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    Find Sailing Charters Near You

    4.9
    (4,730 Reviews)

    Page 2 of 10 • 240 listings

    Sail Lake Michigan from Racine, WI
    Sailing in Racine · 6 guests

    Sail Lake Michigan from Racine, WI

    5.0
    $75/hour
    Sail in downtown Toronto
    Sailing in Toronto · 6 guests

    Sail in downtown Toronto

    5.0
    $121/hour
    Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!
    Powerboats in Washington · 6 guests

    Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

    5.0
    $185/hour
    Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
    Sailing in Washington · 6 guests

    Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

    New
    $280/hour
    SEARAY SLX400 | $550hr | 13 People
    Events in Washington · 13 guests

    SEARAY SLX400 | $550hr | 13 People

    5.0
    Superowner
    $550/hour
    Instant Book
    2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River
    Powerboats in Fort Washington · 6 guests

    2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

    5.0
    $150+/hour
    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
    Sailing in Milwaukee · 6 guests

    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

    New
    $120/hour
    Charter this beautiful Catalina from Milwaukee, WI - Captain Included
    Sailing in Milwaukee · 6 guests

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    4.8
    $150/hour
    Welcome Aboard Optimystic! Create a beautiful memory on the water.
    Sailing in Essex · 6 guests

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    5.0
    $150/hour
    VIKO 30 Premium Sailing Yacht In Deale, MD
    Sailing in Deale · 5 guests

    VIKO 30 Premium Sailing Yacht In Deale, MD

    New
    $925/day
    Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
    Sailing in Mayo · 6 guests

    Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

    5.0
    $150+/hour
    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    Sailing in Deale · 10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    5.0
    $250+/hour
    VIKO S 35 Sailboat in Deale
    Sailing in Deale · 6 guests

    VIKO S 35 Sailboat in Deale

    New
    $298/hour
    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
    Sailing in Annapolis · 13 guests

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    5.0
    $1,100/hour
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Annapolis · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $425/hour
    50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

    5.0
    Snoozed - Active 02 Jul 2026
    38-ft Hunter 376 Sailing Adventure in Annapolis
    Sailing in Annapolis · 6 guests

    38-ft Hunter 376 Sailing Adventure in Annapolis

    5.0
    Superowner
    $100+/hour
    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay
    Sailing in Annapolis · 12 guests

    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

    New
    $334+/hour
    Luxury 2022 Excess 11 Catamaran for 12 in Annapolis
    Sailing in Annapolis · 12 guests

    Luxury 2022 Excess 11 Catamaran for 12 in Annapolis

    New
    $335+/hour
    Luxury Lagoon 42 Catamaran for 12 in Annapolis
    Sailing in Annapolis · 12 guests

    Luxury Lagoon 42 Catamaran for 12 in Annapolis

    New
    $335+/hour
    Durfour 430 Sailing Yacht to Discover the Chesapeake Bay
    Sailing in Annapolis · 12 guests

    Durfour 430 Sailing Yacht to Discover the Chesapeake Bay

    New
    $210+/hour
    34ft Sailing Yacht in Annapolis, Maryland
    Sailing in Annapolis · 4 guests

    34ft Sailing Yacht in Annapolis, Maryland

    New
    $250/hour
    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    5.0
    $136+/hour
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    5.0
    $150/hour

    Top Destinations Nearby

    Local Sailing Reviews

    1. JK

      Jessica

      Charter this beautiful Catalina from Milwaukee, WI - Captain Included

      Patrik was awesome! We did an engagement photo shoot on the boat and he helped us to get the perfect shots! Would highly recommend to anyone looking for a unique date night or fun photo shoot location!

    2. AH

      Alexandra

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Alberto and Grace were the perfect team. They are kind, knowledgeable, respectful, communicative, safe and I would recommend them to anyone. This was our first time sailing in Annapolis, and we could not have asked for a better experience. We hope to share future experiences with them. Everything was perfect.

    3. NS

      Nikolay

      Sail in downtown Toronto

      Amazing trip. Would put 10 stars out of 5. Dom is a great captain, absolutely recommend

    4. BF

      Bruce

      38-ft Hunter 376 Sailing Adventure in Annapolis

      This was our 2nd sail with Capt Alberto. He is super friendly and easy to talk with. And he invites his guests to take an active role in sailing, or to just kick back and relax if they prefer. Great experiences for our family.

    5. HH

      Hannah

      Charter this beautiful Catalina from Milwaukee, WI - Captain Included

      Gorgeous views of the lakefront, knowledgeable captain. Highly recommended

    6. TM

      Thomas

      New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

      This is a great boat and we had an absolute blast. worth every penny!

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