The Chesapeake Bay is a part of the eastern shore of Maryland and Virginia that is known for its charming beauty. There are numerous restaurants, plenty of cute small towns, and plenty of boutique hotels. It is the perfect place for a romantic getaway. 

Chesapeake Bay Romantic Getaways: St. Michael’s

St. Michael’s is a charming waterfront town on Maryland’s Eastern Shore. It is one of the most well known places in the Chesapeake Bay. This small town is famously known for its picturesque views and romantic weekend getaways from Washington DC. 


Indoor Activities

  • Chesapeake Bay Maritime Museum: Dive into the rich maritime history of the Chesapeake Bay. This museum offers a variety of exhibits and collections that showcase the area’s boating history and local culture.
  • Visit Art Galleries: St. Michaels is home to several art galleries featuring works by local and regional artists. Spend a day admiring beautiful paintings, sculptures, and other artworks.
  • Cabin Fever Play Centre: Ideal for families with children, this indoor play center offers a variety of games and activities to keep the little ones entertained, making it a perfect spot for a rainy day.

Outdoor Activities

  • Kayaking and Canoeing: With its abundant shoreline, St. Michaels offers numerous opportunities for kayaking and canoeing. Rent a vessel and explore the serene waters of the Chesapeake Bay at your own pace.
  • Boat Tours Along the Miles River: Take a scenic boat tour to enjoy the natural beauty of the area from a different perspective. These tours offer a relaxing way to learn about the local ecosystem and maritime heritage.
  • Biking: Rent a bike and explore the picturesque landscapes of St. Michaels and its surroundings. There are several trails and paths suitable for cyclists of all levels, offering a healthy and enjoyable way to see the sights.

Hotels & Inns

Here are some notable hotels, inns, and accommodations in St. Michaels:

Inn at Perry Cabin

  • Features: Located on the banks of the Miles River, Inn at Perry Cabin is a luxurious resort offering a serene escape with elegant accommodations, fine dining, and a variety of recreational activities. This luxury property was also the site of the filming of the famous movie Wedding Crashers. In addition to a fitness center, there is also tennis courts, and a full-service spa.
  • Website:

St. Michaels Harbour Inn, Marina & Spa

  • Features: This year-round luxury inn is located on the historic harbor of St. Michaels. It offers waterfront accommodations, a full-service marina, spa services, and dining options.
  • Website:

The Wildset Hotel

  • Features: A modern hotel offering a comfortable and stylish stay with amenities that cater to both relaxation and adventure seekers. It’s situated close to the town’s attractions and dining options.
  • Website: 

Old Brick Inn

  • Location: 401 S. Talbot Street, St. Michaels, MD
  • Features: A historic inn that combines the charm of the past with modern comforts, located in the heart of St. Michaels. It’s known for its warm hospitality and beautiful accommodations.
  • Website:

Parsonage Inn

  • Location: 210 N. Talbot Street, St. Michaels, MD
  • Features: Offering a cozy and intimate setting, the Parsonage Inn is a great choice for those seeking a quiet getaway in a historic setting.
  • Website:

St Michaels Inn

  • Features: This inn provides a comfortable and convenient base for exploring St. Michaels, with amenities designed for family vacations or business trips, including free Wi-Fi and breakfast.
  • Website:


No romantic weekend getaway is complete without some great food. Many of the above hotels have an on-site restaurant. If your boutique hotel does not have the food you are looking for, St. Michael’s is very walkable. You can take a leisurely stroll to one of the many local restaurants in this cute town

Ava’s Pizzeria & Wine Bar

Ava’s Pizzeria & Wine Bar is a favorite among locals and visitors alike, offering a cozy atmosphere with a selection of gourmet pizzas, diverse wines, and other Italian-inspired dishes.

Bistro St. Michaels

Bistro St. Michaels provides a refined dining experience with a menu that emphasizes fresh, local ingredients prepared with a French flair, making it a perfect spot for a romantic dinner or special occasion.

The Crab Claw

The Crab Claw is an iconic seafood restaurant in St. Michaels, known for its waterfront dining and fresh, locally sourced crab dishes. It’s a must-visit for seafood lovers looking to enjoy the Chesapeake Bay’s bounty in a casual, friendly setting.

Chesapeake Bay Romantic Getaways: Tilghman Island

Tilghman Island is a charming waterfront town located that is an ideal destination for a Chesapeake Bay getaway. With its luxurious rooms and a picturesque setting, couples can enjoy the perfect blend of relaxation and adventure.


One of the best ways to experience the beauty of Tilghman Island is through its diverse range of indoor and outdoor activities. Couples can indulge in scenic hikes, horseback riding, and even explore the island’s rich wildlife by spotting ospreys at Osprey Point.


There’s no shortage of romantic rooms in the Chesapeake Bay. Remember that for some of the smaller inns and some of the historic hotels in this area, the best rate will be through their website directly. 

The Black Walnut Point Inn

  • Location: 4417 Black Walnut Point Road, Tilghman Island, MD 21671
  • Features: Situated on a private island, this secluded inn offers stunning sunrise and sunset views over the Chesapeake Bay, surrounded by 52 acres of bird sanctuary. It’s a peaceful retreat with no pets or children under 12 allowed, ensuring a quiet stay.
  • Contact: 410.886.2452
  • Website:

Knapps Narrows Marina & Inn

  • Location: 6176 Tilghman Island Road, Tilghman, MD 21671
  • Features: This inn boasts private balconies with views of the Chesapeake Bay and is located in a quiet marina setting. It’s perfect for family reunions, business meetings, or small weddings, offering a relaxing getaway with plenty of nature and wildlife to observe.
  • Contact: 410.886.2720
  • Website:

Lowes Wharf Marina Inn

  • Location: 21651 Lowes Wharf Rd, Sherwood, Maryland 21665
  • Features: Positioned between St Michaels and Tilghman Island, this inn provides waterfront guest rooms, a restaurant, patio bar, and access to various activities like charter fishing, sunset cruises, crabbing, and kayaking.
  • Contact: 410-745-6684
  • Website:

The Tilghman Island Inn

  • Location: 21384 Coopertown Road, Tilghman Island, MD 21671
  • Features: A newly renovated modern boutique, waterfront hotel offering a luxury experience with stunning views, unique plant materials on the grounds, and a variety of amenities including a restaurant, pool, and waterfront guest rooms with balconies and gas fireplaces.
  • Contact: 410.886.1170
  • Website:

The Wylder Hotel Tilghman Island

  • Location: 21551 Chesapeake House Drive, Tilghman, MD 21671
  • Features: Set on 9 acres of lush grounds and private waterfront property, this hotel offers a saltwater pool, bocce court, lawn games, and a private marina with 25 boat slips. It’s an ideal retreat for those looking to relax and enjoy the Chesapeake Bay’s natural beauty.
  • Contact: 410.886.2121
  • Website:


When in Maryland, trying the crab cakes is a must. The charming beauty of this state and its eastern shore is made even more enjoyable by the variety of food and dining options here. 

Characters Bridge Restaurant

Characters Bridge Restaurant is celebrated for its local seafood and picturesque waterfront dining experience. It’s a favorite spot for both locals and visitors seeking authentic Maryland seafood dishes.

Tickler’s Crab Shack at Wylder Hotel

Tickler’s Crab Shack, located within the Wylder Hotel on Tilghman Island, offers a menu that highlights the freshest local seafood, including dishes prepared with seafood straight from Tilghman Island’s fishing docks.

Two If By Sea

Two If By Sea is renowned for its breakfast and brunch offerings, providing a cozy dining atmosphere. It’s a great place to start your day with a hearty meal before exploring the island.

Chesapeake Bay Romantic Getaways: Annapolis

Annapolis, the capital city of the state of Maryland, is a perfect destination for romantic getaways near Chesapeake Bay. The city, steeped in rich history, boasts a plethora of historic buildings and sites that couples can explore together while admiring the stunning waterfront views.


There’s no better place than Annapolis for a couple thats looking for a more active getaway. 

Indoor Activities

  • Visit the United States Naval Academy: Explore the grounds of this prestigious institution, which offers guided tours that delve into the academy’s rich history and architectural beauty.
  • Art Galleries and Museums: Annapolis is home to numerous art galleries and museums that celebrate local and regional art, maritime history, and more. Spend a leisurely afternoon admiring the artworks and learning about the area’s heritage.
  • Spa Day: Indulge in a relaxing spa day at one of Annapolis’s luxury spas. Many hotels offer spa services, providing the perfect opportunity for couples to unwind and enjoy some pampering.

Outdoor Activities

  • Sailing on the Chesapeake Bay: Annapolis, known as the “Sailing Capital of the U.S.,” offers ample opportunities for sailing adventures. Charter a private sailboat for a romantic excursion on the bay.
  • Stroll through Historic Downtown: Wander the charming streets of downtown Annapolis, where you can explore quaint shops, historic homes, and beautiful gardens.
  • Sunset Cruise: Embark on a sunset cruise from the City Dock to experience the stunning views of the Chesapeake Bay at dusk. It’s a picturesque and memorable way to spend an evening together.

Hotels & Inns

Annapolis offers a wide variety of places to stay. Some feature a waterview and some even have an indoor pool.

Graduate Annapolis Hotel

  • Features: Located in the heart of Annapolis, this hotel combines a collegiate theme with luxury, offering unique and comfortable accommodations. It’s a great base for exploring the city’s attractions.
  • Website: Graduate Annapolis Hotel

The Westin Annapolis

  • Features: This upscale hotel provides guests with modern amenities, spacious rooms, and a convenient location close to all major attractions. The Westin also offers a spa for ultimate relaxation.
  • Website: The Westin Annapolis

Annapolis Waterfront Hotel

  • Features: Situated on the waterfront, this hotel offers stunning views of the harbor and Chesapeake Bay. It’s perfect for couples looking for a romantic setting with easy access to waterfront dining and activities.
  • Website: Annapolis Waterfront Hotel


Annapolis boasts a vibrant culinary scene with a variety of dining options that cater to all tastes. From waterfront dining to cozy, intimate restaurants, couples can enjoy a romantic meal together.

  • Carrol’s Creek Cafe: Enjoy a romantic dinner with waterfront views, offering a menu that features fresh seafood and local ingredients.
  • Vin 909 Winecafe: This wine bar and restaurant offers a cozy atmosphere and a menu with a focus on farm-to-table dishes, perfect for a casual yet intimate dinner.
  • Osteria 177: For a more upscale dining experience, Osteria 177 serves exquisite Italian cuisine in an elegant setting, ideal for a special night out.

The quaint streets of Annapolis exude charm, making it a joy to wander and explore. The city is home to an array of historic buildings, including the Maryland State House, which dates back to the 18th century. Alongside these landmarks, couples can also discover hidden gems and unique local shops while soaking in the atmosphere of this idyllic destination.

Chesapeake Bay Romantic Getaways: Berlin, Maryland

Berlin, a charming town located near Chesapeake Bay, offers a perfect destination for romantic getaways with its unique shops, historic homes, and picturesque Main Street. 

The town is listed on the National Historic Register, adding to its allure and historic charm. It is also the filming site for Julia Roberts movie Runaway Bride. 


Berlin Maryland offers a good mix of indoor and outdoor activities. It is not right on the bay but very close to the water and also close to Ocean City, Maryland which has plenty to do.

Indoor Activities

  • Art Strolls and Gallery Visits: Berlin is home to several art galleries showcasing local and regional artists. Couples can enjoy leisurely strolls through the town’s historic streets, popping into galleries to admire and perhaps purchase a piece of local art.
  • Historic Museum Tours: Explore Berlin’s rich history by visiting local museums. The Calvin B. Taylor House Museum, for example, offers insights into the 19th-century life in Berlin and the architectural elegance of the period.
  • Cooking Classes: Participate in a cooking class together. Some local establishments or chefs may offer private or small group sessions, perfect for learning something new together in a fun, intimate setting.

Outdoor Activities

  • Stroll through Historic Downtown: Berlin’s historic downtown area, with its beautifully preserved buildings and charming streets, is perfect for romantic walks. Explore unique shops, cafes, and the town’s picturesque ambiance.
  • Visit Nearby Assateague Island: Just a short drive from Berlin, Assateague Island offers beautiful beaches, wild horses, and nature trails. It’s ideal for couples seeking outdoor adventure and natural beauty.
  • Golfing: For couples who enjoy golf, Berlin is close to several scenic golf courses where you can enjoy a day on the greens in a beautiful setting.

Hotels & Inns

Berlin is a small town so there are only a few options when it comes to accommodations. 

Atlantic Hotel

  • Features: This historic hotel in the heart of Berlin offers elegantly appointed rooms, a cozy restaurant, and a picturesque setting. It’s a step back in time with modern comforts, perfect for couples seeking a unique and romantic lodging experience.
  • Website: Atlantic Hotel

The Inn Berlin

  • Features: The Inn Berlin, located in the heart of historic Berlin, Maryland, is a boutique bed and breakfast that combines casual luxury with bespoke amenities and services, making it an ideal destination on the Eastern Shore. Set on 1.5 acres of beautiful nature and mature gardens, this grand Victorian estate offers five spacious guest rooms with private baths and organic linens, complimentary gourmet breakfast, and modern amenities for a memorable stay.
  • Website:


Berlin’s dining scene offers a variety of options that cater to all tastes, from casual eateries to fine dining establishments. While specific recommendations were not accessible, couples can expect to find:

  • Farm-to-Table Restaurants: Berlin and the surrounding area are known for their agricultural heritage, offering fresh, locally sourced meals that are both delicious and romantic.
  • Seafood Dining: Given its proximity to the Chesapeake Bay and Atlantic Ocean, seafood lovers can enjoy fresh catches at local restaurants, offering a taste of the region’s best flavors.
  • Intimate Cafes: For a more casual dining experience, Berlin’s cafes offer cozy atmospheres perfect for enjoying a coffee or light meal together.

Berlin, Maryland, with its historic charm, scenic beauty, and welcoming community, provides the perfect setting for a romantic getaway. Whether exploring the town’s cultural offerings, enjoying the natural surroundings, or relaxing in a cozy inn, couples are sure to find Berlin a memorable destination.

Chesapeake Bay Romantic Getaways: Irvington, Virginia

Irvington, Virginia is a hidden gem within the Chesapeake Bay area, making it a perfect destination for romantic getaways. Nestled in the scenic Northern Neck, this charming town offers a serene escape for couples seeking luxurious accommodations and memorable experiences.


There’s lots to do in Irvington. Let’s take a look.

Indoor Activities

  • Wine Tasting at Local Vineyards: The Northern Neck is home to several exquisite vineyards and wineries. Couples can spend a leisurely afternoon wine tasting and enjoying the scenic views of the vineyards.
  • Spa Day: Indulge in a day of relaxation and pampering at one of Irvington’s luxury spas. Many local inns and hotels offer spa services, including couples’ massages and treatments.
  • Visit Art Galleries: Explore Irvington’s art scene by visiting local galleries. The town and its surroundings are known for inspiring artists, offering a range of artwork from paintings to sculptures.

Outdoor Activities

  • Sailing on the Rappahannock River: Take advantage of Irvington’s waterfront location by going on a sailing adventure. Charter services are available for romantic sunset sails or day trips.
  • Explore Historic Sites: Irvington and the Northern Neck are rich in history. Visit historic landmarks and estates to learn about the area’s past and its significance in Virginia’s history.
  • Golfing: Enjoy a round of golf at one of the premier golf courses in the area. The Golden Eagle Golf Club, for instance, offers a challenging yet picturesque course perfect for golf-loving couples.

Hotels & Inns

From luxury to a charming country inn, you can find a variety of places to stay here.

The Tides Inn

  • Features: Situated on a private peninsula, overlooking the beautiful waters of the Rappahannock River, The Tides Inn offers luxurious accommodations, fine dining, and a host of activities. The waterfront grounds here have a beautiful setting for leisurely strolls and amazing sunsets.Couples can indulge in spacious suites, modern amenities, and breathtaking waterfront views. 
  • Website: The Tides Inn

Hope and Glory Inn

  • Features: This charming boutique inn, located in the heart of Irvington, provides a unique and intimate setting. With its beautiful gardens, onsite vineyard, and distinctive accommodations, it’s ideal for couples seeking a quiet escape.
  • Website: Hope and Glory Inn


Irvington’s dining scene offers a variety of options that cater to all tastes, from casual cafes to upscale restaurants. While specific recommendations were not accessible, couples can expect to find:

  • Waterfront Dining: Enjoy a romantic dinner with views of the Rappahannock River. Many restaurants offer fresh seafood and local cuisine with a scenic backdrop.
  • Farm-to-Table Restaurants: The Northern Neck’s agricultural bounty is on full display at local eateries that prioritize fresh, locally sourced ingredients for a truly Virginian dining experience.
  • Cozy Cafes: For a more casual or daytime date, Irvington’s cafes offer the perfect setting to enjoy a coffee and sweet treat together.

Irvington, Virginia, with its blend of natural beauty, historic charm, and serene ambiance, provides the perfect setting for a romantic getaway. Whether exploring the town’s cultural offerings, enjoying the natural surroundings, or relaxing in a cozy inn, couples are sure to find Irvington a memorable destination for a romantic retreat.

Chesapeake Bay Romantic Getaways: Summary

Whether it’s an intimate getaway for a couple or a trip with a group of friends, the Chesapeake Bay has something for everyone. Known as a haven for picturesque waterfront towns, the Chesapeake offers the perfect setting for a romantic couples getaway. It’s an easy road trip from either Washington DC or Baltimore. 

From Rock Hall to Point Lookout State Park, the area provides a diverse selection of scenic stops to explore, each offering its unique features and appeal. One of the great things about this area is that there is plenty to do and you will have plenty of quality time with your partner. 

The picturesque coastal towns of the Chesapeake Bay are famous for their outstanding restaurants, luxury suites, and outdoor activities. If you’re looking for an unforgettable experience on the east coast, plan a trip to one of the romantic destinations above. 

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