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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 49 unique trip itineraries and 213 departures from the world's leading touring operators.
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49 Trips (213 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
Exclusive Savings
Inside
-
Oceanview
$6,790
Balcony
-
Suite
$8,154
From
US$6,790
Save 10,686
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
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,058
Balcony
-
Suite
$6,943
From
US$6,058
Save 9,347
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
$5,330
Suite
$5,875
From
US$5,330
Save 2,870
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
Explore More
Exclusive Savings
Inside
-
Oceanview
$6,096
Balcony
-
Suite
$12,843
From
US$6,096
Save 108
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
$5,920
Suite
$7,170
From
US$5,920
Save 1,480
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
$15,270
Balcony
-
Suite
$18,312
From
US$15,270
Save 20,141
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
-
Suite
$4,670
From
US$4,670
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
$3,886
Oceanview
$4,643
Balcony
-
Suite
$9,289
From
US$3,886
Save 93
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
Explore More
Exclusive Savings
Inside
-
Oceanview
$14,625
Balcony
$19,540
Suite
-
From
US$14,625
Save 249
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
-
Suite
$4,670
From
US$4,670
Per Person
View Trip
20 Day Discover Aegean & Ancient Wonders with Emerald Cruises
New ReleaseCruise

20 Days (19 Nights) Athens to Aqaba
Cruise Line: Emerald Cruises
Ship: Emerald Raiya
Departure: 23 October 2027
Visit: Greece, Turkey, Cyprus, Israel, Egypt, Jordan
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$18,473
Balcony
-
Suite
$24,462
From
US$18,473
Save 19,507
Per Person
View Trip
15 Day Greek Isles & Ephesus with Seabourn
Cruise

15 Days (14 Nights) Athens to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,437
Suite
-
From
US$9,437
Save 222
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
$11,384
Suite
-
From
US$11,384
Save 200
Per Person
View Trip
8 Day Crete, Mykonos & Ephesus with Seabourn
Cruise

8 Days (7 Nights) Athens to Istanbul
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,530
Suite
$9,549
From
US$5,530
Save 128
Per Person
View Trip
9 Day Croatian Island Discovery with APT
Cruise

9 Days (8 Nights) Zagreb to Dubrovnik
Cruise Line: APT
Ship: MV Lady Eleganza
Departures: Jun 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
Inside
-
Oceanview
$5,495
Balcony
-
Suite
-
From
US$5,495
Save 120
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
-
Suite
$13,365
From
US$13,365
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
$2,844
Oceanview
$3,086
Balcony
$4,687
Suite
$6,724
From
US$2,844
Save 2,954
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
$14,622
Balcony
-
Suite
-
From
US$14,622
Save 252
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 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
$4,515
Balcony
$6,930
Suite
$9,763
From
US$4,515
Save 91
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
-
Suite
$12,640
From
US$12,640
Per Person
View Trip
16 Day Hidden Galapagos & Peru with Tauck
Tour + Cruise

16 Days Lima to Guayaquil or Lima to Quito
Operated By: Tauck
Ships: Silver Origin
Departures: May 2026 to Oct 2027
Visit: Peru, Ecuador, Galapagos
Inside
-
Oceanview
-
Balcony
$16,990
Suite
$29,235
From
US$16,990
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
$5,158
Balcony
-
Suite
-
From
US$5,158
Save 131
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
Exclusive Savings
Inside
-
Oceanview
$6,048
Balcony
-
Suite
$6,846
From
US$6,048
Save 21,389
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
$3,293
Oceanview
$3,661
Balcony
$4,612
Suite
$7,677
From
US$3,293
Save 76
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
-
Suite
$5,225
From
US$5,225
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
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,060
Suite
$11,460
From
US$5,060
Save 4,140
Per Person
View Trip
10 Day Treasures of the Aegean with Tauck
Tour + Cruise

10 Days Athens to Athens
Operated By: Tauck
Departures: Jun 2026 to Aug 2026
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visit: Greece, Turkey
From
US$9,990
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: Mar 2026 to Mar 2028
Visit: Ecuador, Galapagos
Last Minute Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,160
Suite
$17,280
From
US$11,160
Save 1,600
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
Exclusive Savings
Inside
-
Oceanview
$6,539
Balcony
-
Suite
$7,695
From
US$6,539
Save 10,607
Per Person
View Trip
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