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 70 unique trip itineraries and 241 departures from the world's leading touring operators.
Filter Results
Departures
Duration
7 Days
37 Days
Regions
Trip Styles
Start & End Cities
Operators
Show More...
Price
$1,400pp
$64,870pp
Countries
Show More...
Filter Results
70 Trips (241 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 (+2 more), Emerald Kaia, Emerald Sakara
Departures: Jul 2027 to Oct 2028
Visit: Croatia, Montenegro, Albania, Greece
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$5,677
Balcony
-
Suite
$7,675
From
US$5,677
Save 2,104
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
Visit: Greece, Turkey
Inside
-
Oceanview
-
Balcony
-
Suite
$8,700
From
US$8,700
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
A Spontaneous Summer Invitation
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,140
From
US$7,140
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
$13,280
From
US$13,280
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
8 Day Greece Intensive Cruise: Rhodes, Patmos & Mykonos with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 14 October 2028
Visit: Greece, Turkey
Azamara Always Included
Inside
$2,269
Oceanview
$2,459
Balcony
$2,999
Suite
$4,199
From
US$2,269
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
A Spontaneous Summer Invitation
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,020
From
US$7,020
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
$7,920
Suite
$13,900
From
US$7,920
Save 5,280
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 Cruises
Ship: Azamara Onward
Departure: 07 October 2028
Visit: Greece, Turkey
Azamara Always Included
Inside
$2,239
Oceanview
$2,429
Balcony
$2,979
Suite
$4,169
From
US$2,239
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
$3,509
Oceanview
$4,189
Balcony
$4,839
Suite
-
From
US$3,509
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
Visit: Greece, Turkey
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$5,778
Balcony
-
Suite
$7,858
From
US$5,778
Save 1,805
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
Inside
-
Oceanview
$6,459
Balcony
$8,499
Suite
$12,324
From
US$6,459
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: Jun 2026 to Oct 2026
Visit: Greece, Croatia, Italy
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,565
From
US$5,565
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
$4,389
Oceanview
$4,979
Balcony
$6,499
Suite
$9,249
From
US$4,389
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
$4,920
From
US$4,920
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
Last Minute Fare
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$3,950
Suite
$10,900
From
US$3,950
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
Visit: Greece, Turkey
Last Minute Fare
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$4,450
Suite
$7,250
From
US$4,450
Per Person
View Trip
25 Day Greece Intensive Combination Cruise: Delphi, Thessaloniki & Rhodes with Azamara Cruises
Cruise
 (3)

25 Days (24 Nights) Venice to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 11 October 2028
Visit: Italy, Slovenia, Croatia, Montenegro, Greece, Turkey
Azamara Always Included
Inside
$7,609
Oceanview
$8,219
Balcony
$10,079
Suite
$14,169
From
US$7,609
Per Person
View Trip
8 Day Greece Intensive Cruise: Chios, Rhodes & Santorini with Azamara Cruises
Cruise
 (3)

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 28 October 2028
Visit: Turkey, Greece
Azamara Always Included
Inside
$2,249
Oceanview
$2,429
Balcony
$2,979
Suite
$4,169
From
US$2,249
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 Cruises
Ship: Azamara Onward
Departure: 07 October 2028
Visit: Greece, Turkey
Azamara Always Included
Inside
$4,549
Oceanview
$4,909
Balcony
$5,999
Suite
$8,389
From
US$4,549
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
$4,610
From
US$4,610
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 Inclusions
Exclusive Savings
Inside
$2,899
Oceanview
$3,099
Balcony
$4,799
Suite
$6,899
From
US$2,899
Save 2,899
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
Inside
-
Oceanview
-
Balcony
$13,004
Suite
$20,399
From
US$13,004
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
Visit: Greece, Albania, Montenegro, Croatia
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$5,839
Balcony
-
Suite
$7,773
From
US$5,839
Save 2,106
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
Inside
-
Oceanview
$14,194
Balcony
-
Suite
$31,364
From
US$14,194
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
Inside
-
Oceanview
$3,399
Balcony
$4,929
Suite
$7,819
From
US$3,399
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
Inside
-
Oceanview
$9,774
Balcony
$14,619
Suite
$21,844
From
US$9,774
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
$13,365
From
US$13,365
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 Cruises
Ship: Azamara Quest
Departure: 14 October 2026
Visit: Greece, Cyprus, Turkey
Azamara Always Included
Inside
$2,779
Oceanview
$3,089
Balcony
$3,529
Suite
$6,469
From
US$2,779
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
Visit: Greece, Croatia, Italy, Montenegro
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$11,590
From
US$11,590
Per Person
View Trip
Results: 1-30 of 70

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 Austria 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 Ireland Italy Japan Jordan Kenya Laos Latin America Malta Middle East Morocco New Zealand Northern Ireland Northern Italy Norway Patagonia Peru Portugal Sardinia Scandinavia Scotland Sicily Slovenia South America South East Asia South Korea Southern Italy Spain Spain & Portugal Sweden Switzerland Tanzania Turkey UK & Ireland Uluru USA Vietnam 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 US dollars.

    

Global Journeys | Terms & Conditions

Global Journeys Travel Inc. is a Member of the American Society of Travel Advisors (ASTA No: 900374670), CLIA (No. 00046729) & is TICO Accredited (No. 50027921).

Travel Industry Associations