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Luxury Island Hopping Trips Starting In May 2027 and 2028

Are you looking to embark on a luxury island hopping trip in May 2027 or 2028? Choose from 37 unique trip itineraries and 172 departures from the world's leading touring operators.
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37 Trips (172 Trip Departures)
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
$4,920
From
US$4,920
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 Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,700
Suite
$9,300
From
US$5,700
Save 1,500
Per Person
View Trip
8 Day Greece Intensive Cruise: Syros, Patmos & Rhodes with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Athens to Athens
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Onward
Departures: Sep 2026 to May 2028
Visit: Greece, Turkey
Azamara Always Included
Inside
$2,199
Oceanview
$2,389
Balcony
$2,919
Suite
$4,079
From
US$2,199
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
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 10 May 2027
Visit: Greece, Turkey
Inside
-
Oceanview
-
Balcony
-
Suite
$9,680
From
US$9,680
Per Person
View Trip
15 Day An Extended Journey Of Island Light & Adriatic Horizons with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Jun 2026
Visit: Greece, Italy, Croatia
Inside
-
Oceanview
-
Balcony
-
Suite
$11,340
From
US$11,340
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: 29 May 2027
Visit: Greece, Turkey
All-Inclusive Fare
All-Inclusive Plus Fare
Inside
-
Oceanview
-
Balcony
$8,800
Suite
$13,300
From
US$8,800
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
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 17 May 2027
Visit: Turkey, Greece
Inside
-
Oceanview
-
Balcony
-
Suite
$5,160
From
US$5,160
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
$5,900
Suite
$9,200
From
US$5,900
Save 1,500
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
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2027 to Jul 2027
Visit: Greece, Croatia, Italy
Inside
-
Oceanview
-
Balcony
-
Suite
$5,225
From
US$5,225
Per Person
View Trip
8 Day Yacht Harbors Of The Aegean Sea with Seabourn
Cruise

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Sep 2028
Visit: Turkey, Greece
Inside
-
Oceanview
-
Balcony
$5,219
Suite
$8,369
From
US$5,219
Per Person
View Trip
22 Day Greek Isles, Evening At Ephesus, Croatia & Slovenia with Seabourn
Cruise

22 Days (21 Nights) Athens to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Jul 2028
Visit: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Inside
-
Oceanview
-
Balcony
$14,129
Suite
$22,679
From
US$14,129
Per Person
View Trip
12 Day Ancient Empires: Istanbul to Athens with Scenic
New ReleaseCruise

12 Days (11 Nights) Istanbul to Athens
Cruise Line: Scenic
Ship: Scenic Ikon
Departures: May 2028 to Aug 2028
Visit: Turkey, Greece
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,093
Suite
$17,654
From
US$15,093
Save 2,370
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
$4,795
Balcony
-
Suite
-
From
US$4,795
Save 4,200
Per Person
View Trip
15 Day Crete, Evening At Ephesus & Aegean Yacht Harbors with Seabourn
Cruise

15 Days (14 Nights) Athens to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2028 to Aug 2028
Visit: Greece, Turkey
Inside
-
Oceanview
-
Balcony
$9,179
Suite
$15,119
From
US$9,179
Per Person
View Trip
15 Day An Extended Journey Through Greek Splendour, Byzantine History & Timeless Piazzas with Explora Journeys
Cruise

15 Days (14 Nights) Venice to Athens
Cruise Line: Explora Journeys
Ship: Explora I
Departures: May 2028 to Aug 2028
Visit: Italy, Slovenia, Croatia, Greece, Turkey
Inside
-
Oceanview
-
Balcony
-
Suite
$9,205
From
US$9,205
Per Person
View Trip
16 Day Hidden Gems Of Turkey, Greece, Croatia & Slovenia with Seabourn
Cruise

16 Days (15 Nights) Istanbul to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 29 May 2027
Visit: Turkey, Greece, Montenegro, Croatia, Slovenia, Italy
Inside
-
Oceanview
-
Balcony
$13,259
Suite
-
From
US$13,259
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: May 2026 to Mar 2028
Visit: Ecuador, Galapagos
Last Minute Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,400
Suite
$17,400
From
US$11,400
Save 1,500
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
29 Day Mediterranean Medley: Italy, Greece & Ephesus with Seabourn
Cruise

29 Days (28 Nights) Rome to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 08 May 2027
Visit: Italy, Sicily, Malta, Croatia, Montenegro, Greece, Turkey
Inside
-
Oceanview
-
Balcony
$27,284
Suite
-
From
US$27,284
Per Person
View Trip
26 Day Best of South America with Galápagos Cruise with APT
New ReleaseTour + Cruise

26 Days Rio de Janeiro to Guayaquil
Operated By: APT
Departures: Apr 2027 to Nov 2028
Visit: Brazil, Argentina, Chile, Peru, Ecuador, Galapagos
From
US$24,795
Per Person
View Trip
15 Day Gardens of the Italian Lakes, Slovenia & Croatian Islands Cruise with APT
Tour + Cruise

15 Days Milan to Dubrovnik
Operated By: APT
Ship: MV Lady Eleganza
Departure: 25 May 2027
Visit: Italy, Slovenia, Croatia
Inside
-
Oceanview
$12,995
Balcony
-
Suite
-
From
US$12,995
Per Person
View Trip
22 Day Mediterranean Mosaic: Italy, Ephesus & Greece with Seabourn
Cruise

22 Days (21 Nights) Dubrovnik to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 15 May 2027
Visit: Croatia, Montenegro, Italy, Greece, Turkey
Inside
-
Oceanview
-
Balcony
$23,080
Suite
-
From
US$23,080
Per Person
View Trip
23 Day Mediterranean Mosaic: Greek Isles, Ephesus & Croatia with Seabourn
Cruise

23 Days (22 Nights) Athens to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 22 May 2027
Visit: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Inside
-
Oceanview
-
Balcony
$20,909
Suite
-
From
US$20,909
Per Person
View Trip
8 Day Hidden Gems Of Turkey & Greece with Seabourn
Cruise

8 Days (7 Nights) Istanbul to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Oct 2027
Visit: Turkey, Greece
Inside
-
Oceanview
-
Balcony
$5,099
Suite
$8,499
From
US$5,099
Per Person
View Trip
15 Day Montenegro, Italy, Mykonos & Turkey with Seabourn
Cruise

15 Days (14 Nights) Dubrovnik to Istanbul
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 15 May 2027
Visit: Croatia, Montenegro, Italy, Greece, Turkey
Inside
-
Oceanview
-
Balcony
$16,293
Suite
-
From
US$16,293
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 Oct 2027
Visit: Croatia
Exclusive Savings
Inside
-
Oceanview
$2,195
Balcony
-
Suite
-
From
US$2,195
Save 2,850
Per Person
View Trip
30 Day Mediterranean Medley: Italy, Turkey, Greece & Balkans with Seabourn
Cruise

30 Days (29 Nights) Dubrovnik to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 15 May 2027
Visit: Croatia, Montenegro, Italy, Greece, Turkey, Slovenia
Inside
-
Oceanview
-
Balcony
$30,416
Suite
-
From
US$30,416
Per Person
View Trip
13 Day Spring In The Aegean with Regent Seven Seas
Cruise

13 Days (12 Nights) Istanbul to Istanbul
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 22 May 2026
Visit: Turkey, Greece
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$17,899
From
US$17,899
Save 17,899
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
Inside
-
Oceanview
-
Balcony
$11,899
Suite
$33,718
From
US$11,899
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: May 2027 to Oct 2027
Visit: Greece, Albania, Montenegro, Croatia
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$5,839
Balcony
-
Suite
$7,773
From
US$5,839
Save 2,217
Per Person
View Trip
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