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Luxury Island Hopping Trips Starting In September 2026 and 2027

Are you looking to embark on a luxury island hopping trip in September 2026 or 2027? Choose from 37 unique trip itineraries and 212 departures from the world's leading touring operators.
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37 Trips (212 Trip Departures)
8 Day A Journey Through Legendary Marvels & Cultural Fusion with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Sep 2026
Visit: Greece, Turkey
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,225
From
US$5,225
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: Jul 2026 to Sep 2026
Visit: Greece, Turkey
All-Inclusive Plus Fare
Last Minute Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,950
Suite
$10,100
From
US$4,950
Save 2,500
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
$11,000
Suite
$17,400
From
US$11,000
Save 2,500
Per Person
View Trip
8 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departures: May 2027 to Sep 2027
Visit: Greece, Turkey
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,200
Suite
$9,200
From
US$6,200
Save 1,500
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$11,590
From
US$11,590
Per Person
View Trip
10 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

10 Days (9 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 03 September 2027
Visit: Greece, Turkey
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,900
Suite
$12,500
From
US$7,900
Save 1,500
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
Multiple Deals Available
Inside
-
Oceanview
$6,276
Balcony
-
Suite
$8,262
From
US$6,512
Save 984
Per Person
View Trip
8 Day Cruising the Greek Islands of the Southern Aegean - with Smithsonian Journeys with Ponant
Cruise
 (2)

8 Days (7 Nights) Athens to Athens
Cruise Line: Ponant
Ship: Le Laperouse
Departure: 08 September 2027
Visit: Greece
Inside
-
Oceanview
-
Balcony
$7,040
Suite
$11,910
From
US$7,040
Per Person
View Trip
8 Day A Journey Through A Tapestry Of Serenity & Island Delights with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 13 September 2027
Visit: Turkey, Greece
Inside
-
Oceanview
-
Balcony
-
Suite
$5,285
From
US$5,285
Per Person
View Trip
8 Day Ephesus & Greek Island Gems with Seabourn
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Seabourn
Ship: Seabourn Quest
Departures: Jul 2026 to Sep 2026
Visit: Greece, Turkey
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
$5,601
Balcony
$6,693
Suite
$8,835
From
US$5,601
Save 150
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
$10,035
From
US$10,035
Per Person
View Trip
14 Day Croatia in Depth with APT
Cruise

14 Days (13 Nights) Zagreb to Dubrovnik
Cruise Line: APT
Ship: MV Lady Eleganza
Departures: Jul 2026 to Sep 2027
Visit: Croatia, Bosnia Herzegovina, Montenegro
Exclusive Savings
Inside
-
Oceanview
$8,047
Balcony
-
Suite
-
From
US$8,047
Save 948
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: 12 September 2026
Visit: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$2,298
Oceanview
$2,686
Balcony
-
Suite
$3,908
From
US$2,298
Save 51
Per Person
View Trip
8 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departures: May 2027 to Sep 2027
Visit: Greece, Turkey
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,000
Suite
$9,300
From
US$6,000
Save 1,500
Per Person
View Trip
36 Day Ultimate Mediterranean: From Spain To Turkey with Seabourn
Cruise

36 Days (35 Nights) Barcelona to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 25 September 2027
Visit: Spain, France, Corsica, Sardinia (+8 more), Italy, Sicily, Malta, Montenegro, Croatia, Slovenia, Greece, Turkey
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$33,088
Suite
$48,572
From
US$33,088
Save 611
Per Person
View Trip
12 Day Athens to Athens with Silversea
Cruise
 (1)

12 Days (11 Nights) Athens to Athens
Cruise Line: Silversea
Ship: Silver Nova
Departure: 20 September 2026
Visit: Greece, Turkey
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,700
Suite
$16,400
From
US$11,700
Save 1,500
Per Person
View Trip
14 Day Croatia & the Dalmatian Coast with Luxury Gold
Tour + Cruise

14 Days Zagreb to Dubrovnik
Operated By: Luxury Gold
Departures: May 2026 to Sep 2026
Visit: Croatia
Exclusive Savings
From
US$8,521
Save 401
Per Person
View Trip
12 Day Greek Islands from the Corinth Canal to the Bosporus with Emerald Cruises
New ReleaseCruise

12 Days (11 Nights) Athens to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Raiya, Emerald Kaia
Departures: Apr 2026 to Sep 2027
Visit: Greece, Turkey
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$10,070
Balcony
-
Suite
$13,552
From
US$10,430
Save 1,415
Per Person
View Trip
20 Day Mediterranean And Greek Islands with Cunard
Cruise

20 Days (19 Nights) London to London
Cruise Line: Cunard
Ship: Queen Anne
Departure: 20 September 2026
Visit: England, Spain, Greece, Sardinia, Gibraltar
Bonus Onboard Credit
Inside
$3,369
Oceanview
$4,669
Balcony
$5,649
Suite
-
From
US$3,369
Per Person
View Trip
10 Day Venice & the Dalmatian Coast with Tauck
Tour + Cruise

10 Days Venice to Venice
Operated By: Tauck
Ship: Le Boréal
Departures: Jun 2026 to Sep 2026
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visit: Italy, Croatia, Montenegro
Inside
-
Oceanview
$10,990
Balcony
$11,365
Suite
$14,690
From
US$10,990
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
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
$4,670
From
US$4,670
Per Person
View Trip
15 Day Sunlight & Stone with Regent Seven Seas
Cruise

15 Days (14 Nights) Trieste to Rome
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 16 September 2027
Visit: Italy, Croatia, Greece, Turkey, Sicily
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$17,723
Suite
$18,017
From
US$17,723
Save 18,375
Per Person
View Trip
11 Day The Greek islands, the Corinth Canal & Adriatic with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Athens to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Kaia, Emerald Azzurra
Departures: May 2026 to Aug 2027
Visit: Croatia, Montenegro, Albania, Greece
Multiple Deals Available
Inside
-
Oceanview
$9,544
Balcony
-
Suite
$12,250
From
US$13,163
Save 1,251
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
29 Day Mediterranean Medley: Spain, France & Ephesus with Seabourn
Cruise

29 Days (28 Nights) Barcelona to Istanbul
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 25 September 2027
Visit: Spain, France, Corsica, Sardinia (+8 more), Italy, Sicily, Malta, Montenegro, Croatia, Slovenia, Greece, Turkey
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$27,394
Suite
-
From
US$27,394
Save 505
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: Jun 2026 to Oct 2027
Visit: Italy, Croatia
Preferred Plus Fare + Air Credit
Select Fare
Exclusive Savings
Inside
-
Oceanview
$7,349
Balcony
-
Suite
$9,257
From
US$7,349
Save 1,035
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
9 Day Croatian Island Discovery with APT
Cruise

9 Days (8 Nights) Dubrovnik to Zagreb
Cruise Line: APT
Ship: MV Lady Eleganza
Departures: Jun 2026 to Sep 2027
Visit: Croatia
Exclusive Savings
Inside
-
Oceanview
$4,905
Balcony
-
Suite
-
From
US$4,905
Save 889
Per Person
View Trip
11 Day Ultimate Aegean Explorer with Regent Seven Seas
Cruise

11 Days (10 Nights) Athens to Istanbul
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 20 September 2027
Visit: Greece, Turkey
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,440
Suite
$12,959
From
US$11,440
Save 11,858
Per Person
View Trip
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