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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 213 departures from the world's leading touring operators.
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39 Trips (213 Trip Departures)
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
$14,092
Balcony
-
Suite
$18,312
From
US$14,092
Save 16,210
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
$5,388
Suite
$9,549
From
US$5,388
Save 111
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
$4,670
Suite
$5,280
From
US$4,670
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
$15,874
Suite
$25,453
From
US$15,874
Save 275
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
$4,960
Suite
$5,610
From
US$4,960
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
$21,302
Suite
-
From
US$21,302
Save 372
Per Person
View Trip
29 Day Mediterranean And Greek Islands with Cunard
Cruise
 (1)

29 Days (28 Nights) Barcelona to Rome
Cruise Line: Cunard
Ship: Queen Victoria
Departure: 04 May 2026
Visit: Spain, Greece, Turkey, Sicily, France, Italy, Corsica
Inside
$4,159
Oceanview
-
Balcony
$6,971
Suite
$10,030
From
US$4,159
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
$22,363
Balcony
-
Suite
$28,692
From
US$22,363
Save 23,607
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
$10,277
Suite
$19,690
From
US$10,277
Save 177
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
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$5,805
Balcony
-
Suite
$6,313
From
US$5,805
Save 21,801
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
$11,020
Suite
$12,540
From
US$11,020
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
$4,670
Suite
$5,280
From
US$4,670
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
$4,764
Suite
$8,096
From
US$4,764
Save 98
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$21,292
Suite
-
From
US$21,292
Save 382
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,880
Suite
$11,540
From
US$6,880
Save 1,720
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,270
Suite
$7,220
From
US$4,270
Save 1,830
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
$4,920
Suite
$5,560
From
US$4,920
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
$5,565
Suite
$6,290
From
US$5,565
Per Person
View Trip
17 Day Discover Mediterranean Gems from Athens to Rome with Emerald Cruises
New ReleaseCruise

17 Days (16 Nights) Athens to Rome
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 01 May 2027
Visit: Greece, Albania, Montenegro, Croatia, Italy, Sicily
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$16,497
Balcony
-
Suite
$21,541
From
US$16,497
Save 17,483
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 182
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,620
Suite
$7,570
From
US$4,620
Save 1,980
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
$16,204
Suite
-
From
US$16,204
Save 285
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 106
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: Jan 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
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
Last Minute Fare
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
11 Day The Greek Islands, Adriatic & Corinth Canal 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
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$8,356
Balcony
-
Suite
$11,363
From
US$8,356
Save 14,574
Per Person
View Trip
8 Day Grecian & Turkish Wonders with Regent Seven Seas
Cruise

8 Days (7 Nights) Athens to Istanbul
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 15 May 2026
Visit: Greece, Turkey
Upgrade Your Horizon
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,224
From
US$7,224
Save 11,674
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
$10,703
Suite
$11,438
From
US$10,703
Save 16,895
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
$9,187
Suite
$19,183
From
US$9,187
Save 195
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
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$6,053
Balcony
-
Suite
$8,163
From
US$6,053
Save 9,558
Per Person
View Trip
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