Annapolis Sailboat Show (Annapolis, MD)
The Annapolis Sailboat Show is an iconic maritime event that takes place every October, attracting sailing enthusiasts from around the world. Set in the historic waterfront of Annapolis, Maryland, this event showcases hundreds of boats, from luxurious yachts to smaller, more nimble sailboats. Visitors can explore new boats, attend seminars, and meet with vendors specializing in boating gear and marine accessories. For new residents and visitors, the event offers a great way to connect with the sailing community and enjoy scenic views of the Chesapeake Bay. Clifton Cabs provides tailored services, ensuring stress-free transportation to and from the event. Whether you’re traveling with a group or solo, Clifton Cabs ensures a comfortable ride through the bustling city streets, with experienced drivers who know the ins and outs of Annapolis traffic. We offer timely pickups and drop-offs to make sure you don’t miss a single moment of the show.
Restaurants near Annapolis Sailboat Show
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Chart House
Seafood
300 2nd St, Annapolis, MD 21403
(410) 268-7166
Chart House offers fresh seafood with stunning views of Spa Creek. With a creative twist on traditional dishes, this upscale eatery provides an excellent dining experience. The restaurant is known for its prime waterfront location and a menu filled with locally-sourced ingredients, ensuring the freshest catch of the day.
Monday
4:00 PM – 9:30 PM
Tuesday
4:00 PM – 9:30 PM
Wednesday
4:00 PM – 9:30 PM
Thursday
4:00 PM – 9:30 PM
Friday
4:00 PM – 10:30 PM
Saturday
3:00 PM – 10:30 PM
Sunday
10:30 AM – 9:00 PM
Carrol’s Creek Café
American, Seafood
410 Severn Ave, Annapolis, MD 21403
(410) 263-8102
Carrol’s Creek Café is a sophisticated waterfront dining spot, serving contemporary American cuisine with an emphasis on fresh seafood. Its outdoor seating offers panoramic views of Annapolis Harbor, providing a serene dining atmosphere, ideal for enjoying Maryland crab cakes and other signature dishes.
Monday
11:30 AM – 9:00 PM
Tuesday
11:30 AM – 9:00 PM
Wednesday
11:30 AM – 9:00 PM
Thursday
11:30 AM – 9:00 PM
Friday
11:30 AM – 10:00 PM
Saturday
11:30 AM – 10:00 PM
Sunday
11:00 AM – 9:00 PM
O’Learys Seafood Restaurant
Seafood
310 Third St, Annapolis, MD 21403
(410) 263-0884
Known for its fresh seafood and intimate ambiance, O’Learys Seafood Restaurant offers a fine dining experience in Eastport. Guests can enjoy inventive dishes like the O’Learys seafood paella, perfectly paired with a curated wine list.
Monday
5:00 PM – 9:00 PM
Tuesday
5:00 PM – 9:00 PM
Wednesday
5:00 PM – 9:00 PM
Thursday
5:00 PM – 9:00 PM
Friday
5:00 PM – 10:00 PM
Saturday
5:00 PM – 10:00 PM
Sunday
5:00 PM – 9:00 PM
Boatyard Bar & Grill
American, Seafood
400 Fourth St, Annapolis, MD 21403
(410) 216-6206
Boatyard Bar & Grill is a casual eatery known for its relaxed atmosphere and seafood-centric menu. Frequented by sailors, this nautical-themed restaurant offers hearty crab cakes, fish tacos, and a range of craft beers, perfect for grabbing a bite after the sailboat show.
Monday
7:30 AM – 11:00 PM
Tuesday
7:30 AM – 11:00 PM
Wednesday
7:30 AM – 11:00 PM
Thursday
7:30 AM – 11:00 PM
Friday
7:30 AM – 12:00 AM
Saturday
7:30 AM – 12:00 AM
Sunday
7:30 AM – 10:00 PM
Vin 909 Winecafe
Wine Bar, American
909 Bay Ridge Ave, Annapolis, MD 21403
(410) 990-1846
Vin 909 Winecafe blends local, organic produce with flavorsome dishes to create an innovative menu, paired with an extensive wine list. The cozy atmosphere makes it a popular spot for both locals and visitors, ideal for an evening of sophisticated dining.
Monday
11:00 AM – 10:00 PM
Tuesday
11:00 AM – 10:00 PM
Wednesday
11:00 AM – 10:00 PM
Thursday
11:00 AM – 10:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
Closed
Cantler’s Riverside Inn
Seafood
458 Forest Beach Rd, Annapolis, MD 21409
(410) 757-1311
Nestled along Mill Creek, Cantler’s Riverside Inn is a seafood lover’s paradise, renowned for its Chesapeake Bay blue crabs. This casual, waterfront restaurant offers patrons a rustic dining experience with some of the freshest local seafood.
Monday
11:00 AM – 10:00 PM
Tuesday
11:00 AM – 10:00 PM
Wednesday
11:00 AM – 10:00 PM
Thursday
11:00 AM – 10:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
11:00 AM – 9:00 PM
Blackwall Hitch
American, Seafood
400 Sixth St, Annapolis, MD 21403
(410) 263-3454
Blackwall Hitch is a chic restaurant with an elegant maritime ambiance. Offering seafood, steaks, and craft cocktails, it provides the perfect mix of modern dining with a nautical twist, featuring rooftop seating with views of the harbor.
Monday
11:30 AM – 10:00 PM
Tuesday
11:30 AM – 10:00 PM
Wednesday
11:30 AM – 10:00 PM
Thursday
11:30 AM – 10:00 PM
Friday
11:30 AM – 12:00 AM
Saturday
11:30 AM – 12:00 AM
Sunday
10:00 AM – 9:00 PM
Lewnes’ Steakhouse
Steakhouse
401 Fourth St, Annapolis, MD 21403
(410) 263-1617
Lewnes’ Steakhouse is a premier destination for lovers of steak and seafood. Known for its high-quality cuts of beef and classic steakhouse atmosphere, it’s an excellent spot for a luxurious meal after a day at the Sailboat Show.
Monday
4:30 PM – 10:00 PM
Tuesday
4:30 PM – 10:00 PM
Wednesday
4:30 PM – 10:00 PM
Thursday
4:30 PM – 10:00 PM
Friday
4:30 PM – 11:00 PM
Saturday
4:30 PM – 11:00 PM
Sunday
4:30 PM – 9:00 PM
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Dulles Airport
Reagan Airport
Baltimore Airport
Chart House
Carrol’s Creek Café
O’Learys Seafood Restaurant
Boatyard Bar & Grill
Vin 909 Winecafe
Cantler’s Riverside Inn
Blackwall Hitch
Lewnes’ Steakhouse
Wedding Venues near Annapolis Sailboat Show
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Annapolis Waterfront Hotel, Autograph Collection
Waterfront Hotel
80 Compromise St, Annapolis, MD 21401
(410) 268-7555
Located right on the harbor, Annapolis Waterfront Hotel offers a stunning backdrop for weddings with views of the Chesapeake Bay. The venue’s outdoor terrace is perfect for ceremonies, while the elegant indoor spaces are ideal for receptions. The hotel’s luxurious amenities provide a seamless experience for couples and guests.
Generic Pricing
Starting at $7,000
Capacity
250 guests
Website
www.marriott.com
Chesapeake Bay Beach Club
Beach Club
500 Marina Club Rd, Stevensville, MD 21666
(410) 604-1933
This award-winning wedding venue offers breathtaking views of the Chesapeake Bay and an upscale, coastal ambiance. Couples can choose from multiple indoor and outdoor event spaces, each offering a romantic, beachside setting. The club is renowned for its attention to detail and exceptional service.
Generic Pricing
Starting at $10,000
Capacity
250 guests
Website
www.baybeachclub.com
Historic Inns of Annapolis
Historic Inn
58 State Cir, Annapolis, MD 21401
(410) 263-2641
For a touch of history, the Historic Inns of Annapolis offer elegant wedding spaces with timeless charm. Couples can exchange vows in historic venues like the Governor Calvert House or the Maryland Inn, each rich with colonial architecture and period details.
Generic Pricing
Starting at $5,000
Capacity
200 guests
Website
www.historicinnsofannapolis.com
The Governor Calvert House
Historic Mansion
58 State Cir, Annapolis, MD 21401
(410) 263-2641
Part of the Historic Inns of Annapolis, The Governor Calvert House offers a unique blend of historical significance and sophisticated elegance. Couples can celebrate their big day amidst antique furnishings and period décor, making it a quintessential Annapolis experience.
Generic Pricing
Starting at $6,500
Capacity
180 guests
Website
www.historicinnsofannapolis.com
Loews Annapolis Hotel
Hotel
126 West St, Annapolis, MD 21401
(410) 263-7777
Loews Annapolis Hotel combines modern sophistication with coastal charm. Its spacious ballroom and multiple event rooms make it a versatile option for weddings of all sizes. The hotel’s on-site event team ensures every detail is taken care of, creating a stress-free experience for couples.
Generic Pricing
Starting at $8,000
Capacity
300 guests
Website
www.loewshotels.com
Quiet Waters Park
Outdoor Park
600 Quiet Waters Park Rd, Annapolis, MD 21403
(410) 222-1777
For couples looking for an outdoor wedding, Quiet Waters Park provides a stunning natural setting. The South River Overlook offers breathtaking views of the water, while the formal gardens and pavilions create a romantic ambiance for both ceremonies and receptions.
Generic Pricing
Starting at $3,000
Capacity
200 guests
Website
www.aacounty.org
The William Paca House & Garden
Historic Garden
186 Prince George St, Annapolis, MD 21401
(410) 990-4543
A National Historic Landmark, The William Paca House & Garden is a beautifully restored colonial mansion with stunning gardens. The romantic garden setting is perfect for intimate outdoor ceremonies, and the elegant mansion provides a lovely backdrop for wedding photos.
Generic Pricing
Starting at $4,500
Capacity
120 guests
Website
www.annapolis.org
London Town & Gardens
Historic Garden Estate
839 Londontown Rd, Edgewater, MD 21037
(410) 222-1919
London Town & Gardens offers a lush garden setting for outdoor ceremonies with the historic William Brown House as a picturesque backdrop. This waterfront venue is ideal for couples looking for a peaceful and scenic location with both elegance and historic charm.
Generic Pricing
Starting at $7,500
Capacity
300 guests
Website
www.historiclondontown.org
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Airport Taxi Transportation near Annapolis Sailboat Show
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