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Sailing yacht rental in Annapolis
9 boats available

Jeanneau Sun Odyssey 389 | 39 North
- Year
- 2018
- Cabins
- 3
- People
- 6
- Air conditioning
- Flat screen TV
- Bathing platform
- Bow thruster
Electric toilets

Dufour 430 | Opportune Moment
- Year
- 2021
- Cabins
- 3
- People
- 6
- Air conditioning
- Flat screen TV
- Bathing platform
- Bow thruster
Electric toilets![Waypoints Yacht Charters]()
![Dufour 530 | La Barca]()
Dufour 530 | La Barca
- Year
- 2024
- Cabins
- 4
- People
- 8
- Air conditioning
- Flat screen TV
- Bow thruster
- Outside GPS plotter
Electric toilets

Jeanneau 51 | Recovery Room
- Year
- 2018
- Cabins
- 3
- People
- 6
- Air conditioning
- Flat screen TV
- Bathing platform
- Bow thruster
Electric toilets

Jeanneau Sun Odyssey 440 | Summer Salt
- Year
- 2018
- Cabins
- 3
- People
- 6
- Air conditioning
- Dinghy engine included
- Flat screen TV
- Bathing platform
Electric toilets

Jeanneau 58 | Padraigin 2
- Year
- 2017
- Cabins
- 4
- People
- 8
- Air conditioning
- Flat screen TV
- Bow thruster
- Outside GPS plotter


Dufour 470 | Unforgettable
- Year
- 2022
- Cabins
- 3
- People
- 6
- Air conditioning
- Flat screen TV
- Bathing platform
- Bow thruster
Electric toilets
![Dufour 530 | Liliana Bella]()
Dufour 530 | Liliana Bella
- Year
- 2021
- Cabins
- 4
- People
- 9
- Air conditioning
- Flat screen TV
- Bathing platform
- Bow thruster
Electric toilets

Dufour 430 | Epiphany
- Year
- 2022
- Cabins
- 3
- People
- 8
- Air conditioning
- Bathing platform
- Bow thruster
- Outside GPS plotter
Electric toilets

Hunter Passage 42 | DreamCatcher
6.2 mi from Annapolis
- Year
- 1995
- Cabins
- 2
- People
- 6
- Final cleaning included
- Deposit insurance included
- Captain included
- Outside GPS plotter
Electric toiletsMainSail Charters & Research, LLC
![Bayliner Ciera 245 | Slip Knot]()
Bayliner Ciera 245 | Slip Knot
29.2 mi from Annapolis
- Year
- 2006
- People
- 6
- Deposit insurance included
- Final cleaning included
- Bathing platform


Sea Ray Sundancer 340 | Destination
29.2 mi from Annapolis
- Year
- 2006
- Cabins
- 1
- People
- 11
- Air conditioning
- Deposit insurance included
- Dinghy engine included
- Final cleaning included


Monterey 335 | Free Spirit
29.2 mi from Annapolis
- Year
- 2015
- Cabins
- 1
- People
- 8
- Air conditioning
- Deposit insurance included
- Final cleaning included
- Flat screen TV

Sailing yacht rental in Annapolis
Charter a sailing yacht and explore Annapolis! Prices start from 5369 kr per day. Experience the authentic charm of Annapolis by renting one of our 9 available sailing yachts. Let the wind lead you and live the true sailing experience during your yacht charter. Sailboat rentals in Annapolis are most popular with groups of friends and offer the best price-comfort ratio.
Sailboats in Annapolis range from 36.1 to 55.8 feet (11 to 17 m) in length. Compared to other types of boats, sailboats are notably fuel-efficient and equipped with a single diesel engine.
Our fleet of monohulls in Annapolis includes popular brands such as Dufour, Jeanneau and Hunter.
These are some of the best places to rent a sailboat in Annapolis:
Whether you’re an experienced sailor seeking a bareboat sailing yacht charter in Annapolis or a novice desiring a skippered sailing yacht in Annapolis, we ensure a seamless and memorable sailing experience.
Most searched
What is the cost of chartering a yacht in Annapolis?
Sailboat charter in Annapolis
A sailing yacht charter in Annapolis usually costs $586 per day. For instance, the most popular 6-berth sailboat costs $586 per day. The most popular sailboat destinations in Annapolis are:
Here are a couple of reasons why to choose a sailboat for your holiday in Annapolis:
Serenity: Sailing yachts provide a tranquil experience, allowing you to glide over the water with only the sound of the wind and waves. This creates a peaceful atmosphere where you can relax and disconnect from the hustle of everyday life.
Authentic Sailing: For sailing enthusiasts, there is nothing quite like the feel of a yacht being powered by the wind. It's an authentic experience that brings you closer to the art of sailing.
Eco-Friendly: With the wind as your primary source of propulsion, sailing yachts are more environmentally friendly than motorized vessels, reducing your carbon footprint while on holiday.
Skill Development: A sailing holiday can be a chance to learn or hone your sailing skills. Participate in managing the sails and steering, and return from your trip with new capabilities.
Onboard Comforts: Modern sailing yachts are equipped with comfortable amenities and living spaces that allow for a luxurious stay without compromising the sailing experience.
Versatile Experiences: Whether you're looking for a romantic getaway, a family adventure, or an exciting trip with friends, a sailing yacht can cater to various types of holidays with the potential for tailored itineraries and activities.
Catamaran charter in Annapolis
A catamaran charter in Annapolis usually costs $944 per day. For instance, the most popular 6-berth catamaran Fountaine Pajot Isla 40, costs $944 per day. Choose a catamaran for a more comfortable and spacious holiday experience. Catamarans feature a shallow draft, enabling you to explore shallow waters and uncover hidden coves. For your next catamaran rental in Annapolis, choose from our most popular destinations:
Power catamaran charter in Annapolis
Chartering a power catamaran in Annapolis starts at around $1,836 per day. For instance, the rental price for a 8-berth power catamaran, such as the Fountaine Pajot MY6 costs $1,836 per day. Power Catamaran is the perfect choice for those looking to cover short distances quickly and without the hassle of a sailboat. Power catamarans are much faster than sailing catamarans and don’t rely on wind conditions, giving you more freedom in your travels. The most popular destinations to charter a power catamaran in Annapolis are:
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