24 ft (7 m) · 11 guests
2005, 24’ Chaparral sport boat with open bow
City Of Annapolis, U.S.A.
From US$778 /day

220 boats available to charter in City Of Annapolis, U.S.A. — compare motor yachts, catamarans and sailing boats from verified operators.
Yacht chartering in City Of Annapolis is a Chesapeake Bay departure with easy access to sheltered creeks, historic waterfronts, and open-water sailing. It suits everything from relaxed day cruises to private celebrations and fishing trips.
The main boarding area is the Annapolis waterfront, especially the historic City Dock, with other departures commonly using Eastport marinas, Back Creek, Spa Creek, and Liberty Marina on the South River. These locations put you close to the bay while keeping pick-up practical for both sailing yachts and motor yachts.
A day trip from City Of Annapolis can reach the broader Chesapeake Bay, quiet anchorages, and nearby harbor towns such as St. Michaels and Oxford. Longer day windows also allow scenic runs toward Baltimore or a comfortable loop around the bay’s central sailing waters.
Captained or bareboat. Book direct with verified operators.
24 ft (7 m) · 11 guests
City Of Annapolis, U.S.A.
From US$778 /day
38 ft (12 m) · 6 guests · 2 cabins
City Of Annapolis, U.S.A.
From US$1,860 /day
47 ft (14 m) · 12 guests · 3 cabins
City Of Annapolis, U.S.A.
From US$10,639 /day
19 ft (6 m) · 6 guests
City Of Annapolis, U.S.A.
From US$623 /day
43 ft (13 m) · 12 guests · 4 cabins
City Of Annapolis, U.S.A.
From US$1,038 /day
65 ft (20 m) · 12 guests · 4 cabins
City Of Annapolis, U.S.A.
From US$2,923 /day
29 ft (9 m) · 11 guests
City Of Annapolis, U.S.A.
From US$717 /day
71 ft (22 m) · 12 guests · 3 cabins
City Of Annapolis, U.S.A.
From US$3,906 /day
45 ft (14 m) · 12 guests · 2 cabins
City Of Annapolis, U.S.A.
From US$3,272 /day
46 ft (14 m) · 10 guests · 5 cabins
City Of Annapolis, U.S.A.
From US$1,368 /day
54 ft (16 m) · 9 guests · 4 cabins
City Of Annapolis, U.S.A.
From US$795 /day
40 ft (12 m) · 13 guests · 2 cabins
City Of Annapolis, U.S.A.
From US$4,055 /day
46 ft (14 m) · 30 guests
City Of Annapolis, U.S.A.
From US$2,989 /day
37 ft (11 m) · 6 guests · 2 cabins
City Of Annapolis, U.S.A.
From US$1,209 /day
25 ft (8 m) · 12 guests
City Of Annapolis, U.S.A.
From US$1,153 /day
42 ft (13 m) · 6 guests · 1 cabin
City Of Annapolis, U.S.A.
From US$1,436 /day
34 ft (10 m) · 8 guests · 1 cabin
City Of Annapolis, U.S.A.
From US$1,353 /day
39 ft (12 m) · 12 guests · 1 cabin
City Of Annapolis, U.S.A.
From US$2,657 /day
42 ft (13 m) · 13 guests
City Of Annapolis, U.S.A.
From US$4,019 /day
36 ft (11 m) · 12 guests
City Of Annapolis, U.S.A.
From US$2,492 /day
24 ft (7 m) · 12 guests
City Of Annapolis, U.S.A.
From US$1,246 /day
20 ft (6 m) · 6 guests
City Of Annapolis, U.S.A.
From US$733 /day
Live availability from verified operators; day rates converted to USD.
| Boat type | Available | From (per day) |
|---|---|---|
| Yacht | 146 | $233 |
| Boat | 24 | $372 |
| Sailing yacht | 23 | $349 |
| Catamaran | 21 | $913 |
| Fishing boat | 5 | $558 |
| Mega yacht | 1 | $2,325 |
Most charters depart from the Annapolis City Dock, Eastport marinas, Spa Creek slips, or Back Creek boarding points. Liberty Marina on the South River is another verified staging point for Chesapeake Bay charters.
These departures are useful because they give fast access to the bay while staying close to Annapolis’ waterfront core. That makes them suitable for both captained cruises and bareboat-style outings where permitted.
A day charter from City Of Annapolis is ideal for sailing on the Chesapeake Bay, cruising to quiet anchorages, or visiting historic waterfront towns. Verified nearby day-trip destinations include St. Michaels, Oxford, and Baltimore.
Charter styles in the area include fishing trips, overnight cruises, and private parties, so the route can be matched to a relaxed family outing or a more social event. The bay’s sheltered waters are especially useful for comfortable half-day and full-day trips.
The clearest verified seasonal window for Chesapeake Bay catamaran charters in this area is May to October. That is the main period explicitly listed for local sailing charters.
Outside that range, weather and operating schedules can vary by operator and vessel. For planning purposes, late spring through early autumn is the most supported season for charter activity around Annapolis.
If you book a captained charter in the U.S.A., no licence is required from the guest. For self-operation in Maryland, anyone born on or after July 1, 1972 must hold a state-approved boating safety education certificate or an accepted equivalent.
That makes City Of Annapolis a practical choice for mixed groups, because you can choose either a skippered trip or a self-driven option where local rules allow it. The right format depends on whether you want a fully crewed experience or independent control.
The most practical airport for Annapolis charter guests is Baltimore/Washington International, which is commonly used for access to the city. From there, transfer time to Annapolis is roughly 40 to 50 minutes by car in normal traffic.
That short transfer helps make City Of Annapolis workable for day charters, weekend trips, and event bookings. The downtown waterfront departure points are then within easy reach of the city center.
Boat rentals in City Of Annapolis start from around $233 per day.
A day charter can reach the Chesapeake Bay, local anchorages, and nearby towns such as St. Michaels and Oxford. Some itineraries also include Baltimore, depending on time and conditions.
Common boarding points include Annapolis City Dock, Eastport marinas, Back Creek, Spa Creek, and Liberty Marina on the South River. These spots give fast access to the Chesapeake Bay.
The clearest verified charter season is May to October. That is the main window listed for Chesapeake Bay sailing catamarans in the area.
Not if you book a captained charter. If you operate a motorized vessel yourself in Maryland and were born on or after July 1, 1972, you need a state-approved boating safety education certificate or equivalent.
Yes. Verified charter options in Annapolis include family outings, private parties, fishing trips, and overnight cruises, so the port works for both small and larger groups.
Boat types
From RIBs and motorboats to catamarans and crewed superyachts.
YachtLuxury cruising with full crew
8–16 guests ·
from $480/day
CatamaranStable, spacious, perfect for groups
10–12 guests ·
from $280/day
SailboatWind, sails and slow island hopping
6–10 guests ·
from $130/day
MotorboatFast day cruises without the captain
4–10 guests ·
from $90/day
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