We've been fleeing Boston winters every two or three years for 15 years now. We head to Sanibel Island, a long thin strip of sand just off the coast from Fort Myers' strip malls and fake canals. Sanibel has a huge nature reserve, biking trails, gorgeous seashell beaches, some low-rise condos, timeshares and hotels, overpriced restaurants (it is a resort, after all), all surrounded by the Gulf of Mexico. The Island has very strict zoning controls, so it retained its large swaths of natural areas, flat footprint, and lack of high-rises on the beaches.
We love it here, and bought into a timeshare called Casa Ybel around 12 years ago. We usually rent it out, but elected to use it ourselves this year, probably for the last time before it gets sacrificed to Dan's college bills. It's a lovely, extremely well cared for place with one and two bedroom apartments with screened porches overlooking the Gulf.
We always call ahead to Billy's Rentals, and have bikes and beach chairs delivered. We also book ahead for any boating we want to do, as this is a very crowded week from cold-weather school vacations. Restaurant reservations are a good idea as well, although some places don't take them. However, many places have 'call ahead" where you call up to get on the waiting list before heading over.
On Saturday morning, we did our grocery shopping. We try to do the "big shop" on our way over from Fort Myers where prices are much cheaper, but we didn't arrive till 10 Friday night. The island tends to roll up the sidewalks at 7:30. Food prices at both island supermarkets are staggering, especially when you're feeding teenage boys. Produce is twice what I'm used to in Boston, except for local citrus. Food for a week of breakfasts, lunches, and snacks was over $100!
Lazing at the beach, riding bikes, and having the first pina colada on the beach at sunset took up the afternoon. We rented a tandem bike and two singles, and the tandem was a blast--especially for the member of your family who gets distracted while bikeriding, and has a history of riding into things.
For dinner, we bought some fresh tuna and mahi-mahi from the fish market at Timbers restaurant. We grilled it, and I made a sauce of garlic, butter, and peach-jalapeno jam. Delicious, especially when eaten on the porch, with cool white wine and the sound of the waves. The resort was hosting a wedding, and we mortified the kids by dancing on the porch until the music stopped at 9:30.