn't get much better than that!
    Afternoon / Sunset Sail (Individual Ticket)

    955 Harbor Island Dr, San Diego

    • Embark on a 3-hour afternoon excursion aboard a 32-foot, 1914-style sail boat that has a wooden mast and teak accents
    • Check out the San Diego skyline and other vessels, including the Navy Fleet
    • Enjoy complimentary craft beer, wine, soda, and snacks
    • Let loose with thrilling exploration of San Diego's famed bay
    • For weekday afternoon charters and availability and child pricing, please contact Sail Liberty directly.
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    City Highlights Tour and Cruise

    Explore beautiful San Diego and Coronado on this narrated sightseeing tour. Aboard a comfortable coach, explore sites like Old Town, Balboa Park, the Gaslamp Quarter and Seaport Village, and enjoy time to walk around and take photos. Explore beautiful San Diego and Coronado on this narrated sightseeing tour. Aboard a comfortable coach, explore sites like Old Town, Balboa Park, the Gaslamp Quarter and Seaport Village, and enjoy time to walk around and take photos --- and don't forget about a scenic 1-hour cruise on San Diego Bay! You'll be picked up from your San Diego hotel in the morning and taken on a narrated coach tour of sunny San Diego, stunning La Jolla and scenic Coronado. First, visit Old Town, the birth place of San Diego. Now a state-protected historical park, this area commemorates the early days of the city and is home to Heritage Park, where you'll see well-preserved Victorian buildings. Continue to Balboa Park, a 1,200-acre (490-hectacre) park named after Spanish maritime explorer Vasco Núñez de Balboa. Then, discover the Gaslamp Quarter, the historic heart of San Diego where the nightlife happens. Learn how the name refers to the gas lamps that were common here in the late 19th and early 20th centuries. Drive along downtown's Green Dragon Colony, a collection of cottages that once served as a retreat for writers, actors, artists and musicians. These buildings now house quaint galleries and boutiques. Then, relax on a comfortable boat and soak in amazing sights from the water as you listen to interesting onboard commentary. Throughout your tour of these beautiful places, you'll have several photo stops along the way, as well as time to walk around.
    City Highlights Tour and Cruise

    Downtown, San Diego

    • Relax on a comfortable coach as you explore San Diego, La Jolla, and Coronado
    • See historical sites like Old Town, Balboa Park, the Gaslamp Quarter and Seaport Village
    • Admire incredible coastal views and elaborate Victorian architecture aboard an hour long harbor cruise
    • Relax knowing hotel pickup and drop-off are included
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