Home > Cruises > Luxury Cruises > Island Hopping Cruises & Sailing Trips > October

Luxury Island Hopping Trips Starting In October 2026, 2027 and 2028

Are you looking to embark on a luxury island hopping trip in October 2026, 2027 or 2028? Choose from 69 unique trip itineraries and 234 departures from the world's leading touring operators.
Filter Results
69 Trips (234 Departures)
69 Trips (234 Departures)
Departures
Duration
7 Days
37 Days
Regions
Trip Styles
Start & End Cities
Operators
Show More...
Price
$2,000pp
$80,995pp
Countries
Show More...
8 Day Mediterranean Enchantment with Emerald Cruises
Cruise

8 Days (7 Nights) Dubrovnik to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya +2 more, Emerald Kaia, Emerald Sakara
Departures: Jul 2027 to Oct 2028
Visits: Croatia, Montenegro, Albania, Greece
Exclusive Savings
Inside
-
Oceanview
$8,099
Balcony
-
Suite
$10,867
From (Per Person)
A$8,099
Save 2,225
Per Person
View Trip
15 Day An Extended Journey Of Greek Isles, Turkish Landmarks & Classic Legends with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 04 October 2027
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$13,377
From (Per Person)
A$13,377
Save 273
Per Person
View Trip
12 Day Ionian & Aegean Wonders with Oceania Cruises
Cruise
 (3)

12 Days (11 Nights) Rome to Athens
Cruise Line: Oceania
Ship: Oceania Marina
Departure: 26 October 2028
Visits: Italy, Sicily, Malta, Greece
Your World Inclusions
Exclusive Savings
Inside
$4,621
Oceanview
$5,970
Balcony
$7,124
Suite
$10,432
From (Per Person)
A$4,621
Save 2,129
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
Visits: Italy, Croatia, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$10,746
From (Per Person)
A$10,746
Save 219
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: Sep 2026 to Oct 2026
Visits: Greece, Croatia, Italy, Montenegro
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$17,689
From (Per Person)
A$17,689
Save 384
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
Visits: Italy, Croatia, Montenegro, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$20,374
From (Per Person)
A$20,374
Save 416
Per Person
View Trip
8 Day Mediterranean Enchantment with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Athens to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya, Emerald Kaia
Departures: Jun 2027 to Sep 2028
Visits: Greece, Albania, Montenegro, Croatia
Exclusive Savings
Inside
-
Oceanview
$8,246
Balcony
-
Suite
$11,406
From (Per Person)
A$8,246
Save 2,649
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
Visits: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
$3,674
Balcony
$5,007
Suite
$10,671
From (Per Person)
A$3,674
Save 87
Per Person
View Trip
15 Day Greece Intensive Combination Cruise: Volos, Santorini & Mykonos with Azamara Cruises
Cruise
 (4)

15 Days (14 Nights) Athens to Athens
Cruise Line: Azamara
Ship: Azamara Journey
Departure: 21 October 2028
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$6,754
Oceanview
$7,293
Balcony
$8,920
Suite
$12,507
From (Per Person)
A$6,754
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,187
Suite
$19,502
From (Per Person)
A$10,187
Save 8,713
Per Person
View Trip
8 Day Greece Intensive Cruise: Chios, Rhodes & Santorini with Azamara Cruises
Cruise
 (4)

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Azamara
Ship: Azamara Journey
Departure: 28 October 2028
Visits: Turkey, Greece
Azamara Always Included
Exclusive Savings
Inside
$3,382
Oceanview
$3,656
Balcony
$4,480
Suite
$6,263
From (Per Person)
A$3,382
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
Ship: Azamara Onward
Departure: 06 October 2026
Visits: Italy, Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$7,149
Oceanview
$8,247
Balcony
-
Suite
$20,183
From (Per Person)
A$7,149
Save 120
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: Sep 2026 to Oct 2026
Visits: Greece, Croatia, Italy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$8,232
From (Per Person)
A$8,232
Save 184
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
Visits: Croatia, Italy, Albania, Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$24,688
Suite
-
From (Per Person)
A$24,688
Save 475
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
Ship: Azamara Quest
Departure: 03 October 2026
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$4,424
Oceanview
$4,963
Balcony
$6,119
Suite
-
From (Per Person)
A$4,424
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
Visits: Greece, Montenegro, Italy, Croatia
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$22,364
From (Per Person)
A$22,364
Save 456
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,484
Suite
$23,716
From (Per Person)
A$15,484
Save 316
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, Emerald Sakara
Departures: Jul 2026 to Oct 2028
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
$8,249
Balcony
-
Suite
$10,401
From (Per Person)
A$8,249
Save 3,497
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
Departures: Oct 2026
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,125
Suite
$8,967
From (Per Person)
A$6,125
Save 6,150
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
Visits: Greece, Montenegro, Italy, Croatia
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$10,628
From (Per Person)
A$10,628
Save 217
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
Visits: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,723
From (Per Person)
A$6,723
Save 137
Per Person
View Trip
15 Day Greece Intensive Combination Cruise: Santorini, Rhodes & Patmos with Azamara Cruises
Cruise
 (8)

15 Days (14 Nights) Athens to Athens
Cruise Line: Azamara
Ship: Azamara Onward
Departure: 07 October 2028
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$6,815
Oceanview
$7,354
Balcony
$8,990
Suite
$12,577
From (Per Person)
A$6,815
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
Visits: Turkey, Greece, Albania, Italy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,678
Suite
$28,007
From (Per Person)
A$15,678
Save 301
Per Person
View Trip
21 Day Discover Western Mediterranean with Emerald Cruises
New ReleaseCruise
 (3)

21 Days (20 Nights) Athens to Valletta
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 18 October 2028
Visits: Greece, Turkey, Sicily, Malta
Exclusive Savings
Inside
-
Oceanview
$22,002
Balcony
-
Suite
$29,352
From (Per Person)
A$22,002
Save 6,388
Per Person
View Trip
11 Day Greece, Cyprus & Turkey: Paros, Limassol & Antalya with Azamara Cruises
Cruise
 (5)

11 Days (10 Nights) Athens to Athens
Cruise Line: Azamara
Ship: Azamara Quest
Departure: 14 October 2026
Visits: Greece, Cyprus, Turkey
Azamara Always Included
Exclusive Savings
Inside
$3,678
Oceanview
$4,079
Balcony
$4,667
Suite
$8,538
From (Per Person)
A$3,678
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
Visits: Italy, Croatia, Greece, Montenegro, Albania
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$19,326
From (Per Person)
A$19,326
Save 394
Per Person
View Trip
8 Day Greece Intensive Cruise: Rhodes, Patmos & Mykonos with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Athens to Athens
Cruise Line: Azamara
Ship: Azamara Onward
Departure: 14 October 2028
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$3,422
Oceanview
$3,706
Balcony
$4,520
Suite
$6,313
From (Per Person)
A$3,422
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
$4,673
Balcony
-
Suite
$16,918
From (Per Person)
A$4,673
Save 86
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
Visits: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,526
From (Per Person)
A$7,526
Save 158
Per Person
View Trip
8 Day Greece Intensive Cruise: Athens, Santorini & Crete with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Athens to Athens
Cruise Line: Azamara
Ship: Azamara Onward
Departure: 07 October 2028
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$3,382
Oceanview
$3,666
Balcony
$4,480
Suite
$6,273
From (Per Person)
A$3,382
Per Person
View Trip
Results: 1-30 of 69

No trips found. Try adjusting the search filters.




Trips found! Scroll up to view.

Luxury Travel

Luxury Tours Luxury Cruises Luxury River Cruises Luxury Small Group Tours

Luxury Trips By Region

Africa Alaska Amazon Arctic Argentina Asia Australia Balkans Botswana Brazil Cambodia Canada & Alaska Central America Central Europe Chile Corsica Costa Rica Croatia Denmark Eastern Europe Eastern Med Ecuador Egypt England Europe Finland France Galápagos Germany Greece Greenland Iceland India Indonesia Ireland Italy Japan Jordan Kenya Latin America Malta Mexico Middle East Morocco New South Wales New Zealand Northern Ireland Northern Italy Norway Patagonia Peru Portugal Queensland Sardinia Scandinavia Scotland Sicily Slovenia South America South Australia South East Asia South Korea Southern Italy Spain Spain & Portugal Sweden Switzerland Tanzania Turkey UK & Ireland USA Vietnam Western Australia Western Europe

Cruise Themes

Adults Only Cruises Christmas & New Year Cruises Expedition Cruises Family Cruises Island Hopping Cruises Luxury Cruises Northen Lights Cruises Sailing Trips Short Cruises Last Minute Cruise Deals

© 2010-2026. Global Journeys. You're viewing our site in Australian dollars.

    

Global Journeys | Terms & Conditions

Global Journeys Pty Ltd. Accredited Member of The Australian Travel Industry Association (ATIA). No. A11351.

Travel Industry Associations