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Luxury Island Hopping Trips Starting In May 2026, 2027 and 2028

Are you looking to embark on a luxury island hopping trip in May 2026, 2027 or 2028? Choose from 39 unique trip itineraries and 208 departures from the world's leading touring operators.
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39 Trips (208 Trip Departures)
11 Day The Eternal Aegean with Ponant
Cruise
 (2)

11 Days (10 Nights) Valletta to Istanbul
Cruise Line: Ponant
Ship: Le Boreal
Departure: 14 May 2026
Visit: Malta, Sicily, Italy, Greece, Turkey
Inside
-
Oceanview
-
Balcony
$9,970
Suite
-
From
US$9,970
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 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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$4,670
From
US$4,670
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
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$4,960
From
US$4,960
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
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
Upgrade Your Horizon
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$12,369
From
US$12,369
Save 18,629
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$17,790
Suite
-
From
US$17,790
Save 314
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
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
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
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,360
Suite
$20,440
From
US$11,360
Save 199
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
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
$4,550
Suite
$7,590
From
US$4,550
Save 2,450
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
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,280
Suite
$11,900
From
US$7,280
Save 1,820
Per Person
View Trip
22 Day Epic Voyage: Athens to Venice with Emerald Cruises
New ReleaseCruise
 (3)

22 Days (21 Nights) Athens to Venice
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 29 May 2027
Visit: Greece, Turkey, Albania, Montenegro, Croatia, Slovenia, Italy
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$28,692
From
US$28,692
Save 30,328
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
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$11,590
From
US$11,590
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
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$8,870
Balcony
-
Suite
$11,877
From
US$12,188
Save 31,209
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$18,703
Suite
-
From
US$18,703
Save 336
Per Person
View Trip
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
A Suite Invitation
Sky & Sea
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 Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,615
Suite
$7,765
From
US$4,615
Save 2,485
Per Person
View Trip
11 Day Wonders of the Greek Islands & Aegean Riviera with Scenic
New ReleaseCruise

11 Days (10 Nights) Athens to Athens
Cruise Line: Scenic
Ship: Scenic Ikon
Departure: 27 May 2028
Visit: Greece, Turkey
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,413
Suite
$15,789
From
US$13,413
Save 17,177
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$24,301
Suite
-
From
US$24,301
Save 433
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
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,464
Suite
$17,083
From
US$14,464
Save 18,851
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,775
Suite
-
From
US$13,775
Save 253
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,888
Suite
$8,346
From
US$4,888
Save 112
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: May 2026 to Sep 2027
Visit: Croatia, Bosnia Herzegovina, Montenegro
Exclusive Savings
Inside
-
Oceanview
$7,851
Balcony
-
Suite
-
From
US$7,851
Save 605
Per Person
View Trip
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