Do: Sail on the Charles River Sailboats dot the Charles River all year long -- sailing is a popular pastime for locals and tourists alike. If you're looking to rent a boat for a few hours on your own, or would like to get a lesson from an instructor before you hit the open seas, head to Community Boating (the oldest public sailing facility in the country) right on the Charles. They offer rentals, lessons, and sailing programs from April through November -- you can even rent kayaks or Windsurfers if you'd rather attempt to manage something a little smaller. Stay: Liberty Hotel Occupying a former jail, the 298-room Liberty Hotel is truly unique, with a playful design that incorporates the incarceration theme in fun ways. The stunning lobby, comfortable rooms, and quality on-site restaurants make this hotel a good choice. The hotel, located about two blocks from the Charles River, offers guests discounted rates on kayak rentals.