Sightseeing Adventures
Traveling to Washington, D.C. or Southwest Florida? Here are some spots worth exploring.
RSW International Airport offers a multitude of direct flights to appealing destinations. JetBlue, for example, has daily flights that connect Southwest Florida travelers to many northeast locations for quick getaways. Washington, D.C., is one of those. It’s an easy flight from Fort Myers up to Washington, D.C.’s, Reagan National, but your most relaxing getaway might lie beyond the district. Historic (and beautiful) Annapolis—only 45 minutes from the airport—is a great fit for anyone who loves history, seafood or sailing. Average lows are 50 degrees or higher May through October, while daytime temps are typically pleasant, by Floridian standards, all but three months a year.
The magnificent U.S. Naval Academy campus—worth a trip on its own—anchors downtown Annapolis. Settled in 1649, this small city, brimming with Colonial-era architecture, maintains a vibrant mix of polite midshipmen; tanned and lean recreational sailors; visitors of all kinds; D.C. weekenders; and locals. You can easily explore this small but memorable American city on foot, further adding to its relaxation factor.
The academy is fascinating and offers patriotic visitors several goose-bump moments. Situated where the Severn River spills into the Chesapeake Bay, the navy’s legendary campus is open to the public, and a guided tour is the way to go. Led by a certified docent, these informative tours give a glimpse into the life of midshipmen, while viewing significant landmarks, such as the crypt of naval hero John Paul Jones.
Plan a midday visit and you’ll get to enjoy Noon Formation, one of “the Yard’s” great attractions. Weather and schedule permitting, this impressive assemblage of midshipmen takes place weekdays during much of the academic year, and on Saturdays during Plebe Summer.
Whatever you do, don’t skip the USNA Museum in Preble Hall. It’s chock-full of naval history treasures, including the famous handmade Revolutionary flag that implored, “Don’t give up the ship,” inspiring the unofficial navy motto.
Rising above the heart of downtown Annapolis, the iconic Maryland State House remains the oldest state capitol in continuous legislative use and briefly served as the nation’s capital. History buffs might remember George Washington’s momentous occasion here, as well as another that marked the end of the Revolutionary War.
This national historic landmark, which you can tour on your own, is a pleasant stroll from any number of quaint shops, galleries, restaurants and pubs. You’ll discover Galway Bay Irish Restaurant and Pub, popular Chick and Ruth’s Delly, and Mason’s Lobster Rolls. Maritime art is in good supply at local galleries.
For a true rite of passage, find your way to Cantler’s Riverside Inn, a decades-old landmark restaurant for blue crabs. If you’ve never tackled this meal—served in a pile on a brown paper tablecloth—it’s best to get a little coaching from a server, lest you provide entertainment for the regulars as you attempt to eat what you’ve ordered.
It’s easy to while away time just exploring the Annapolis harbor front, with its countless powerboats and sailing yachts. A five-minute ride across Spa Creek takes you to Carrol’s Creek Café or the Chart House, both offering nice views of local docks.
To get the full-on Chesapeake Bay experience, book a trip with Schooner Woodwind Annapolis Sailing Cruises. These four-star excursions take place aboard one of two 74-foot wooden schooners. Sunset is a captivating time to unwind while watching the sun sink behind one of America’s most treasured small cities.
For a most unique lodging experience, Schooner Woodwind offers a “Boat and Breakfast” option, in which guests spend the night aboard. Plenty of traditional lodging options are available in Annapolis as well: everything from 18th-century buildings to a Hilton and some airbnbs.
It’s easy to while away time just exploring the Annapolis harbor front, with its countless powerboats and sailing yachts.