Ranked #8 in the U.S.A. on TripAdvisor, our award-winning Wine, Cocktail & Food Experience is the ultimate way to discover why St. Augustine was named Southern Living’s #1 Small Town Food City. In a relaxed, small-group setting, you’ll explore the city’s historic streets with a local guide who quickly becomes a new friend, stopping at some of our favorite restaurants, bars, and boutique spots along the way. Indulge in handcrafted cocktails, boutique wines, and dishes worth talking about, carefully selected to highlight the best flavors this foodie city has to offer. Each stop is thoughtfully chosen to complement the next, creating a journey of taste, story, and history. From savory bites to perfectly paired drinks, laughter to insider tips, this tour isn’t just about tasting, it’s about discovering the city through its flavors. By the end, you’ll understand why locals and visitors alike keep coming back.

Get lost with the glorious wonder of St. Augustine's attractions. Our Adults Only 21+ option on vessel GREAT BLUE HERON is specifically made for the adult crowd and welcomes anyone 21 and older. We have a beer and wine bar on board, with a fantastic selection, and non-alcoholic beverages available for purchase as well. Feel free to bring small appetizers and snacks on board, but no outside alcohol allowed please! The Sunset Eco Cruise option on our vessel OSPREY is family friendly for ages 7+. This vessel also has a bar on board for purchase of drinks.

Join local guides on a tour of St. Augustine's walled city featuring the city's 450-plus-year history. This 90-minute, personally narrated tour occurs on the comfort and ease of an electric cart. This private tour is for groups of 1 to 7 people, ages 7 and up. Your group will not be combined with other people. Seatbelts and no alcohol permitted per regulations. This tour is a detailed and educational tour of historic St. Augustine. Focusing on the colonial walled city of St. Augustine, highlights of the tour include the Castillo de San Marcos, Flagler's Hotels and Churches, the Oldest House, the Plaza, and Aviles St. During the tour, your guide will share the interesting and storied history of St. Augustine.

Experienced Naturalist on board as your guide, you will be sure to leave with a new passion for our marine life. This part of Florida is beaming with estuary delights, all of which come together to form quite an ecosystem. We regularly see dolphin playing and hunting during our tours! Although nature is never guaranteed, we bring you to the best locations to observe the wildlife including dolphins, sea turtles and Florida birds such as the pelican, osprey and roseate spoonbill. This tour is great for any age! Our vessels OSPREY and GREAT BLUE HERON have a bar on board with an excellent variety of beer and wine including mimosa's! We also have snacks and soft drinks available! No outside alcohol allowed, but you are welcome to bring your own food and drink as long as non-alcoholic. On the ISLAND BREEZE, you are more than welcome to BYOB! We have plenty of free parking at our location and a restroom on board for your convenience.

A 'Progressive Style', Seated Food Adventure (Strolling): This tasting experience takes you to four (4) handpicked venues — with each stop offering a dish featuring bold flavors, unique pairings, and unforgettable hospitality. From savory beginnings to sweet endings - you will enjoy one bite, one sip, and one story at a time. Highlights: CULINARY DELIGHTS: Each dish is thoughtfully paired with an exquisite wine or artisanal cocktail (pairings are subject to vary). INSIDER INSIGHTS: Get the scoop from a local culinary insider who'll be your guide throughout the journey. LEISURELY EXPLORATION: Stroll through St. Augustine's charming streets, soaking in its beauty and vibrant food scene, at casual pace. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.

Start your evening out by winding down on the water! Let us take you on an adventure to the bay-front, where our experienced guides will give you a tour on nature, wildlife, and famous historic landmarks. We are lucky to see a plethora of wildlife during this cruise including dolphin and birds like the famous Roseate Spoonbill! Remember, this entertaining cruise is during the sunset in the winter months, and in the early evening the rest of the year! You will receive a presentation and sampling of 6 fabulous wines (including local favorites) as we cruise past the famous historic bayfront. Our bar on board has an excellent variety of beer, wine, bubbly and soft drinks for purchase at very reasonable prices. There are no other tours like this in St. Augustine!

Step into 460 years of history on the most popular walking tour of St. Augustine. On this engaging small-group experience, explore America’s oldest city with a knowledgeable local guide who is part-historian and part-new friend and brings the streets, buildings, and stories to life. Discover how five different flags once flew above the Castillo de San Marcos and shaped the city’s unique past. Walk along the historic harbor, take in views of the oldest masonry fort in the United States, and explore the oldest grid street system in the country. Along the way, you’ll learn about the people who left their mark on St. Augustine, including Juan Ponce de León, Pedro Menéndez de Avilés, Henry Flagler, and Dr. Martin Luther King Jr. Designed to orient you to the city, this tour gives you the context and confidence to explore St. Augustine on your own after the walk, and we also highlight our favorite spots to eat and drink along the way in the "Best Food Town in the South"!

This is a food and wine tour that celebrates our history, today. Not only do we focus on local establishments to provide the best of the true St. Augustine cuisine, our licensed guides are fully knowledgeable in all aspects of our town's history. This will immerse our guests with an understanding of the people who have resided here throughout the ages as well as the food they've enjoyed. Wine or beer are provided with each food stop.

A 'Progressive Style' Foodie Adventure (ROLLING): This unique food tour invites you to explore the vibrant neighborhoods BEYOND the historic core. Satisfy your appetite with four progressive style stops, each offering a seated tasting experience in one of our city’s hidden gems. From savory starters to sweet finishes, every course is paired with a boutique wine or artisanal cocktails. Bonus: arrive via the comfort of our chauffeured vehicle. Highlights: ELEVATED EXPERIENCE: Delve into St. Augustine's culinary scene with exclusive tastings at four (4) top-tier venues. LOCAL INSIGHT: Benefit from insider knowledge shared by a local culinary guide. CHAUFFEURED COMFORT: Explore the city's charm in comfort aboard our open-air electric vehicle. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.

Best first way to see St. Augustine. See the highlights of St. Augustine the easy way on a small group golf cart tour. The best first way to see St. Augustine is with Explore Tours and PickUps, especially if it’s your first time visiting. You’ll cover more ground than walking tours while enjoying a personal, guided experience through the nation’s oldest city. Perfect for couples, families, and anyone wanting a relaxed but informative overview before exploring on their own. Cruise through the historic district while learning the stories behind St. Augustine’s most important landmarks. Your guide shares history, local insight, and recommendations so you know exactly what to do after the tour. Many guests choose this as their first activity to get a feel for the city and often search for us again after to plan future visits or recommend us to friends.

There is not a better way to witness the sunset of St. Augustine, then on our boat tour. Our tour guides will educate you on some of the historic sites in Saint Augustine. While we’re on the water, hopefully we will see dolphins playing in the water.

The Wicked St. Augustine tour delves into the unwritten history of the nation's oldest city. You will hear stories of the illicit industries that made the town a financial success, all while avoiding the reputation of a sinful city. From its founding St. Augustine had a thriving tavern, gambling and prostitution industry, even while portraying a city founded on religious principles. See the locations of high stakes gambling, speak easy taverns, and private clubs which skirted around the laws of the day, like prohibition. Learn how the political powers knew of these activities, secretly supported their providers, all while keeping a squeaky clean image.

Support small local businesses and see more availability by looking us up directly on the web at 'ExploreToursAndPickUps' dot com. Personable tour of the holiday light display with a twist of history throughout the Historic District of St. Augustine! Venture down the smaller streets with our unique carts that others can not pass through! We venture off the beaten path which display beautiful holiday decorations at the famous bed & breakfasts!

Support small local businesses and see more availability by looking us up directly on the web at 'ExploreToursAndPickUps' dot com. Personable tour of the holiday light display with a twist of history throughout the Historic District of St. Augustine! Venture down the smaller streets with our unique carts that others can not pass through! We venture off the beaten path which display beautiful holiday decorations at the famous bed & breakfasts.

Nightly Spirits Historic Haunted Booze & Boos Tours look at some of the spookiest places in St. Augustine while allowing time to really enjoy the "spirits" along the way. Our tours stop at several different local bars and give you a look into their haunted and historic past. The Ancient City has a rich history, filled with tales of epic battles, violent bloodshed, and eccentric individuals. St. Augustine is notoriously haunted. If you’re brave enough to meet some ancient ghosts, join Nightly Spirits for an up-close look at just what makes this city so spirited! Come try us out, this isn't your ordinary ghost tour, and we are confident that you will love our pirate guides!

WEEKENDS: Join us for an ultimate Brunch Tour experience in the heart of St. Augustine! Indulge in four of the city's most sought-after brunch spots, each offering a unique and delectable menu. Whether you're a local or a visitor, our tour promises to be a delicious adventure! BRUNCH BONANZA: Dive into the flavors of the most beloved brunch spots, indulging in everything from savory dishes to sweet treats. BRUNCH BUNCH CRUISE: Relax & enjoy the ride in our chauffeured open-air electric vehicle, with a local culinary insider, while soaking in the city's sights and sounds. BRUNCH BLISS: Don't miss out on this brunch affair, complete with amazing libations, that promises to leave your tummy blissfully satisfied! Note: 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history & sightseeing sprinkled in.

Maybe you've taken one of the many tours offered in the wonderful city of St. Augustine previously. Would you like to hear about things you have NOT heard before? Learn something new for a change? Little secrets not usually talked about? Perhaps you will know some of them but pretty certain not all of them. This is not your typical "history" tour. You will hear about, and be shown, things on a variety of topics from history, crime, our many dead, buildings, plans, myths and truths. Group size limited to 12 for a more personal, intimate experience. This will take you little over a mile of walking, in the historic downtown area, and last about an hour. Tour takes place rain or shine.

As the sun dips below the horizon and darkness cloaks the ancient city of St. Augustine, the bayfront tells a different story—one of restless spirits, eerie legends, and the lingering echoes of centuries past. Join us on our Haunted History Cruise, where spooky tales and history comes alive on the water. Led by our captivating guides, you’ll cruise along the Matanzas Bay and hear chilling tales tied to America’s oldest city. From the haunted lighthouse to the ghostly shores of the Castillo, this journey is steeped in spine-tingling lore. What you should know: This cruise is geared towards adults and teens, 13 and up.

DINE LIKE A LOCAL ON ISLAND TIME with a laid-back, tropical party on wheels - as we explore the hidden gems of the BOULEVARD! Slip on your tropical attire & flip-flops as we cross the historic Bridge of Lions! What’s Included: AUTHENTIC VIBES: Indulge in mouthwatering culinary delights, at 4 of the island's hottest destinations, that unveil the authentic flavors beyond the bustling downtown! INSIDER INSIGHT: Expertly guided by a local insider who knows all the best spots to eat, drink, and chill. LAID BACK TRANSPORTATION: Chauffeured, open-air vehicle that'll have you feeling like you're cruising with Jimmy Buffett himself! PARADISE FARE: Dive into delectable island fare that offers a nice size lunch experience - plus games, limbo & more! Note: 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the cocktail and culinary scene with a bit of history & sightseeing sprinkled in.

ENJOY BRUNCH ALL WEEKEND LONG! This leisurely strolling tour blends food, fun, and history — a unique way to explore the oldest city while indulging in everyone’s favorite weekend tradition: brunch. Enjoy seated sweet and savory tastings at each stop, perfectly paired with craft mimosas, bold Bloody Mary's, or locally brewed coffee cocktails — elevated, yet effortlessly relaxed. BRUNCH BITES: Sweet and savory tastings at 4+ favorite brunch spots — each with their own delicious spin on morning classics. SIPS THAT SHINE: Perfectly paired pours, from crisp bubbly to bold Bloody Mary's and handcrafted cocktails. SCENIC STROLL: Explore the charming streets of the Nation’s Oldest City with a local foodie guide sharing hidden gems, history, and culture along the way. Note: 24-HOUR ADVANCED NOTICE REQUIRED FOR FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history & sightseeing sprinkled in.