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Cycling along the contours of Southie

Boston's skyline and the John F. Kennedy Library and Museum bracket a bicyclist on a weekday morning. (Michael Bailey/Globe Staff)Michael Bailey/Globe Staff

Biking in Boston is improving, but it still is too often a white-knuckle ride through narrow streets plied by aggressive, inattentive motorists and, maddeningly, clueless cyclists. For an alternative Hub-and-spokes reality, try a ride along Southie’s beaches.

Dawn is the ideal time, when the horizon holds ribbons of reds and a breeze can twist your sweat into a quick shiver. If your schedule or body rhythm argues for later, aim for 10 a.m., preferably on a weekday.

Start your trek at iconic Castle Island and head south along Day Boulevard. The road is flat, the sightlines exceptional. You’ll pick up an unprotected bike lane at I Street but post-rush hour traffic, both for cars and other bikes, tends to be light.


A massive granite slab holds a map of Boston Harbor and the islands and a timeline of the city's history. (Michael Bailey/Globe Staff)Michael Bailey/Globe Staff

Follow the contours of the coast until you reach Moakley Park on your right. You’ll want to cross over to the Harborwalk, taking that along the Harbor Point housing development. This area offers several inviting places to stop, including a massive, round granite map with Boston Harbor and the islands in the middle and a timeline along the circumference. If you stop at a gazebo at the point, your eyes take in a terrific view of the JFK Library and Museum, its white and black building bordered in blue waters in three directions. Across the waters are Spectacle and Thompson islands.

Continue on to behind JFK, about four miles from your starting point, and take a few minutes to saunter along the grounds and winding stairs that hug I.M. Pei’s architectural gem. The library remains closed due to the pandemic.

Dilson Silva, of Brighton, often takes morning swims at Carson Beach in South Boston.Craig F. Walker/Globe Staff

As you return along largely the same path, keep an eye out for a spot to take a dip in Dorchester Bay. Unlike the horror of the hordes of people packing M Street Beach on sultry weekends, Carson Beach on a warm weekday morning offers vast tracts of open sand, with social distancing not even a consideration. Check tide tables before your trip: If it’s mid to high tide, jump in. If it’s low tide, you’ll have to walk out far before the water even reaches your thighs and you’ll want water shoes to traverse jagged rocks.


Hop back on the bike. Because most parking spots have been removed on the seaside section of Day Boulevard, you’ll have your own path, protected by barrels. If you decide to extend the trip around the Castle Island causeway, you’ll need to walk your bike. You’ll also need to decide whether it is too crowded for comfort.

If inbound planes for Logan are overhead, you have another option: Find a spot right under the flight path. After the largest planes pass, the air often crackles overhead. By then, you should feel energized in all directions.

Michael Bailey can be reached at michael.bailey@globe.com.