The Jamaica Plain Boathouse and the Arnold Arboretum were selected as two of the top 10 places to propose to a loved one in Boston by the WeekendPick website. We couldn't agree more! The boathouse can be very romantic, whether it's at sunset or during a beautiful day. Heck, even a rainy day can be very romantic at Jamaica Pond. Of course, you'll want to make sure there aren't any musical performances happening at the boathouse during your planned proposal time -- unless that works well with your proposal.