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2026

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2027

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2028

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Who is travelling?

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From
US $1,065 per person

Dodecanese Sailing Explorer

8 days
Start and end in Rhodes
4.5
905 traveler reviews
From
US $1,065 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

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2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
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Plan your adventure:
Sailing
Catch the wind and set sail for new horizons
Guided in English
Group Size 2 - 25
All Ages Welcome
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Rhodes

    Your sailing adventure starts in Rhodes. You'll board the gulet after 4:00 PM and get settled into your cabin. Before the boat departs, there's time to check out Rhodes Harbour's waterfront tavernas, local markets, and shops, or wander through the UNESCO-listed Old Town with its medieval cobblestone streets and Gothic architecture. You'll have a welcome dinner on board and then rest up for the week ahead.

    Meals
    Dinner (Welcome dinner on board)

    Included Activities

    • Explore Rhodes Harbour waterfront
    • Visit UNESCO World Heritage Old Town of Rhodes

    Optional Activities

    • Shopping in local antique shops
    • Dining at waterfront tavernas
    Landmarks
    Rhodes Old Town
    Rhodes Harbour
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  2. Day 2

    Nanou Bay - Symi

    You depart Rhodes between 10:00-13:00 and sail toward Symi. The boat stops at Nanou Bay, a secluded cove you can only reach by water, where you'll swim and snorkel in clear turquoise waters. By late afternoon around 16:00, you arrive at Symi Port and see the colorful Neoclassical mansions cascading down the hillside. After settling in, you can walk along the charming waterfront with its tavernas.

    Meals
    Breakfast, Lunch

    Included Activities

    • Swimming and snorkeling at Nanou Bay
    • Visit Symi Port

    Optional Activities

    • Dining at Symi Port tavernas
    Landmarks
    Nanou Bay
    Symi Port
    Itinerary Image 1
  3. Day 3

    Symi - St George Bay - Panormitis

    After breakfast, you depart Symi Port between 09:00-10:00 AM and sail along the dramatic coastline to St. George Bay, a swimming spot accessible only by sea. You'll anchor there for swimming, snorkeling, and lunch served on deck. Later around 4:00 PM, you head to Panormitis to visit the Monastery of the Archangel Michael, an 18th-century Greek Orthodox site with small museums. Note that loud music is prohibited here to respect the holy location.

    Meals
    Breakfast, Lunch (Served on deck)

    Included Activities

    • Swimming and snorkeling at St. George Bay
    • Lunch on deck at St. George Bay
    • Visit Monastery of the Archangel Michael Panormitis
    Landmarks
    St. George Bay
    Monastery of the Archangel Michael Panormitis
  4. Day 4

    Symi - Akrogiali Bay - Tilos

    You depart between 09:00-10:00 AM toward Tilos, an island with high rocky mountains and steep coastlines. Most of the day is spent at Akrogiali Bay with its clear waters for swimming and snorkeling. By late afternoon around 16:00, you dock at Tilos Harbor in Livadia and explore the quiet port town streets, or take a taxi or bus to the abandoned ghost village of Mikro Chorio where ruins are lit up at night.

    Meals
    Breakfast (On deck), Lunch

    Included Activities

    • Swimming and snorkeling at Akrogiali Bay
    • Visit Tilos Harbor (Livadia)

    Optional Activities

    • Visit Mikro Chorio ghost village by taxi or bus
    • Dinner at traditional tavern in Tilos Harbor
    Landmarks
    Akrogiali Bay
    Tilos Harbor (Livadia)
    Mikro Chorio
  5. Day 5

    Tilos - Trakhia Bay - Chalki

    You set course for Chalki, a serene island northwest of Rhodes. Depending on sea conditions, you depart between 06:00-10:00 AM and spend the day anchored at Trakhia Bay in clear waters. By late afternoon around 16:00, you arrive at Nimporio, the island's only village and main port. You can admire the colorful mansions around the harbor, walk along the waterfront promenade with cafeterias and taverns, and optionally visit the village church for a traditional mass between 7:30-8:00 PM.

    Meals
    Breakfast, Lunch

    Included Activities

    • Swimming and snorkeling at Trakhia Bay
    • Visit Nimporio village and port

    Optional Activities

    • Visit village church for traditional mass (7:30-8:00 PM)
    • Dinner at family-run waterfront taverns
    Landmarks
    Trakhia Bay
    Nimporio
  6. Day 6

    Chalki - Anthony Quinn Bay - Kalithea

    You begin your final full day with an early departure heading back toward Rhodes coastline. Depending on weather, you'll have breakfast while cruising or upon arrival at Anthony Quinn Bay, named after the legendary actor who filmed The Guns of Navarone there. From there, you continue to Kalithea, a coastal area known for its thermal springs history. You'll spend the rest of the day exploring coves, swimming, or relaxing on deck before a special dinner on board.

    Meals
    Breakfast, Lunch, Dinner (Special dinner on board)

    Included Activities

    • Visit Anthony Quinn Bay
    • Explore Kalithea coves
    • Swimming in Kalithea waters
    Landmarks
    Anthony Quinn Bay
    Kalithea Beach
  7. Day 7

    Rhodes

    You arrive back at Rhodes New Marina between 09:00-10:00 AM. The day is yours to explore. Walk through the Medieval Old Town, a UNESCO World Heritage Site, checking out cobblestone streets, the Palace of the Grand Master, the Street of the Knights, or grabbing a gelato in the shadow of ancient walls. There's an optional Farewell Dinner at a traditional taverna in town for Greek food, music, and time with other travelers. You'll return to the gulet for your final night on board.

    Meals
    Breakfast, Lunch

    Included Activities

    • Explore Rhodes Old Town
    • Visit Palace of the Grand Master (optional)
    • Walk Street of the Knights (optional)

    Optional Activities

    • Farewell Dinner at traditional taverna in town
    Landmarks
    Rhodes Old Town
    Palace of the Grand Master
    Street of the Knights
    Itinerary Image 1Itinerary Image 2
  8. Day 8

    Rhodes

    You wake up one final time on the gulet and have a last Mediterranean breakfast on board while enjoying the marina view. Disembarkation happens at 09:00 AM where you say goodbye to the crew and fellow travelers before heading home.

    Meals
    Breakfast (Final breakfast on board)
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What's Included

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  • Accommodation
  • Meals
  • Additional Services
  • Transport
  • Free eSIM
    TourRadar offers the lead traveler (the person who booked) a free 1GB eSIM for the trip. The eSIM is redeemable only through the TourRadar app 72 hours before departure.

What's Not Included

  • Flights
  • Insurance
  • Additional Services

Number of tours

104

Age Range

5 to 99 years old

Response time

within 2 days

Response rate

79%

Encounters Travel is an adventure tour operator, based in the UK but with...

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Your Peace of Mind Options

Cancellation Policy

A transparent overview of applicable fees.

Travel Insurance

Be covered for any unforseen circumstances.

Reviews About This Operator

  • Jaime
    · September 14th, 2024
    Excellent introduction to Classical Greece. Our guide, Georgina, was super knowledgeable , capable, and friendly.
    Show more
  • Anthony
    · September 25th, 2023
    These tours start with the itinerary, but are made or busted with the guide. Ours was Dominique (sp?). She was excellent! A lot of energy and passion, as well as information. She is an archaeologist, so she really knows the facts and can bring the ancient ruins to life. She is also very respectful of the monasteries and their inhabitants. The tour was well organized and run very well. Plus, we left a tablet in a hotel, and the hotel called to let her know. They went 5 minutes of their way in a busy schedule to get it back for us. Bravo for the extra effort!
    Show more
  • Paula
    · December 28th, 2024
    Operated by Fez travel, an all round wonderful experience, our tour guide Halil and driver were excellent. Highly recommended.
    Show more

Dates & Availability

Select departure month and travellers

Select Date

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Upcoming departures
  • From Saturday
    2 May, 2026
    To Saturday
    9 May, 2026
    English
    From:
    US $1,065 per person
  • From Saturday
    9 May, 2026
    To Saturday
    16 May, 2026
    English
    From:
    US $1,065 per person
  • From Saturday
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    To Saturday
    23 May, 2026
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    From:
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  • From Saturday
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    To Saturday
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  • 1 Other Unavailable Departure
  • From Saturday
    30 May, 2026
    To Saturday
    6 Jun, 2026
    English
    From:
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  • From Saturday
    6 Jun, 2026
    To Saturday
    13 Jun, 2026
    This departure date is not available or sold out
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    From:
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  • From Saturday
    13 Jun, 2026
    To Saturday
    20 Jun, 2026
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    From:
    US $1,130 per person
  • From Saturday
    20 Jun, 2026
    To Saturday
    27 Jun, 2026
    English
    From:
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  • From Saturday
    27 Jun, 2026
    To Saturday
    4 Jul, 2026
    This departure date is not available or sold out
    Sold out
    From:
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  • From Saturday
    4 Jul, 2026
    To Saturday
    11 Jul, 2026
    English
    From:
    US $1,265 per person
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More benefits
Can’t find the answer to your question?
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From
US $1,065 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select Date

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Save and compare this adventure

Best price guarantee Learn More

Plan your adventure:

Good to Know

Tour ID: 334393

  • Currency
    Euro
    Greece
  • Plugs & Adapters

  • Vaccines
    • These are only indications, so please visit your doctor before you travel to be 100% sure.
    • Hepatitis A - Recommended for Greece. Ideally 2 weeks before travel.
    • Hepatitis B - Recommended for Greece. Ideally 2 months before travel.
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before April 11th, 2026 a full payment is necessary. For tours departing after April 11th, 2026, a minimum payment of $250 is required to confirm your booking with Encounters Travel. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 65 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Encounters Travel will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Encounters Travel" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec