Sailing•O'Day Javelin Rentals •Rhodes Sailboat Rentals •Cape Dory Sailboat Rentals •Windsurfer Rentals •Sailing Lessons •Willow Sailboat Trips •Old Quarry Sailing School •What to Bring Sailing Enjoy sailing through some of the most beautiful islands along the Maine coast. The Stonington archipelago is second to none and offers some of the very best sailing in Maine, boasting over 60 islands. O'Day Javelin Rentals Centerboard, seats up to 4.If you have limited experience, haven't sailed in a while, or are new to the area, we suggest you consider a short lesson to familiarize yourself with the boat and learn about the area. Old Quarry reserves the right to refuse rental equipment to those with insufficient knowledge or ability for the activity in question. Before you depart, we will discuss wind and sea conditions, weather, route options, channel crossings, hazards, and ask you to file a float plan with us. We'll provide all the necessary sailing gear - pfd, pump, extra line, paddle, anchor, VHF radio, and chart. We'll assist you in rigging the boat. Depending on the extent of your experience and the weather conditions, we may ask you to stay within a designated area. Old Quarry's charterboat, Nigh Duck, is available for rescue as needed. What to Bring Half Day Rentalsare for a 4 hour period from when you arrive.RATES: $80/half day Full Day Rentalsare for an 8 hour period from when you arrive.RATES: $110/full day Please call ahead for reservations or add to your shopping cart below to reserve a sailboat. Renters must prove competency in a sailboat. |
Rhodes 19' Sailboat RentalsRhodes 19' Sailboat: Centerboard, seats 6 or more. If you have limited experience, haven't sailed in a while, or are new to the area, we suggest you consider a short lesson to familiarize yourself with the boat and learn about the area. Old Quarry reserves the right to refuse rental equipment to those with insufficient knowledge or ability for the activity in question. Before you depart, we will discuss wind and sea conditions, weather, route options, channel crossings, hazards, and ask you to file a float plan with us. We'll provide all the necessary sailing gear - pfd, pump, extra line, paddle, anchor, VHF radio, and chart. We'll assist you in rigging the boat. Depending on the extent of your experience and the weather conditions, we may ask you to stay within a designated area. Old Quarry's charterboat, Nigh Duck, is available for rescue as needed. What to Bring Half Day Rentalsare for a 4 hour period from when you arrive.RATES: $110/half day Full Day Rentalsare for an 8 hour period from when you arrive.RATES: $175/full day Please call ahead for reservations or add to your shopping cart below to reserve a sailboat. Renters must prove competency in a sailboat. |
Cape Dory 19' Sailboat RentalsCape Dory 19' Sailboat: Fixed keel, seats 4, cabin sleeps 2. If you have limited experience, haven't sailed in a while, or are new to the area, we suggest you consider a short lesson to familiarize yourself with the boat and learn about the area. Old Quarry reserves the right to refuse rental equipment to those with insufficient knowledge or ability for the activity in question. Before you depart, we will discuss wind and sea conditions, weather, route options, channel crossings, hazards, and ask you to file a float plan with us. We'll provide all the necessary sailing gear - pfd, pump, extra line, paddle, anchor, VHF radio, and chart. We'll assist you in rigging the boat. Depending on the extent of your experience and the weather conditions, we may ask you to stay within a designated area. Old Quarry's charterboat, Nigh Duck, is available for rescue as needed. What to Bring Half Day Rentalsare for a 4 hour period from when you arrive.RATES: $110/half day Full Day Rentalsare for an 8 hour period from when you arrive.RATES: $185/full day Please call ahead for reservations or add to your shopping cart below to reserve a sailboat. Renters must prove competency in a sailboat. |
Windsurfer Rentals You must have windsurfing experience and have the ability to rig the boat in order to rent a windsurfer. The Stonington archipelago is a relatively sheltered area, however windsurfing on the ocean presents a number of challenges. Old Quarry reserves the right to refuse rental equipment to those with insufficient knowledge or ability for the activity in question. Before you depart, we will discuss wind and sea conditions, weather, route options, channel crossings, hazards, and ask you to file a float plan with us. Depending on the extent of your experience and the weather conditions, we may ask you to stay within a designated area. Old Quarry's charterboat, Nigh Duck, is available for rescue as needed. We'll provide all the necessary windsurfing gear including a pfd. We suggest you wear booties, watershoes, or sneakers. Wetsuits, drysuits, booties, and gloves are available for rent in our campstore. Half Day Rentalsare for a 4 hour period from when you arrive.RATES: $40/half day Full Day Rentalsare for an 8 hour period from when you arrive.RATES: $70/full day Please call ahead for reservations or add to your shopping cart below to reserve a windsurfer. |
Sailing LessonsLearn how to sail in an O'Day Javelin, a sturdy 14' fiberglass boat that is great for beginners. Lessons are also given on our Rhodes 19' and Cape Dory 19'. Experienced instructors will teach you the fundamentals of sailing, from rigging the boat to getting underway to planning a day trip. Topics covered include points of sail, terminology, weather, seamanship, and safety. Private lessons are given by the hour, with a maximum number of three people, in Webb Cove and around the nearby islands. RATES: $50/hour for one person - $10/hour for each additional person |
Sailboat Cruises aboard "Willow" Come and experience sailing aboard Willow, a beautiful classic 1959 32' wooden sloop. We will tack through some of the most scenic waters in the world, here off the coast of Stonington! Three hour and six hour excursions will be offered. You can learn basic sailing skills or sit back and enjoy the scenery. Wildlife sightings include basking seals, sea birds and eagles. Drawing classes and gourmet lunches are being introduced this year provided by Captain Geoff and his first mate Iana. Drawing classes will have the same pricing structure as regular charters and be at the same times. What to bring aboard: white soled sneakers, water, sun block, hat, warm layers, wind breaker, sun glasses. Please use the bathroom facilities on shore before sailing. We only have facilities for emergencies. Willow takes a maximum of six passengers on all cruises and charters. Half Day Cruises:11:00am-2:00pm & 2:30pm-5:30pmRATES: $250/1-4 passengers; $62.50/each additional passenger Full Day Cruises:11:00am-5:00pmRATES: $500/1-4 passengers; $125/each additional passenger Private Charters for up to 6 People:RATES: $375/half day; $750/full day; $100/each additional hour (applies to 6 hour charters only) Please call ahead for reservations or add to your shopping cart below. Reservations made at least a day in advance are appreciated. |






Centerboard, seats up to 4.
If you have limited experience, haven't sailed in a while, or are new to the area, we suggest you consider a short
If you have limited experience, haven't sailed in a while, or are new to the area, we suggest you consider a short
You must have windsurfing experience and have the ability to rig the boat in order to rent a windsurfer. The Stonington archipelago is a relatively sheltered area, however windsurfing on the ocean presents a number of challenges. Old Quarry reserves the right to refuse rental equipment to those with insufficient knowledge or ability for the activity in question.
Come and experience sailing aboard Willow, a beautiful classic 1959 32' wooden sloop. We will tack through some of the most scenic waters in the world, here off the coast of Stonington!