Living aboard in the Chesapeake Bay means finding a marina that actually fits your lifestyle and budget. The challenge? Sorting through vague online listings, outdated reviews, and conflicting information about slip availability, liveaboard policies, and amenities that matter when you’re calling your boat home.
Liveaboard marinas in Chesapeake Bay range from urban hotspots with restaurants at your doorstep to resort-style havens with pools and beaches, plus budget-friendly options with small-town charm.
Here’s the straight scoop on seven top marinas with real pricing, actual amenities, and honest pros and cons so you can find your perfect slip.
Table of Contents
- Anchorage Marina (Baltimore)
- Herrington Harbour North & South (Deale, MD)
- Annapolis Landing Marina (Annapolis)
- Tidewater Marina (Havre de Grace)
- Port Annapolis Marina
- Piney Narrows Yacht Haven (Chester)
- Baltimore Marine Center (Inner Harbor)
- Your Perfect Liveaboard Marinas in Chesapeake Bay Await
Anchorage Marina (Baltimore)
When you’re looking for liveaboard life that puts city conveniences literally within walking distance, Anchorage Marina in Baltimore’s Canton neighborhood delivers that perfect balance. The marina’s floating docks come with finger piers and gated access, giving you that extra layer of security. You’ve got a Safeway right across the street for grocery runs, and West Marine is one block away.
Anchorage Marina accommodates boats up to 250 feet with 565 total slips, and liveaboards are welcome here. Saturday cookouts with free burgers, dogs, and drinks have become something of a tradition. The location puts you five miles from the Key Bridge and about half a mile from Fort McHenry.
Pros:
- Over 100 restaurants are within walking distance of Baltimore Harbor
- Safeway grocery store and West Marine are immediately accessible
- Gated security with keycard access for slip holders
- Pool, WiFi, laundry facilities, and metered electric are included
Cons:
- Urban noise and congestion from the city location
- Annual marina rates are around $4,750 for a 50-foot slip plus $2,200 annual dues
- Limited green space compared to resort marinas
Herrington Harbour North & South (Deale, MD)
These sister marinas have been named Best Resort Marina, Best Clean Marina, and Best Overall Marina. At Herrington Harbour South, you’ll find an Olympic-size swimming pool, private beaches with complimentary kayaks and paddleboards, and a mile-long eco-trail. Herrington Harbour North sits just 25 minutes from the Capital Beltway and features a saltwater pool with views, a jacuzzi spa, and a pool bar.
Both marinas host 60-80 complimentary training classes, social events, seminars, and parties annually. On-site restaurants—Dockside at North and Ketch 22 at South—mean you can grab three meals a day. You’ve got access to complimentary bicycles, outdoor movie nights, and yoga classes.
Pros:
- Resort-level amenities, including an Olympic pool and private beaches
- Two full-service restaurants on-site
- 60-80 complimentary events and classes per year
- Strong environmental stewardship and clean marina certifications
Cons:
- Deale lacks urban walkability and nightlife
- Winter liveaboards need to run long hoses for water access
- Premium pricing reflects resort amenities
Related: Top 7 Liveaboard Marinas in Maryland for Year-Round Living
Annapolis Landing Marina (Annapolis)
Located at the corner of Back Creek and the Chesapeake Bay, you can leave your slip and be out on the Bay in less than 10 minutes. The marina offers serenity while sidestepping the congestion, bridges, and noise of downtown, yet you’re just minutes away from all the excitement of Annapolis Harbor. The US Naval Academy sits nearby, and during sailing season, you’re surrounded by major sailing events.
Annapolis Landing welcomes liveaboards year-round with a $150 liveaboard fee. The marina has 123 slips handling vessels up to 110 feet, with rates that include electric, water, Wi-Fi, cable, pool access, bathhouse with laundry, fuel discounts, and free pumpouts. The fuel dock features high-speed diesel pumps that can fill vessels at up to 35 gallons per minute.
Pros:
- Bridge-free Bay access in under 10 minutes
- Comprehensive amenities are included in the slip rates
- Strong, established liveaboard community
- Water taxi/shuttle service to downtown Annapolis
Cons:
- Winter pump-out relies on an ice-prone pump-out boat
- More boatyard feel than resort atmosphere
- Recent management changes have drawn mixed reviews
Tidewater Marina (Havre de Grace)
At the head of the Chesapeake Bay in historic Havre de Grace, Tidewater Marina offers full-service facilities with that small-town feel. You’re about an hour from Baltimore, Philadelphia, and central Pennsylvania via I-95 and US-40. The marina sits right in the middle of historic Havre de Grace, putting restaurants, paddle-boarding, groceries, laundry, and a public library within walking distance.
Daily transient rates run $2.00 per foot, and annual rates come in at $175 per foot—significantly more affordable than Annapolis or Baltimore. The marina offers over 158 slips plus 120 Hi & Dri stalls. Full-service capabilities include a discount marine store, complete repairs, a fuel dock, and well-maintained individual bathrooms.
Pros:
- Extremely affordable slip rates at $175 per foot annually
- Charming walkable historic town with restaurants and shops
- Protected basins eliminate waves and currents
- Full-service boatyard and marine store on-site
Cons:
- Liveaboards are not currently allowed
- Northern location means longer runs to popular cruising grounds
- Limited nightlife compared to urban marinas
Port Annapolis Marina
Port Annapolis Marina spans 16 acres of park-like settings on Back Creek, offering quick, bridge-free access to the Chesapeake. With over 250 slips catering to larger vessels, including catamarans, Port Annapolis has built a reputation for quality service. Facilities include a pool, playground, workout center with weights and cardio equipment, a lounge with full-service bar and Wi-Fi, and Black Market Bakery on-site.
Port Annapolis offers more amenities than many competing marinas and includes unmetered power. The marina is better protected than alternatives and has a superior winter pump-out system. Pet owners welcome—Port Annapolis is pet-friendly. Dockmaster Scott and his team have earned consistent praise for being helpful and accommodating.
Pros:
- Resort amenities include a pool, a workout center, and an on-site bakery
- Unmetered power and a reliable winter pump-out system
- Thriving liveaboard community
- Pet-friendly with 16 acres of landscaped grounds
Cons:
- Premium pricing reflects upscale amenities
- Short docks with multiple pilings can challenge docking
- Requires a dinghy or transportation to reach downtown Annapolis
Related: Top 9 Liveaboard Marinas in Mississippi
Piney Narrows Yacht Haven (Chester)
Nestled along the banks of Kent Narrows on Kent Island, Piney Narrows Yacht Haven has provided a sheltered haven for over 30 years. You’re just minutes from the great restaurants, bars, and nightlife that make Kent Narrows a premier boating destination. The marina provides easy access to Annapolis, Baltimore, Philadelphia, Wilmington, and Washington, D.C.
Piney Narrows welcomes liveaboards year-round across their 278 slips, with covered and open dock options for vessels up to 67 feet. The pet-friendly marina features pristine shower houses that are key-coded to each dock, cable and WiFi, laundry facilities, slip-assigned parking, a sparkling pool, and a snack shop. Transient rates run around $2.00 per foot daily.
Pros:
- Prime access to Kent Narrows restaurant and nightlife scene
- Key-coded private shower houses for each dock section
- Slip-assigned parking included
- Quiet Eastern Shore atmosphere with a community feel
Cons:
- Less urban walkability than the western shore marinas
- Fewer year-round amenities than resort-style marinas
- 7-foot approach depth limits larger vessels
Baltimore Marine Center (Inner Harbor)
Baltimore Marine Center at Inner Harbor West offers an exclusive setup with just 25 annual slips in downtown Baltimore. You’re steps away from restaurants, bars, shops, and countless activities, with the National Aquarium across the way and Camden Yards minutes from your slip. The Baltimore Water Taxi stops right at the marina, connecting you easily to all of Baltimore’s diverse neighborhoods—Fells Point, Canton, and Federal Hill.
Baltimore Marine Centers operates multiple locations, including Lighthouse Point Marina in Canton, where liveaboard communities have thrived for years. Lighthouse Point provides gated security, water delivery year-round, free haul-outs, and gym and pool memberships. Inner Harbor West features amenities, including a pool and fitness center.
Pros:
- Prime downtown location with walkability to everything
- Water taxi access to all Baltimore neighborhoods
- Pool and fitness center access included
- Gated security in an urban environment
Cons:
- Extremely limited availability with only 25 slips
- Premium urban pricing
- City noise and activity levels
- High annual costs approaching $10,000 plus liveaboard fees
Your Perfect Liveaboard Marinas in Chesapeake Bay Await
Want city vibes? Urban marinas put you steps from restaurants and nightlife—at premium prices. Craving resort amenities? High-end spots deliver pools, beaches, and nonstop social events. Need quick Bay access? Bridge-free locations get you sailing in minutes with thriving liveaboard communities. On a budget? Northern marinas offer rates as low as $175 per foot, though some restrict liveaboards. Prefer small-town charm? Eastern Shore options keep you near great restaurants with quieter vibes.
You’ve got the intel on what’s out there—now go find your slip and start living the dream.
