Cruises & Sailing · Tomorrow

(14 activities)
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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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    Sunset Sailing Cruise

    If San Diego knows how to do one thing, it knows how to stay classy, and all other cities should take note. For two hours, you can live the high life on a yacht and forget about everything else sitting in your inbox. Climb aboard and capture the romance of the sun setting into the Bay with cool breezes and breathtaking views. Enjoy the beauty of the San Diego skyline with your friends or that special someone as the sun dips into the sea while on this private sunset sail. You can be completely stationary for the trip or you can get your hands a little dirty and help the captain trim the sails -- or even take your turn behind the wheel. Don’t forget to keep an eye out for wildlife marine, because there is a very good chance you will get to see dolphins and seals in their organic and natural habitat. Fall in love with this city all over again (or for the first time!) from a different point of view.
    Sunset Sailing Cruise

    1880 Harbor Island Dr, San Diego

    • Sail around San Diego aboard a classic racing yacht
    • Relish the sunset and downtown skyline like you never have before
    • Nibble on complimentary snacks and bring a bottle of your favorite champagne to enjoy as the sun sets
    • Snuggle up at the spacious settee down below in the cabin
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    3 Hour Sailing Adventure

    Got a sinking feeling that you’re missing out on the finer things in life? Well, this unique sailing experience ought to really float your boat! You’ll charter a 37-foot sailing vessel for yourself and up to five others to explore the breathtaking waters of San Diego Bay. Launching from Harbor Island, you’ll sail past the North Island Naval Station on Coronado, the Midway Museum, and more! The El Barco, your impressive vessel for the evening, is equipped with ample seating both above and below deck, so you can sit back and comfortably enjoy the ride with your fellow seafarers. And adding to the fun, champagne is included, so you can offer a toast to your own intrepid, and highly sophisticated, spirit!
    3 Hour Sailing Adventure

    955 Harbor Island Dr, San Diego

    • Charter a six-passenger, 37-foot sailing vessel for a tour of San Diego Bay
    • Enjoy fabulous views in style with your closest friends or family by your side
    • Embark on your journey from Harbor Island and sail past the North Island Naval Station and more!
    • Treat yourself to a luxurious adventure that includes complimentary champagne
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    Signature Sailing Tour (2hr)

    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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    1 positive reviews
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    Marine Wildlife Tour (4hr)

    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 with a focus on whale watching. If working the adventure is not your thing, everyone can still enjoy craft beer, chilled white wine, lunch 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 watch as surrounding whales create blow-spouts for a spectacular splash out on the water. Whether you want to work the mast or work your jaw, this unique whale watching experience has something for everyone.
    Marine Wildlife Tour (4hr)

    1450 Harbor Island Dr, San Diego

    • Sail on a beautiful sail boat through the San Diego Bay for a whale watching experience
    • 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 and complimentary lunch
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    1 positive reviews
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    Hot Tub Anchored Cruise - 2Hr

    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 - 2Hr

    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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    Adventure Daytime Sailing Tour

    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

    2051 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
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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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    Rum Runner Sail Tour Bar Crawl

    You have never experienced San Diego Bay bars this way. Take a sailboat with friends on this unique sailing bar crawl. First stop at a local pub and inspire you with a classic, refreshing drink with a little Captain Morgan. Next, you’ll sail to two of three other bars: C- level lounge on Harbor Island (for a shot/drink to head off the spins) or, we can sail west to the “Bali Hai” for the world famous Mia Tia (for the brave at heart) or Jimmy’s world famous Gastro Pub where we’ll try not to get “3 sheets to the wind”. You will not get in trouble on this rum run, but you may need a designated driver to take you home after enjoying all the delicious concoctions.
    Rum Runner Sail Tour Bar Crawl

    2051 Shelter Island Dr, San Diego

    • Experience the San Diego Bay in this unique sailing bar crawl
    • Enjoy San Diego’s bars and restaurants at 2 incredible stops
    • Drinks are included
    • Great for bachelor and bachelorette parties
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    Couples Sailing Cruise

    What better way to appreciate the San Diego coast than from the comfort of a cruise with your significant other? From the smooth, steady sail of your boat you will be overwhelmed with beautiful coastal views. On this cruise you will set sail for a full day: You can decide whether you would like to spend a relaxing day moving about the bay or do a full sail to the Coronado Islands (a Mexican wildlife refuge). You will have the opportunity to see many different types of wildlife including birds, sea lions, otters, seals, and whales. The Coronado Islands offer a lot of unique wildlife including whales, brown pelicans, cormorants, oystercatchers, brown and blue-footed boobies (go ahead and laugh), sea lions, otters, seals, elephant seals, dolphins, and burros (yes, burros). The islands offer many interesting visuals including the wildlife that are not typically seen on land surrounded by water. If you’re comfortable leading the way, you’ll be more than encouraged to take the wheel yourself, or let your partner do all the work! For the most elegant and romantic sailing experience, join a full day trip with snacks and drinks included. Feel free to BYOB to make this experience that much more special.
    Couples Sailing Cruise

    1880 Harbor Island Dr, San Diego

    • Experience a couples sailing cruise on the bay or to the Coronado islands
    • Behold a variety of surrounding views and wildlife, including sea lions and otters
    • Take a crack with your partner at steering the boat as you drift across the open waters
    • Enjoy complimentary snacks and water with remarkable views
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