Culinary Cruises: Brunch, Dinner, Wine Tastings & More on the Water

After an unforgettable kayaking experience, why not take your adventure back out to the water for food and drinks? Whether you’re in the mood for a relaxed brunch, a gourmet dinner at sunset, or a fun wine or rum tasting, these cruises offer the perfect blend of food, drink, and scenic beauty.

Discover a new way to experience St. Augustine’s waterways. Book your culinary cruise today and indulge in a unique dining adventure on the water! 

$45
Wine Tasting Cruise

Wine Tasting Cruise



1.5 Hours • Ages 21+ | Taste a curated selection of wines or craft beer paired with charcuterie and stunning waterfront views.

Enjoy an unforgettable evening on the water with a charcuterie spread and six curated wines or local craft beers. Take in stunning views of St. Augustine’s iconic landmarks like the Castillo de San Marcos and Lighthouse. Elevate your night with gourmet delights and scenic beauty.

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$40
Rum Runner Cruise

Rum Runner Cruise

2 Hours • Ages 21+ | Sip rum cocktails and immerse yourself in the lively and interactive pirate history of St. Augustine.

Ready for a wild night? This adult-only Rum Runner Cruise is bold, bawdy, and anything but tame! Our pirate crew delivers raunchy skits, songs, and jokes tailored to your tastes. How explicit? That’s up to you! This unique party on the water isn’t for the faint of heart. Grab your crew and book now for an unforgettable night!

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$149
Sip & Sail Cruise

Sip & Sail


1 Hour • Ages 21+ | Relax with a refreshing beverage as you sail into the sunset aboard a luxury sailing yacht.

Gather your friends for an unforgettable sailing adventure! Whether you’re sipping mimosas on a morning cruise or sampling 3-5 seasonal wines at sunset, this luxurious yacht tour offers stunning views of St. Augustine’s historic waterways. Relax, indulge, and make memories on the water—book your Sip & Sail experience now and elevate your day to extraordinary!

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$179
Shared Brunch Sail Experience

Shared Brunch Sail Experience


Enjoy a delicious brunch with friends as you sail through calm morning waters.

Hop aboard our luxury yacht for a one-of-a-kind brunch sail through St. Augustine! Enjoy a delicious individually wrapped brunch and mimosas while soaking in stunning views from the water. With a private captain and crew handling every detail, you can relax, indulge, and make lasting memories.

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$1,500
Private Luxury Brunch Sail

Private Luxury Brunch Sail


Treat your family to a private, luxurious brunch experience on the water.

Enjoy a delectable chef inspired brunch aboard our luxury yacht with stunning views of St. Augustine. Your private captain and crew handle all the details, ensuring you relax, savor the meal, and enjoy time with loved ones. Includes family-style brunch and bottomless mimosas on our luxury catamaran.”

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$1995
Private Sunset Dinner Cruise

Private Sunset Dinner Cruise


Indulge in a gourmet dinner while taking in the beauty of a St. Augustine sunset.

Set sail for an unforgettable dining experience aboard a private luxury yacht. Enjoy front-row views of St. Augustine’s bayfront as the sun sets, while indulging in a Chef-prepared 4-course dinner with wine, beer, or other beverages. Relax and savor this exclusive 3-hour charter with your guests!

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Discover St. Augustine’s Most Luxurious Culinary Cruises: Sipping, Sailing, and Scenic Beauty

St. Augustine’s ancient waterways offer more than just picturesque views—they present the perfect setting for an extraordinary culinary journey. Imagine sailing through history, with gourmet food and drink in hand, as you take in iconic landmarks like the Castillo de San Marcos and the St. Augustine Lighthouse. From exclusive wine tastings to indulgent brunches and sunset dinners, these carefully curated cruises offer unforgettable experiences that combine luxury, relaxation, and adventure.

Imagine gliding through St. Augustine’s iconic waterways, a glass of fine wine in hand, a fresh sea breeze in your face, and the sun slowly dipping behind the historic skyline. Whether you’re looking to savor a chef-curated meal, sip on expertly selected wines, or indulge in a relaxing brunch on the water, these exclusive culinary cruises will elevate your St. Augustine experience to new heights. Join us for a luxurious and unforgettable journey that blends gourmet food and drink with the beauty of the Ancient City.

Wine Tasting Cruise

For those who appreciate the finer things in life, the Wine Tasting Cruise, guests can expect to embark on a 1.5-hour voyage through St. Augustine’s storied waterways. While passing by historic sites such as the Castillo de San Marcos and the St. Augustine Lighthouse, passengers will enjoy a curated selection of fine wines or local craft beers, paired with an artisanal charcuterie spread. This cruise is designed for those who appreciate the finer things in life—each sip of wine, each taste of charcuterie, perfectly complements the scenic beauty of the city’s bayfront. As the sun sets, the soft hues reflect off the water, transforming the cruise into a serene, indulgent experience. The Wine Tasting Cruise offers a harmonious blend of history, culture, and refined tastes.

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Rum Runner Cruise: Pirate-Themed Fun with a Splash of Rum

For those seeking a livelier adventure, the Rum Runner Cruise promises two hours of spirited fun on the water. This adults-only experience is a riot of rum cocktails, rowdy entertainment, and pirate-themed antics. Led by a pirate crew skilled in delivering raunchy skits, jokes, and songs, the cruise brings St. Augustine’s pirate history to life with plenty of laughs. Guests on the Rum Runner Cruise are encouraged to join in the fun, as the interactive show is fueled by the audience’s energy. As the sun dips behind the city, the cruise becomes a lively evening of music, humor, and plenty of rum. It’s a perfect choice for those who enjoy bold entertainment, and it’s unlike any other cruise in the region.

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Sip & Sail: A Relaxing Escape on the Water

The Sip & Sail cruise offers a more relaxed and refined experience, perfect for unwinding as you sail through St. Augustine’s calm waters. This one-hour yacht tour is a great way to start your day with a mimosa in hand, or to toast the evening with a selection of seasonal wines. As the yacht glides along the bayfront, guests can expect stunning views of St. Augustine’s historic landmarks, including the Bridge of Lions and the iconic Lighthouse. Whether it’s the morning sun or the evening’s golden glow, the Sip & Sail cruise creates a serene atmosphere for reflection, indulgence, and pure enjoyment of the city’s natural beauty.

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Shared Brunch Sail Experience

There’s no better way to start the day than aboard a Shared Brunch Sail. Gather your friends or family and set sail through calm morning waters while enjoying a delightful brunch, perfectly curated for your journey. Picture an individually wrapped gourmet brunch paired with mimosas, enjoyed on deck as the sun rises over St. Augustine’s historic skyline. With a private captain and crew catering to your needs, all you have to do is relax and savor every moment. This experience is perfect for anyone looking to combine relaxation, great food, and stunning views.

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Private Luxury Brunch Sail

For those seeking the ultimate indulgence, the Private Luxury Brunch Sail delivers an unforgettable experience. Imagine cruising aboard a sleek, luxurious yacht with your closest friends or family, savoring a chef-prepared, family-style brunch with bottomless mimosas. As you sail through St. Augustine’s picturesque waters, your private captain and crew ensure every detail is handled, so you can relax, dine, and create lasting memories. With sweeping views of the Ancient City and the tranquility of the open water, this sail is the epitome of elegance and luxury.

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Private Sunset Dinner Cruise

If there’s one way to top off a perfect day in St. Augustine, it’s with a Private Sunset Dinner Cruise. As the sun dips below the horizon, casting a golden glow over the city, you’ll enjoy a chef-prepared four-course dinner aboard a private luxury yacht. With a front-row seat to one of the most beautiful sunsets you’ll ever witness, and a selection of fine wines, beer, and other beverages to complement the meal, this three-hour cruise is a feast for the senses. Ideal for special occasions, romantic getaways, or simply treating yourself to something extraordinary, this is a dining experience like no other.

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Why Choose a Culinary Cruise in St. Augustine?

St. Augustine is known for its rich history and stunning coastal views, but experiencing it from the water takes things to another level. Whether you’re a foodie, a wine lover, or simply someone looking for an extraordinary adventure, these cruises combine the best of both worlds: indulgence and exploration. From intimate dining experiences to lively, adult-only entertainment, each cruise offers something unique.

Elevate your next visit to the Ancient City by booking one of these exclusive culinary cruises and treat yourself to an experience you’ll never forget.

dinner cruises in St Augustine on sailboats luxury yachts

The Timeless Dance Between Sailing and the Sea’s Bounty: A Culinary Voyage Through History

For centuries, the ocean has provided not only a means of exploration and discovery but also sustenance. As humankind ventured further into the unknown, the art of sailing and the craft of preparing food on the water evolved in tandem. Today, these traditions converge in an entirely new way—through water-based dining and drinking experiences that transport you to a bygone era, all while offering modern luxuries and gourmet cuisine.

A Legacy of Exploration and Survival

The history of sailing is one of adventure, discovery, and survival. Ancient mariners like the Phoenicians, Greeks, and Vikings braved the open seas, navigating by the stars and the wind. For these sailors, the sea was a vast and unpredictable place, but it was also a provider. Early seafarers developed ingenious ways to store and prepare food aboard their ships, often turning to the ocean itself for fresh fish, crustaceans, and seaweed to sustain them during long voyages.

Salted and dried fish were staples of these early diets, along with hardtack (a simple biscuit made from flour and water), fermented vegetables, and whatever fresh fruits could be kept from spoiling. The cuisine of the sea was born out of necessity, but it also laid the foundation for culinary traditions that would flourish centuries later.

From Practical to Indulgent: The Birth of Seafaring Cuisine

As technology advanced and ships grew larger and more capable, life aboard a vessel became less about mere survival and more about enjoyment. The great age of exploration, beginning in the 15th century, brought with it a new focus on the pleasures of food at sea. European explorers, such as Christopher Columbus and Vasco da Gama, not only charted new territories but also traded spices, fruits, and other exotic ingredients that would transform maritime cuisine.

By the time of the 18th century, the concept of dining aboard ships had shifted dramatically. The officers and wealthy passengers of naval and merchant vessels dined in relative luxury, feasting on fresh seafood caught from the surrounding waters, complemented by imported delicacies such as wines, cheeses, and breads. Lavish meals became part of the allure of sea voyages, and the pairing of good food with scenic ocean views became a tradition that still thrives today.

The Modern Culinary Voyage: Dining Afloat

Today, water-based dining experiences have taken this maritime tradition to new heights. Far removed from the humble salted fish and hardtack of centuries past, modern sailors—and their guests—are treated to gourmet meals prepared by chefs who specialize in cuisine that celebrates both the sea and its bounty.

Imagine this: You board a sleek sailing yacht, greeted by the salt air and the promise of an evening spent on calm waters. As the vessel sets sail, you’re treated to the sight of an expert chef at work in the galley, preparing fresh seafood dishes paired with seasonal ingredients. Your senses are tantalized by the smell of grilled fish, garlic butter drizzling over lobster tails, and the bright, fresh aroma of citrus-infused salads.

This is what makes today’s water-based dining experiences so special—they offer not only the chance to enjoy a fine meal but also the opportunity to experience the connection between the ocean and the food on your plate.

A Feast from the Sea: The Cuisine of Sailing

There is something timeless and romantic about dining on the water. Whether it’s a seafood feast or a wine tasting cruise, the ocean becomes part of the experience, with its rhythm and sounds creating a natural, soothing backdrop. In modern water-based dining, fresh seafood often takes center stage. From oysters harvested just miles away to delicately prepared shrimp, the flavors of the sea are brought to life in dishes that speak to the region’s unique maritime history.

On a sunset dinner cruise, for instance, you might begin with a platter of briny oysters, followed by a delicate, lemon-scented halibut or pan-seared scallops served with roasted vegetables. These dishes are complemented by carefully selected wines or craft beers that pair perfectly with the briny, fresh flavors of the ocean. Each bite is a reminder of the ancient relationship between humanity and the sea—a relationship built on respect, survival, and now, indulgence.

The Art of Pairing: Wine, Rum, and the Sea

Of course, no maritime dining experience would be complete without the right drink in hand. Sailors of old often drank rum, wine, and beer, not just for pleasure but for practicality—these beverages stayed fresh longer than water and were easy to store aboard ship. Today, wine tastings and rum cruises pay homage to this tradition, offering guests a chance to sip their way through history while enjoying the coastal views.

A Wine Tasting Cruise on a luxury yacht, for example, might feature locally sourced wines paired with cheeses, fruits, and even seafood dishes. Each sip complements the sights around you, as the colors of the sunset reflect off your glass and the city’s historic landmarks glow in the distance. Similarly, a Rum Runner Cruise might evoke the spirit of the pirates who once prowled these waters, with rum-based cocktails served alongside lively tales of pirate lore.

Why a Water-Based Culinary Experience is Unmatched

What makes these dining and drinking experiences so special isn’t just the food or the views—it’s the combination of both, creating a sense of escape that you simply can’t replicate on land. As you sail past historic landmarks, the sea breeze mingles with the aromas of your meal, heightening your senses and creating an immersive experience that transports you to a different time.

Whether you’re indulging in a leisurely brunch on a Luxury Brunch Sail, sipping wine on a Private Sunset Dinner Cruise, or enjoying a lively rum tasting with friends, dining on the water connects you to the ocean in a way that feels both timeless and deeply modern. It’s a celebration of the sea’s bounty, the art of sailing, and the simple pleasure of a good meal enjoyed in the right setting.

Set Sail on Your Own Culinary Journey

For those looking to experience the romance of sailing and the indulgence of fine dining, there is no better way than to book a water-based culinary experience. These cruises offer a perfect blend of history, culture, and cuisine, allowing you to explore the waterways of St. Augustine or other coastal cities in a way that elevates both the palate and the soul.

As you sit back, drink in hand, and watch the coastline drift by, you’ll understand why sailors throughout history have always found comfort—and joy—in the union of the sea and its cuisine. Whether it’s a casual brunch or an elegant dinner, a wine tasting or a rum-soaked pirate adventure, these experiences are sure to leave you with memories as rich as the food itself.