I'm not sure exactly where Shakespeare's is...in Calabash? If so,everything is walking distance. We stay at a sunset Resort who has a pool and I know people come to eat lunch and swim. Sunset also has a cottage right on the water with a kitchen at a very reasonable rare. Its a nice safe place to stay and a two minute walk to jakes and 4 to jack sprats. Jakes has a weird kind of a pool, nestled into the bar- restaurant...you're kind of on display and I've eaten there four times and went to spa twice and never saw anyone in it!?