Overnight Sailing Charters & Multi-Day Trips on the Chesapeake Bay

Sail from Irvington, Virginia aboard our 36' monohull Galene or 58' cruising catamaran Pisces. Choose a 2-to-7-day adventure passage—available as a private boat charter, by-the-cabin booking, or liveaboard ASA certification course.

Check 2027 Availability

2027 Multi-Day Sailing Trips at a Glance

All overnight voyages depart from The Tides Inn Marina (480 King Carter Dr., Irvington, VA) and include onboard provisions while underway.

  
    
        Trip
        Galene (36' Monohull · Max 3)
        Pisces (58' Catamaran · Max 5)
        Overnight Style
        Optional ASA Course
      

    
        2-Day Weekender
(1 Night)
        $3,200 Private
        $5,500 Private
        Marina (Galene) / Anchorage or Marina (Pisces)
        N/A
      

        3-Day Chesapeake Circle
(2 Nights)
        $4,200 Private
        $6,800 Private
        Marina (Galene) / Anchorage or Marina (Pisces)
        N/A
      

        4-Day Chesapeake Cat Cruise
(3 Nights)
        Not offered
        $9,600 Private
(or from $2,500/cabin)
        Anchorage & Marina Mix
        ASA 104 / 114
      

        7-Day Delmarva Loop
(6 Nights)
        Not offered
        $14,000 Private
(or from $3,800/cabin)
        Offshore + Chesapeake Bay
        ASA 105 / 106
      

  

Trip	Galene (36' Monohull · Max 3)	Pisces (58' Catamaran · Max 5)	Overnight Style	Optional ASA Course
2-Day Weekender (1 Night)	$3,200 Private	$5,500 Private	Marina (Galene) / Anchorage or Marina (Pisces)	N/A
3-Day Chesapeake Circle (2 Nights)	$4,200 Private	$6,800 Private	Marina (Galene) / Anchorage or Marina (Pisces)	N/A
4-Day Chesapeake Cat Cruise (3 Nights)	Not offered	$9,600 Private (or from $2,500/cabin)	Anchorage & Marina Mix	ASA 104 / 114
7-Day Delmarva Loop (6 Nights)	Not offered	$14,000 Private (or from $3,800/cabin)	Offshore + Chesapeake Bay	ASA 105 / 106