Home > Cruises > Luxury Cruises > Island Hopping Cruises & Sailing Trips > May

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 40 unique trip itineraries and 178 departures from the world's leading touring operators.
Filter Results
40 Trips (178 Departures)
40 Trips (178 Departures)
Departures
Duration
8 Days
31 Days
Regions
Trip Styles
Start & End Cities
Operators
Show More...
Price
$2,900pp
$80,995pp
Countries
Show More...
8 Day Mediterranean Enchantment with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Dubrovnik to Athens
Cruise Line: 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
Suite
$10,867
From (Per Person)
A$8,099
Save 2,225
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
Visits: Greece, Turkey
Exclusive Savings
Balcony
$10,530
Suite
$18,130
From (Per Person)
A$10,530
Save 4,820
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
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia +2 more, Emerald Raiya, Emerald Sakara
Departures: Jun 2027 to Oct 2028
Visits: Italy, Croatia
Exclusive Savings
Oceanview
$8,498
Suite
$11,267
From (Per Person)
A$8,498
Save 2,661
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
Visits: Turkey, Greece
Exclusive Savings
Suite
$7,879
From (Per Person)
A$7,879
Save 161
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
Visits: Greece, Croatia, Italy
Exclusive Savings
Suite
$7,526
From (Per Person)
A$7,526
Save 174
Per Person
View Trip
17 Day Greece & Croatia Combination Cruise: Rhodes, Santorini & Hvar with Azamara Cruises
Cruise
 (4)

17 Days (16 Nights) Athens to Venice
Cruise Line: Azamara
Ship: Azamara Journey
Departure: 06 May 2028
Visits: Greece, Turkey, Montenegro, Croatia, Italy
Azamara Always Included
Exclusive Savings
Inside
$6,814
Oceanview
$7,364
Balcony
$9,011
Suite
$12,633
From (Per Person)
A$6,814
Save 455
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
Ship: Emerald Azzurra
Departure: 29 May 2027
Visits: Greece, Turkey, Albania, Montenegro, Croatia
Exclusive Savings
Oceanview
-
Suite
$39,281
From (Per Person)
A$39,281
Save 2,759
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
Departure: 15 May 2027
Visits: Greece, Turkey
Exclusive Savings
Balcony
$9,408
Suite
$15,925
From (Per Person)
A$9,408
Save 2,592
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
Ships: Silver Nova, Silver Ray
Departures: May 2027 to Sep 2028
Visits: Greece, Turkey
Exclusive Savings
Balcony
$7,203
Suite
$15,239
From (Per Person)
A$7,203
Save 5,047
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
Ships: Azamara Journey, Azamara Onward
Departures: Sep 2026 to May 2028
Visits: Greece, Turkey
Azamara Always Included
Exclusive Savings
Inside
$3,028
Oceanview
$3,280
Balcony
$3,996
Suite
$5,588
From (Per Person)
A$3,028
Save 201
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
Visits: Greece, Turkey
Exclusive Savings
Suite
$18,620
From (Per Person)
A$18,620
Save 380
Per Person
View Trip
8 Day Greek Islands & Turkish Coastlines with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) Athens to Athens
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 29 May 2027
Visits: Greece, Turkey
Exclusive Savings
Oceanview
-
Suite
$12,831
From (Per Person)
A$12,831
Save 1,739
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
Visits: Greece, Turkey
Exclusive Savings
Suite
$7,174
From (Per Person)
A$7,174
Save 155
Per Person
View Trip
14 Day Croatia in Depth with APT
Cruise

14 Days (13 Nights) Zagreb to Dubrovnik
Tour Operator: APT
Ships: MV Lady Eleganza
Departures: Jul 2026 to Sep 2028
Visits: Croatia, Bosnia Herzegovina, Montenegro
Exclusive Savings
Oceanview
$10,064
From (Per Person)
A$11,779
Save 3,181
Per Person
View Trip
16 Day Hidden Galapagos & Peru with Tauck
Tour + Cruise

16 Days Lima to Quito
Cruise Line: Silversea
Tour Operator: Tauck
Ship: Silver Origin
Departures: Apr 2027 to Sep 2027
Trip Styles: Coach, Cruise, Island Hopping, Wildlife, Scenic
Visits: Peru, Ecuador, Galapagos
From (Per Person)
A$27,413
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
Tour Operator: APT
Departures: Apr 2027 to Nov 2028
Trip Styles: Small Group, Cruise, Island Hopping, Wildlife, Scenic
Visits: Brazil, Argentina, Chile, Peru, Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$33,141
Save 2,354
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
Visits: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Balcony
$34,034
Suite
-
From (Per Person)
A$34,034
Save 664
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
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 13 May 2028
Visits: Greece, Turkey, Montenegro, Croatia, Italy
Exclusive Savings
Suite
$14,274
From (Per Person)
A$14,274
Save 291
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
Visits: Greece, Turkey, Montenegro, Croatia, Slovenia, Italy
Exclusive Savings
Balcony
$22,779
Suite
$35,323
From (Per Person)
A$22,779
Save 493
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
Visits: Italy, Sicily, Malta, Croatia, Montenegro, Greece, Turkey
Exclusive Savings
Balcony
$44,528
Suite
-
From (Per Person)
A$44,528
Save 870
Per Person
View Trip
9 Day Croatian Island Discovery with APT
Cruise

9 Days (8 Nights) Dubrovnik to Zagreb
Tour Operator: APT
Ships: MV Lady Eleganza
Departures: May 2027 to Sep 2028
Visits: Croatia
Exclusive Savings
Oceanview
$8,438
From (Per Person)
A$8,438
Save 1,567
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
Visits: Croatia, Montenegro, Italy, Greece, Turkey
Exclusive Savings
Balcony
$27,467
Suite
-
From (Per Person)
A$27,467
Save 541
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 Aug 2027
Visits: Greece, Turkey
Exclusive Savings
Balcony
$15,207
Suite
$27,163
From (Per Person)
A$15,207
Save 431
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: Oct 2026 to Mar 2028
Visits: Ecuador, Galapagos
Exclusive Savings
Balcony
$16,758
Suite
$28,861
From (Per Person)
A$16,758
Save 5,497
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
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Sep 2027 to Oct 2028
Visits: Greece, Turkey
Exclusive Savings
Oceanview
$11,051
Suite
$14,726
From (Per Person)
A$11,051
Save 3,230
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
Visits: Turkey, Greece
Exclusive Savings
Balcony
$21,330
Suite
$23,270
From (Per Person)
A$21,330
Save 5,909
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
Visits: Greece, Turkey
Exclusive Savings
Balcony
$15,414
Suite
$23,548
From (Per Person)
A$15,414
Save 352
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
Visits: Greece, Turkey
Exclusive Savings
Balcony
$18,312
Suite
$21,840
From (Per Person)
A$18,312
Save 4,833
Per Person
View Trip
11 Day Adriatic Gems & Greece with Oceania Cruises
Cruise

11 Days (10 Nights) Trieste to Athens
Cruise Line: Oceania
Ship: Oceania Allura
Departure: 11 May 2028
Visits: Italy, Croatia, Montenegro, Greece
Your World Inclusions
Exclusive Savings
Balcony
$6,108
Suite
$9,891
From (Per Person)
A$6,108
Save 2,172
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
Tour Operator: APT
Departures: May 2027 to Oct 2028
Trip Styles: Small Group, Cruise, Island Hopping, Wildlife, Scenic
Visits: Brazil, Argentina, Chile, Peru, Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$42,061
Save 3,234
Per Person
View Trip
Results: 1-30 of 40

No trips found. Try adjusting the search filters.




Trips found! Scroll up to view.

Luxury Travel

Luxury Tours Luxury Cruises Luxury River Cruises Luxury Small Group Tours

Luxury Trips By Region

Africa Alaska Amazon Arctic Argentina Asia Australia Balkans Botswana Brazil Cambodia Canada & Alaska Central America Central Europe Chile Corsica Costa Rica Croatia Czech Republic Denmark Eastern Europe Eastern Med Ecuador Egypt England Europe Finland France Galápagos Germany Greece Greenland Iceland India Indonesia Ireland Italy Japan Jordan Kenya Latin America Malta Mexico Middle East Morocco New South Wales New Zealand Northern Ireland Northern Italy Norway Patagonia Peru Poland Portugal Queensland Sardinia Scandinavia Scotland Sicily Slovenia South America South Australia South East Asia South Korea Southern Italy Spain Spain & Portugal Sweden Switzerland Tanzania Turkey UK & Ireland USA Victoria Vietnam Western Australia Western Europe

Cruise Themes

Adults Only Cruises Christmas & New Year Cruises Expedition Cruises Family Cruises Island Hopping Cruises Luxury Cruises Northen Lights Cruises Sailing Trips Short Cruises Last Minute Cruise Deals

© 2010-2026. Global Journeys. You're viewing our site in Australian dollars.

    

Global Journeys | Terms & Conditions

Global Journeys Pty Ltd. Accredited Member of The Australian Travel Industry Association (ATIA). No. A11351.

Travel Industry Associations