Discover the Chesapeake Bay, Maryland - America's Great Estuary Adventure

Day 1: Annapolis — Historic Harbors & Crab Delights

• Morning (9:30 AM - 12:30 PM) Arrive in Annapolis and check into your accommodation. Consider a charming B&B or a hotel like Graduate Annapolis (often around $200-250/night depending on season) for its prime location and vibrant atmosphere. Kick off your historical journey with a guided walking tour of the U.S. Naval Academy. Entry to the grounds is free, but guided tours from the Visitor Center at Gate 1 (52 King George St) cost around $15-20 per person and last about 1.5-2 hours. You’ll explore iconic landmarks such as Bancroft Hall and the Naval Chapel.
  • Distance: Most central Annapolis hotels are within a 10-15 minute walk to Gate 1 of the Academy.
  • Practical Tip: Bring a photo ID for entry to the Naval Academy. Wear comfortable walking shoes.
• Afternoon (12:30 PM - 5:00 PM)
  • Lunch (12:30 PM - 1:30 PM): Head towards the Annapolis City Dock area for lunch. Enjoy a classic Maryland crab cake sandwich or fresh oysters at a casual spot like Buddy’s Crabs & Ribs on Main Street or Market House (a historic public market with various food vendors). Expect to spend around $40-60 for two.
  • Activities (1:30 PM - 5:00 PM): Immerse yourself in the city’s history. Visit the Maryland State House (free entry, allow 1 hour), the oldest state capitol in continuous legislative use. Then, stroll down Main Street and State Circle, browsing the unique boutiques, art galleries, and historic architecture. For a different perspective, consider a scenic 40-minute narrated harbor cruise with Watermark Cruises (approx. $25-30 per person) departing from City Dock, offering picturesque views of the Severn River and the Bay.
  • Distance: All these attractions are within easy walking distance from City Dock, making it perfect for exploring on foot.
• Evening (5:00 PM onwards)
  • Relaxation & Dinner: Enjoy some downtime at your hotel to freshen up.
  • Dinner (7:00 PM): Indulge in an authentic Maryland seafood experience. For a lively and quintessential crab house experience, drive a short distance (about 10 minutes) to Mike’s Crab House on the South River, known for its steamed crabs and waterfront views. Expect to spend around $100-130 for two for a full crab feast. Alternatively, stay downtown and enjoy the vibrant atmosphere and delicious, moderately priced seafood at The Point Crab House & Grill.
  • Post-Dinner: If you have energy left, enjoy a nightcap at a cozy pub on West Street or by the City Dock.

Day 2: Eastbound Charm — From State Capital to Island Oasis

• Morning (8:30 AM - 12:00 PM)
  • Breakfast (8:30 AM - 9:30 AM): Enjoy a delicious breakfast at a local Annapolis cafe. Consider City Dock Coffee or Iron Rooster (known for their homemade pop-tarts and hearty breakfast dishes) on Market Space. Expect to spend $30-50 for two.
  • Scenic Drive (9:30 AM - 11:30 AM): Begin your journey to St. Michaels, a charming waterfront town on the Eastern Shore. The drive is approximately 1 hour 15 minutes to 1 hour 30 minutes (55-60 miles). You’ll cross the iconic Chesapeake Bay Bridge (toll for eastbound traffic, approx. $4-6 via E-ZPass or cash). Enjoy the scenic views as you traverse rural landscapes and charming small towns.
  • Arrival in St. Michaels (11:30 AM): Check into your St. Michaels accommodation. The St. Michaels Inn or one of the many charming local B&Bs offer comfortable stays often in the $200-250/night range.
• Afternoon (12:00 PM - 5:30 PM)
  • Lunch (12:00 PM - 1:00 PM): Settle into St. Michaels with a casual lunch by the water. The Crab Claw is a local institution right on the harbor, famous for its outdoor seating and fresh, no-frills seafood. Expect to spend $50-70 for two.
  • Cultural Immersion (1:00 PM - 4:30 PM): Spend your afternoon at the Chesapeake Bay Maritime Museum (CBMM). This incredible museum spans 18 acres of waterfront property, featuring historic boats, a working boatyard, and the iconic Hooper Strait Lighthouse. Allow 2.5-3 hours to explore all the exhibits and learn about the Bay’s rich history and culture. Entrance is $20 per person.
  • Stroll & Shop (4:30 PM - 5:30 PM): Walk along Talbot Street, the main thoroughfare of St. Michaels, browsing the charming boutiques, art galleries, and antique shops.
• Evening (5:30 PM onwards)
  • Relaxation & Refresh (5:30 PM - 7:00 PM): Head back to your hotel for a brief rest and to freshen up.
  • Dinner (7:00 PM): Enjoy an upscale dining experience at Limoncello, an authentic Italian restaurant with a focus on fresh, local ingredients (including seafood), or Foxy’s Harbor Grille for a more casual upscale feel with great water views. Expect to spend around $130-160 for two.
  • Optional: Enjoy a peaceful evening stroll along the harbor as the sun sets, or grab a drink at a local establishment like St. Michaels Winery.

Day 3: St. Michaels Serenity & Bay Farewell

• Morning (9:00 AM - 12:00 PM)
  • Breakfast (9:00 AM - 10:00 AM): Enjoy a leisurely breakfast at your hotel or a local cafe like Justine’s Ice Cream Parlor & Cafe (offers breakfast sandwiches and pastries) or Blue Heron Coffee for quality coffee and light bites. Expect to spend $30-40 for two.
  • Morning Activity (10:00 AM - 12:00 PM):
    • Option 1 (Active): Rent kayaks or paddleboards from St. Michaels Harbor Shuttle & Kayak Rental to explore the tranquil waters of the Miles River at your own pace. (Cost: ~$30-40 per hour for a double kayak).
    • Option 2 (Relaxed): Take a relaxing and informative cruise on the Patriot, a 1920s-style tour boat offering narrated historical and ecological tours of the Miles River. (Cost: ~$25-30 per person for a 1-hour cruise).
    • Option 3 (Shopping & Exploration): Revisit any shops on Talbot Street you wanted to explore further or discover new ones, or simply enjoy a final walk through the charming streets of St. Michaels.
• Afternoon (12:00 PM - 2:00 PM)
  • Lunch (12:00 PM - 1:00 PM): Enjoy a final Chesapeake Bay-inspired meal before departing. Try Ava’s Pizzeria & Wine Bar for a more casual but delicious option, featuring fresh ingredients and local flavors, or grab a quick and tasty bite from another spot on Talbot Street. Expect to spend $40-60 for two.
  • Departure (1:00 PM - 2:00 PM): Depending on your next destination, begin your journey home, carrying delicious memories of Chesapeake culinary delights and coastal charm. The drive back towards Annapolis/Baltimore/Washington D.C. will take approximately 1.5 - 2 hours, crossing the Bay Bridge westbound (no toll).

Day 1: Annapolis Charm & Bay Bridge Gateway

• Morning (9:00 AM - 1:00 PM) Arrive in Annapolis, Maryland’s charming capital. Park at a central garage like the Knighton Garage (estimated cost: $15-20 for a few hours). Begin your exploration with a self-guided tour of the historic downtown area, including Ego Alley and the stunning Maryland State House (free admission, allow ~1 hour to walk the grounds and view the exterior/interior if open). Stroll the cobblestone streets, admire the colonial architecture, and browse the unique shops. The main attractions are within a 1-2 mile walkable radius.
• Afternoon (1:00 PM - 5:00 PM) Enjoy lunch at a quintessential Annapolis eatery. Options include Chick & Ruth’s Delly (classic diner fare, expect ~$30 for two) or Iron Rooster (known for its all-day breakfast and comfort food, ~$45 for two). After lunch, depart Annapolis and head east on US-50 to cross the iconic Chesapeake Bay Bridge. The scenic drive across the 4.3-mile bridge offers panoramic views of the Bay (Toll: ~$4-6, pay-by-plate or EZ-Pass). Upon arrival on Kent Island, check into your accommodation. Recommended options include Hilton Garden Inn Kent Island or Best Western Kent Island (estimated cost: ~$180-250/night). Distance: Annapolis to Kent Island is approximately 20 miles (30-45 minutes drive).
• Evening Relax after your journey, then head out for dinner on Kent Island. Experience the waterfront atmosphere at The Jetty Dock Bar (casual, live music often, $60-80 for two) or enjoy classic seafood at Fisherman’s Inn ($80-100 for two). After dinner, a leisurely stroll along the Kent Narrows waterfront is a perfect way to end the day.

Day 2: Kent Island’s Natural & Nautical Side

• Morning (9:00 AM - 12:00 PM) Start your day with breakfast at your hotel or a local spot like K-Coast Coffee Cafe (estimated cost: ~$20-25 for two). Next, immerse yourselves in nature at Terrapin Nature Park (free admission, allow 1.5-2 hours). Enjoy easy walking trails, a sandy beach, and stunning views of the Chesapeake Bay and the Bay Bridge. Afterward, visit the Chesapeake Exploration Center (free admission, allow ~1 hour) to learn about the Bay’s ecosystem, history, and the impact of the bridge. Distances: All attractions are within a short 5-10 mile drive on Kent Island.
• Afternoon (12:00 PM - 5:00 PM) Have lunch at a Kent Narrows institution: Harris Crab House (iconic, casual, expect ~$70-100 for two if enjoying steamed crabs) or Bridges Restaurant (more upscale with water views, lunch entrees ~$60-80 for two). In the afternoon, consider renting kayaks or paddleboards at Kent Narrows (seasonal, estimated cost: ~$30-50 per hour per person) to explore the calm waters. Alternatively, browse the local boutiques and art galleries or simply relax by the water.
• Evening For dinner, savor another taste of the Chesapeake. Options include Libbey’s Coastal Kitchen & Cocktails (upscale casual with fresh, local ingredients, ~$90-120 for two) or Annie’s Paramount Steak & Seafood (a beloved local favorite, ~$80-110 for two). Conclude your day by finding a spot for a beautiful sunset view over the Bay.

Day 3: Eastern Shore Gems & Tilghman’s Call

• Morning (9:00 AM - 12:30 PM) Enjoy breakfast at your accommodation before checking out. Embark on a scenic drive south on US-50 and MD-331 towards the charming town of Easton. Spend a couple of hours exploring historic downtown Easton (free to walk around). Discover its vibrant arts scene by visiting galleries like the Academy Art Museum (admission ~$15/person) or browsing unique shops. Distance: Kent Island to Easton is approximately 30 miles (45-60 minutes drive).
• Afternoon (12:30 PM - 5:00 PM) Dine in Easton for lunch. Choices range from The Wardroom (a popular deli/cafe, ~$30-40 for two) to Out of the Fire (an upscale casual eatery with delicious dishes, ~$60-80 for two). After lunch, continue your journey to Tilghman Island via the picturesque MD-33. Check into your accommodation, such as the Tilghman Island Inn (estimated cost: ~$180-220/night) or Harrison’s Chesapeake House for an authentic waterman’s experience. Spend the late afternoon exploring the quaint fishing village and observing the working watermen. Distance: Easton to Tilghman Island is approximately 25 miles (30-40 minutes drive).
• Evening Experience true island dining. Enjoy dinner at Harrison’s Chesapeake House (renowned for its classic seafood and waterman vibe, expect $70-100 for two, be sure to try the crab cakes) or indulge in a finer dining experience at the Tilghman Island Inn Restaurant ($100-140 for two). Take in the peaceful, star-filled island evening.

Day 4: Tilghman Island’s Watermen & Tranquility

• Morning (9:00 AM - 1:00 PM) Start your day with breakfast at your lodging or a local cafe like Two if By Sea (seasonal, limited hours, ~$20-25 for two). Begin your island exploration at the Phillips Wharf Environmental Center (small admission fee, ~$5/person, allow ~1 hour) to learn about the Bay’s marine life and conservation efforts. If available and seasonal (check ahead!), consider a unique Skipjack tour on the historic Rebecca T. Ruark (estimated cost: ~$50-75/person for a few hours) for an immersive look at traditional oyster dredging. This offers a deep dive into watermen’s heritage.
• Afternoon (1:00 PM - 5:00 PM) For lunch, consider a casual meal at a local spot like Mike’s Crab House (seasonal, ~$60-80 for two for lunch) or grab supplies from the Schooner Landing Store for a scenic picnic by the water. Spend the afternoon taking a leisurely drive or bike ride around the island, observing the drawbridge as it opens for boats, and visiting Dogwood Harbor to watch the working skipjacks and buy fresh seafood from local docks. Embrace the tranquil pace of island life.
• Evening Enjoy a farewell dinner on Tilghman Island. You might revisit a favorite from the previous night or try another local gem. If seeking a change of scenery, nearby St. Michaels (approx. 20-minute drive) offers more dining options, but staying on Tilghman maintains the island’s unique charm. Consider a casual crab feast if available and in season. Relax and enjoy the quiet sounds of the Bay.

Day 5: Island Farewell & Bay Views

• Morning (9:00 AM - 12:00 PM) Enjoy a final breakfast on Tilghman Island before checking out of your accommodation. Take one last stroll to soak in the island’s serene atmosphere or pick up any last-minute souvenirs. Begin your drive north, heading towards the Chesapeake Bay Bridge. Optional Stop: Consider a brief stop in the charming town of St. Michaels (approximately 20 minutes from Tilghman Island). You could visit the renowned Chesapeake Bay Maritime Museum (admission ~$18/person, allow 2-3 hours) or simply enjoy a walk along its picturesque main street and harbor. Distance: Tilghman Island to St. Michaels is about 15 miles.
• Afternoon (12:00 PM - 3:00 PM) If you stopped in St. Michaels, have lunch there at a place like Ava’s Pizzeria & Wine Bar (casual, ~$40-50 for two) or the iconic The Crab Claw (waterfront, ~$80-120 for two). Otherwise, grab a quick bite on your way. Continue your journey towards the Chesapeake Bay Bridge for your return crossing. (Note: Westbound tolls are typically only charged when eastbound, so the return should be free unless you have an EZ-Pass for automatic deductions).
• Evening Depart for home, carrying memories of the Bay’s charming towns, iconic bridges, and tranquil island retreats.