Annapolis City Dock
Matthew Mckinney

Annapolis City Dock

Unique Chesapeake Experiences: Bayside Adventure and Luxury

Annapolis City Dock
Matthew Mckinney

Annapolis City Dock


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

 

Broadway Market in Fells Point, Baltimore

Broadway Market in Fells Point, Baltimore

Baltimore Water Taxi

Baltimore Water Taxi

Day 1 - City Lights, City Sights

Fells Point, Baltimore

 

View of the Wednesday night sailboat races on board the Schooner Woodwind

View of the Wednesday night sailboat races on board the Schooner Woodwind

Shopping in Annapolis

Shopping in Annapolis

Day 2 - Strolling, Sailing and Sunsets

Baltimore to Annapolis, Maryland’s historic capital city

 

Sunset at Big Owls Tiki Bar in Kent Narrows

Sunset at Big Owl Tiki Bar in Kent Narrows

Sunrise Kayaker

Capital SUP Sunrise Kayaker

Day 3 - Catch the Action on the Water

Annapolis to Kent Island

 

Downtown Easton with Avalon Theatre and Banning’s Tavern

Downtown Easton with Avalon Theatre and Banning’s Tavern

Dining Outside at the Tidewater Inn

Outdoor dining and happy hour at the Tidewater Inn

Day 4 - Immerse Yourself in Art & Culture

Kent Narrows to Easton

 

Sail Selina Charters

Sail Selina Charters

Oxford Bellvue Ferry at Sunset

Oxford Bellevue Ferry at Sunset

Day 5 - Soak Up the Water Views

Easton to Oxford and St. Michaels and back to Easton

Maryland's Great Chesapeake Bay Loop Getaway Guide

Maryland's Great Chesapeake Bay Loop Getaway Guide

Find a treasure trove of ways to explore the Bay, and meet our skilled Chesapeake Bay Storytellers.

Download Guide