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Luxury Island Hopping Trips Starting In October 2026 and 2027

Are you looking to embark on a luxury island hopping trip in October 2026 or 2027? Choose from 58 unique trip itineraries and 200 departures from the world's leading touring operators.
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58 Trips (200 Trip Departures)
8 Day Mediterranean Enchantment with Emerald Cruises
Cruise

8 Days (7 Nights) Dubrovnik to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Jul 2027 to Oct 2027
Visit: Croatia, Montenegro, Albania, Greece
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$6,477
Balcony
-
Suite
$8,639
From
US$6,477
Save 1,420
Per Person
View Trip
12 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

12 Days (11 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 26 October 2026
Visit: Greece, Turkey
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,000
Suite
$12,800
From
US$9,000
Save 2,500
Per Person
View Trip
8 Day Turkey & Greek Isle Gems with Seabourn
Cruise
 (1)

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Seabourn
Ship: Seabourn Quest
Departures: Jun 2026 to Oct 2026
Visit: Turkey, Greece
Yours to Explore
Inside
-
Oceanview
$4,999
Balcony
$6,899
Suite
$9,199
From
US$4,999
Per Person
View Trip
8 Day A Journey Of Ancient Echoes & Island Grace with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 11 October 2027
Visit: Turkey, Greece
Inside
-
Oceanview
-
Balcony
-
Suite
$4,380
From
US$4,380
Per Person
View Trip
11 Day Autumn Adventure with Oceania Cruises
Cruise
 (1)

11 Days (10 Nights) Venice to Athens
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 15 October 2027
Visit: Italy, Croatia, Greece
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$2,899
Oceanview
$3,149
Balcony
$4,799
Suite
$6,899
From
US$2,899
Save 2,899
Per Person
View Trip
22 Day An Extended Journey Across Stories, Shores & Changing Seasl with Explora Journeys
Cruise
 (1)

22 Days (21 Nights) Venice to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 29 October 2026
Visit: Italy, Croatia, Greece, Montenegro, Albania
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$12,450
From
US$12,450
Per Person
View Trip
11 Day A Journey Through Greece’s Icons To Italy’s Hidden Coastlines with Explora Journeys
Cruise
 (1)

11 Days (10 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 19 October 2026
Visit: Greece, Montenegro, Italy, Croatia
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,480
From
US$7,480
Per Person
View Trip
12 Day Greece & Turkey Cruise: Istanbul, Thessaloniki & Athens with Azamara Cruises
Cruise
 (5)

12 Days (11 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 03 October 2026
Visit: Greece, Turkey
Azamara Always Included
Inside
$3,599
Oceanview
$4,299
Balcony
$4,979
Suite
$7,819
From
US$3,599
Per Person
View Trip
22 Day Ephesus, Turkey, Grecian Gems & Dalmatian Delights with Seabourn
Cruise
 (1)

22 Days (21 Nights) Dubrovnik to Athens
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 04 October 2026
Visit: Croatia, Italy, Albania, Greece, Turkey
Yours to Explore
Inside
-
Oceanview
-
Balcony
$26,399
Suite
-
From
US$26,399
Per Person
View Trip
15 Day Greek Isles, Ephesus & Turquoise Coast with Seabourn
Cruise
 (1)

15 Days (14 Nights) Athens to Athens
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 11 October 2026
Visit: Greece, Turkey
Yours to Explore
Inside
-
Oceanview
$11,499
Balcony
$18,319
Suite
-
From
US$11,499
Per Person
View Trip
12 Day A Journey Through Seaside Legends & Living History with Explora Journeys
Cruise
 (1)

12 Days (11 Nights) Venice to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 29 October 2026
Visit: Italy, Croatia, Greece
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,520
From
US$7,520
Per Person
View Trip
8 Day A Journey Of Lush Landscapes & Golden Enchantment with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Oct 2026
Visit: Greece, Croatia, Italy
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,840
From
US$5,840
Per Person
View Trip
12 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

12 Days (11 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departures: Jun 2027 to Oct 2027
Visit: Greece, Turkey
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,400
Suite
$12,500
From
US$8,400
Save 2,500
Per Person
View Trip
8 Day A Journey Through Mythical Isles & Captivating Shores with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Istanbul
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Inside
-
Oceanview
-
Balcony
-
Suite
$4,670
From
US$4,670
Per Person
View Trip
24 Day Turkey, Greece & Andalusia with Seabourn
Cruise
 (1)

24 Days (23 Nights) Istanbul to Lisbon
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 18 October 2026
Visit: Turkey, Greece, Albania, Italy (+4 more), Corsica, Sardinia, Spain, Portugal
Yours to Explore
Inside
-
Oceanview
$16,999
Balcony
$24,299
Suite
$37,899
From
US$16,999
Per Person
View Trip
8 Day Greek Isles & Ephesus with Seabourn
Cruise
 (1)

8 Days (7 Nights) Athens to Istanbul
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 11 October 2026
Visit: Greece, Turkey
Yours to Explore
Inside
-
Oceanview
$7,599
Balcony
$9,999
Suite
$14,499
From
US$7,599
Per Person
View Trip
12 Day Greece Cruise: Crete, Mykonos & Santorini with Azamara Cruises
Cruise
 (8)

12 Days (11 Nights) Venice to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 06 October 2026
Visit: Italy, Greece, Turkey
Azamara Always Included
Inside
$4,149
Oceanview
$4,779
Balcony
-
Suite
-
From
US$4,149
Per Person
View Trip
15 Day An Extended Journey of Marble Cities & Sapphire Seas with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Oct 2026
Visit: Greece, Croatia, Italy, Montenegro
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$11,590
From
US$11,590
Per Person
View Trip
8 Day Greek Islands & Turkish Coastlines with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Athens to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Jun 2026 to Oct 2027
Visit: Greece, Turkey
Preferred Fare + Bonus Savings
Select Fare
Exclusive Savings
Inside
-
Oceanview
$5,450
Balcony
-
Suite
$7,498
From
US$5,450
Save 1,926
Per Person
View Trip
8 Day Athens to Athens with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 12 October 2026
Visit: Greece, Turkey
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,300
Suite
$9,300
From
US$6,300
Save 2,500
Per Person
View Trip
15 Day Discover the Eastern Mediterranean with Emerald Cruises
New ReleaseCruise
 (3)

15 Days (14 Nights) Athens to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Jul 2027 to Oct 2027
Visit: Greece, Turkey, Albania, Montenegro, Croatia
Inside
-
Oceanview
$15,190
Balcony
-
Suite
$19,530
From
US$15,190
Per Person
View Trip
22 Day An Extended Journey Of Returning Tides & New Shores with Explora Journeys
Cruise
 (1)

22 Days (21 Nights) Athens to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 19 October 2026
Visit: Greece, Montenegro, Italy, Croatia
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$14,480
From
US$14,480
Per Person
View Trip
11 Day Greece & Turkey Cruise: Mykonos, Paros & Antalya with Azamara Cruises
Cruise
 (5)

11 Days (10 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 14 October 2026
Visit: Greece, Cyprus, Turkey
Azamara Always Included
Inside
$3,049
Oceanview
$3,379
Balcony
$4,889
Suite
$7,469
From
US$3,049
Per Person
View Trip
15 Day Athens to Athens with Silversea
Cruise
 (1)

15 Days (14 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 12 October 2026
Visit: Greece, Turkey
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$10,000
Suite
$15,600
From
US$10,000
Per Person
View Trip
13 Day Greece & Turkey Cruise: Thessaloniki, Istanbul & Rhodes with Azamara Cruises
Cruise
 (8)

13 Days (12 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 30 October 2027
Visit: Greece, Turkey
Azamara Always Included
Inside
$3,119
Oceanview
$3,539
Balcony
$4,599
Suite
$6,529
From
US$3,119
Per Person
View Trip
18 Day An Extended Journey Of Changing Light & Coastal Lives with Explora Journeys
Cruise
 (1)

18 Days (17 Nights) Venice to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 12 October 2026
Visit: Italy, Croatia, Montenegro, Greece
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$13,640
From
US$13,640
Per Person
View Trip
8 Day Lavrion (Athens) to Athens (Piraeus) with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 05 October 2026
Visit: Greece, Turkey
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,300
Suite
$10,900
From
US$6,300
Save 2,500
Per Person
View Trip
15 Day Turkey, Greece & Roman Gems with Seabourn
Cruise
 (1)

15 Days (14 Nights) Istanbul to Rome
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 18 October 2026
Visit: Turkey, Greece, Albania, Italy
Yours to Explore
Inside
-
Oceanview
$10,649
Balcony
$15,999
Suite
$27,599
From
US$10,649
Per Person
View Trip
8 Day Athens to Athens with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 19 October 2026
Visit: Greece, Turkey
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,200
Suite
$9,200
From
US$6,200
Save 1,500
Per Person
View Trip
8 Day San Cristóbal to San Cristóbal with Silversea
Cruise

8 Days (7 Nights) Quito to Guayaquil
Cruise Line: Silversea
Ship: Silver Origin
Departures: May 2026 to Mar 2028
Visit: Ecuador, Galapagos
Last Minute Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,400
Suite
$18,100
From
US$10,400
Save 2,500
Per Person
View Trip
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