St. Augustine Old Town - Tours by Air & Boat


Fly high in a 1930s bi-plane as you loop and roll over St. Augustine. A splurge, yes, but a memorable activity for just the two of you - especially at sunset.


The only ship of its kind in St. Augustine, you'll see it from a distance and want be on board. Enjoy a day or sunset cruise aboard this 76-foot Tall Ship (or - with good timing - a Full Moon sail) with a group of up to 49 people. Kids are very welcome on the day cruise and will love imagining they're savvy sailors, dodging blockades in the 1800s. Will you help to raise the sails, or just sit back, enjoy a drink and keep watch for dolphins?

  • Website:
  • Address: 111 Avenida Menendez, Suite. D, St. Augustine, FL 32084
  • Children: The day cruise is suited for kids
  • Keep in mind: While beautiful, it can be windy during the winter. Dress appropriately for the water.


Leave your pregnant wives and elderly parents content at the beach while you, and any thrill-seeking buddies (or teenagers), hang on tightly for this fast-as-lightning zip across St. Augustine's water. If you're pressed for time, you'll see plenty during an hour's cruise - including the St. Augustine Pier and the Castillo de San Marcos (page 22). Fancy sightseeing at speed? You won't go faster than this.

  • Website:
  • Address: 111- E Avenida Menendez, Slip 73, St. Augustine, FL 32084
  • Children: Four and up
  • Keep in mind: Military discounts available


A slow and steady cruise, sit at tables on deck and look for dolphins. If you choose a later sailing, you get a sunset thrown in for free.

  • Website:
  • Address: 4125 Coastal Hwy., St. Augustine, FL 32084
  • Children: Very family-friendly
  • Pets: Pet-friendly
  • Keep in mind: Check the website for coupons