The answers to the place descriptions are:
| A beautiful birdwatching spot on Cape Ann, as featured in a local birding journal in October 2001 | Andrew's Point |
| A gathering space in Swansea, Wales that provides a focal point for the city, featuring live music and entertainment on summer days. | Castle Square |
| A prime snorkeling spot in the fjords of Arabia | Telegraph Island |
| A quiet Indianapolis neighborhood bordered by Edgewood Road on the south, Gray Road and Sherman Drive on the east, Keystone on the west, and I-465 on the north. | Carson Square |
| A small seaport community in the Bronx surrounded by the Long Island Sound and Eastchester Bay. | City Island |
| Archeological site at Cullompton, Devon, UK believed to be remnants of a Roman military camp | St. Andrew's Hill |
| Boutique retail district in the heart of downtown in Nevada's capital city | Telegraph Square |
| Charlestown park bordered by a famous English restaurant | City Square |
| Community north of the holiday town of Port Macquarie on the beautiful mid-north coast of New South Wales | Telegraph Point |
| Florida panhandle coastal area that gave its name to an endangered species of mouse | St. Andrew's Beach |
| Ghost town also known as Melones on the Mother Lode belt in Calaveras County | Carson Hill |
| Harney County, Oregon, summit 43118-E6 | Carson Point |
| Historic park and symbolic gathering place in a planned city founded in 1913 | City Hill |
| North Carolina estuary site named after an environmental activist | Carson Island |
| Pristine Alaskan territory in the Stikine River, 15 miles Northeast of Wrangell. | Andrew Island |
| Quaint seaside resort in the heart of Hua Hin, Thailand | City Beach |
| Remote Tasmanian seashore at 40: 25' S 144: 52' E | Telegraph Beach |
| Rocky basin in New Zealand popular for climbing and bouldering | Castle Hill |
| Scenic New Jersey site, named for a glorious Victorian mansion, that now houses a technological university | Castle Point |
| Seaside location in Falmouth, Cornwall where visitors can climb up on a foot path to Pendennis Point | Castle Beach |
The places start with Andrew/Carson/Castle/City/Telegraph and end with Beach/Hill/Island/Point/Square:
| (St.) Andrew | Beach | #10 |
| (St.) Andrew('s) | Hill | #6 |
| Andrew | Island | #16 |
| Andrew('s) | Point | #1 |
| Carson | Hill | #12 |
| (Rachel) Carson | Island | #15 |
| Carson | Point | #13 |
| Carson | Square | #4 |
| Castle | Beach | #11 |
| Castle | Hill | #19 |
| Castle | Point | #20 |
| Castle | Square | #2 |
| City | Beach | #17 |
| City | Hill | #14 |
| City | Island | #5 |
| City | Square | #8 |
| Telegraph | Beach | #18 |
| Telegraph | Island | #3 |
| Telegraph | Point | #9 |
| Telegraph | Square | #7 |
The five places not on the list are Telegraph Hill, Andrew Square, Carson Beach, City Point, and Castle Island. These can all be found in SOUTH BOSTON.
Training:
The training for this puzzle is VIRGINIA COUNTY. South Boston is in the Virginia county of HALIFAX.