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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 53 unique trip itineraries and 220 departures from the world's leading touring operators.
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53 Trips (220 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
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$6,644
Balcony
-
Suite
$8,154
From
US$6,644
Save 11,852
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 Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,440
Suite
$10,030
From
US$4,440
Save 2,960
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
Explore More
Exclusive Savings
Inside
-
Oceanview
$8,777
Balcony
$12,109
Suite
$22,271
From
US$8,777
Save 147
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,670
Suite
$5,280
From
US$4,670
Per Person
View Trip
11 Day Aegean Odyssey: Athens to Istanbul with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Athens to Istanbul
Cruise Line: Emerald Cruises
Ship: Emerald Raiya
Departure: 06 October 2027
Visit: Greece, Turkey
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$8,106
Balcony
-
Suite
$11,259
From
US$8,106
Save 10,884
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
Exclusive Savings
Inside
-
Oceanview
$4,537
Balcony
-
Suite
-
From
US$4,537
Save 112
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
Explore More
Exclusive Savings
Inside
-
Oceanview
$4,265
Balcony
$6,514
Suite
$10,596
From
US$4,265
Save 84
Per Person
View Trip
22 Day Ephesus, Grecian Gems, Turkey & Rome with Seabourn
Cruise
 (1)

22 Days (21 Nights) Athens to Rome
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 11 October 2026
Visit: Greece, Turkey, Albania, Italy
Explore More
Exclusive Savings
Inside
-
Oceanview
$14,514
Balcony
$19,037
Suite
$30,116
From
US$14,514
Save 249
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: Jul 2026 to Oct 2027
Visit: Greece, Turkey
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$5,805
Balcony
-
Suite
$6,313
From
US$5,805
Save 21,801
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: May 2027 to Oct 2027
Visit: Greece, Turkey, Albania, Montenegro, Croatia
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$14,092
Balcony
-
Suite
$18,312
From
US$14,092
Save 16,210
Per Person
View Trip
12 Day Greece & Turkey Cruise: Istanbul, Thessaloniki & Athens with Azamara Cruises
Cruise
 (4)

12 Days (11 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 03 October 2026
Visit: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$3,430
Oceanview
$4,090
Balcony
$4,720
Suite
$7,757
From
US$3,430
Save 79
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: Apr 2026 to Mar 2028
Visit: Ecuador, Galapagos
Last Minute Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,200
Suite
$17,930
From
US$11,200
Save 2,800
Per Person
View Trip
22 Day An Extended Journey of Iconic Cities, Blue Horizons & Ancient Soul 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, Turkey, Cyprus
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$12,640
Suite
$14,280
From
US$12,640
Per Person
View Trip
11 Day Greece & Turkey Cruise: Mykonos, Paros & Antalya with Azamara Cruises
Cruise
 (4)

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
Exclusive Savings
Inside
$2,914
Oceanview
$3,225
Balcony
$3,681
Suite
$6,717
From
US$2,914
Save 65
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,444
Suite
-
From
US$9,444
Save 160
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
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$2,844
Oceanview
$3,086
Balcony
$4,687
Suite
$6,724
From
US$2,844
Save 2,954
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
A Suite Invitation
Sky & Sea
Inside
-
Oceanview
-
Balcony
$5,565
Suite
$6,290
From
US$5,565
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,670
Suite
$5,280
From
US$4,670
Per Person
View Trip
12 Day Adriatic, the Greek Islands & Corinth Canal with Emerald Cruises
New ReleaseCruise

12 Days (11 Nights) Dubrovnik to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Kaia, Emerald Azzurra
Departures: May 2026 to Sep 2027
Visit: Croatia, Montenegro, Albania, Greece
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$9,464
Balcony
-
Suite
$11,140
From
US$9,972
Save 15,306
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$11,020
Suite
$12,540
From
US$11,020
Per Person
View Trip
18 Day An Extended Journey Through Bewitching Isles & Glittering Shores 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, Turkey
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$12,735
Suite
$14,445
From
US$12,735
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
15 Day Greece Intensive Cruise: Volos, Mykonos & Santorini with Azamara Cruises
Cruise
 (8)

15 Days (14 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 02 October 2027
Visit: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$4,111
Oceanview
$4,693
Balcony
-
Suite
$8,330
From
US$4,111
Save 88
Per Person
View Trip
15 Day Peru & the Galapagos Islands with Tauck
Tour + Cruise

15 Days Lima to Guayaquil
Operated By: Tauck
Departures: Mar 2027 to Oct 2027
Visit: Peru, Ecuador, Galapagos
From
US$14,790
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,460
Suite
$6,340
From
US$5,460
Save 2,340
Per Person
View Trip
22 Day Mediterranean Mosaic: Dalmatian Gems, Malta & Ephesus with Seabourn
Cruise

22 Days (21 Nights) Rome to Istanbul
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 02 October 2027
Visit: Italy, Sicily, Malta, Montenegro (+4 more), Croatia, Slovenia, Greece, Turkey
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,032
Suite
$22,695
From
US$14,032
Save 247
Per Person
View Trip
8 Day Croatian Coast and the Best of the Adriatic with Emerald Cruises
Cruise

8 Days (7 Nights) Venice to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia
Departures: Jul 2026 to Oct 2027
Visit: Italy, Croatia
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$5,852
Balcony
-
Suite
$7,646
From
US$6,442
Save 10,444
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
Explore More
Exclusive Savings
Inside
-
Oceanview
$9,111
Balcony
$12,776
Suite
-
From
US$9,111
Save 153
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
8 Day Greece Intensive Cruise: Thessaloniki, Volos & Mykonos with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 02 October 2027
Visit: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$2,909
Oceanview
$3,316
Balcony
$4,102
Suite
$5,974
From
US$2,909
Save 70
Per Person
View Trip
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