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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 57 unique trip itineraries and 212 departures from the world's leading touring operators.
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37 Days
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57 Trips (212 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 Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$7,477
Balcony
-
Suite
$9,571
From
US$7,477
Save 474
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
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
$6,100
Suite
$9,100
From
US$6,100
Save 2,500
Per Person
View Trip
11 Day A Voyage from Greece to Cyprus with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Athens to Larnaca
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 21 October 2026
Visit: Greece, Turkey, Cyprus
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$10,950
From
US$10,950
Save 1,745
Per Person
View Trip
15 Day Dalmatian Gems, Malta, Italy, Greece & Turkey with Seabourn
Cruise

15 Days (14 Nights) Venice to Istanbul
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 09 October 2027
Visit: Italy, Slovenia, Croatia, Montenegro, Greece, Turkey
Yours to Explore
Inside
-
Oceanview
-
Balcony
$14,999
Suite
-
From
US$14,999
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
$10,299
Balcony
$16,399
Suite
$27,599
From
US$10,299
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
Multiple Deals Available
Inside
-
Oceanview
$6,450
Balcony
-
Suite
$7,536
From
US$6,450
Save 1,926
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
$11,000
Suite
$17,400
From
US$11,000
Save 2,500
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
$13,460
From
US$13,460
Per Person
View Trip
22 Day Discover the Wonders of the Mediterranean & Red Sea with Emerald Cruises
New ReleaseCruise

22 Days (21 Nights) Athens to Aqaba
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 21 October 2026
Visit: Greece, Turkey, Cyprus, Israel, Egypt, Jordan
Inside
-
Oceanview
-
Balcony
-
Suite
$25,740
From
US$25,740
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
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
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,000
Suite
$12,800
From
US$9,000
Save 2,500
Per Person
View Trip
14 Day Aegean Voyage: Istanbul to Athens - Southbound with Tauck
Tour + Cruise

14 Days Istanbul to Athens
Operated By: Tauck
Departure: 13 April 2026
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visit: Turkey, Greece
From
US$12,790
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
$3,369
Oceanview
$3,929
Balcony
-
Suite
$8,669
From
US$3,369
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
10 Day Treasures of the Aegean with Tauck
Tour + Cruise

10 Days Athens to Athens
Operated By: Tauck
Departures: Jul 2026 to Aug 2026
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visit: Greece, Turkey
From
US$9,990
Per Person
View Trip
11 Day Glamorous Grecian Nights with Regent Seven Seas
Cruise

11 Days (10 Nights) Athens to Istanbul
Cruise Line: Regent Seven Seas
Ship: Seven Seas Voyager
Departure: 24 October 2026
Visit: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,699
Suite
$12,099
From
US$11,699
Save 11,699
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
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
8 Day San Cristóbal to San Cristóbal with Silversea
Cruise

8 Days (7 Nights) Quito to Guayaquil
Cruise Line: Silversea
Ship: Silver Origin
Departures: Jun 2026 to Mar 2028
Visit: Ecuador, Galapagos
Last Minute Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,000
Suite
$17,400
From
US$11,000
Save 2,500
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
$6,100
Suite
$9,100
From
US$6,100
Save 1,500
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
$10,199
Suite
$14,499
From
US$7,599
Per Person
View Trip
8 Day Istanbul to Athens Adventure with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Raiya, Emerald Azzurra
Departures: Jun 2026 to Oct 2027
Visit: Turkey, Greece
Preferred Plus Fare + Air Credit
Select Fare
Exclusive Savings
Inside
-
Oceanview
$6,452
Balcony
-
Suite
$8,484
From
US$6,452
Save 876
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
$5,099
Balcony
$7,799
Suite
$10,999
From
US$5,099
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
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
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
-
Oceanview
$5,549
Balcony
-
Suite
-
From
US$5,549
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
22 Day Mediterranean Mosaic: Greece, Ephesus, Italy & Spain with Seabourn
Cruise

22 Days (21 Nights) Athens to Barcelona
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 16 October 2027
Visit: Greece, Turkey, Malta, Sicily, Sardinia, Spain
Yours to Explore
Inside
-
Oceanview
-
Balcony
$19,799
Suite
$27,899
From
US$19,799
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
-
From
US$15,190
Per Person
View Trip
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