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At a Glance
We currently have the complete Boston Whaler boat line available and are eager to help you find the perfect boat to fit your needs. Whether it is a day offshore fishing the canyons, a day waterskiing and swimming with family and friends, or searching the Chesapeake's amazing back creeks and shallows, we have a Boston Whaler to take you there.
Outstanding experience in purchasing our first Whaler. We interacted with TommyO, Ashley, and Bart over a period of months as we talked through the decision and ultimate purchase. All were great to work with and helped us find the boat that fit us the best. I highly recommend going to see them.
Great experience, especially being first time boat owners. Tommy O took good care of us from start to finish. We feel like we can call on him anytime with any questions at all. We love the boat!
Great experience in purchasing a boat. The knowledge Tommy O provided made the sale a pleasure. He ensured I was purchasing the best boat for me and my family working magic to find my boat during a time when inventory is slim. These guys at Whalertowne are second to none.
Great customer service and very accommodating staff. TommyO took care of us through our entire shopping/purchasing experience and was always on call to answer our questions. We are very happy with our new boat and will purchase here again when we size up in the future.
Its said that "adversity builds character." True, but first it reveals it. In business, adversity reveals a business' true ethos. With the current and unprecedented social distancing restrictions in place, I got caught-up between the placing a deposit and traveling to perform a sea-trial and pick-up my boat. With no sense of how long or how severe the health and economic impacts will be, I requested that my deposit be returned. TommyO (whom I have yet to personally meet) immediately empathized and did not hesitate to assure me that Whalertowne's business practices place people first; that's just who they are. As pleasant as he was during the sale, he cheerfully returned my deposit in full. I see what TommyO meant; not by word but by deed. When things return to normal, its Whalertowne where I will return; they have earned my trust.
We currently have the complete Boston Whaler boat line available and are eager to help you find the perfect boat to fit your needs. Whether it is a day offshore fishing the canyons, a day waterskiing and swimming with family and friends, or searching the Chesapeake's amazing b…
Chesapeake Whalertowne - Annapolis works with financing partners to help buyers secure loans for boats and watercraft. Contact Chesapeake Whalertowne - Annapolis to ask about current financing promotions, available lenders, and whether pre-qualification is available. You can also use Searchshop's built-in payment estimator on any listing to model monthly payments before reaching out.
Chesapeake Whalertowne - Annapolis is located at 110 Compromise St, Annapolis, Maryland, 21401. They serve buyers in Annapolis, Maryland and surrounding areas.
Chesapeake Whalertowne - Annapolis specializes in boats and watercraft. Browse their full inventory on Searchshop to see all available listings with year, make, model, photos, and pricing.
You can contact Chesapeake Whalertowne - Annapolis through the contact form or reveal their phone number on their Searchshop profile page. Include the year, make, and model you are interested in for a faster response.
Buying a boat from Chesapeake Whalertowne - Annapolis in Annapolis, Maryland? Use this guide to evaluate any listing before you commit.
Match the boat to your waters
Pontoons and deck boats suit calm lakes. Deep-V hulls handle chop on larger lakes and coastal water. Center consoles are versatile for fishing. Ask Chesapeake Whalertowne - Annapolis which models suit the waterways near Annapolis, Maryland.
Inspect the hull carefully
Look for stress cracks, blistering, or repairs on fiberglass hulls. Check the transom for soft spots by pressing firmly — a solid transom feels rigid. Osmotic blistering costs thousands to repair.
Check engine hours
Inboard and outboard engines are typically rated to 1,500–3,000 hours. Low-hour engines with service records are worth more. Ask to see oil change and winterization records for any boat at Chesapeake Whalertowne - Annapolis.
Request a sea trial
Test the boat on the water before buying. Run it at full throttle. Listen for unusual noises. Check that the throttle and steering respond smoothly. Reputable dealers like Chesapeake Whalertowne - Annapolis will accommodate this request.
Verify title and registration
Ask for the current title and confirm the hull identification number (HIN) matches. Check for any liens with your state boating agency. Chesapeake Whalertowne - Annapolis should be able to walk you through the paperwork.
Marine financing has unique terms. Here is what to know before financing a boat through Chesapeake Whalertowne - Annapolis in Annapolis, Maryland.
Typical Loan Terms
10 to 20 years for larger boats. Smaller boats are typically financed over 5 to 10 years.
Down Payment
10% to 20% is standard. Some lenders require more for older vessels.
Pro Tip
Get pre-approved by your bank before visiting Chesapeake Whalertowne - Annapolis — it gives you a rate to compare against dealer financing.
Marine lenders (USAA, SunTrust, Essex Credit) specialize in boat loans and often offer better rates than general banks. Get a pre-approval before visiting Chesapeake Whalertowne - Annapolis to compare against dealer-arranged financing.
Chesapeake Whalertowne - Annapolis is a boat dealer in Annapolis, Maryland listed on Searchshop. Browse their full boats and watercraft inventory, view detailed photos, compare prices, and get in contact directly from this page. Searchshop aggregates boat dealer listings across the country so you can compare stock and pricing in one place before you visit or call.
Buyers in and around Annapolis, Maryland can browse the full inventory at Chesapeake Whalertowne - Annapolis, read verified buyer reviews, and reach out through the contact form on this page. Each listing at Chesapeake Whalertowne - Annapolis shows year, make, model, condition, mileage or hours, and current asking price. Use the monthly payment estimator on any listing to model financing before stepping on the lot.
The inventory at Chesapeake Whalertowne - Annapolis is updated regularly on Searchshop. Each listing shows high-resolution photos alongside the year, make, model, trim, and price. Mileage, condition notes, and available options are listed on each vehicle detail page. A built-in loan calculator lets you estimate your monthly payment based on purchase price, down payment, and loan term before you call or visit. Save listings you like to compare them side by side. If a unit you are interested in is no longer showing, contact Chesapeake Whalertowne - Annapolis directly — dealers often have incoming trades and new arrivals not yet listed.
Buying from a local boat dealer in Maryland has practical advantages. Local dealers handle state title, registration, and sales tax in-house. Warranty and service work are easier to coordinate nearby. Local dealers carry inventory suited to the region — boats suited to local waterways and seasons. Visiting in person lets you inspect and test ride before you commit. Use the Searchshop dealer directory to compare Maryland boat dealers by city, brand, or inventory.
Use the contact form on this page to ask about a specific listing, request more photos, or schedule a visit. Include the year, make, and model for a faster response. Ask about trade-in valuations, financing promotions, and upcoming inventory. Chesapeake Whalertowne - Annapolis is in the Searchshop boat dealer directory serving Annapolis, Maryland and surrounding areas. Browse other boat dealers on Searchshop to compare inventory and pricing near you.
Many boat dealers accept trade-ins as part of a purchase. Contact Chesapeake Whalertowne - Annapolis directly to ask about their trade-in program, how they value trade-in units, and how a trade-in would apply toward your next boat purchase.
