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Luxury Island Hopping Trips Starting In May 2027, 2028 and 2029

Are you looking to embark on a luxury island hopping trip in May 2027, 2028 or 2029? Choose from 38 unique trip itineraries and 99 departures from the world's leading touring operators.
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38 Trips (99 Departures)
38 Trips (99 Departures)
Departures
Duration
8 Days
31 Days
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Price
$3,500pp
$81,315pp
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8 Day Mediterranean Enchantment with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Dubrovnik to Athens
Operator: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia +2 more, Emerald Raiya, Emerald Sakara
Departures: Jul 2027 to Oct 2028
Visits: Croatia, Montenegro, Albania, Greece
Exclusive Savings
Oceanview
$8,099
Balcony
$10,867
Suite
$10,867
From (Per Person)
A$8,099
Save 5,505
Per Person
View Trip
8 Day A Journey from Sunlit Cyclades to Adriatic Elegance with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Venice
Operator: Explora Journeys
Ship: Explora II
Departures: May 2027 to Jul 2027
Visits: Greece, Croatia, Italy
Exclusive Savings
Suite
$9,898
From (Per Person)
A$7,918
Save 221
Per Person
View Trip
8 Day Greek Islands & Turkish Coastlines with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) Athens to Athens
Operator: Emerald Cruises
Ship: Emerald Azzurra
Departure: 29 May 2027
Visits: Greece, Turkey
Exclusive Savings
Oceanview
-
Balcony
-
Suite
$13,312
From (Per Person)
A$13,312
Save 1,748
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
Operator: Explora Journeys
Ship: Explora II
Departures: May 2027 to Oct 2027
Visits: Greece, Turkey
Exclusive Savings
Suite
$8,546
From (Per Person)
A$7,644
Save 180
Per Person
View Trip
8 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Operator: Silversea
Ships: Silver Nova, Silver Ray
Departures: May 2027 to Sep 2028
Visits: Greece, Turkey
Exclusive Savings
Balcony
$8,722
Suite
$12,495
From (Per Person)
A$8,722
Save 1,948
Per Person
View Trip
8 Day Croatian Coast and the Best of the Adriatic with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Venice to Dubrovnik
Operator: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia +2 more, Emerald Raiya, Emerald Sakara
Departures: Jun 2027 to Oct 2028
Visits: Italy, Croatia
Free Night
Exclusive Savings
Oceanview
$8,498
Balcony
$11,711
Suite
$11,267
From (Per Person)
A$8,498
Save 3,221
Per Person
View Trip
15 Day An Extended Journey From The Shores Of Athens To The Island Of Mykonos with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Athens
Operator: Explora Journeys
Ship: Explora II
Departure: 10 May 2027
Visits: Greece, Turkey
Exclusive Savings
Suite
$17,130
From (Per Person)
A$16,204
Save 331
Per Person
View Trip
8 Day A Journey Of Aegean Allure & Ancient Echoes with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Istanbul to Athens
Operator: Explora Journeys
Ship: Explora II
Departure: 17 May 2027
Visits: Turkey, Greece
Exclusive Savings
Suite
$8,193
From (Per Person)
A$8,193
Save 167
Per Person
View Trip
10 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise
 (1)

10 Days (9 Nights) Athens to Athens
Operator: Silversea
Ship: Silver Nova
Departure: 29 May 2027
Visits: Greece, Turkey
Exclusive Savings
Balcony
$10,976
Suite
$14,749
From (Per Person)
A$10,976
Save 1,974
Per Person
View Trip
8 Day Greece Intensive Cruise: Syros, Patmos & Rhodes with Azamara Cruises
Cruise
 (6)

8 Days (7 Nights) Athens to Athens
Operator: Azamara
Ship: Azamara Journey
Departure: 06 May 2028
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$3,639
Oceanview
$3,942
Balcony
$4,815
Suite
$6,745
From (Per Person)
A$3,639
Per Person
View Trip
17 Day Greece & Croatia Combination Cruise: Rhodes, Santorini & Hvar with Azamara Cruises
Cruise
 (6)

17 Days (16 Nights) Athens to Venice
Operator: Azamara
Ship: Azamara Journey
Departure: 06 May 2028
Visits: Greece, Turkey, Montenegro, Croatia, Italy
Azamara Always Included
Exclusive Savings
Inside
$8,765
Oceanview
$9,470
Balcony
$11,577
Suite
$16,223
From (Per Person)
A$8,765
Per Person
View Trip
22 Day Greek Isles, Evening At Ephesus, Croatia & Slovenia with Seabourn
Cruise

22 Days (21 Nights) Athens to Venice
Operator: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Jul 2028
Visits: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Balcony
$21,799
Suite
$41,203
From (Per Person)
A$21,799
Save 529
Per Person
View Trip
15 Day Peru & the Galapagos Islands with Tauck
Tour + Cruise

15 Days Lima to Guayaquil
Operator: Tauck
Departures: Apr 2027 to Oct 2027
Interests: Coach, Cruise, Island Hopping, Wildlife
Visits: Peru, Ecuador, Galapagos
Complimentary Hotel Night
From (Per Person)
A$22,166
Per Person
View Trip
15 Day Montenegro, Italy, Mykonos & Turkey with Seabourn
Cruise

15 Days (14 Nights) Dubrovnik to Istanbul
Operator: Seabourn
Ship: Seabourn Ovation
Departure: 15 May 2027
Visits: Croatia, Montenegro, Italy, Greece, Turkey
Exclusive Savings
Balcony
$26,771
Suite
-
From (Per Person)
A$26,771
Save 527
Per Person
View Trip
15 Day Crete, Evening At Ephesus & Aegean Yacht Harbors with Seabourn
Cruise

15 Days (14 Nights) Athens to Athens
Operator: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Sep 2029
Visits: Greece, Turkey
Exclusive Savings
Balcony
$13,081
Suite
$21,460
From (Per Person)
A$13,081
Save 400
Per Person
View Trip
11 Day Yachting the Less-travelled Greek Isles, Mykonos and Turkey with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Athens to Athens
Operator: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Sep 2027 to Oct 2028
Visits: Greece, Turkey
Exclusive Savings
Oceanview
$11,051
Balcony
$16,135
Suite
$14,726
From (Per Person)
A$11,051
Save 3,230
Per Person
View Trip
16 Day Hidden Gems Of Turkey, Greece, Croatia & Slovenia with Seabourn
Cruise

16 Days (15 Nights) Istanbul to Venice
Operator: Seabourn
Ship: Seabourn Ovation
Departure: 29 May 2027
Visits: Turkey, Greece, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Balcony
$23,710
Suite
-
From (Per Person)
A$23,710
Save 463
Per Person
View Trip
12 Day Ancient Empires: Istanbul to Athens with Scenic
New ReleaseCruise

12 Days (11 Nights) Istanbul to Athens
Operator: Scenic
Ship: Scenic Ikon
Departures: May 2028 to Aug 2028
Visits: Turkey, Greece
Complimentary 20min Heli Flight
Exclusive Savings
Balcony
$20,026
Suite
$23,270
From (Per Person)
A$20,026
Save 5,895
Per Person
View Trip
30 Day Mediterranean Medley: Italy, Turkey, Greece & Balkans with Seabourn
Cruise

30 Days (29 Nights) Dubrovnik to Venice
Operator: Seabourn
Ship: Seabourn Ovation
Departure: 15 May 2027
Visits: Croatia, Montenegro, Italy, Greece, Turkey, Slovenia
Exclusive Savings
Balcony
$52,222
Suite
-
From (Per Person)
A$52,222
Save 1,026
Per Person
View Trip
22 Day Mediterranean Mosaic: Italy, Ephesus & Greece with Seabourn
Cruise

22 Days (21 Nights) Dubrovnik to Athens
Operator: Seabourn
Ship: Seabourn Ovation
Departure: 15 May 2027
Visits: Croatia, Montenegro, Italy, Greece, Turkey
Exclusive Savings
Balcony
$35,895
Suite
-
From (Per Person)
A$35,895
Save 703
Per Person
View Trip
16 Day Hidden Galapagos & Peru with Tauck
Tour + Cruise

16 Days Lima to Quito
Operator: Tauck
Cruise Line: Silversea
Ship: Silver Origin
Departures: May 2027
Interests: Coach, Cruise, Island Hopping, Wildlife
Visits: Peru, Ecuador, Galapagos
Complimentary Hotel Night
From (Per Person)
A$27,413
Per Person
View Trip
31 Day Best of South America with Belmond Andean Explorer Train and Galápagos Cruise with APT
New ReleaseTour + Cruise

31 Days Rio de Janeiro to Guayaquil
Operator: APT
Departures: May 2027 to Oct 2028
Interests: Small Group, Cruise, Island Hopping, Wildlife
Visits: Brazil, Argentina, Chile, Peru, Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$42,257
Save 3,126
Per Person
View Trip
11 Day Wonders of the Greek Islands & Aegean Riviera with Scenic
New ReleaseCruise

11 Days (10 Nights) Athens to Athens
Operator: Scenic
Ship: Scenic Ikon
Departure: 27 May 2028
Visits: Greece, Turkey
Complimentary 20min Heli Flight
Exclusive Savings
Balcony
$20,076
Suite
$21,840
From (Per Person)
A$20,076
Save 4,869
Per Person
View Trip
23 Day Mediterranean Mosaic: Greek Isles, Ephesus & Croatia with Seabourn
Cruise

23 Days (22 Nights) Athens to Venice
Operator: Seabourn
Ship: Seabourn Ovation
Departure: 22 May 2027
Visits: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Balcony
$37,562
Suite
-
From (Per Person)
A$37,562
Save 736
Per Person
View Trip
15 Day An Extended Journey Of Lush Island Vistas, Roman Ruins & Hidden Coves with Explora Journeys
Cruise

15 Days (14 Nights) Athens to Venice
Operator: Explora Journeys
Ship: Explora I
Departure: 13 May 2028
Visits: Greece, Turkey, Montenegro, Croatia, Italy
Exclusive Savings
Suite
$12,372
From (Per Person)
A$12,372
Save 253
Per Person
View Trip
15 Day Greek Isles & Ephesus with Seabourn
Cruise

15 Days (14 Nights) Athens to Athens
Operator: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Aug 2027
Visits: Greece, Turkey
Exclusive Savings
Balcony
$18,441
Suite
$35,910
From (Per Person)
A$18,441
Save 491
Per Person
View Trip
13 Day Athens (Piraeus) to Athens (Piraeus) with Silversea
Cruise

13 Days (12 Nights) Athens to Athens
Operator: Silversea
Ship: Silver Shadow
Departure: 28 May 2028
Visits: Greece, Turkey
Exclusive Savings
Oceanview
$10,241
Balcony
$13,034
Suite
$20,041
From (Per Person)
A$10,241
Save 1,959
Per Person
View Trip
8 Day Yacht Harbors Of The Aegean Sea with Seabourn
Cruise

8 Days (7 Nights) Istanbul to Athens
Operator: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Sep 2029
Visits: Turkey, Greece
Exclusive Savings
Balcony
$7,246
Suite
$11,920
From (Per Person)
A$7,246
Save 211
Per Person
View Trip
8 Day A Journey Of Ancient Myths & Island Serenity with Explora Journeys
Cruise

8 Days (7 Nights) Athens to Athens
Operator: Explora Journeys
Ship: Explora I
Departure: 13 May 2028
Visits: Greece, Turkey
Exclusive Savings
Suite
$6,198
From (Per Person)
A$6,198
Save 127
Per Person
View Trip
14 Day Croatia & the Dalmatian Coast with Luxury Gold
Tour + Cruise

14 Days Zagreb to Dubrovnik
Operator: Luxury Gold
Departures: May 2027 to Sep 2027
Interests: Coach, Small Group, Cruise, Island Hopping
Visits: Croatia
Exclusive Savings
From (Per Person)
A$13,327
Save 1,308
Per Person
View Trip
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