Vacation Charter Packages
Sail, Explore, Unwind
Escape the everyday and step into an unforgettable journey with Captain Dave’s Vacation Charter Packages. These multi-day charters offer the perfect way to immerse yourself in the wonders of the sea, exploring beautiful destinations from the comfort and adventure of a sailing yacht. Ideal for those new to yachting or seasoned travelers, our vacation packages bring you closer to pristine beaches, secluded coves, and vibrant island culture.
7 or 14 Day Charters
Greece – Saronic Islands
Embark on a week-long sailing journey through Greece’s stunning Saronic Islands, with Captain Dave guiding you to hidden coves and charming coastal towns. Each stop promises a blend of history and local culture:
Aegina: Wander through historic sites like the Temple of Aphaia and enjoy Aegina’s famous pistachios.
Poros: Swim in secluded bays and explore pine-covered hills.
Hydra: Step back in time on this car-free island filled with art galleries and waterfront cafes.
Spetses: Discover the elegant atmosphere, boutique shops, and tranquil beaches.
Ermioni: Conclude in this quiet village, rich in history and natural beauty.
What’s Included: Professional skipper, tailored itineraries, and local insights.
Greece – Ionian Islands
Set sail on a week-long journey through Greece’s lush Ionian Islands, known for their stunning greenery, turquoise waters, and rich mythology. With Captain Dave as your guide, experience both vibrant islands and serene bays at your own pace:
Lefkada: Begin your adventure in Lefkada, famous for its stunning beaches and clear waters. Swim in Porto Katsiki, explore charming villages, and enjoy local cuisine.
Ithaca: Visit the legendary home of Odysseus, where history and myth blend seamlessly. Wander its peaceful harbors and take in the island’s unique, rugged beauty.
Kefalonia: Marvel at Kefalonia’s turquoise beaches and dramatic landscapes. Discover hidden caves, Venetian castles, and the charming town of Fiskardo.
What’s Included: Professional skipper, tailored itineraries, and local insights.
Greece – Sporades Islands
”Mamma Mia” Tour
Live out your “Mamma Mia!” dreams in the magical Sporades Islands, where sparkling waters and lush landscapes set the perfect scene for adventure. With Captain Dave as your guide, explore the islands that inspired the iconic movie, visiting charming harbors, hidden beaches, and quaint villages that capture the spirit of Greece.
Skopelos: The famous island from Mamma Mia!, where you can visit the stunning Agios Ioannis chapel, perched high above the sea. Wander the winding streets of Skopelos town and enjoy the island’s relaxed, cinematic charm.
Skiathos: Known for its beautiful beaches and vibrant atmosphere, Skiathos is perfect for a blend of relaxation and exploration. Enjoy golden sands and lively tavernas, then explore hidden coves by boat.
Alonissos: Discover this quieter, picturesque island, home to the National Marine Park. It’s ideal for nature lovers, with crystal-clear waters, secluded beaches, and scenic hiking trails.
What’s Included: Skilled skipper, flexible itinerary, and “Mamma Mia!”-inspired stops for an unforgettable Greek island experience.
Greece – Cyclades Islands
Mykonos & Santorini
Set sail with Captain Dave through the enchanting Cyclades, an island group where each stop offers a different take on Greek charm, culture, and beauty. From the glamorous scenes of Mykonos to the awe-inspiring sunsets of Santorini, experience the best of Greece’s iconic islands along with hidden gems in the smaller Cyclades.
Mykonos: Begin your journey on the “Island of the Winds,” where vibrant nightlife, stylish boutiques, and iconic windmills create an unforgettable energy. Lounge on golden beaches by day and explore Mykonos Town’s winding, lively streets by night.
Santorini: Known worldwide for its breathtaking sunsets and whitewashed cliffside villages, Santorini is a highlight of any Cyclades adventure. Stroll through Oia, savor local wines, and take in views that capture the magic of the Aegean Sea.
Paros: Find the perfect blend of tradition and trendiness on Paros. Known for its charming harbor towns and sandy beaches, Paros offers everything from lively beach clubs to quiet, authentic villages.
Naxos: Explore the largest island of the Cyclades, filled with lush landscapes, ancient temples, and rich history. Known for its fresh local produce, Naxos also boasts some of the best beaches in Greece.
The Smaller Cyclades: Discover the tranquility of lesser-known islands like Koufonisia and Iraklia, where quiet coves, local tavernas, and pristine beaches offer a peaceful escape from the crowds.
What’s Included: Professional skipper, customizable itineraries, and insider knowledge to create a personalized Cyclades experience.
Note: This route is only available in late Autumn.
Italy & French Riviera
Embark on an unforgettable voyage along the iconic coasts of Italy and the French Riviera, where glamour, history, and breathtaking scenery come together. From the pastel-hued villages of the Cinque Terre to the glitzy harbors of Monaco, let Captain Dave guide you through Europe’s most stylish and storied shores.
Cinque Terre, Italy: Start your journey along Italy’s stunning Ligurian coast, where the colorful villages of Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore dot the cliffs. Marvel at the dramatic landscapes, sample local wines, and experience the charm of these UNESCO-protected villages.
Portofino, Italy: Known for its elegance and celebrity appeal, Portofino combines luxury with the beauty of a charming fishing village. Stroll its chic boutiques, visit historic sites, and soak up the Mediterranean allure of this iconic Italian gem.
Monaco: Enter the glamour of Monaco, where sleek yachts and high-end casinos meet stunning Mediterranean views. Explore the famed Monte Carlo district, take in the royal history, and enjoy world-class dining and entertainment in the heart of the Riviera.
Nice, France: The gateway to the French Riviera, Nice offers a blend of Old-World charm and French sophistication. Wander along the Promenade des Anglais, savor Provençal cuisine, and soak up the sun on the region’s pebbled beaches.
St. Tropez, France: Known for its lively atmosphere and sun-drenched beauty, St. Tropez is perfect for those seeking both relaxation and excitement. Lounge on golden beaches, explore the bustling market, and enjoy a taste of Riviera nightlife.
What’s Included: Experienced skipper, tailored itineraries, and local recommendations to immerse you in the Mediterranean lifestyle.
Note: Limited availability, discuss for options.
Southern Italy – Naples to Sicily
Embark on an adventure from Naples to Sicily, experiencing some of Italy’s most captivating coastal gems along the way. This journey combines ancient history, dramatic landscapes, and the raw beauty of volcanic islands, making for an unforgettable Mediterranean escape.
Naples: Begin your voyage in Naples, a city steeped in history and famous for its vibrant energy and rich culinary traditions. Visit the ancient ruins of Pompeii, enjoy authentic Neapolitan pizza, and take in views of Mount Vesuvius as you set sail southward along the Italian coast.
Tropea: Sail to the stunning coastal town of Tropea, known for its dramatic cliffs, medieval architecture, and sandy beaches. Wander the narrow streets, visit the famous Santa Maria dell’Isola monastery, and enjoy local delicacies like red onion and nduja, a Calabrian specialty.
Stromboli: Next, head to the volcanic island of Stromboli, one of the Aeolian Islands. This active volcano offers an awe-inspiring view, especially at night when the “Sciara del Fuoco” (Stream of Fire) lights up the sky. Enjoy a hike up to the observation point or relax in the charming village below, where black-sand beaches and traditional Sicilian hospitality await.
Lipari: Continue to Lipari, the largest of the Aeolian Islands, known for its beautiful beaches, historic castles, and archaeological sites. Wander through Lipari’s old town, visit the Aeolian Archaeological Museum, or relax on Canneto Beach, soaking in the beauty of this volcanic archipelago.
Taormina, Sicily: Conclude your journey in Taormina, Sicily’s jewel on the eastern coast. With its ancient Greek theatre offering views of Mount Etna and the sparkling Ionian Sea, Taormina combines historical intrigue with natural beauty. Stroll through the town’s picturesque streets, dine on Sicilian specialties, and toast to your adventure with a glass of local Etna wine.
What’s Included: Professional skipper services, customizable stops, and local insights for an authentic Italian experience.
Note: Limited availability, discuss for options.
