Greece & Turkey Bike & Cruise: Sail the Greek Islands by Yacht

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

A VBT representative will greet you at the airport to start your adventure off right. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

After breakfast at your hotel, meet your local VBT guide at 8:30 a.m. in the lobby. After brief introductions, board a private motorcoach for a short drive to a scenic location outside Athens. Here, you will meet your trip leaders for a safety and bike-fitting session, followed by a relaxed warm-up ride designed to get you comfortable on your bike and acquainted with the terrain.

Later this afternoon, transfer to the stunning Wind Spirit, a graceful four-masted sailing yacht that will be your home for the week. Upon boarding, enjoy a light lunch provided onboard and the remainder of the afternoon settling into your cabin and exploring the yacht before setting sail. This evening, gather with your fellow travelers for a festive welcome dinner and toast the adventure ahead.

Today's Ride Choices

Morning: Warm-Up Ride — 12.3 km (8 miles)

What to Expect:

This short warm-up ride offers a chance to get comfortable with your bike. The route is flat and follows roads with some light traffic.

Cumulative Distance Range: 12.3 km (8 miles)

Included Meals: Breakfast, Lunch, Dinner

This morning, your yacht sails into the Bay of Argos, passing the Venetian-era Bourtzi island fortress. From the yacht, take a tender to the pier in Nafplio—a bustling port city during the Middle Ages and today one of the most romantic towns on the fabled Peloponnese Peninsula. It also serves as a gateway to some of ancient Greece’s most important classical sites.

Upon reaching the pier, meet your trip leaders and set out on a breathtaking ride through fertile farmlands, neatly tended olive groves, charming farmhouses, and remote churches, with rugged mountains rising in the distance. Your cycling journey leads you inland to Mycenae—the oldest city on mainland Greece—set amid a picturesque, rocky landscape.

At Mycenae, an archaeologist guide joins you for an in-depth tour of the site’s remarkable highlights, including the famed Lion Gate and the Treasury of Atreus, an incredible feat of ancient engineering.

After your visit, return by motorcoach to Nafplio and board your yacht. Enjoy a leisurely lunch onboard, then take advantage of the yacht’s amenities—perhaps lounging by the pool, relaxing at the spa, or heading into Nafplio to explore its cobbled lanes, neoclassical mansions, and inviting shops. The yacht sets sail in the early evening, followed by dinner onboard.

Today's Ride Choices

Morning: Nafplio to Mycenae — 25.1 km (16 miles)

What to Expect:

Today’s ride begins from the pier in Nafplio. Expect some traffic as you exit the port, with portions of the city ride following designated bike paths. There will be additional traffic near the archaeological site of Mycenae. The route is generally easy, with some rolling hills. Most of the cycling takes place on quiet country roads through small villages after leaving Nafplio.

Cumulative Distance Range: 25.1 km (16 miles)

Included Meals: Breakfast, Lunch, Dinner

Today, go ashore at Mykonos to explore one of the most magnificent of the Cyclades Islands. Join a local guide for an inspiring walking tour of the main town of Chora, passing iconic sugar-cube houses adorned with deep-blue doors and bougainvillea-draped balconies. Stroll the town’s coastal path, admire sweeping Aegean vistas, visit the island’s Archaeological Museum, and stop by the renowned thatch-roof windmills perched scenically on a ridge above the sea. Continue to the charming waterfront fishing houses of “Little Venice,” originally built to give fishermen direct access to the sea from their lower floors. Along the way, enjoy tastings at a local bakery and a café, where ouzo and meze are on the menu.

Return to your yacht for lunch. This afternoon, enjoy time to further explore picture-perfect Mykonos at your leisure. Dinner is once again served on board.

What to Expect:

Non-Biking Day

Included Meals: Breakfast, Lunch, Dinner

Arrive in the Turkish resort town of Kusadasi early this morning. After breakfast, a shuttle delivers you to the starting point of your ride, a thrilling route among some of Turkey’s seldom-visited villages and rural landscapes. This coastal region is a patchwork of farms, pastures, and hills, and it’s a true privilege to glimpse its beauty and tranquility from a bicycle.

Your afternoon is once again yours to follow your own whims. Relax on deck or in the hot tub if you wish or explore the colorful pier-side shops of Kusadasi. Later, join our private walking tour of the ancient, incredibly preserved streets of Ephesus, steeped in history and Biblical lore. Savor every moment over a magical dinner this evening under the moonlight, in the embrace of the historic site.

Today's Ride Choices

Morning: Turkish Countryside — 24 km (15 miles)

What to Expect:

Today, travel by bus from the port to the nearby foothills outside of Kusadasi, where your ride begins in the scenic Turkish countryside. You’ll follow mostly quiet country roads through orchards and forests, with occasional traffic as you pass through villages. After your ride, return to the port by bus. Note: Today’s ride will be on non-VBT bikes.

Cumulative Distance Range: 24 km (15 miles)

Included Meals: Breakfast, Lunch, Dinner

After another delicious breakfast on board, disembark in Patmos for a morning ride to one of the Greek Islands’ most sacred sites—the Monastery of St. John. This peaceful island is famously where St. John wrote the Book of Revelation in 95 AD. Your ride to the monastery is nothing short of inspiring, passing gleaming whitewashed villages, shady pine forests, and terraced farms. A few challenging hills reward you with sweeping sea views.

There will be time to explore the monastery, a vast complex of churches and courtyards revered as the centerpiece of the “Jerusalem of the Aegean.” Later, enjoy an invigorating downhill ride to a seaside taverna, where you’ll savor a lunch of Greek specialties.

In the afternoon, pedal back to the pier along a spectacular coastal route, then take the tender back to your yacht in time to relax before dinner.

Today's Ride Choices

Morning & Afternoon: Patmos Loop — 22.8 km (14 miles)

What to Expect:

Today’s ride begins and ends at the pier in Patmos. You’ll start with an uphill climb of approximately 5 km, navigating some traffic as you depart the port. At the top, enjoy a rest and a private walking tour of the Monastery of St. John in Chora. Afterward, continue your ride with a downhill stretch into the town of Patmos, then cycle on to a nearby beach for an included lunch. Following lunch, ride back to the pier to conclude the day. Today’s route follows the island’s primary two-lane roads, with traffic expected when entering and exiting the town of Patmos and the monastery’s parking area.

Cumulative Distance Range: 22.8 km (14 miles)

Included Meals: Breakfast, Lunch, Dinner

Boasting one of the most dramatic settings of any Greek Island, Santorini is an awe-inspiring spectacle of nature and culture. This crescent-shaped island sits on the rim of an ancient volcano whose caldera collapsed into the sea after a massive eruption. The main town of Fira clings to cliffs 1,000 feet above the water, offering breathtaking views.

Leave your bikes behind today as you join a local guide for an insider’s tour. Stroll among the terraced, whitewashed houses of Oia, adorned with iconic blue accents. Take in panoramic island views before continuing to the ancient Minoan city of Akrotiri, often called the “Pompeii of the Aegean,” which was destroyed by a volcanic eruption in 1600 BC. Pause for lunch at Canava Roussos Winery, where you’ll learn about ancient wine-making techniques and sample the island’s famed Assyrtiko wine.

After some time to browse the pedestrian streets of Fira, return to your yacht.

This evening, join your fellow travelers for a festive onboard BBQ dinner—a signature event aboard the Wind Spirit.

What to Expect:

Non-Biking Day

Included Meals: Breakfast, Lunch, Dinner

After a morning of scenic cruising in the Aegean, you arrive in Monemvasia—one of Europe’s oldest continuously inhabited fortified towns, founded in the sixth century. Once a vital medieval port, its massive rock formation served as a strategic lookout over the sea. Today, it remains an imposing and iconic wonder, connected to the mainland by a narrow isthmus.

After lunch, set out on a scenic coastal ride offering some of the most breathtaking views of your tour. Pedal along the shoreline, with the sparkling Aegean on one side and soaring cliffs on the other, and enjoy spectacular vistas of Monemvasia—often called “Greece’s Rock of Gibraltar.”

Your ride concludes at the main city gate of the walled village, where you’ll meet your leaders for a short walking tour through Monemvasia’s charming medieval streets.

If you wish, you’ll have a bit of free time to explore independently before returning to the yacht. This evening, celebrate your Aegean adventure during a private farewell reception and dinner on board.

Today's Ride Choices

Afternoon: Monemvasia to Agios Fokas Out-and-Back — 27.5 km (17 miles)

What to Expect:

Today’s ride begins at the pier in Monemvasia’s small port. After navigating some traffic as you depart, you’ll follow a scenic and flat coastal route to the picturesque seaside cemetery of Agios Fokas. Enjoy views of the rugged coastline and, on your return, sweeping vistas of Monemvasia—nicknamed “Greece’s Rock of Gibraltar.” The ride concludes at the main city gate of the walled village, where you’ll meet your leaders for a short walking tour.

Cumulative Distance Range: 27.5 km (17 miles)

Included Meals: Breakfast, Lunch, Dinner

VBT Air Package Guests:
After breakfast, disembark one final time and conclude your Aegean odyssey with a guided tour of the Temple of Poseidon. Perched dramatically above the Aegean on a high promontory, it was constructed around 700 BC to venerate the god of the sea. After time to marvel at the 2,700-year-old site during a walking tour, continue to a nearby seaside taverna for a lunch of fresh seafood and Greek dishes.

Later, arrive at the Sofitel Athens Airport Hotel, conveniently located within Athens International Airport, for your final night in Greece. You have the remainder of the afternoon and evening free to enjoy the hotel’s amenities, which include a heated indoor pool, sauna, massage services, and a modest gym. On-site dining features two restaurants offering gourmet and international cuisine.

VBT Post-Tour Extension Guests:
After breakfast, disembark one final time and conclude your Aegean odyssey with a guided tour of the Temple of Poseidon. Perched dramatically above the Aegean on a high promontory, it was constructed around 700 BC to venerate the god of the sea. After time to marvel at the 2,700-year-old site during a walking tour, continue to a nearby seaside taverna for a lunch of fresh seafood and Greek dishes.

Later, arrive at the Athens Airport for your evening flight to Istanbul. Upon arrival, you will be met and transferred to your hotel for the next four nights—the historic Pera Palace Hotel. Originally built to host passengers of the Orient Express, this opulent and centrally located property is set in the heart of Beyoğlu. Guests enjoy easy access to top bars, shops, and restaurants. Galata Tower and Istiklal Street are less than a 10-minute walk away, with Taksim Square just beyond. The nearby metro or Tünel funicular offers convenient access to Sultanahmet and the Old City.

Included Meals: Breakfast, Lunch

After an included breakfast this morning, simply walk across the street to the international departure terminal and check in for your return flight home.

Included Meals: Breakfast

You are responsible for making your own way to Athens, Greece, to begin your bicycling vacation. Your tour starts at 8:30 a.m. at the Electra Palace Hotel in Athens. A local VBT guide will meet you in the lobby holding a VBT sign. Please be dressed in your riding attire and have any essentials with you.

VBT highly recommends arriving in Greece at least one day prior to the tour start. This allows time to rest and recover from jet lag before beginning your sightseeing and cycling adventure.

After brief introductions, board a private motorcoach for a short drive to a scenic location outside Athens. Here, you will meet your trip leaders for a safety and bike-fitting session, followed by a relaxed warm-up ride designed to get you comfortable on your bike and acquainted with the terrain.

Later this afternoon, transfer to the stunning Wind Spirit, a graceful four-masted sailing yacht that will be your home for the week. Upon boarding, enjoy a light lunch provided onboard and the remainder of the afternoon settling into your cabin and exploring the yacht before setting sail. This evening, gather with your fellow travelers for a festive welcome dinner and toast the adventure ahead.

Today's Ride Choices

Morning: Warm-Up Ride — 12.3 km (8 miles)

What to Expect:

This short warm-up ride offers a chance to get comfortable with your bike. The route is flat and follows roads with some light traffic.

Cumulative Distance Range: 12.3 km (8 miles)

Included Meals: Lunch, Dinner

This morning, your yacht sails into the Bay of Argos, passing the Venetian-era Bourtzi island fortress. From the yacht, take a tender to the pier in Nafplio—a bustling port city during the Middle Ages and today one of the most romantic towns on the fabled Peloponnese Peninsula. It also serves as a gateway to some of ancient Greece’s most important classical sites.

Upon reaching the pier, meet your trip leaders and set out on a breathtaking ride through fertile farmlands, neatly tended olive groves, charming farmhouses, and remote churches, with rugged mountains rising in the distance. Your cycling journey leads you inland to Mycenae—the oldest city on mainland Greece—set amid a picturesque, rocky landscape.

At Mycenae, an archaeologist guide joins you for an in-depth tour of the site’s remarkable highlights, including the famed Lion Gate and the Treasury of Atreus, an incredible feat of ancient engineering.

After your visit, return by motorcoach to Nafplio and board your yacht. Enjoy a leisurely lunch onboard, then take advantage of the yacht’s amenities—perhaps lounging by the pool, relaxing at the spa, or heading into Nafplio to explore its cobbled lanes, neoclassical mansions, and inviting shops. The yacht sets sail in the early evening, followed by dinner onboard.

Today's Ride Choices

Morning: Nafplio to Mycenae — 25.1 km (16 miles)

What to Expect:

Today’s ride begins from the pier in Nafplio. Expect some traffic as you exit the port, with portions of the city ride following designated bike paths. There will be additional traffic near the archaeological site of Mycenae. The route is generally easy, with some rolling hills. Most of the cycling takes place on quiet country roads through small villages after leaving Nafplio.

Cumulative Distance Range: 25.1 km (16 miles)

Included Meals: Breakfast, Lunch, Dinner

Today, go ashore at Mykonos to explore one of the most magnificent of the Cyclades Islands. Join a local guide for an inspiring walking tour of the main town of Chora, passing iconic sugar-cube houses adorned with deep-blue doors and bougainvillea-draped balconies. Stroll the town’s coastal path, admire sweeping Aegean vistas, visit the island’s Archaeological Museum, and stop by the renowned thatch-roof windmills perched scenically on a ridge above the sea. Continue to the charming waterfront fishing houses of “Little Venice,” originally built to give fishermen direct access to the sea from their lower floors. Along the way, enjoy tastings at a local bakery and a café, where ouzo and meze are on the menu.

Return to your yacht for lunch. This afternoon, enjoy time to further explore picture-perfect Mykonos at your leisure. Dinner is once again served on board.

What to Expect:

Non-Biking Day

Included Meals: Breakfast, Lunch, Dinner

Arrive in the Turkish resort town of Kusadasi early this morning. After breakfast, a shuttle delivers you to the starting point of your ride, a thrilling route among some of Turkey’s seldom-visited villages and rural landscapes. This coastal region is a patchwork of farms, pastures, and hills, and it’s a true privilege to glimpse its beauty and tranquility from a bicycle.

Your afternoon is once again yours to follow your own whims. Relax on deck or in the hot tub if you wish or explore the colorful pier-side shops of Kusadasi. Later, join our private walking tour of the ancient, incredibly preserved streets of Ephesus, steeped in history and Biblical lore. Savor every moment over a magical dinner this evening under the moonlight, in the embrace of the historic site.

Today's Ride Choices

Morning: Turkish Countryside — 24 km (15 miles)

What to Expect:

Today, travel by bus from the port to the nearby foothills outside of Kusadasi, where your ride begins in the scenic Turkish countryside. You’ll follow mostly quiet country roads through orchards and forests, with occasional traffic as you pass through villages. After your ride, return to the port by bus. Note: Today’s ride will be on non-VBT bikes.

Cumulative Distance Range: 24 km (15 miles)

Included Meals: Breakfast, Lunch, Dinner

After another delicious breakfast on board, disembark in Patmos for a morning ride to one of the Greek Islands’ most sacred sites—the Monastery of St. John. This peaceful island is famously where St. John wrote the Book of Revelation in 95 AD. Your ride to the monastery is nothing short of inspiring, passing gleaming whitewashed villages, shady pine forests, and terraced farms. A few challenging hills reward you with sweeping sea views.

There will be time to explore the monastery, a vast complex of churches and courtyards revered as the centerpiece of the “Jerusalem of the Aegean.” Later, enjoy an invigorating downhill ride to a seaside taverna, where you’ll savor a lunch of Greek specialties.

In the afternoon, pedal back to the pier along a spectacular coastal route, then take the tender back to your yacht in time to relax before dinner.

Today's Ride Choices

Morning & Afternoon: Patmos Loop — 22.8 km (14 miles)

What to Expect:

Today’s ride begins and ends at the pier in Patmos. You’ll start with an uphill climb of approximately 5 km, navigating some traffic as you depart the port. At the top, enjoy a rest and a private walking tour of the Monastery of St. John in Chora. Afterward, continue your ride with a downhill stretch into the town of Patmos, then cycle on to a nearby beach for an included lunch. Following lunch, ride back to the pier to conclude the day. Today’s route follows the island’s primary two-lane roads, with traffic expected when entering and exiting the town of Patmos and the monastery’s parking area.

Cumulative Distance Range: 22.8 km (14 miles)

Included Meals: Breakfast, Lunch, Dinner

Boasting one of the most dramatic settings of any Greek Island, Santorini is an awe-inspiring spectacle of nature and culture. This crescent-shaped island sits on the rim of an ancient volcano whose caldera collapsed into the sea after a massive eruption. The main town of Fira clings to cliffs 1,000 feet above the water, offering breathtaking views.

Leave your bikes behind today as you join a local guide for an insider’s tour. Stroll among the terraced, whitewashed houses of Oia, adorned with iconic blue accents. Take in panoramic island views before continuing to the ancient Minoan city of Akrotiri, often called the “Pompeii of the Aegean,” which was destroyed by a volcanic eruption in 1600 BC. Pause for lunch at Canava Roussos Winery, where you’ll learn about ancient wine-making techniques and sample the island’s famed Assyrtiko wine.

After some time to browse the pedestrian streets of Fira, return to your yacht.

This evening, join your fellow travelers for a festive onboard BBQ dinner—a signature event aboard the Wind Spirit.

What to Expect:

Non-Biking Day

Included Meals: Breakfast, Lunch, Dinner

After a morning of scenic cruising in the Aegean, you arrive in Monemvasia—one of Europe’s oldest continuously inhabited fortified towns, founded in the sixth century. Once a vital medieval port, its massive rock formation served as a strategic lookout over the sea. Today, it remains an imposing and iconic wonder, connected to the mainland by a narrow isthmus.

After lunch, set out on a scenic coastal ride offering some of the most breathtaking views of your tour. Pedal along the shoreline, with the sparkling Aegean on one side and soaring cliffs on the other, and enjoy spectacular vistas of Monemvasia—often called “Greece’s Rock of Gibraltar.”

Your ride concludes at the main city gate of the walled village, where you’ll meet your leaders for a short walking tour through Monemvasia’s charming medieval streets.

If you wish, you’ll have a bit of free time to explore independently before returning to the yacht. This evening, celebrate your Aegean adventure during a private farewell reception and dinner on board.

Today's Ride Choices

Afternoon: Monemvasia to Agios Fokas Out-and-Back — 27.5 km (17 miles)

What to Expect:

Today’s ride begins at the pier in Monemvasia’s small port. After navigating some traffic as you depart, you’ll follow a scenic and flat coastal route to the picturesque seaside cemetery of Agios Fokas. Enjoy views of the rugged coastline and, on your return, sweeping vistas of Monemvasia—nicknamed “Greece’s Rock of Gibraltar.” The ride concludes at the main city gate of the walled village, where you’ll meet your leaders for a short walking tour.

Cumulative Distance Range: 27.5 km (17 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, disembark one final time and conclude your Aegean odyssey with a guided tour of the Temple of Poseidon. Perched dramatically above the Aegean Sea on a high promontory, this iconic sanctuary was built around 700 BC to honor the god of the sea. Enjoy time to explore and marvel at the 2,700-year-old site during a walking tour, followed by lunch at a nearby seaside taverna featuring fresh seafood and classic Greek dishes.

Later, arrive at the Sofitel Athens Airport Hotel, conveniently located within Athens International Airport, where your tour concludes at approximately 3:00 p.m.

Important: Train or air departures prior to 6:00 p.m. are not recommended. If you have an earlier departure, you will need to make your own transportation arrangements to your next destination from the yacht in Athens.

Included Meals: Breakfast, Lunch