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US: Annapolis, MD – Sail Away on a Wine Tasting Cruise on Chesapeake Bay
Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.”
August Wine in the Wind – Along the Douro is a true sailing experience. Unwind on a two hour sail around the Chesapeake Bay while sampling wonderful wines from Portugal. You will be able to help raise the sails, steer the boat, or simply sit back and relax with your wine and food.
The beautiful, wooden, 74-foot schooner departs at 4:00pm and returns at 6:00 pm. A representative from the winery will be on board to introduce you to four special wines while you are under sail. The cruise will include 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (referred to as magnificent morsels) for you to enjoy with each wine. 
Wines being featured:
Mapreco Vinho Verde
Mapreco Vinho Verde Rose
Barao De Vilar Reserva, Douro
Noval Black Porto
You get to take-home your boat friendly, wine glass by Go Vino with the Woodwind’s logo on it as a souvenir of the day.
Location: Annapolis Waterfront Hotel, 80 Compromise Street, Annapolis, MD 21401
Date: Sun, Aug 12 2018
Time: 4pm -6pm
Tel: 410-263-7837
schoonerwoodwind.com
For Regional Accommodations, Restaurants & Attractions: visitannapolis.org
US: Annapolis, MD – A Week Long Celebration of the Arts and the Irish
Celebrating Annapolis’ Diverse Arts Scene, Annapolis Arts Week was created to bring together the area’s local artists and musicians for a week of art, food, block parties, events, music, and festivals.
The week includes major events: Paint Annapolis, a county-wide, juried, plein air competition celebrating its 15th year with 30 distinguished artists from around the globe. The artists will create 300 landscape works, highlighting the special colonial architecture, marine atmosphere, and overall energy of Annapolis. p a i n t a n n a p o l i s . o r g
Paint Annapolis features special events every day:
Sunday, June 3: Dueling Brushes – Quick Draw at Susan B Campbell Park
Monday June 4: Artist paint in Anne Arundel County
Tuesday, June 5: Paint the Bay Reception at Annapolis Maritime Museum
6-8pm
Wednesday, June 6: Artists paint in the city of Annapolis
Nocturne at dusk – Dinner Under the Stars
Thursday, June 7: Artists paint in the historic district
Art on the Avenue, Maryland Avenue, 5-7pm
Friday, June 8: Collector’s Award Reception, 6:30 – 9pm
Saturday June 9 & Sunday June 10: Reception & Sales at Circle Gallery
Mimosas & Muffins: Sunday 11am – 1pm
Here are some additional events going on throughout Annapolis Arts Week:
The Annapolis Irish Festival where you can enjoy traditional Celtic music and Irish rock bands on three different stages, along with workshops and exhibits. Try some delicious Irish beef stew and other Irish favorites. Little Leprechaun Land (open on Saturday only 11am– 4pm) provides pony rides, face painting and other free activities for the kids. June 1 & 2, 2018 at Anne Arundel County Fairgrounds annapolisirishfestival.com
16th Annual First Sunday Arts Festival Shop among the creations of 130 local and regional artisans; dine at outdoor cafes; and enjoy the music of more than seven live bands. It’s a great time to explore art galleries, take a game room challenge and/or create your own artwork at shops on West Street taking place on First block of West and Calvert Streets, Sunday, June 3 – 11am – 5pm – Admission: Free firstsundayarts.com
Dinner Under the Stars is a place for families and friends to come together and for couples to experience a romantic evening under the stars. Artists will paint from sundown to sunrise alongside the hundreds who come to dine, drink, and dance under the night sky. Spend Wednesday evenings dining, dancing and listening to live bands in the middle of the first block of West Street, just off Church Circle. Wednesdays, June 6, 13, 20, 27, 6pm – 10pm dinnerunderthestars.org
Photo Credit: VisitAnnapolis.org & Kenneth Tom Photography
Location: Various
Date: June 1 -10, 2018
Hours: Various
Tel: 410-268-4566
annapolisartsweek.com
For Regional Accommodations, Restaurants & Attractions: visitannapolis.org
US: Annapolis, MD – Win Designer Handbags Playing Bingo
Now here’s a unique and stylish fundraiser that I can really get behind; it’s bingo, but how about Designer Handbag Bingo! 
Enjoy an afternoon of Bingo fun with chances to win designer handbags from Coach, Kate Spade, Michael Kors, Vera Bradley and more. Fun festivities includes: 50/50 Raffle, Special Games, Door Prizes, Silent Auction and Concessions.
Proceeds will benefit The Bernie House and the Zonta Club of Annapolis Scholarship Foundation.
Admission includes 20 bingo games, with extra games sold at the door. Tickets are limited. To buy your ticket: whatsuptix.com/events/designer-handbag-bingo/
Location: The Annapolis Elks Lodge #622, 2 Pythian Drive, Edgewater, MD 21037
Date: Sunday, March 18, 2018
Time: 1pm (Doors open at 12 noon, Bingo starts at 1pm)
Tel: 410-573-0201
elks622.com
For Regional Accommodations, Restaurants & Attractions: visitannapolis.org
US: Annapolis, MD – Support the USO and Honor the U.S. Military by Attending the Military Bowl
on’t miss the 10th Anniversary Military Bowl presented by Northrop Grumman Corporation, benefiting the USO of Metropolitan Washington-Baltimore (USO-Metro), a military support organization. Kick off is on Thursday, Dec. 28 at 1:30 pm at Navy-Marine Corps Memorial Stadium in Annapolis matching a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC) and will be televised nationally on ESPN. 
The game day festivities kicks off at 9:30 am with one of Annapolis’ newest traditions: the Military Bowl Parade, featuring The world-famous Budweiser Clydesdales. They will lead the parade procession – along with Medal of Honor recipients, mascots, and team bands – from City Dock in downtown Annapolis to the Navy-Marine Corps Memorial Stadium as part of the many special events throughout the day.
The Official Military Bowl Tailgate kicks off in the Blue Lot on the west side of Navy-Marine Corps Memorial Stadium. Admission to the tailgate is free and will feature music, games, food & beverages from fantastic Annapolis restaurants, and exciting giveaways for the first arrivals. In addition, there’s also the 3rd Annual Bud & Burger Battle (held from 10:30 am-12:30 pm) where you can sample some of Annapolis’ favorite burgers before voting for your favorite.
Fan Bowl Week in Annapolis:
Wednesday, December 27
Thursday, December 28
For more than 70 years, the USO (United Service Organizations) has been the way for the American people to say thank you to our nation’s service men and women and their families.
To purchase tickets: militarybowl.org/tickets/#!
Location: U.S. Navy-Marine Corps Memorial Stadium, 550 Taylor Avenue, Annapolis
Date: Thurs, December 28, 2017
Time: Kick off 1:30 (doors open at 12:00)
Tel: 202-776-2919
militarybowl.org
For Regional Accommodations, Restaurants & Attractions: visitannapolis.org
US: Annapolis, MD – Celebrate and Bring Awareness to Clean Up Efforts in Spa Creek
The 2nd annual Clean Water PaddleFEST in Annapolis is to celebrate and bring awareness to clean up efforts in Spa Creek while enjoying a day full of fun.
Paddle at your own pace or take a guided on-water tour of Spa Creek. Guided tours available at 2pm. See educational stops along Spa Creek detailing conservation efforts which aim to make it again fishable and swimmable. Afterwards attend the Eco-Fest with informative exhibits from area environment groups with plenty of activities for kids.
All human powered paddlers and vessels are welcome to attend. Bring your own craft or use a stand up paddle board or kayak from Capital SUP. There will be a mass paddle and foot show of support for clean water in Spa Creek at 12 noon, on and in the water around the Spa Creek bridge.
Fun activities and prizes for all ages. Kid and dog friendly. All proceeds benefit Spa Creek Conservancy.
Your ticket includes:
On-water guided or self tour
Food BBQ beverages
Wine and beer
Event tee shirt
Admission to EcoFEST
Dry Bags to first 200 ticket holders
Live Music from 1-3pm
Location:Capital SUP on Spa Creek, 808 Boucher Avenue, Annapolis, MD 21403
Date: Sat, Sept 16, 2017
Time: 11 – 4pm
spacreek.net/index.php/events/special-events
For Regional Accommodations, Restaurants & Attractions: visitannapolis.org
US: Annapolis, MD – Plunge In to the Boating Season at Annapolis Sailboat Show
Head to Annapolis City Dock at the end of April and catch the Annapolis Spring Sailboat Show. Set in the historic seaport of Annapolis, the sixth annual in-water sailboat show kicks off the boating season with displays: catamarans, mono hulls, racing boats, family cruisers, day sailors, and inflatables—a total of over 100 new and brokerage boats. 
The sailboat show is for experienced and novice sailors alike, showcasing every new model present in the market, on display in the water and on land, allowing you opportunity to talk to the industry experts about buying and owing a boat. Shop for the latest in marine equipment, electronics, clothing and boating accessories at more than one hundred on-land nautical exhibits.
Cruisers University features hands-on workshops providing lessons from professionals and firsthand experience. The event will also include in-water demos, and the 3rd Annual Annapolis Junior Keelboat Regatta, where on April 29th at noon regional high school sailing teams will compete for the traveling cup.
Take a break from touring boats to enjoy live music, continuous entertainment, free food and beer and wine tastings, prizes, plus magnificent water views.
This venue is a one of a kind opportunity for sailors to be with sailors. There are very few places where you will find so many sailors congregated; the Annapolis Spring Sailboat Show is one of them.
Location: City Dock, Annapolis, MD (GPS address: 1 Dock Street, Annapolis, MD 21401)
Date: April 28 – 30, 2017
Hours: Fri, Sat 10 – 6 pm, Sun 10 -5 pm
Tel: 410-268-8828
annapolisboatshows.com/annapolis-spring-sailboat-show
For Regional Accommodations, Restaurants & Attractions: visitannapolis.org
US: Annapolis, MD – Binge on Chocoholic Sushi with Chocolate Martinis at Annapolis Festival
Under the warm glow of lights you’ll be served a FREE toasty cup of hot chocolate while you enjoy listening to music. Indulge in some family-fun, there is something for everyone including shopping, art, drinks, food, prizes, and fun for kids of all ages and did I mention chocolate.
Take a chocolate tour along West Street with a dozens of vendors selling various chocolate specialties , including chocolate caramels, bars, truffles, fudge, cookies, rice crispies, fondue, chocolate fountain, candy apples, chocolate sushi, and even chocolate martinis. Chocoholics, get ready to binge!
Entertainment includes: Moon Bounce, Balloon Sculptures, Face Painting, Meet Santa, McGruff the crime fighting dog, and Sparky the fire department dog, Music performances, Comedy, Ugly Sweater Contest, holiday shopping, the lighting of the West Street Light Canopy. You can roast marshmallows and make s’mores at the fire pit in the middle of West Street sponsored by the Annapolis Fire Department.
Chocolate, holiday vendors, music, family friendly entertainment and holiday light canopy. All this makes for a great street party in Annapolis. Support the local arts and and We Care and Friends . Suggested $5 donation to the Annapolis Arts District-Kids are free with a paid parent donation.
Location: West St and Calvert St (Intersection) ,Annapolis, MD 21401
Date: Sun, Dec 4th, 2016
Time: noon-5pm
Tel: 410-858-5884
annapolischocolatefestival.com
For Regional Accommodations, Restaurants & Attractions: visitannapolis.org