Charter Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay. Sailing yacht, 3 cabins, 2 bathrooms, 6 berths. Select dates to see live availability, exact pricing, and optional add‑ons (e.g., skipper, extras) Ideal for: adventure seekers. Available experiences: fishing, sail & bike, wellness on the water.
Charter Option: BAREBOAT
When the Sun Odyssey 440 came onto the market, it revolutionized how sailors live on board and move around the boat. The Sun Odyssey features an interior optimized for cruising comfort and sailing performance, along with an on-deck experience like never before.
The high-performance platform incorporates a full-length, hard-chined hull to promote fast cruising while minimizing heeling. The generous sail plan is easily handled by the inboard winches and lowered gooseneck height. Sailing this boat is an experience like none other. She is fast, powerful, and nimble on the wheel.
The 440 features the Walk Around Decks, an incredible feature. This, combined with unobstructed side decks from bow to stern, make movement on the deck easier than ever before. The huge cockpit is perfect for entertaining guests, and the convertible cockpit lounge turns the aft eight feet of the boat into a gigantic sun pad!
The open-concept interior is bathed in light, as the main salon features a multitude of windows and hatches. The interior layout features two large cabins and a smaller cabin. The central U-shaped galley is optimally placed for comfort while underway, centralizing the weight of the appliances for optimized sailing performance and serving meals in the salon. In the 440, the nav station is particularly emphasized, elevating this feature into a coffee nook or home office.
Approx. 30 min by Car from Baltimore/Washington International Airport (BWI).
📍 Travel Tip: Located 30 minutes from Baltimore/Washington International Airport (BWI).
Some boats just feel right the moment you ease the sheets and let the sails fill. The Sun Odyssey 440 - 3 cab. is one of them — a sailing yacht that rewards patience and delivers you, properly, into the waters around Annapolis. It sleeps up to 6 guests across 3 cabins and 2 bathrooms, making it a solid choice for Adventure & Nature. The base puts you within easy reach of Harbors near Annapolis, Chesapeake Bay, Coastal towns — and Jun–Sep is when these waters are at their best.
Location & Details
Marina:Annapolis, Chesapeake Bay
Charter Option:SailBoat, Sailing yacht
Local Guide
Harbors near Annapolis, Chesapeake Bay | Coastal towns | Scenic anchorages | Island routes
Best Season:
Jun–Sep (Jul–Aug is peak), May & Sep are popular shoulder months.
Jeanneau Sun Odyssey 440 - 3 cab. — 6 guests max, 3 cabins, 2 bathrooms, 6 berths. A sailing yacht puts the experience in your hands — or your skipper's. Responsive in a breeze, economical on fuel, and genuinely satisfying to passage-make. Ideal for: Adventure & Nature. Available experiences: Yoga & Wellness on the Water, Sunset and Sunrise Cruises, Photography Cruises. Vibe: Balanced Mediterranean Discovery.
Frequently Asked Questions
How much does it cost to rent the Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, pricing depends on your dates, trip length, and any add‑ons (e.g., skipper, fuel, extras). Select your dates to see the exact quote for this listing.
Is the Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay available for my dates?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, choose your preferred dates and trip length on the page to see live availability and the current price for those dates.
Do I need a license to charter it for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, rules depend on the country and whether you charter bareboat or with a skipper. If a license is required, you’ll see that clearly during the quote/booking flow.
Can I add a skipper or full crew for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, skipper/crew options depend on the listing and local regulations. If available, you can add them during the quote/booking flow (or request them in your inquiry).
What’s included, and what usually costs extra for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, inclusions vary by operator. Common extras can include fuel, marina/port fees, cleaning, linens, and optional equipment. Your quote will itemize what’s included and what’s optional.
How do booking and payments work for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, you’ll see the payment schedule, cancellation terms, and any security deposit requirements during checkout before you confirm the booking. Reference: KymmaBoats listing #25901.
How many people can stay on board for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, capacity depends on this specific listing: 6 berths, 3 cabins, 2 bathrooms.
Which airport should we fly into for the departure base for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, after you select dates, we’ll show the exact departure address and recommended nearby airports/transfer options for this listing.
What’s a great 7‑day itinerary from the base for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, once you pick your dates, you can use the map and nearby destinations on the page to plan stops that match your pace (relaxed vs. explorer vs. social).
What are the best months to start from the base for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, seasonality varies by region. You’ll get the best guidance by considering local wind patterns and your preferred crowd/temperature level for your travel month.
What sailing experience do I need to charter bareboat (without a skipper) for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, local regulations vary but typically require a valid coastal sailing qualification (such as RYA Coastal Skipper, ICC, or national equivalent) and may require a VHF radio certificate. If you're unsure whether you qualify, adding a professional skipper is the right choice — it's often a much better experience anyway.
What happens if the weather turns bad during our charter for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, safety always comes first. Your skipper (or you, bareboating) will always choose a safe anchorage over pushing through rough conditions. On most popular charter routes, a sheltered Plan B is never far away. Strong winds can actually make for exhilarating sailing — the final call is always made based on real-time conditions and your group's comfort.
How long does it typically take to sail between islands for Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, on most popular routes (Croatia, Greece, BVI), island hops range from 1 to 4 hours under sail. A typical day involves a morning departure, 2–3 hours of sailing, and arriving at your next anchorage by early afternoon. Your skipper plans realistic legs based on your group's pace and preferences.
What adventure and nature activities can we do from the Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay?
For Jeanneau Sun Odyssey 440 - 3 cab. from Annapolis, Chesapeake Bay, directly from most boats: snorkeling and swimming in pristine bays, kayaking, paddleboarding (equipment may be onboard or hireable locally). Depending on your destination, you can arrange day trips for scuba diving, sea caves exploration, hiking to clifftop villages, and wildlife watching. Ask your charter partner what's available locally and what equipment the boat carries.