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Explore Greetwell

Curated local experiences in 500+ destinations

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Questions? We're here to help.Real people, 7 days a week.

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  • 15 Best Stuff to Do in Atlanta, GA in 2026
  • Best results for

    Sailing in Harbor Dr, CA

    Showing 1-24 of 35 results
    2.5-Hour Private Sunset Sail in San Diego

    2.5-Hour Private Sunset Sail in San Diego

    Sail San Diego Bay at sunset on a private 2.5-hour charter

    5.0 • 323 reviews
    $525& up
    Private Sailing & Swim Charter in San Diego

    Private Sailing & Swim Charter in San Diego

    Pair time under sail with a swim stop and paddleboard play

    5.0 • 284 reviews
    $1,037
    Private San Diego Bay Sailing Charter

    Private San Diego Bay Sailing Charter

    Make room for your own celebration on a fully private sail

    5.0 • 131 reviews
    $636/ boat
    Private Midday Sailing Charter in San Diego

    Private Midday Sailing Charter in San Diego

    See San Diego’s historic waterfront on a private daytime sail

    4.9 • 877 reviews
    $631& up
    Sail San Diego Bay Catamaran Cruise With Drinks

    Sail San Diego Bay Catamaran Cruise With Drinks

    Sail San Diego Bay on a small-group catamaran with drinks included

    4.9 • 258 reviews
    $660
    Classic Yacht Afternoon Sail on San Diego Bay

    Classic Yacht Afternoon Sail on San Diego Bay

    Sail a classic yacht past San Diego Bay landmarks with drinks and snacks

    4.9 • 113 reviews
    $125/ person
    2.5-Hour Private Sailing Charter in San Diego Bay

    2.5-Hour Private Sailing Charter in San Diego Bay

    Sail, swim, and toast aboard a private yacht

    $1,018
    Private Sunset Sailing Tour in San Diego

    Private Sunset Sailing Tour in San Diego

    Sail into sunset with views of the Pacific and San Diego skyline

    $694& up
    2.5-Hour Sailing Charter in San Diego

    2.5-Hour Sailing Charter in San Diego

    Take the helm on a private sail past San Diego’s waterfront landmarks

    5.0 • 323 reviews
    $525& up
    Private Sail & Swim Charter With Paddle Boards in San Diego

    Private Sail & Swim Charter With Paddle Boards in San Diego

    Enjoy sailing and time in the water without choosing between them

    5.0 • 284 reviews
    $1,309
    Early Afternoon Sailing Tour in San Diego

    Early Afternoon Sailing Tour in San Diego

    Trade the city streets for coastal views under sail

    5.0 • 131 reviews
    $116/ person
    Private 3-Hour Sailing Lesson in San Diego

    Private 3-Hour Sailing Lesson in San Diego

    Learn to sail in a private 3-hour lesson with a US Coast Guard certified captain

    4.9 • 877 reviews
    $689
    Morning Sailing Charter in San Diego

    Morning Sailing Charter in San Diego

    Private bay sailing with Point Loma or Coronado routes

    5.0 • 323 reviews
    $525& up
    Private Sailing Charter to Point Loma in San Diego

    Private Sailing Charter to Point Loma in San Diego

    Relax at sea with your own crew and views of the California coast and Mexico

    5.0 • 284 reviews
    $1,091
    Midday Sailing Tour in San Diego

    Midday Sailing Tour in San Diego

    Take in San Diego’s city views under sail

    5.0 • 131 reviews
    $116/ person
    Private Sailing Charter in San Diego

    Private Sailing Charter in San Diego

    Customize a private sail with your own captain and crew

    4.9 • 877 reviews
    $1,198& up
    Private Catamaran Sailing Charter on San Diego Bay

    Private Catamaran Sailing Charter on San Diego Bay

    Charter a private catamaran for your special occasion on San Diego Bay

    4.9 • 258 reviews
    $660
    Sunset Sailing Cruise in San Diego

    Sunset Sailing Cruise in San Diego

    Unwind on an evening sail with drinks and skyline views

    4.9 • 258 reviews
    $119/ person
    Sunset Sail on a Classic Yacht in San Diego Bay

    Sunset Sail on a Classic Yacht in San Diego Bay

    A classic-yacht sunset sail with drinks and San Diego Bay views

    4.9 • 113 reviews
    $125/ person
    4-Hour Sailing Charter in San Diego

    4-Hour Sailing Charter in San Diego

    Sail the coastline, swim in a calm bay, and relax on the water

    $1,479
    Private Sailing Tour in San Diego

    Private Sailing Tour in San Diego

    Take your next date out on the Pacific

    $633& up
    San Diego 4-Hour Sail & Swim Charter

    San Diego 4-Hour Sail & Swim Charter

    Cruise San Diego Bay, swim in Glorietta Bay, and explore your preferred route

    5.0 • 323 reviews
    $795& up
    San Diego Sunset Sail on San Diego Bay

    San Diego Sunset Sail on San Diego Bay

    Wind down with a sunset sail, city views, and drinks included

    5.0 • 131 reviews
    $116/ person
    Bottomless Mimosa Sailing Cruise in San Diego

    Bottomless Mimosa Sailing Cruise in San Diego

    Sail San Diego Bay with bottomless mimosas on a 2-hour morning cruise

    4.9 • 877 reviews
    $80/ person
    12
    Harbor Dr Things To Do
    SailingYacht Charters45Boat Rentals35Bike Rentals25Fishing Charters22
    More
    • Stand Up Paddle Boarding21
    • Whale Watching21
    • Equipment Rental17
    • Boat Tours14
    • Wine Tours14
    • Food Tours11
    • Paddleboarding10
    City Tours
    9
  • Ghost and Haunted8
  • Surfing Lessons8
  • Guided Tours7
  • Brewery Tours6
  • Day Trips6
  • Dinner Cruises6
  • Kayaking Tours6
  • Scuba Diving6
  • Bike Tours5
  • Motorcycle Tours5
  • Seasonal and Holiday5
  • Self Guided and Passes5