Land and Sea Packages

Join us by LAND AND SEA to experience all the Best that St. Augustine has to Offer!

St. Augustine Sailing has joined St. Augustine Experiences to present you with unique excursions that bring the city to life on foot and onboard! See St. Augustine up-close and personal through guided walking tours that focus on local specialties, and take in the sights of St. Augustine from the sea as you board a luxury sailing yacht for a private 2-hour charter.


Start the day winding your way through historic downtown discovering St. Augustine’s sweeter side at five local sweet shops. You’ll step back in time with tales of mom and pop candy shops, local bakeries, and why we love the nation’s oldest city. Our personable guides share fascinating stories about local history as well as the reasons why we find chocolate so addicting!
The treats continue with beer and wine as you set sail for 2-hours of salty sea life aboard a luxury yacht. You’ll be mesmerized by both the scenery, the sailboat, and the salt air as you see the city from a whole new perspective. What a wonderful finale to the sweetest of days!


It’s anchors aweigh for adventure on the high seas aboard a luxury yacht complete with a selection of fun cocktail mixes and local craft brews! Rest your sea legs as you sip and sail on your 2-hour luxury sailboat charter, while feasting on the sights of St Augustine from a uniquely inspiring perspective along the Intracoastal Waterway.

After your escapades on the water, stroll around the charming streets of the nation’s oldest city learning how the business of beer has evolved in St Augustine to become one of the fastest growing and most highly regarded beer producing regions in the country. As part of this journey, you visit notable landmarks, unique brew pubs, and state-of-the-art tap rooms while sampling an abundance of delicious beer along the way.


What could be better than the perfect pairing of St Augustine sea and land experiences, starting with light bites and Mimosas onboard a luxury yacht. Imagine seeing the city of St Augustine bathed in morning light as you relax and soak up the scenery when you set sail on a 2-hour charter excursion.

Back in port, it’s off to the beautiful downtown historic district for an immersion in St Augustine’s eclectic culinary scene. You’ll visit three of the city’s best venues for imbibing with friends in America’s oldest city, savoring wine, charcuterie boards, and colorful cocktails. Between delicious drinks and food, view sites such as the Old City Gates, Castillo de San Marcos, Plaza de la Constitución, and America’s oldest thoroughfare, Aviles Street.

This experience is a perfect pairing that will send you on an unforgettable surf and turf exploration of charming St Augustine!

Meet Your Crew

Chuck Points
Cindy Campbell Taylor
Chief Brand Builder