Unique Chesapeake Experiences: Bayside Adventure and Luxury

Who says you can’t do it all? Try active Bay adventures, sample local and authentic culinary delights, experience exciting nightlife and entertainment, and relax and pamper yourself at luxury hotels and spas.

Baltimore to Annapolis and Easton, 106 miles, 5 days, 6 nights

Day 1 - City Lights, City Sights

Fells Point, Baltimore

• Wake up to luxury at the Sagamore Pendry Hotel Baltimore on the waterfront in Fells Point
• Ride the Water Taxi in spring, summer and fall across the Inner Harbor, taking in stunning views of the city skyline
• Land at Fort McHenry National Monument and Historic Shrine to see the fort where “the flag was still there”
• Ride the Water Taxi back to Fells Point and board the taxi to the Rusty Scupper to enjoy lunch with a view, or check out the restaurants in Federal Hill
• Explore the American Visionary Art Museum in Federal Hill, a quirky and fascinating museum featuring the work of self-taught artists
• Travel back to Fells Point on the Water Taxi
• Dine on the waterfront patio at Ampersea Restaurant for a modern culinary experience featuring local and seasonal ingredients
• Experience the nightlife in Fells Point. Start at The Cat’s Eye Pub or the Waterfront Hotel, both  favorites for live music
• OR catch a broadway show at the Hippodrome in downtown Baltimore
• End your day with a nightcap and a spectacular view of the city at The Bygone in Harbor East

Day 2 - Strolling, Sailing and Sunsets

Baltimore to Annapolis, Maryland’s historic capital city

• Wake up in Fells Point at the Sagamore Pendry Hotel Baltimore
• Stroll the charming and historic cobbled streets in Fells Point and browse the shops
• Drive to Annapolis (50 minutes)
• Amble around the Annapolis Harbor at City Dock and watch yachts cruise Ego Alley
• Stop into the shops on Main Street
• Watch the Wednesday night sailboat races or take a sunset cruise aboard the Schooner Woodwind, a Chesapeake Bay Storyteller
• Treat yourself to a meal at The Choptank OR eat with the locals at Cantler’s Riverside Inn - a traditional dock-to-table crab shack
• Croon with your favorite artists at Rams Head on Stage OR take in a show at Annapolis Summer Garden Theatre
• Rest for the night at The Graduate Hotel

Day 3 - Catch the Action on the Water

Annapolis to Kent Island

• Take a Morning Paddle to see dolphins with Chesapeake Bay Storyteller Capital SUP
• OR go Charter fishing with Chesapeake Bay Storyteller Tuna the Tide at Kent Narrows
• Bike the Cross Island Trail and/or the South Island Trail to see gorgeous Bay views
• Experience the glow of the magic hour at Matapeake Beach
• Check out the culinary experience and nightlife on Kent Island: Join the locals for dinner, drinks and live music at The Big Owl Tiki Bar, or feast on seafood favorites with a twist at Bridges Restaurant while soaking up the sunset
• Relax and unwind at The Inn at the Chesapeake Bay Beach Club & Spa

Day 4 - Immerse Yourself in Art & Culture

Kent Narrows to Easton

• Enjoy a rejuvenating spa treatment at The Inn at Chesapeake Bay Beach Club
• Drive to Easton (30 minutes)
• Grab a scratch-made healthy snack at Sprout
• Explore art from the 17th century to today at the Academy Art Museum (free admission)
• Shop, stroll and see the art galleries and boutiques in Easton
• Check into the Tidewater Inn
• Dine at Out of the Fire Restaurant for creative, sustainably-sourced cuisine
• Catch a concert or show at Avalon Theater

Day 5 - Soak Up the Water Views

Easton to Oxford and St. Michaels and back to Easton

• Drive from Easton to Oxford on the Chesapeake Views Road Bike Route (cars allowed and bike rentals available from Easton Cycle and Sport)
• Take a sightseeing cruise with Chesapeake Bay Storyteller Tumblehome Cruises in Oxford
• Explore the waterfront colonial town of Oxford
• Ride the historic Oxford - Bellevue Ferry to Bellevue (cars and bikes included)
• Take a scenic ride or drive to St. Michaels and have lunch at Ava’s Pizzeria and Wine Bar
• Continue your scenic ride or drive to Tilghman Island to watch the sunset across the Bay
• Return to Easton
• Dine on Northern Italian cuisine on the elegant terrace at Scossa Restaurant & Lounge 
• Retire for the night at The Tidewater Inn and reflect on your Chesapeake Bay memories