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

9 boats available to charter in Annapolis, U.S.A. — compare motor yachts, catamarans and sailing boats from verified operators.
Chartering in Annapolis offers a quintessential American sailing experience on the world-renowned Chesapeake Bay, where pristine anchorages meet historic seaside villages. You depart from prime marinas like Annapolis City Marina or Port Annapolis Marina, both providing full services including fuel, pump-out, and ship stores with easy access to downtown Annapolis. A day trip from Annapolis reaches the vibrant ports of Baltimore, the quaint towns of St. Michaels and Oxford, and over 11,000 miles of shoreline to explore across the Bay.
The setting is defined by the celebrated Naval Academy overlooking the harbor and the quiet, unspoiled nature of Whitehall Bay. Charterers can enjoy on-site dining at the Chart House restaurant near Annapolis City Marina before heading out on their adventure. The Bay delivers a long, enjoyable sailing season from early Spring to late Fall, making it a top cruising destination for sailors of all levels.
Captained or bareboat. Book direct with verified operators.
24 ft (7 m) · 11 guests
City Of Annapolis, U.S.A.
From US$778 /day
40 ft (12 m) · 12 guests · 2 cabins
City Of Annapolis, U.S.A.
Price on request
37 ft (11 m) · 6 guests · 2 cabins
City Of Annapolis, U.S.A.
From US$1,209 /day
42 ft (13 m) · 6 guests · 1 cabin
City Of Annapolis, U.S.A.
From US$1,436 /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
23 ft (7 m) · 10 guests
City Of Annapolis, U.S.A.
From US$2,325 /day
71 ft (22 m) · 12 guests · 3 cabins
City Of Annapolis, U.S.A.
From US$3,906 /day
34 ft (10 m) · 8 guests · 1 cabin
City Of Annapolis, U.S.A.
From US$1,353 /day
54 ft (16 m) · 9 guests · 4 cabins
City Of Annapolis, U.S.A.
From US$795 /day
43 ft (13 m) · 12 guests · 4 cabins
City Of Annapolis, U.S.A.
From US$1,038 /day
44 ft (13 m) · 12 guests · 4 cabins
City Of Annapolis, U.S.A.
From US$1,972 /day
46 ft (14 m) · 30 guests
City Of Annapolis, U.S.A.
From US$2,989 /day
39 ft (12 m) · 12 guests · 1 cabin
City Of Annapolis, U.S.A.
From US$2,657 /day
47 ft (14 m) · 12 guests · 3 cabins
City Of Annapolis, U.S.A.
From US$10,639 /day
47 ft (14 m) · 12 guests · 2 cabins
City Of Annapolis, U.S.A.
From US$5,208 /day
40 ft (12 m) · 8 guests · 2 cabins
City Of Annapolis, U.S.A.
From US$2,790 /day
33 ft (10 m) · 8 guests
City Of Annapolis, U.S.A.
From US$1,063 /day
22 ft (7 m) · 12 guests
City Of Annapolis, U.S.A.
From US$1,869 /day
18 ft (5 m) · 6 guests
City Of Annapolis, U.S.A.
From US$779 /day
58 ft (18 m) · 8 guests · 4 cabins
City Of Annapolis, U.S.A.
From US$853 /day
46 ft (14 m) · 10 guests · 5 cabins
City Of Annapolis, U.S.A.
From US$1,368 /day
Live availability from verified operators; day rates converted to USD.
| Boat type | Available | From (per day) |
|---|---|---|
| Catamaran | 4 | $1,116 |
| Sailing yacht | 3 | $419 |
| Yacht | 2 | $5,890 |
The primary departure points include Annapolis City Marina at 410 Severn Ave and Port Annapolis Marina at 7074 Bembe Beach Rd, both offering full services like fuel and ship stores. Other popular options are Chesapeake Harbour Marina and Whitehall Marina, which features a quiet, scenic location on Whitehall Bay with floating docks. These marinas provide easy access to downtown Annapolis and the Naval Academy, allowing you to stroll into town for shops and restaurants before sailing.
From Annapolis, you can sail to historic seaside towns like St. Michaels and Oxford, as well as the vibrant port of Baltimore. The Bay offers over 11,000 miles of shoreline, including quiet, pristine anchorages perfect for overnight stays or relaxing weekends. Short dinghy rides or strolls into Eastport or downtown Annapolis let you enjoy world-class restaurants and quaint shops before continuing your adventure.
The sailing season in Annapolis runs from early Spring to late Fall, providing a long and enjoyable window for bareboat or captained charters. The Chesapeake Bay is a top cruising destination with favorable weather conditions throughout these months. This extended season allows charterers to explore the Bay's diverse waters, from unspoiled anchorages to historic towns, without significant weather interruptions.
In the U.S.A., you must be at least 25 years old to rent a bareboat charter, while 18 years is required for a captained boat. For bareboat charters, you typically need to demonstrate sailing competence or hold a recognized licence, though USCG licensed captains are available if you prefer not to drive. Always verify specific operator requirements, as some may request proof of experience or certification before handing over the yacht.
The nearest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI), located roughly 30 miles from Annapolis. The transfer time is approximately 45 minutes to 1 hour by car, depending on traffic conditions. Once in Annapolis, you can easily access the marinas like Annapolis City Marina or Port Annapolis Marina to begin your Chesapeake Bay adventure.
A sailing yacht charter in Annapolis usually costs from around $615 per day. The cost varies depending on the size of the boat and the length of time you will be using it.
The sailing season in Annapolis runs from early Spring to late Fall. This long window allows you to explore the Chesapeake Bay's 11,000 miles of shoreline comfortably.
Yes, for bareboat charters you typically need to demonstrate sailing competence or hold a recognized licence. Alternatively, you can hire a USCG licensed captain to drive the yacht for you.
You can sail to historic seaside towns like St. Michaels and Oxford, as well as the vibrant port of Baltimore. These destinations offer quaint shops, world-class restaurants, and pristine anchorages.
Yes, Annapolis is perfect for families and groups, offering private charters for special occasions, cocktail cruises, or relaxing weekends. The Bay provides diverse waters suitable for all ages and experience levels.
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
Nearby ports
Compare departure points and fleets across the coast.
Other destinations
Compare nearby coasts and plan your next charter.
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from $145/hour
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from $220/hour
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from $180/hour
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Croatia ·
from $130/hour