Annapolis Neck, Maryland

Marco Polo on December 12, 2023

Exploring Annapolis Neck: Maryland’s Charming Jewel

Welcome to Annapolis Neck, a hidden gem nestled on Maryland’s breathtaking Chesapeake Bay! This charming and historic region offers a delightful blend of colonial beauty, maritime heritage, and a vibrant culinary scene. Join me on this three-day weekend trip as we uncover the top-rated attractions, restaurants, and sights that make Annapolis Neck an irresistible destination.

Day 1: Immersed in Maritime History

Morning: Discover the United States Naval Academy

Our adventure begins with a visit to the United States Naval Academy, a prestigious institution that has shaped the country’s naval officers since 1845. Take a guided tour to explore the stunning campus, including the awe-inspiring Bancroft Hall, the Academy Chapel, and the captivating Naval Academy Museum. Don’t miss the must-see attraction, the U.S. Naval Academy Museum, where you can delve into the history of the Navy through fascinating exhibits and artifacts.

  • United States Naval Academy Website: usna.edu

Afternoon: Stroll along City Dock and Main Street

After a delicious lunch at a local hotspot like Iron Rooster or Carrol’s Creek Cafe, take a leisurely walk along City Dock and Main Street. Immerse yourself in the charming atmosphere as you explore the boutiques, art galleries, and specialty stores that line the streets. Marvel at the picturesque views of the Chesapeake Bay and the sailboats gliding by.

Evening: Dinner at Osteria 177

For an unforgettable dining experience, head to Osteria 177, a refined Italian restaurant known for its exceptional cuisine and elegant ambiance. Indulge in their exquisite handmade pastas, fresh seafood, and decadent desserts. Pair your meal with a fine wine from their extensive collection, and savor every bite in this intimate setting.

Day 2: Historic Charm and Natural Beauty

Morning: Tour the Historic Maryland State House

Start your day with a journey through history as you explore the Maryland State House. This magnificent building, dating back to 1772, served as the nation’s first peacetime capital and is the oldest state capitol in continuous legislative use. Marvel at the grand architecture and soak in the stories that echo within the walls. Don’t miss the famous Old Senate Chamber, where George Washington resigned his commission as commander-in-chief of the Continental Army.

Afternoon: Escape to Quiet Waters Park

Embrace nature’s tranquility at Quiet Waters Park, a picturesque haven offering scenic trails, lush greenery, and serene waterfront views. Take a leisurely hike or rent a kayak to explore the idyllic waters of the South River. Pack a picnic and savor a delightful lunch amidst the park’s beauty. If you’re visiting during the summer, be sure to catch one of their popular concerts at the outdoor amphitheater.

Evening: Dining Delights at Preserve

Nestled in the heart of Annapolis Neck, Preserve is an exceptional restaurant that celebrates the flavors of Mid-Atlantic cuisine. Their menu showcases locally-sourced ingredients, creatively prepared to offer a unique dining experience. From their tantalizing small plates to their innovative entrees, each dish is a masterpiece. Pair your meal with one of their craft cocktails or select from their thoughtfully curated wine list.

Day 3: Nautical Adventures and Unforgettable Views

Morning: Sail the Chesapeake Bay

No visit to Annapolis Neck is complete without experiencing the beauty of the Chesapeake Bay. Embark on a sailing adventure with Sailing Cruises on the Bay and let the wind carry you across the sparkling waters. Whether you choose a daytime cruise or a sunset sail, you’ll be mesmerized by the stunning views of the coastline, lighthouses, and charming waterfront homes.

Afternoon: Explore the Chesapeake Bay Maritime Museum

Immerse yourself in the maritime heritage of the Chesapeake Bay at the Chesapeake Bay Maritime Museum. This captivating museum offers a fascinating collection of historic boats, exhibits, and interactive displays that transport you back in time. Don’t miss the chance to tour the iconic Hooper Strait Lighthouse for panoramic views of the Bay.

  • Chesapeake Bay Maritime Museum Website: cbmm.org

Evening: Farewell Dinner at Vin 909

As our three-day adventure draws to a close, indulge in a memorable farewell dinner at Vin 909, a cozy and rustic wine bar and bistro. Known for its farm-to-table philosophy, Vin 909 serves up delectable dishes made with locally sourced ingredients. Pair your dinner with a glass of wine from their impressive selection, and toast to the unforgettable memories you’ve made in Annapolis Neck.

We hope this meticulously curated itinerary helps you make the most of your three-day weekend trip to Annapolis Neck. From exploring historic landmarks to savoring culinary delights, this charming region promises an experience you will cherish for a lifetime. Safe travels and bon voyage!

Please note that attractions and restaurants may have specific COVID-19 protocols and hours of operation. Be sure to check their respective websites for the most up-to-date information before your visit.

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