Both my grandparents, my husband and myself, and my sister are toying with the idea of going on a sailboat for about a week. Weve done this years ago around the Virgin Islands where we had a crew (captain, chef, dont remember what else) and it was a blast. Wed love something exactly like that: where we can stay on the boat the entire time, go swimming, see nature (landscape and animals), etc.

Problem: About a decade ago, during the last sailing trip my grandmother went on, she had a medical emergency and she and my grandfather didnt think shed make it. The hospital nearby wasnt equipped well enough for her case. Thankfully they were able to get an emergency medical flight back to the US and she pulled through. She is 100% ok now, but my grandfather worries when shes not near a major hospital and so wont go on trips like that anymore. But my grandmother really wants this sailing trip. And health wise, she is fine, and theres no medical reason why she cant go.

Were hoping theres a compromise where she can still go sailing, but wont need so long in a private medical plane to get to a major hospital, and then my grandfather wont worry so much. Anyone here have any destination ideas?

As for trip specifics:

Budget: Honestly dont have one. My grandparents have more money than they know what to do with.

Duration: A week, but were flexible. The exact dates are also flexible. So long as the water is warm the date is fine.

Where were starting from: My grandparents and sister are in Florida, US, and my husband and I am in Ontario, Canada. My family lives in a city with an international airport and I do not so Ill need at least two flights but thats not really a problem for me.

Preferences: Wed prefer to hire a crew but it isnt required. My grandparents prefer a crew to drive, cook, and clean, but if anyone here has a great destination that doesnt offer a crew thats fine too. My husband and I can drive the boat and I wouldnt mind cooking and cleaning.

Interests: Sightseeing. Pretty nature and wildlife. Swimming. If we can stop at little towns by the shore for lunch and some walking thatd be a plus. No hiking though. Sleep on the boat.