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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 204 departures from the world's leading touring operators.
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39 Trips (204 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
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
Departures: May 2027 to Oct 2027
Visit: Italy, Slovenia, Croatia
Exclusive Savings
Inside
-
Oceanview
$12,354
Balcony
-
Suite
-
From
US$12,354
Save 249
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
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$16,136
Suite
$18,620
From
US$16,136
Save 1,259
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: 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: 29 May 2027
Visit: Greece, Turkey
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,300
Suite
$11,900
From
US$7,300
Save 1,500
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
$4,670
From
US$4,670
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
12 Day A Journey Of Sunlit Island Idylls & Timeless Cities with Explora Journeys
Cruise
 (1)

12 Days (11 Nights) Istanbul to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 28 May 2026
Visit: Turkey, Greece, Croatia, Italy
Inside
-
Oceanview
-
Balcony
-
Suite
$10,735
From
US$10,735
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
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
$17,269
From
US$17,269
Save 17,929
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
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,190
Suite
$9,816
From
US$6,190
Save 143
Per Person
View Trip
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
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
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
$4,380
From
US$4,380
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
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
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$28,765
Suite
-
From
US$28,765
Save 534
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$6,276
Save 984
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
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
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$21,607
Suite
-
From
US$21,607
Save 392
Per Person
View Trip
11 Day Aegean & Turkish Awakening with Oceania Cruises
Cruise

11 Days (10 Nights) Athens to Istanbul
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 07 May 2026
Visit: Greece, Turkey
Your World Included Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,660
Suite
$16,808
From
US$8,660
Save 238
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
Departure: 25 May 2026
Visit: Greece, Turkey
Inside
-
Oceanview
-
Balcony
-
Suite
$5,805
From
US$5,805
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
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
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,143
Suite
-
From
US$14,143
Save 256
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
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$29,265
Suite
-
From
US$29,265
Save 534
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
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