Private Multi-Island Cruises in the Cyclades

Premium island-hopping charters connecting Milos to Santorini, Mykonos, Paros, and the Cyclades

Experience a seamless, tailor-made private trip across the Aegean. Navy Blue provides premium boat transfers with a fleet of modern motor yachts offering direct, port-to-port services from Santorini to Milos and Milos to Santorini.

Select Departure/Arrival Island:

Select Departure/Arrival Island:

Milos

Aerial view of white volcanic rock formations and turquoise sea channels in the Western Cyclades

Western Cyclades Cruise

Departure/Arrival: Milos

Cruise through the western Cyclades and visit up to four islands in a single day. Explore Kimolos, Sifnos, Serifos, and Kythnos. Enjoy chef-prepared Mediterranean meals and an open bar with premium wines and local beers.

Islands you will explore:

Kimolos

Sifnos

Serifos

Kithnos

Duration:
9h
Fuel Costs:
Included
Round Trip:
Yes

Starting from

4,100€

+50€ / Person

Book Western Cyclades Cruise
Traditional whitewashed syrmata boathouses built into the rocky shore of Milos over clear turquoise water

Central Cyclades Cruise

Departure/Arrival: Milos

Cruise through the central Cyclades on a multi-island hopping yacht tour, with stops in Kimolos, Poliegos, Folegandros, and Sikinos. Enjoy chef-prepared Mediterranean meals and a full open bar on board.

Islands you will explore:

Sifnos

Despotiko

Antiparos

Paros

Duration:
9h
Fuel Costs:
Included
Round Trip:
Yes

Starting from

4,100€

+50€ / Person

Book Central Cyclades Cruise
Santorini caldera view at sunset with blue-domed churches and whitewashed buildings on the cliff edge

Southern Cyclades Cruise

Departure/Arrival: Milos

Cruise south through the Cyclades on a multi-island hopping yacht tour, with stops in Folegandros, Sikinos, Ios, and Santorini. Enjoy gourmet platters with local wines, beers, and refreshments in our open bar.

Islands you will explore:

Poliegos

Folegandros

Sikinos

Santorini

Duration:
10h
Fuel Costs:
Included
Round Trip:
Yes

Starting from

4,400€

+50€ / Person

Explore Southern Cyclades Cruise
Stone medieval castle with Greek flag above a Cyclades harbor with small boats and white cubic buildings

South-Central Cyclades Cruise

Departure/Arrival: Milos

Chart a course through the central Cyclades. Explore up to four distinct islands: the uninhabited shores of Poliegos, the peaceful bays of Kimolos, the clifftop villages of Folegandros, and the serene harbors of Sikinos.

Islands you will explore:

Kimolos

Poliegos

Folegandros

Sikinos

Duration:
8h
Fuel Costs:
Included
Round Trip:
Yes

Starting from

3,900€

+50€ / Person

Book South-Central Cyclades Cruise
Sailboats moored in a Cyclades island marina with whitewashed village and green hillside above

Eastern Cyclades Cruise

Departure/Arrival: Milos

Navigate east through the Cyclades and visit Paros, Naxos, Iraklia, and Ios on a full-day journey at sea. Mediterranean dishes and an open bar with wines, beers, and chilled refreshments are available throughout the day.

Islands you will explore:

Paros

Naxos

Iraklia

Ios

Duration:
10h
Fuel Costs:
Included
Round Trip:
Yes

Starting from

4,700€

+50€ / Person

Book Eastern Cyclades Cruise

Premium Island-Hopping Experience

Luxury sea travel across the Cyclades with modern yachts and refined comfort

NAVYGON Specifications
Maker:
Navygon
Engine:
600 hp
Year Built:
2026
WC:
Yes
Crew:
Yes
Model:
N 400 S
Length:
12 m / 40ft
Cruising Speed: Speed:
35 Knots
Max Speed:
50 Knots
Guests:
Up to 10

Exclusive Trips to Multiple Greek Islands

Private Yacht Travel from Milos, Kimolos, or Sifnos to the most popular Cyclades destinations

Aerial view of a Cyclades island town with a yacht-filled marina, whitewashed buildings, and mountain backdrop

What is an Island-Hopping Cruise

Boat Trips Across the Aegean's Top Destinations

A Multi-Island Cruise is a full-day boat trip designed to reveal the Cyclades in a single, seamless tour. Our luxury yachts carry you comfortably through the Aegean Sea, stopping at up to four of Greece's most renowned island destinations, each with its own unique beauty. Every route is shaped by our captains with years of experience navigating these waters.

An attentive crew caters to your every need, sharing stories and traditions of each island along the way. Swim in hidden coves, pause for lunch beside scenic shorelines, and discover secret spots that only local sailors know. Continue your trip through the picturesque Cyclades, passing some of the most breathtaking photography spots.

Secluded Cyclades coastline with rocky cliffs, turquoise water, and a small whitewashed chapel

Who Are Multi-Island Tours Best For

A Private Greek-Islands Exploration

Celebrate a honeymoon, anniversary, or simply each other with a Private Cruise through the Cyclades. Secluded coves, Santorini sunsets, and moments designed for two create an ideal setting for romance. Families enjoy spacious decks, calm swim stops at Poliegos, and chef-prepared meals with every detail thoughtfully handled by our crew.

Whether you are marking a birthday, planning a reunion, or gathering with friends, a Multi-Island Cruise becomes the highlight of your Greek Islands experience. From Naxos to Santorini, Navy Blue's luxury yacht cruises provide premium service, local expertise, and access to destinations that ferries simply cannot reach.

Cyclades Map & Island Destinations

Plan your Private Round-Trip Cruise within the Greek Islands

Navy Blue Multi-Island Cruise route map of the Cyclades showing Milos, Santorini, Naxos, and Paros in the Aegean Sea

Our South Aegean Yacht Routes

The Cyclades scatter like pearls across the Aegean Sea. Each island holds its own character, from volcanic cliffs and whitewashed harbors to turquoise bays away from the crowds.

Navy Blue's Multi-Island Cruises connect these destinations in seamless full-day trips. Depart from Milos, Kimolos, or Sifnos and visit up to four islands in a single day. Every route is a round-trip, designed to bring you back to your starting point with memories of places most travelers never reach.

Supported Island Tours

  • Kimolos

  • Sikinos

  • Sifnos

  • Serifos

  • Milos

  • Santorini

  • Folegandros

  • Paros

  • Poliegos

  • Ios

  • Antiparos

  • Naxos

Why Choose a Private Multi-Island Cruise

See more islands in one day than most visitors see in a week

Aerial view of white limestone sea caves and a hidden turquoise cove in the Greek Islands

Private Yacht vs Ferry: What’s the Difference

A Private Multi-Island Cruise is built around your preferences. Visit up to four Cyclades islands, swim in bays only reachable by boat, and enjoy a freshly prepared meal on board between stops. Our modern luxury yachts make the journey between islands smooth and enjoyable, meaning more time exploring and less time in transit. No fixed timetables, no crowded departures. You just enjoy the day.

  • Four islands in a single day

  • Curated routes with local captains

  • Flexible pace, no rigid schedules

IDEAL FOR

Couples, Families & Groups


Four Islands

in One Day

Private Vessel

& Crew

Meals

Included

Curated

Routes Only

Open Bar

Included

Stops at

Hidden Coves

Cyclades Private Multi-Island Cruise Rates

Explore pricing for Private Multi-Island Cruises across the Cyclades

Select Departure/Arrival Island:

Departure/Arrival Island:

Milos

Route Departure/Arrival Islands You Will Visit Starting From
Western Cyclades Cruise Milos Kimolos – Sifnos – Serifos – Kithnos €4,100
Central Cyclades Cruise Milos Sifnos – Despotiko – Paros – Antiparos €4,100
Southern Cyclades Cruise Milos Folegandros – Sikinos – Ios – Santorini €4,400
South-Central Cyclades Cruise Milos Kimolos – Poliegos – Folegandros – Sikinos €3,900
Eastern Cyclades Cruise Milos Paros – Naxos – Iraklia – Ios €4,700

Western Cyclades Cruise

Kimolos – Sifnos – Serifos – Kithnos

Departure/Arrival

Milos

Price

€4,100

Central Cyclades Cruise

Sifnos – Despotiko – Paros – Antiparos

Departure/Arrival

Milos

Price

€4,100

Southern Cyclades Cruise

Folegandros – Sikinos – Ios – Santorini

Departure/Arrival

Milos

Price

€4,400

South-Central Cyclades Cruise

Kimolos – Poliegos – Folegandros – Sikinos

Departure/Arrival

Milos

Price

€3,900

Eastern Cyclades Cruise

Paros – Naxos – Iraklia – Ios

Departure/Arrival

Milos

Price

€4,700

Navy Blue | Analytics & Metrics

Milestones from every season across Milos, Kimolos, Poliegos and the Cyclades

Satisfied Guests

10,400+

Cruises Performed

1,600+

Nautical Miles

45,000+

Supported Islands

25+

Top Destinations

Milos, Kimolos, Poliegos

Kleftiko, Milos

Sarakiniko, Milos

Rema, Kimolos

Blue Bay, Poliegos

Gerakas, Milos

Private Cruises

Semi-Private

Guests Nationality

Country of Origin

USA (43%)

Australia (14%)

Greece (6%)

Canada (5%)

UK (4%)

Other (28%)

USA (43%)

Australia (14%)

Greece (6%)

Canada (5%)

UK (4%)

Other (28%)

Milos Weather

Summer Season | May ~ Oct

Sunny (87%)

Cloudy (9%)

Rainy (4%)

Multi-Island Cruises FAQs

Everything you need to know about our Island-Hopping Tours in the Cyclades

How Many Islands Can You Visit on a Multi-Island Cruise?

A Navy Blue multi-island cruise visits up to four Cyclades islands in a single full-day boat tour. Each route departs from Milos, Kimolos, or Sifnos in the morning and returns to your starting island by evening. Five curated routes cover the western, central, southern, and eastern Cyclades.

The number of island stops depends on distance, sea conditions, and how long you choose to stay at each location. Our local captains know these waters well and adjust the pace to suit your group. You might spend an hour exploring a quiet village harbor, then cruise to a sheltered bay for swimming and lunch on board. We plan around your preferences and confirm the best route based on sea conditions, so every day feels relaxed rather than rushed. Whether you visit three islands or four, the route is designed for a smooth, memorable voyage through the Greek Islands.

What Is Included in a Private Multi-Island Cruise?

Every Navy Blue private multi-island cruise includes a luxury yacht with a professional crew, curated Mediterranean meals, an open bar, snorkeling gear, and premium on-board amenities. Fuel and all port fees are covered. You simply board in the morning and enjoy the day with nothing extra to arrange.

Meals are served in stages throughout the cruise so you stay light and energized between swim stops. Expect fresh local ingredients, seasonal salads, and seafood prepared on board. The open bar runs all day with wine, beer, soft drinks, and water. For special occasions, upgrades such as champagne, cake, flowers, or a professional photographer are available on request. Our crew handles every detai seamlessly, from setting up shaded lounging areas to guiding you to the best snorkeling spots near each island. The experience is designed to feel effortless from the moment you step on deck.

Can You Customize the Route on a Multi-Island Cruise?

Yes. Every Navy Blue multi-island cruise is flexible by design. We plan around your preferences and confirm the best route based on sea conditions. You can request longer stops, extra swim time, or a focus on specific islands. Your captain adjusts the itinerary throughout the day to match your group’s pace.

Before your cruise, our team reviews your wishes and suggests the route that fits best. On the water, your captain reads the conditions in real time. If the wind shifts or a cove is too crowded, the crew knows alternative bays and secret spots that most visitors never see. Families often ask for calm, shallow swim stops, while couples may prefer a longer pause at a scenic village. Groups celebrating birthdays or anniversaries can add custom touches like a champagne toast at sunset. This kind of flexibility is what sets a private luxury yacht cruise apart from a fixed ferry schedule.

Which Cyclades Islands Can You Reach on a Day Cruise from Milos?

From Milos, Navy Blue’s day cruise routes reach over a dozen Cyclades islands. Popular stops include Kimolos, Sifnos, Poliegos, Folegandros, Sikinos, Ios, Santorini, Paros, Naxos, Antiparos, Despotiko, Serifos, Kithnos, and Iraklia. Five curated routes group these islands by region so you cover the most ground in a single day.

Each route follows a regional path through the Aegean. The Western Cyclades route passes Kimolos, Sifnos, Serifos, and Kithnos, where you find thermal shores and artisan villages. The Central route heads toward Poliegos and Folegandros, known for pristine waters and dramatic clifftop trails. Heading south, the route reaches Sikinos, Ios, and Santorini’s volcanic caldera. The Eastern route covers Paros, Naxos, and the quiet beauty of Iraklia. All routes are round-trip, starting and ending at your departure island. Your captain selects the best stops based on sea conditions and your interests, so no two cruises feel the same.

What Makes Navy Blue’s Multi-Island Cruises Different?

Navy Blue is a premium yacht cruise company based in Milos with local captains, modern luxury open-yachts, and a food-led on-board experience. Every cruise includes curated Mediterranean meals, an open bar, and a professional crew that values privacy and comfort. The focus is on refined service, not crowded group tours.

The difference starts with the yacht itself: a modern open-yacht built for comfort, shade, and relaxed space on board. Meals are prepared fresh and served in stages so you feel energized between swim stops, not weighed down by a single heavy lunch. Our captains have navigated these waters for years and know which coves are calm, which villages are worth a walk, and where to find the best light for photos. Guests rate us 5.0 on Google, Tripadvisor, and GetYourGuide because we treat every cruise as a private occasion, whether you are a couple on a honeymoon or a family reunion of twelve. That combination of local expertise, premium equipment, and quiet, high-touch hosting is difficult to replicate.

Explore More FAQs

Navy Blue Multi-Island Cruises Reviews

Real guest experiences from our Multi-Island Trips around the Aegean

Ama Okafor, Navy Blue island-hopping cruise guest in the Cyclades

Ama Okafor

12 May, 2025

Absolutely perfect. Four islands in one day and every moment felt unhurried. The crew anticipated everything. Already planning our return.

Camila, Navy Blue island-hopping cruise guest in the Cyclades

Camila

18 August, 2025

Our honeymoon highlight. Champagne as we watched the sunset near Santorini. A private cove for just the two of us at Folegandros. The captain knew exactly when to give us space and when to share local stories. Romantic beyond words.

William J., Navy Blue island-hopping cruise guest in the Aegean

William J.

9 October, 2025

Navy Blue just delivered us the perfect island-hopping. Four islands, great food, and a crew that made everything easy. Amazing experience.

Pedro Fernandez, Navy Blue island-hopping cruise guest in the Cyclades

Pedro Fernandez

5 November, 2025

We visited Milos for a week and saved the multi-island cruise for our final day. It was the right decision. Everything we had seen from land became even more beautiful from the sea.

Rahman Linnea, Navy Blue multi-island cruise guest in the Cyclades

Rahman Linnea

27 June, 2025

We were a bit nervous about a multi-island cruise with two young children. Completely unnecessary worry. The crew made the kids feel like VIPs. A family memory we will never forget.

Kateryna N., Navy Blue multi-island cruise guest in the Cyclades

Kateryna N.

7 September, 2025

Booked for my 40th birthday. Eight of us on the yacht, visiting Kimolos, Poliegos, and ending with sunset drinks near Sifnos. The playlist was perfect, the food was incredible, and the crew made us feel like celebrities. My friends are still talking about it weeks later. If you are considering a group celebration, stop considering and just book.

Noura Diallo, Navy Blue multi-island cruise guest in the Cyclades

Noura Diallo

14 March, 2025

The lunch alone was worth booking. Fresh, Greek, beautifully presented. Add the swimming, the views, the seamless service. Perfection.

Irena Pereira, Navy Blue multi-island cruise guest in the Greek Islands

Irena Pereira

22 June, 2025

We already think about our next visit. Three islands in one day with amazing food and a crew that made it all feel easy. Highlight of our summer!

Leila Costa, Navy Blue multi-island cruise guest in the Aegean

Leila Costa

3 July, 2025

I have chartered yachts across the Mediterranean. Navy Blue's service matches anything I have experienced. Impeccable attention to detail.

Elif Youssef, Navy Blue multi-island cruise guest in the Greek Islands

Elif Youssef

21 April, 2025

I came to photograph Sarakiniko and the Cyclades. The captain positioned the yacht perfectly for golden hour. The light at Sikinos was extraordinary. For any photographer, this is the only way to capture the Greek Islands.

Nadia, Navy Blue multi-island cruise guest in the Aegean

Nadia

30 July, 2025

Quiet luxury. No pretense. Just a beautiful yacht, exceptional crew, and the Aegean unfolding before you. Exactly as travel should be.

Zain Rangel, Navy Blue island-hopping cruise guest in the Cyclades

Zain Rangel

11 August, 2025

We visited 4 islands in just one day. Unbelievable! Thank you Navy Blue!!!

Ama Okafor, Navy Blue island-hopping cruise guest in the Cyclades

Ama Okafor

12 May, 2025

Absolutely perfect. Four islands in one day and every moment felt unhurried. The crew anticipated everything. Already planning our return.

Camila, Navy Blue island-hopping cruise guest in the Cyclades

Camila

18 August, 2025

Our honeymoon highlight. Champagne as we watched the sunset near Santorini. A private cove for just the two of us at Folegandros. The captain knew exactly when to give us space and when to share local stories. Romantic beyond words.

William J., Navy Blue island-hopping cruise guest in the Aegean

William J.

9 October, 2025

Navy Blue just delivered us the perfect island-hopping. Four islands, great food, and a crew that made everything easy. Amazing experience.

Pedro Fernandez, Navy Blue island-hopping cruise guest in the Cyclades

Pedro Fernandez

5 November, 2025

We visited Milos for a week and saved the multi-island cruise for our final day. It was the right decision. Everything we had seen from land became even more beautiful from the sea.

Rahman Linnea, Navy Blue multi-island cruise guest in the Cyclades

Rahman Linnea

27 June, 2025

We were a bit nervous about a multi-island cruise with two young children. Completely unnecessary worry. The crew made the kids feel like VIPs. A family memory we will never forget.

Our Premium Partners

A trusted partner community of hotels, travel agencies, concierge, and more

Viator logo – Navy Blue booking partner
BednBlue logo – Navy Blue yacht booking partner
Travel to Milos logo – Navy Blue tourism partner
Click&Boat logo – Navy Blue yacht rental partner
Booking Manager (MMK) logo – Navy Blue booking software partner
Artemis Seaside Resort logo – Navy Blue accommodation partner
GetYourGuide logo – Navy Blue booking partner
Horizon Suites Milos logo – Navy Blue accommodation partner
Breeze Milos Boutique Hotel logo – Navy Blue accommodation partner
Volcano Luxury Suites logo – Navy Blue accommodation partner
Solus logo – Navy Blue accommodation partner
Noma logo – Navy Blue accommodation partner
Milos Cove logo – Navy Blue accommodation partner
Obsidian Suites Milos logo – Navy Blue accommodation partner
Milos Concierge logo – Navy Blue local services partner
Tripadvisor logo – Navy Blue review platform partner
Nostos Seafood Experience logo – Navy Blue restaurant partner

Join our community by becoming a Navy Blue Partner

Luxury Round-Trip Cruises in the Greek Islands

Navy Blue connects the most popular islands in the Cyclades through five curated routes departing from Milos, Kimolos, and Sifnos. Each cruise visits up to four islands in a single day. Swim in hidden coves, enjoy fresh Mediterranean meals, and sip from an open bar between stops. Our captains plan your trip based on your preferences and weather conditions to make the most of your day and let you experience the Aegean at its finest.

Reserve Your Multi-Island Cruise

Luxury Round-Trip Cruises in the Greek Islands

Navy Blue connects the most popular islands in the Cyclades through five curated routes departing from Milos, Kimolos, and Sifnos. Each cruise visits up to four islands in a single day. Swim in hidden coves, enjoy fresh Mediterranean meals, and sip from an open bar between stops. Our captains plan your trip based on your preferences and weather conditions to make the most of your day and let you experience the Aegean at its finest.

Reserve Your Multi-Island Cruise