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Greece Sailing Adventure: Cyclades Islands

5.0/5 Based on 1 Reviews No Booking FeesDedicated Travel Advisor
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US$2,464
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 Trip Length
10 Days
 Trip Starts
Santorini
 Trip Finishes
Santorini
10 Day Greece Sailing Adventure: Cyclades Islands Itinerary (Intrepid)
Countries Explored: Greece
Trip Style
Original
Departures
Max. Group Size
11
Pace
Moderate
Trip Code
ZSRV

Overview

Read reviews and enjoy exclusive savings on Intrepid's 10 Day Greece Sailing Adventure: Cyclades Islands. Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in turquoise seas and get the lay of the land from a local leader who’s got all read more the people in the right places.

Itinerary

Kalimera! Welcome to Greece. Your adventure begins in Santorini, where you’ll meet your skipper and fellow travellers at Cafe Spartakos at 1 pm at Athinios Port. If you’ve got time, consider arriving a couple of days early to see all that Santorini has to offer. There’s heaps of amazing restaurants, shops and bars in the island's capital, Thira, not to mention some of the most beautiful beaches and landscapes. Check out the volcanic beaches or take a walk along the caldera's rim to Firostefani, Imerovigli and Oia – this walk is also recommended at sunset, especially! After meeting your crew, you’ll board your yacht – your home for the next seven nights. You’ll sail to Ios’ port, where you’ll have some free time to explore the nearby beaches or check out Hora's shops, restaurants and bars – it’s all accessible within a short walk from the harbour.

Sail to the rugged island of Amorgos. This is the stunning location of Luc Bresson's film, 'The Big Blue'. Stop for a swim at Paradisi Beach before continuing along the coast to the port of Katapola. The restaurants, cafes and bars along the waterfront are an excellent place to relax and enjoy views of classic Cycladic windmills and an old Venetian castle. You might like to explore the ancient Minoan Settlement or drive up to the 11th-century monastery, Moni Hozoviotissis, for beautiful views of the Aegean Sea. Maybe head to the village of Hora, sitting high up in the rocky mountainside. Stroll through the labyrinth of stone laneways and Byzantine churches surrounding the town square. The Amorgos Archaeological Collection is housed nearby in Gavros Tower.

Cast off and sail to the Small Cyclades this morning. This group of islands are home to some small fishing villages as well as beautifully clear waters and beaches. While all these islands once harboured communities, the Middle Ages saw this reduced to just pirates and goats! Today, only Koufonisia, Iraklia, Schinoussa and Donousa have permanent residents, with the largest population said to be around 300. In the evening, maybe sample some fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.

Today you'll make your way to the largest Cycladic Island of Naxos. There’s the option of taking a daytrip around the island, but you can always stay behind and relax. The island’s best beaches are to the south, where water sports are also on offer. Maybe hike up to the old Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches all retain a medieval feel. While here, stop by the Roman Catholic Cathedral in the square, and the nearby Archaeological Museum, in the former Jesuit School of Commerce. Take an optional trip to the countryside to observe rural life, see one of the oldest temples in Greece and have lunch in the hills at a family tavern. Tonight, taste the local brew with a shot of Kitron (lemon liquor).

Sail to the island of Syros, dropping by the Bay of Gaidharos for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek Revolution made it a safe haven for the persecuted. Over the next two days, maybe catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleys (the views of the Aegean are stunning from up here). Sample authentic Greek food and culture in the capital of Syros and the Cyclades, Ermoupoli and check out the town hall in the main square. At night, maybe immerse yourself in local island life with an optional group dinner at a neighbourhood family's home. Tuck into some homemade cuisine made with fresh, seasonal ingredients and enjoy the views from the seafront.

Head to Mykonos today – with a history of around 5000 years, the island is said to be named after Apollo's grandson. It was also the mythological base for a deadly battle between Zeus and the Titans, their giant petrified bodies forming the rocks of the island. Browse the galleries and boutiques in town, see the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. Tonight, maybe wander down to Little Venice, where colourful wooden balconies hang precariously over the sea – this is the ideal spot to sit back with a cocktail and enjoy the Aegean sunset. After, join the fun of Mykonos’ notorious nightlife.

Set sail for the island of Sifnos, known for its production of high-quality ceramics. The island's bare hills contrast the fertile valleys of wild juniper, terraced olive groves and almond trees. The beach in the main port of Kamares is one of the best on the island and the ideal place to swim. Wander among the whitewashed houses, churches and chapels of the village of Apollonia – the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland for panoramic ocean views and see the medieval architecture of the fortress of Kastro.

Sail towards the tranquil island of Folegandros this morning. Named after the son of a former King of Crete, Folegandros has suffered a long history of colonisation and occupation like many of the surrounding islands. In the port of Karavostasis, the pebbly beach or waterfront tavernas are nice places to relax. Take a stroll through the island’s capital of Hora – one of the oldest villages in the Cyclades. The area in and around the Kastro is the most striking. In the evening, maybe wander up the hill to the Church of the Panagia – an excellent vantage point to view the sunset.

Bid farewell to the open water as you catch the ferry back from Ios to Santorini, arriving back at Athinios Port just before 12 pm. With no other activities planned, your adventure ends today in Santorini. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini International Airport. If you would like to extend you stay, just get in touch with your booking agent ahead of time.

Trip Inclusions

  • Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
  • Walk along the volcanic rim of Santorini, past white villages that cling to cliffs and watch as day turns to night during sunset at the caldera – this is a memory you’ll bring home!
  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village.
  • Visit Mykonos for the quintessential Greek Islands experience. Embrace your hedonistic side with the boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

  • Overnight boat (9 nights)

  • No meals are included on this trip.

  • Kitty: A compulsory payment of 110.00 EUR must be paid locally on your trip. This amount may change up to 48 hours before departure - please check your Essential Trip Information for the latest details. An Intrepid “kitty” is a central fund required on certain trips, used to cover shared costs such as group meals, local tips (for guides, drivers and hotel staff), and miscellaneous expenses not included in the main tour price. We include the kitty amount in the advertised price for transparency, but it will not appear in your quote since it is payable locally.
  • Accommodation, itinerary and inclusions subject to change.
  • Price is for land, cruise and internal flights as specified. Flights not specified are not included
  • Intrepid regularly update their itineraries throughout the year based on feedback and local conditions. Therefore the itinerary you see now may differ from when you booked. Global Journeys will provide you with detailed trip notes at the time of quoting, along with a finalised itinerary and trip notes before your trip departs.
5.0
Average Rating 5.0 / 5
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Sailing the Cyclades 1 , VIC, Australia, Sep 2023
Fantastic sailing trip, visited 8 beautiful islands. You sail in the morning wind permitting for around 4/6 hours arriving at the next island in plenty of time to explore and enjoy dinner. Our skipper Fotis was local and we always felt safe in his capable hands. The yacht is 56 feet so you don’t have very much sleeping and bathroom space, you need to read more be prepared for that. Highly recommend this Intrepid trip.

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Wednesday 23 Sep 2026 23 Sep 26 Santorini
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Tuesday 29 Sep 2026 29 Sep 26 Santorini
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Saturday 01 May 2027 01 May 27 Santorini
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Friday 21 May 2027 21 May 27 Santorini
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Tuesday 25 May 2027 25 May 27 Santorini
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Monday 31 May 2027 31 May 27 Santorini
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Friday 04 Jun 2027 04 Jun 27 Santorini
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Thursday 10 Jun 2027 10 Jun 27 Santorini
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Monday 14 Jun 2027 14 Jun 27 Santorini
Wednesday 23 Jun 2027 23 Jun 27 Santorini
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Was: $3,106
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Sunday 20 Jun 2027 20 Jun 27 Santorini
Tuesday 29 Jun 2027 29 Jun 27 Santorini
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Was: $3,106
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Thursday 24 Jun 2027 24 Jun 27 Santorini
Saturday 03 Jul 2027 03 Jul 27 Santorini
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Wednesday 30 Jun 2027 30 Jun 27 Santorini
Friday 09 Jul 2027 09 Jul 27 Santorini
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Sunday 04 Jul 2027 04 Jul 27 Santorini
Tuesday 13 Jul 2027 13 Jul 27 Santorini
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Saturday 10 Jul 2027 10 Jul 27 Santorini
Monday 19 Jul 2027 19 Jul 27 Santorini
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Wednesday 14 Jul 2027 14 Jul 27 Santorini
Friday 23 Jul 2027 23 Jul 27 Santorini
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Was: $3,106
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Save $93
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Tuesday 20 Jul 2027 20 Jul 27 Santorini
Thursday 29 Jul 2027 29 Jul 27 Santorini
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Exclusive Savings
Was: $3,106
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Save $93
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Saturday 24 Jul 2027 24 Jul 27 Santorini
Monday 02 Aug 2027 02 Aug 27 Santorini
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Was: $3,106
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Save $93
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Friday 30 Jul 2027 30 Jul 27 Santorini
Sunday 08 Aug 2027 08 Aug 27 Santorini
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Was: $3,106
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Save $93
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Tuesday 03 Aug 2027 03 Aug 27 Santorini
Thursday 12 Aug 2027 12 Aug 27 Santorini
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Exclusive Savings
Was: $3,106
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Save $93
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Monday 09 Aug 2027 09 Aug 27 Santorini
Wednesday 18 Aug 2027 18 Aug 27 Santorini
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Exclusive Savings
Was: $3,106
US$3,013
Save $93
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Friday 13 Aug 2027 13 Aug 27 Santorini
Sunday 22 Aug 2027 22 Aug 27 Santorini
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Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Thursday 19 Aug 2027 19 Aug 27 Santorini
Saturday 28 Aug 2027 28 Aug 27 Santorini
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Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Monday 23 Aug 2027 23 Aug 27 Santorini
Wednesday 01 Sep 2027 01 Sep 27 Santorini
Details
Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Sunday 29 Aug 2027 29 Aug 27 Santorini
Tuesday 07 Sep 2027 07 Sep 27 Santorini
Details
Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Thursday 02 Sep 2027 02 Sep 27 Santorini
Saturday 11 Sep 2027 11 Sep 27 Santorini
Details
Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Wednesday 08 Sep 2027 08 Sep 27 Santorini
Friday 17 Sep 2027 17 Sep 27 Santorini
Details
Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Sunday 12 Sep 2027 12 Sep 27 Santorini
Tuesday 21 Sep 2027 21 Sep 27 Santorini
Details
Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Saturday 18 Sep 2027 18 Sep 27 Santorini
Monday 27 Sep 2027 27 Sep 27 Santorini
Details
Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Wednesday 22 Sep 2027 22 Sep 27 Santorini
Friday 01 Oct 2027 01 Oct 27 Santorini
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Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Tuesday 28 Sep 2027 28 Sep 27 Santorini
Thursday 07 Oct 2027 07 Oct 27 Santorini
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Definite Departure
Exclusive Savings
Was: $3,106
US$3,013
Save $93
Twin Share (Per Personpp)
Saturday 02 May 2026 02 May 26 Santorini
Monday 11 May 2026 11 May 26 Santorini
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US$6,006
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Friday 22 May 2026 22 May 26 Santorini
Sunday 31 May 2026 31 May 26 Santorini
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Tuesday 26 May 2026 26 May 26 Santorini
Thursday 04 Jun 2026 04 Jun 26 Santorini
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US$6,006
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Monday 01 Jun 2026 01 Jun 26 Santorini
Wednesday 10 Jun 2026 10 Jun 26 Santorini
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Was: $6,006
US$5,469
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Friday 05 Jun 2026 05 Jun 26 Santorini
Sunday 14 Jun 2026 14 Jun 26 Santorini
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Thursday 11 Jun 2026 11 Jun 26 Santorini
Saturday 20 Jun 2026 20 Jun 26 Santorini
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Was: $6,006
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Save $537
Solo (Own Room)
Monday 15 Jun 2026 15 Jun 26 Santorini
Wednesday 24 Jun 2026 24 Jun 26 Santorini
Details
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Was: $5,946
US$5,419
Save $527
Solo (Own Room)
Sunday 21 Jun 2026 21 Jun 26 Santorini
Tuesday 30 Jun 2026 30 Jun 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Thursday 25 Jun 2026 25 Jun 26 Santorini
Saturday 04 Jul 2026 04 Jul 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Wednesday 01 Jul 2026 01 Jul 26 Santorini
Friday 10 Jul 2026 10 Jul 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Sunday 05 Jul 2026 05 Jul 26 Santorini
Tuesday 14 Jul 2026 14 Jul 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Saturday 11 Jul 2026 11 Jul 26 Santorini
Monday 20 Jul 2026 20 Jul 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Wednesday 15 Jul 2026 15 Jul 26 Santorini
Friday 24 Jul 2026 24 Jul 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Tuesday 21 Jul 2026 21 Jul 26 Santorini
Thursday 30 Jul 2026 30 Jul 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Saturday 25 Jul 2026 25 Jul 26 Santorini
Monday 03 Aug 2026 03 Aug 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Friday 31 Jul 2026 31 Jul 26 Santorini
Sunday 09 Aug 2026 09 Aug 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Tuesday 04 Aug 2026 04 Aug 26 Santorini
Thursday 13 Aug 2026 13 Aug 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Monday 10 Aug 2026 10 Aug 26 Santorini
Wednesday 19 Aug 2026 19 Aug 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Friday 14 Aug 2026 14 Aug 26 Santorini
Sunday 23 Aug 2026 23 Aug 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Thursday 20 Aug 2026 20 Aug 26 Santorini
Saturday 29 Aug 2026 29 Aug 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Monday 24 Aug 2026 24 Aug 26 Santorini
Wednesday 02 Sep 2026 02 Sep 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,806
US$5,304
Save $502
Solo (Own Room)
Sunday 30 Aug 2026 30 Aug 26 Santorini
Tuesday 08 Sep 2026 08 Sep 26 Santorini
Details
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Was: $5,976
US$5,443
Save $533
Solo (Own Room)
Thursday 03 Sep 2026 03 Sep 26 Santorini
Saturday 12 Sep 2026 12 Sep 26 Santorini
Details
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Exclusive Savings
Was: $5,976
US$5,443
Save $533
Solo (Own Room)
Wednesday 09 Sep 2026 09 Sep 26 Santorini
Friday 18 Sep 2026 18 Sep 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,976
US$5,443
Save $533
Solo (Own Room)
Sunday 13 Sep 2026 13 Sep 26 Santorini
Tuesday 22 Sep 2026 22 Sep 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,976
US$5,443
Save $533
Solo (Own Room)
Saturday 19 Sep 2026 19 Sep 26 Santorini
Monday 28 Sep 2026 28 Sep 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,976
US$5,443
Save $533
Solo (Own Room)
Wednesday 23 Sep 2026 23 Sep 26 Santorini
Friday 02 Oct 2026 02 Oct 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,976
US$5,443
Save $533
Solo (Own Room)
Tuesday 29 Sep 2026 29 Sep 26 Santorini
Thursday 08 Oct 2026 08 Oct 26 Santorini
Details
Definite Departure
Exclusive Savings
Was: $5,976
US$5,443
Save $533
Solo (Own Room)
Show more dates...
Note
A definite departure means minimum numbers have been reached for this departure to operate. Your Global Journeys Travel Advisor will check the availability of your departure date when you Inquire. Additional savings may apply. T&C’s apply.
Note
Tour & cruises prices are per person. Prices shown have savings applied, are subject to availability and may be withdrawn at any time without notice. Pricing and trip details are correct at this point in time, however are subject to confirmation at the time of booking and are subject to change by Intrepid. For cruise itineraries, cabin images are sourced from the cruise-line and should be treated as indicative only. Cabin inclusions, upholsteries and room layout may differ to the image(s) shown depending on the ship selected and your sailing dates.

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