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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 51 unique trip itineraries and 208 departures from the world's leading touring operators.
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37 Days
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51 Trips (208 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
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$7,267
Balcony
-
Suite
$9,042
From
US$7,267
Save 723
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$18,661
Suite
$27,383
From
US$18,661
Save 338
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
Inside
-
Oceanview
-
Balcony
-
Suite
$11,590
From
US$11,590
Per Person
View Trip
14 Day Aegean Voyage: Athens to Istanbul with Tauck
New ReleaseTour + Cruise

14 Days Athens to Istanbul
Operated By: Tauck
Departures: Apr 2026 to Oct 2026
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visit: Greece, Turkey
From
US$12,790
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
Exclusive Savings
Inside
-
Oceanview
$14,776
Balcony
-
Suite
-
From
US$14,776
Save 454
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,045
Suite
-
From
US$14,045
Save 254
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
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
$16,414
Balcony
$24,254
Suite
$37,190
From
US$16,414
Save 285
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
$5,820
From
US$5,820
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
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
10 Day Treasures of the Aegean with Tauck
Tour + Cruise

10 Days Athens to Athens
Operated By: Tauck
Departures: May 2026 to Aug 2026
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visit: Greece, Turkey
From
US$9,990
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
Inside
-
Oceanview
-
Balcony
-
Suite
$12,620
From
US$12,620
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
Exclusive Savings
Inside
-
Oceanview
$19,166
Balcony
-
Suite
-
From
US$19,166
Save 524
Per Person
View Trip
8 Day Mediterranean Enchantment with Emerald Cruises
Cruise

8 Days (7 Nights) Athens to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia, Emerald Raiya
Departures: Apr 2026 to Oct 2027
Visit: Greece, Albania, Montenegro, Croatia
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$7,050
Balcony
-
Suite
$9,050
From
US$7,050
Save 778
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
$4,380
From
US$4,380
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
Inside
-
Oceanview
-
Balcony
-
Suite
$11,850
From
US$11,850
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
Exclusive Savings
Inside
-
Oceanview
$10,124
Balcony
$16,102
Suite
$27,078
From
US$10,124
Save 175
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
Exclusive Savings
Inside
-
Oceanview
$5,158
Balcony
-
Suite
-
From
US$5,158
Save 131
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
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,160
Suite
$16,920
From
US$11,160
Save 1,600
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
Exclusive Savings
Inside
$3,293
Oceanview
$3,836
Balcony
$5,281
Suite
$8,055
From
US$3,293
Save 76
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
Exclusive Savings
Inside
-
Oceanview
$5,186
Balcony
$7,857
Suite
$11,483
From
US$5,186
Save 118
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
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$6,278
Balcony
-
Suite
$8,265
From
US$6,278
Save 868
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: Jul 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
Inside
-
Oceanview
$5,689
Balcony
-
Suite
-
From
US$5,689
Save 106
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
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: Sep 2026 to Oct 2027
Visit: Peru, Ecuador, Galapagos
Inside
-
Oceanview
-
Balcony
$16,990
Suite
$29,235
From
US$16,990
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
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,300
Suite
$12,460
From
US$6,300
Save 4,200
Per Person
View Trip
37 Day Ultimate Mediterranean: From Balkan Gems To Spain with Seabourn
Cruise

37 Days (36 Nights) Venice to Lisbon
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 09 October 2027
Visit: Italy, Slovenia, Croatia, Montenegro (+7 more), Greece, Turkey, Malta, Sicily, Sardinia, Spain, Portugal
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$31,539
Suite
$45,259
From
US$31,539
Save 560
Per Person
View Trip
12 Day A Journey Of Enchanting Mediterranean Discovery & Cultural Depth with Explora Journeys
Cruise
 (1)

12 Days (11 Nights) Istanbul to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Oct 2026
Visit: Turkey, Greece, Croatia, Italy
Inside
-
Oceanview
-
Balcony
-
Suite
$9,855
From
US$9,855
Per Person
View Trip
15 Day Peru & the Galapagos Islands with Tauck
Tour + Cruise

15 Days Lima to Guayaquil
Operated By: Tauck
Departures: Mar 2026 to Oct 2027
Visit: Peru, Ecuador, Galapagos
From
US$14,690
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
$6,080
Suite
$7,610
From
US$6,080
Save 1,520
Per Person
View Trip
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