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An Annapolis bachelorette party weekend, in four lines
What decides an ultimate weekend in this small sailing town.
- The sail
- $76 to $84Per person for a two hour Woodwind public sail, all in
- Parking
- $15 to $23A day in the garages, and no charge on Sunday between 6 a.m. and 2 p.m.
- Getting around
- Free shuttleThe shuttle runs to midnight on Friday and Saturday
- On the street
- No open drinksAn open container on any street or in a public lot is a misdemeanor
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Guests on a Schooner Woodwind public sail
A sail takes the whole group, and a private charter takes up to 40 per schooner.
Schooner Woodwind publishes a cap of 30 guests on its two hour public sails and says private charters give a group exclusive use of one or both 74 foot schooners, up to 40 guests aboard each. The six passenger limit people quote belongs to uninspected charter vessels under 100 gross tons under Coast Guard rules, so ask any small charter whether it is inspected before you book for nine.
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Fun things to do on an Annapolis bachelorette party weekend
The bay, the town and the Yard, with published terms.
A sail on the Chesapeake
Schooner Woodwind runs two hour public sails from the Annapolis Waterfront Hotel docks; soft soled shoes only, and no refunds once tickets are bought.
A private charter
Exclusive use of a schooner, with catering and a bar as options, booked through the sales line.
The water taxi
Watermark's Annapolis Water Taxi runs daily to 10 p.m., $4 to $9 a person one way, with 54 stops.
Explore Main Street
Shops and boutiques in downtown Annapolis, on the way to City Dock.
Visit the Naval Academy
Everyone 18 and over needs a REAL ID, a passport or an enhanced license; the public walks in through Gate 1 and cannot drive on.
Live music
Rams Head Tavern offers free weekly local music, and Rams Head On Stage runs ticketed shows.
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Where to drink and eat on an Annapolis night out
Spots the group will want, with published hours and rules.
Dry 85
Whiskey flights and craft beer on Main Street, open to 2 a.m. Friday and Saturday, with Sunday bacon brunch; reservations accepted.
Rams Head Tavern
Serving on West Street since 1989, with a wisteria covered patio.
Level, A Small Plates Lounge
Shareable small plates and craft cocktails on West Street, with private rooms for up to 200 and girls night out on its list.
Jimmy Cantler's Riverside Inn
Steamed blue crabs on Mill Creek, open daily; reservations only for parties of 25 or more, Monday to Thursday, so a smaller group queues.
Boatyard Bar & Grill
Weekend brunch in Eastport from 9 or 10 a.m.; no reservations, and it is a walk over the Spa Creek Bridge or a water taxi ride away.
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Where to stay for an Annapolis bachelorette party
Hotels on the harbor, and what the city requires of rentals.
Annapolis Waterfront Hotel
At City Dock, with balcony rooms; most room types sleep four, and the Woodwind sails from its docks.
A licensed rental
Every short-term rental needs a city license, the license number must appear in the listing, and one occupant must be over 21.
How many can sleep there
Annapolis sets space by floor area: nine adults need about 825 square feet of habitable space, and a room for four needs 200.
Keep it quiet
Noise limits at home are 65 dBA by day and 55 dBA from 10 p.m. to 7 a.m.; three verified nuisances can cost the host the license.
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Annapolis bachelorette party ideas the bride will enjoy
Experiences that make the weekend special, from the afternoon to the night out.
A photo walk
Main Street, the docks and the brick lanes, the perfect photo stop in late afternoon light.
A wine or whiskey tasting
Dry 85 pours whiskey flights and three ounce beer flights to share.
A walking tour
Take the bride through the historic streets on foot before dinner.
A cozy evening in
A suite with a sitting room and a wet bar, so the girls can stay in.
Matching style
Nautical stripes for the sail, then something new for the evening.
A group toast on deck
A charter can add a drinks package, so share the plan with the crew.
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Planning tips for Annapolis bachelorette parties
Local details that decide how the travel weekend runs.
Book the sail first
Public sails sell by the seat; charters go through the sales line.
Pick the hotels early
Boat show weekends in October and April fill the town, so book rooms early.
Plan the crab run
Cantler's is a drive, so arrange a ride and go before the dinner rush.
Bring the right ID
Everyone 18 and over needs a REAL ID or passport for the Naval Academy, which is a unique stop.
Leave the car parked
The free shuttle and the water taxi cover downtown and Eastport.
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An Annapolis bachelorette party itinerary
One way to plan the weekend.
Check in
The Annapolis Waterfront Hotel at City Dock.
Drinks
Dry 85 on Main Street.
Music
Rams Head Tavern on West Street.
Brunch
Boatyard Bar & Grill in Eastport, by water taxi.
On the bay
A two hour sail on Schooner Woodwind.
Crabs
Jimmy Cantler's Riverside Inn, first come, first served.
Dinner and cocktails
Level's small plates and a private room.
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Planning an Annapolis bachelorette weekend
The rules, the parking and the calendar.
An Annapolis bachelorette party is a walkable harbor town trip: a sail on the Chesapeake, crabs, Main Street bars and a room or licensed rental at City Dock. Nothing here needs a car once you arrive, which is part of the fun.
Drinks and the law
The drinking age is 21. Annapolis sets bar hours by license class: taverns close at midnight, while restaurant, hotel and club classes with the extended license can serve to 2 a.m. Dancing and music in a public place are not allowed between 1 a.m. and 8 a.m. City code bans open containers on the street, in a City lot and in any vehicle; a separate section exempts a passenger in a registered for hire vehicle, so get a party bus operator's written answer before you plan drinks on board.
Parking and the shuttle
Gott's Court tops out at $18 a day, Knighton at $15 and Mills Hillman at $23.25, with no charge on Sunday if you enter after 6 a.m. and leave before 2 p.m. The free shuttle runs Monday to Thursday 6 a.m. to 11 p.m., Friday to midnight, Saturday 7 a.m. to midnight and Sunday 8 a.m. to 8 p.m.
When to go
NOAA normals give highs of about 68 degrees in April, 77 in May and 69 in October, against 89 in July. Hurricane season runs June 1 to November 30. The boat shows fill the town: the Powerboat Show is October 8 to 11 and the Sailboat Show October 15 to 18, 2026, with the Spring Sailboat Show April 23 to 25, 2027.
A sail booked for the whole group, a free shuttle, and nothing open in hand on Main Street.
The Annapolis ruleBefore booking
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Annapolis bachelorette party, answered
What the group asks before booking.
How many people fit on an Annapolis bachelorette party boat?
Schooner Woodwind caps public sails at 30 and private charters at up to 40 per schooner.
Uninspected charter boats under 100 gross tons carry six passengers.
How much is a sail in Annapolis?
Woodwind lists $76.10 to $84.20 a person for a two hour public sail, all in.
Private charter prices come from the sales line.
Can you drink on the street in Annapolis?
No. An open container on a street, sidewalk or City lot is a misdemeanor under city code.
Bars cannot let you leave with a drink.
Do we need a car in Annapolis?
Not downtown: the shuttle and the taxi on the harbor cover it.
Cantler's is a drive, so plan a ride.
Can we book a table for nine for crabs?
Cantler's takes reservations only for 25 or more, Monday to Thursday, and Boatyard takes none.
Go early or split the group.
What should we know about visiting the Naval Academy?
Every visitor 18 and over needs a REAL ID, passport or enhanced license, and the public cannot drive on.
The visitor route is not open to non US citizens.
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What to read next
Chartering a boat, Washington, the east coast and more.
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Where this comes from
The places and rules are as published in September 2026.
The places named here
Every hotel, bar, restaurant and operator on this page is named by at least three independent sources, at least one of them authoritative, and its hours, prices and group rules are as published on its own website in September 2026. Revelwick has not visited them, does not rate them and is not paid by them.
What the figures are
Prices quoted from an operator are that operator's published price. Any per head figure given as a Revelwick estimate is an editorial estimate rather than a quote, so check current prices before you book.
Where the rules come from
Rental, alcohol, open container, noise and parking rules are from the Annapolis City Code and the official Annapolis parking guide, the passenger vessel rule from Coast Guard regulations, Naval Academy access from the Academy, the water taxi from Watermark, weather from NOAA climate normals, hurricane season from the National Hurricane Center, and event dates from their organizers.