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Are reservations necessary?

Hi there!

Visiting mid-May and would like to, if possible, play our days somewhat by ear. We have things we want to do for sure but don’t have it down to a specific day or time. Example is guided tour kayaking mangrove, sea life encounter cruise, of course eating out (not fine dining). Is it possible to have a loose itinerary or will we lose out if we don’t book in advance?

Thanks for any tips!

Visiting Siesta Key in mid-May gives you some flexibility, but whether you can “play it by ear” depends on the type of activity and how busy things are likely to be.

Guided tours (like kayaking through mangroves or sea life encounters) are popular and often have limited slots each day. While mid-May is slightly before the peak summer crowds, weekends and popular time slots can fill up quickly.

  • Kayak mangrove tours – Many operators allow walk-ups if space is available, but morning tours are very popular and can sell out. Booking at least a day or two in advance is safer.
  • Sea life encounter cruises – Tours that involve snorkeling or wildlife encounters often have limited capacities due to boat size. Booking in advance is recommended if you have specific days in mind.
  • Dining – For casual, non-fine-dining restaurants, reservations are generally not required, but busy lunch spots or highly rated places can have a wait, especially on weekends.

If you prefer a flexible itinerary:

  • Book your must-do tours in advance to guarantee a spot. You can leave restaurants and some beach time unplanned.
  • Check cancellation policies – Many tours allow changes or cancellations 24–48 hours in advance, giving you flexibility.
  • Consider arriving early for popular activities if you prefer not to book, but this can be stressful if you’re relying on last-minute availability.

Overall, a loose itinerary is possible, but for guided tours and popular activities, booking at least a day or two ahead is strongly recommended to avoid disappointment. Casual dining and beach activities can remain spontaneous.

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