A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki - cover photo

A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki

  • Rhodes
  • 7 days cruise
  • Gulet
  • 4 reviews
  • Shared cruises may require a minimum number of guests.
  • Price may vary depending on the cabin type, occupancy and cruise date.
  • Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
 Price per Person
€ 829
  • Price may vary depending on the cruise date.
  • Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
 Price per Boat
€ 11000
Gallery
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
From
€ 829 per Person
or € 11000 entire boat

Your sailing trip

A relaxed gulet sailing route from Rhodes exploring Symi, Tilos and Chalki with swimming bays, historic villages and authentic Greek island life

This 7 day gulet cruise from Rhodes offers an immersive sailing experience through the heart of the Dodecanese Islands, combining short navigations, crystal clear waters and time ashore in some of the region’s most characterful destinations. Departing from Rhodes Harbour, the itinerary follows a balanced circular route including Symi, Tilos and Chalki, with carefully selected bays and ports that reflect the authentic rhythm of Greek island life.

The cruise begins in Rhodes, where guests have time to explore the UNESCO listed Old Town before setting sail. The route then unfolds through a series of scenic island stops, from the colorful harbor of Symi to the quiet landscapes of Tilos and the unspoiled atmosphere of Chalki. Daily swimming stops in sheltered bays such as Nanou Bay, St George Bay and Trakhia Bay are combined with relaxed afternoons in traditional ports, allowing time for local walks, tavernas and cultural visits.

Navigation distances are kept moderate to ensure comfort and an easygoing pace on board. The captain adapts the route according to weather and sea conditions, choosing the best anchorages each day to maximize safety, enjoyment and time spent at sea. Life on board follows a natural flow, with mornings dedicated to sailing or swimming, afternoons for island exploration and evenings spent at anchor or in small harbors.

This Rhodes gulet cruise is ideal for travelers seeking a social and authentic sailing holiday rather than a formal luxury experience. It suits couples, solo travelers and small groups who want to discover the Dodecanese from the sea, enjoying traditional navigation, clear waters and genuine Greek hospitality.
The itinerary is indicative and may vary in order or choice of stops, without compromising the overall sailing experience.

Itinerary

Day 1
Rhodes Harbour
Boarding takes place in Rhodes Harbour from 16:00. Guests are welcomed on board and settle into their cabins before the cruise officially begins. Rhodes Harbour is a lively area, rich in traditional Greek tavernas, local markets and small antique shops. Before dinner, there is time to explore the UNESCO-listed Old Town of Rhodes, one of the best-preserved medieval towns in Europe, famous for its stone streets, fortifications and historic atmosphere. Dinner and overnight stay on board at Rhodes New Marina.
Day 2
Rhodes, Nanou Bay, Symi
After completing port formalities and refueling between 10:00 and 13:00, the gulet sails toward Symi, one of the most picturesque islands of the Dodecanese. The first stop is Nanou Bay, a secluded anchorage surrounded by green hills, ideal for swimming and relaxing in crystal-clear waters. In the afternoon, around 16:00, the cruise continues to Symi Port. The colorful neoclassical houses rising above the harbor create one of the most iconic views in Greece. Dinner is served on board, with the option to dine ashore at one of the charming waterfront tavernas. Overnight in Symi.
Day 3
Symi, St George Bay, Panormitis or Pedi
Departure from Symi takes place after breakfast between 09:00 and 10:00. The morning is spent anchoring at St George Bay or nearby coves, offering time for swimming, snorkeling and lunch in pristine waters. In the afternoon, around 16:00, the gulet sails south to Panormitis, home to the renowned Monastery of Archangel Michael. This important Greek Orthodox pilgrimage site dates back to the 18th century and remains an active monastery. A respectful and tranquil atmosphere is maintained throughout the visit. If sea conditions do not allow access to Panormitis, the alternative stop will be Pedi. Dinner and overnight stay in the area.
Day 4
Symi, Akrogiali Bay, Tilos
After breakfast, the cruise heads toward Tilos between 09:00 and 10:00. The island is known for its rugged mountains, transparent waters and unspoiled character. The day is spent anchored at Akrogiali Bay, perfect for swimming and enjoying the dramatic coastal scenery. In the late afternoon, around 16:00, arrival at Tilos Harbour allows time to explore the quiet island village. Guests may visit Mikro Chorio, an abandoned hilltop village offering panoramic views and a unique evening atmosphere. Dinner is typically enjoyed at a local tavern ashore and is not included in the cruise package. Overnight in Tilos.
Day 5
Tilos, Trakhia Bay, Chalki
Depending on weather conditions, the gulet departs Tilos between 06:00 and 10:00, sailing toward Chalki, one of the least-developed islands in the Dodecanese. The day begins with a stop at Trakhia Bay or a similar secluded anchorage, ideal for swimming and relaxing in clear, calm waters. In the late afternoon, arrival at Nimporio, Chalki’s main village and port. The waterfront promenade is lined with traditional cafés and tavernas, and the island’s slow pace offers a peaceful contrast to more touristic destinations. Overnight stay in Chalki.
Day 6
Chalki, Anthony Quinn Bay, Kalithea
An early departure brings the gulet back toward Rhodes Island. Breakfast is served either during navigation or upon arrival at Anthony Quinn Bay, a famous swimming spot named after the actor who once owned land in the area. Later, the cruise continues to Kalithea Beach, known for its beautiful coves and inviting waters. The afternoon is dedicated to swimming, relaxation and enjoying the surrounding coastline. Dinner and overnight stay in Kalithea.
Day 7
Kalithea, Rhodes Port
The gulet arrives at Rhodes New Marina between 09:00 and 10:00, allowing time for guests to explore the island independently. This final day is ideal for visiting the medieval Old Town, museums, local markets or enjoying a last walk along the harbor. In the evening, guests gather for a farewell dinner, either on board or at a local restaurant, celebrating the end of the Dodecanese sailing experience. Overnight on board in Rhodes. Disembarkation takes place the following morning by 09:00. Note The itinerary may be modified by the captain depending on weather conditions, sea state or operational requirements. Changes may include visiting destinations in a different order or replacing stops with equally beautiful alternatives, without affecting the overall quality of the cruise.

Cruise price details

Price per person

€ 829

Accomodation on selected shared cabin, check out single use and details

Entire yacht price

€ 11000

Book the entire yacht for a private trip

Yacht - Roulette Formula Rhodes

Traditional Gulet Cabin Charter in Greece, Roulette Formula

This cabin charter is operated on board a traditional wooden gulet selected from a small fleet of carefully maintained sailing yachts cruising in Greek waters. The exact gulet is assigned close to departure, following a roulette formula, but all boats used for this itinerary share the same comfort level, onboard services and sailing style, ensuring a consistent experience for all guests.

The gulets used for this cruise range between approximately 23 and 28 meters in length and accommodate small groups in private guest cabins with en-suite bathrooms. Depending on the specific yacht assigned, the layout typically includes between 7 and 9 guest cabins, designed for couples, friends or solo travelers joining a shared sailing experience. Interiors are classic and functional, with warm wooden finishes, comfortable sleeping areas and private bathrooms with shower and WC.

Outdoor spaces are a key feature of these gulets. All yachts offer a spacious aft deck with shaded seating and dining area, ideal for meals on board and relaxed social moments. The forward deck is dedicated to sunbathing, with cushions or mattresses allowing guests to enjoy navigation, anchorages and quiet afternoons at sea. The overall atmosphere on board is informal and friendly, focused on comfort, slow sailing and shared experiences rather than luxury or formality.

Each gulet is operated by a professional local crew, typically including a captain, chef and deckhands, all experienced in Greek cruising areas. The crew takes care of navigation, meals, daily routines and safety, adapting the itinerary according to weather conditions and sea state to ensure a smooth and enjoyable cruise. Meals are freshly prepared on board and served in a convivial setting, contributing to the relaxed onboard rhythm.

While the specific yacht is assigned shortly before departure, all gulets used for this cruise meet the same standards in terms of space, services and overall comfort. In some cases, another gulet of equivalent or higher category from the same fleet may be selected, without affecting the quality or structure of the experience.

Yacht
Model
2010 Roulette Formula Rhodes
Length
25 m
Yacht services
Tender size
5.4 m
Snorkeling equipment
Yes
Fishing equipment
Yes
Toys on board
Yes
Accommodations
Max guests
16
Double cabins
6
Triple cabins
2
Bathrooms
8
Private Bathrooms
Yes
Crew
4
Chef on board
No
Other facilities
Expansive sun deck with shaded and open areas for relaxing and sunbathing
Comfortable indoor lounge and bar area
Onboard WiFi connection (subject to coverage)
Air conditioned en suite cabins located on deck
Cabins available as double, twin or triple depending on the assigned gulet
Storage space, reading lights and comfortable mattresses in all cabins
Air conditioning operating while docked, up to 8 hours per day
Snorkeling masks available on board
Tender available for easy and safe access to shore
Professional English speaking crew including captain, chef and steward
2010 Roulette Formula Rhodes
Cabins
Standard double Twin Cabin
Double cabin with private bathroom
4
  • cabin capacity
  • double bed
  • private bathroom
Triple
Three persons cabin with private bathroom
2
  • cabin capacity
  • private bathroom

Cruise activities and tips

Travel activities

Cruise activity Exploring Symi Town and Harbor Life

Exploring Symi Town and Harbor Life

Arriving in Symi by sea is considered one of the most scenic moments of the cruise. The entrance into the harbor reveals rows of pastel colored neoclassical houses rising amphitheatrically from the water, creating one of the most photographed views in the Dodecanese. Once ashore, guests can enjoy a relaxed walk along the waterfront promenade, explore narrow stone-paved alleys, and browse small artisan shops selling sponges, ceramics and local products. Symi also offers a pleasant culinary scene, with traditional tavernas and cafés overlooking the marina, ideal for a coffee break, aperitif or dinner ashore. The town combines refined architecture, maritime history and a lively yet unhurried island atmosphere, making it a highlight for guests who enjoy culture, photography and authentic Greek harbor life.

Cruise activity Monastery Visit at Panormitis

Monastery Visit at Panormitis

In the southern part of Symi, guests may have the opportunity to visit the Monastery of Archangel Michael Panormitis, one of the most important religious landmarks in the Dodecanese. Set in a quiet bay surrounded by hills, the monastery dates back to the early 18th century and remains an active place of worship, still inhabited by monks today. Visitors can explore the courtyard, church and small museum, learning about Greek Orthodox traditions and the strong local devotion to Archangel Michael. The peaceful surroundings and simple architecture create a calm, reflective atmosphere that contrasts beautifully with the lively ports visited during the cruise. Silence and respectful behavior are observed, preserving the spiritual character of the site.

Cruise activity Island Walks and Village Life on Tilos

Island Walks and Village Life on Tilos

Tilos is known for its unspoiled character and relaxed rhythm, offering a genuine island experience away from mass tourism. Guests can take an easy walk through the small harbor town, stopping at local cafés, bakeries or family run tavernas. The village atmosphere is friendly and informal, allowing visitors to observe everyday island life at a slow pace. For those interested in exploring further, a short taxi or bus ride leads to Mikro Chorio, an abandoned hilltop village overlooking the island. Here, stone houses, narrow paths and panoramic views create a unique setting, especially in the evening when the area is softly lit. Tilos combines nature, history and local hospitality, making it an ideal stop for travelers seeking quiet moments and authentic Greek island culture.

Travel organizer tips

What to pack for a sailing holiday?
Pack smart for your yacht charter: choose a soft bag instead of a hard suitcase, bring lightweight layers, reef-safe sunscreen, and non-slip shoes for onboard use. A couple of swimsuits and motion sickness remedies can also make a big difference. Each boat has limited storage, so pack light, but wisely! Need help building the perfect list? Read our full guide: What to pack in a suitcase for a yacht charter
What’s a Typical Day Like on a Yacht Charter?
Start your day with a swim in a quiet bay, sail to hidden beaches or seaside villages, and enjoy a slow lunch on deck. Afternoons mean snorkeling, sunbathing, or exploring ashore. As the sun sets, your boat anchors in a scenic cove or near a harbor, ready for a relaxed dinner and a night under the stars. Curious about the full experience? Discover more in our guide: What’s a typical day like on a sailing holiday?
Who Handles Cooking and Cleaning on a Yacht Charter?
On skipper-only charters, guests usually share cooking and cleaning duties, think salads, pasta, and good teamwork. If there's a hostess, light meals and tidying are included, but it's still a casual, collaborative vibe. On fully crewed yachts, you’ll enjoy full service with a chef and crew managing everything. Want to know what’s included in your setup? Read the full guide: Who takes care of cooking and cleaning on a sailing charter?
What Happens in Case of Bad Weather During a Sailing Holiday?
Summer sailing holidays rarely face major weather issues, but when the sea gets rough, skippers adjust the route for your safety. Expect protected bays, marina stops, or a change in plan. These moments often lead to unexpected gems: local towns to explore, time to relax on board, or cozy dinners ashore. Curious about how crews handle these changes? Read the full FAQ: What to do in case of adverse weather conditions or changes to the itinerary

Traveler reviews

Michael C. 2026-01-10

This cruise exceeded my expectations. The islands are beautiful, but what made the difference was the rhythm of the trip. Swimming in clear bays during the day, walking through small ports in the evening, and discovering places like Panormitis and Chalki that you’d probably skip on your own. It felt genuine and unspoiled. I’d recommend this itinerary to anyone who wants to experience the Dodecanese beyond the usual tourist paths.

Anna G. 2025-06-14

I loved how peaceful and authentic this journey felt. Symi was stunning, but Tilos was my favorite stop. Quiet villages, friendly locals and a completely different pace of life. The balance between sailing, swimming and time ashore was perfect, and I never felt overwhelmed or tired. It’s ideal if you want to disconnect, enjoy nature and still experience local culture in a very natural way.

James U. 2024-09-14

I’ve sailed in Greece before, but this itinerary really stood out. Arriving in places like Symi and Tilos by boat gives you a completely different perspective compared to visiting by ferry. The mix of quiet anchorages, small authentic islands and cultural stops made the week feel well balanced. It never felt rushed, and every stop had its own character. If you’re looking for a relaxed sailing experience with real Greek atmosphere, I’d absolutely recommend this route.

Sophie A. 2023-05-20

This cruise was exactly what I hoped for. Arriving by sea into small islands like Symi and Chalki was magical, especially in the late afternoon light. I appreciated that the itinerary wasn’t about luxury, but about atmosphere, scenery and shared experiences. Every day felt different, yet relaxed. I would definitely recommend this cruise to couples or solo travelers looking for a friendly, authentic Greek island experience.

A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
A 7 Day Sailing Itinerary Between Symi, Tilos and Chalki
Featured cruises
€ 829
  • Shared cruises may require a minimum number of guests.
  • Price may vary depending on the cabin type, occupancy and cruise date.
  • Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
 per Person
€ 11000
  • Price may vary depending on the cruise date.
  • Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
 per Boat