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

Island Hopping Cruises Starting In May 2027, 2028 and 2029

Are you looking to embark on an island hopping cruise in May 2027, 2028 or 2029? Choose from 269 unique cruise itineraries and 6,417 departures from the world's leading cruise lines.
Filter Results
269 Cruises (6,417 Departures)
269 Cruises (6,417 Departures)
Departures
Duration
4 Days
45 Days
Regions
Ship Size
Trip Styles
Show More...
Budget
Start & End Cities
Operators
Show More...
Price
$500pp
$80,995pp
Countries
Show More...
8 Day Idyllic Greece with Celestyal Cruises
Cruise

8 Days (7 Nights) Athens to Athens
Cruise Line: Celestyal Cruises
Ship: Celestyal Journey
Departures: Aug 2026 to Oct 2027
Visits: Greece, Turkey
Exclusive Savings
Inside
$1,596
Oceanview
$1,576
Suite
$2,155
From (Per Person)
A$1,576
Save 40
Per Person
View Trip
10 Day Footsteps of Apostle Paul with Globus
Tour + Cruise
 (4)

10 Days Athens to Athens
Cruise Line: Celestyal Cruises
Tour Operator: Globus
Departures: Aug 2026 to Sep 2027
Trip Styles: Coach, Cruise, Island Hopping, Religious, Scenic
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$6,139
Save 197
Per Person
View Trip
15 Day Greece & Aegean Islands Cruise with Cosmos
Tour + Cruise
 (15)

15 Days Athens to Athens
Cruise Line: Celestyal Cruises
Tour Operator: Cosmos
Departures: Aug 2026 to Oct 2027
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visits: Greece, Turkey
Single Supplement Waivers
Exclusive Savings
From (Per Person)
A$6,495
Save 387
Per Person
View Trip
14 Day Country Roads of Croatia with Insight Vacations
Tour
 (13)

14 Days Zagreb to Dubrovnik
Operator: Insight Vacations
Departures: Aug 2026 to Oct 2027
Trip Styles: Coach, Island Hopping, Scenic
Visits: Croatia, Slovenia
Exclusive Savings
From (Per Person)
A$6,242
Save 1,694
Per Person
View Trip
26 Day Northern Italy, Slovenia & Croatia with Bunnik Tours
Tour + CruiseFlights Included
 (6)

26 Days Milan to Dubrovnik
Operator: Bunnik Tours
Departures: Sep 2026 to Sep 2027
Trip Styles: Coach, Small Group, Cruise, Island Hopping, Scenic
Visits: Italy, Slovenia, Croatia
Exclusive Savings
From (Per Person)
A$18,188
Save 1,161
Per Person
View Trip
13 Day Grand Hawaii Vacation with Globus
Tour
 (5)

13 Days Honolulu to Maui
Operator: Globus
Departures: Sep 2026 to Dec 2027
Trip Styles: Coach, Island Hopping, Scenic
Visits: USA
Exclusive Savings
From (Per Person)
A$10,789
Save 554
Per Person
View Trip
24 Day Turkey & Greece with Bunnik Tours
Tour + CruiseFlights Included
 (5)

24 Days Istanbul to Athens
Operator: Bunnik Tours
Departures: Sep 2026 to Sep 2027
Trip Styles: Coach, Small Group, Cruise, Island Hopping, Scenic
Visits: Turkey, Greece
Exclusive Savings
From (Per Person)
A$15,782
Save 821
Per Person
View Trip
16 Day Classical Greece with Idyllic Aegean 7-night Cruise with Globus
Tour + Cruise
 (3)

16 Days Athens to Athens
Cruise Line: Celestyal Cruises
Tour Operator: Globus
Departures: Sep 2026 to Sep 2027
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$9,111
Save 266
Per Person
View Trip
9 Day Dalmatian Elegance with Insight Vacations
Cruise
 (3)

9 Days (8 Nights) Split to Split
Operator: Insight Vacations
Departures: Aug 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$5,603
Save 384
Per Person
View Trip
10 Day Greek Island Hopper with Globus
Tour
 (3)

10 Days Athens to Athens
Operator: Globus
Departures: Aug 2026 to Sep 2027
Trip Styles: Coach, Island Hopping, Scenic
Visits: Greece
Exclusive Savings
From (Per Person)
A$5,021
Save 184
Per Person
View Trip
14 Day Greek Island Wanderer with Explore Worldwide
Tour
 (3)

14 Days Athens to Santorini
Operator: Explore
Departures: Sep 2026 to Oct 2027
Trip Styles: Adventure, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$4,394
Save 517
Per Person
View Trip
30 Day Ultimate South America with Brazil's Amazon & Galapagos Cruise with Cosmos
Tour + Cruise
 (3)

30 Days Manaus to Guayaquil
Tour Operator: Cosmos
Departures: Sep 2026 to Oct 2027
Trip Styles: Coach, Cruise, Island Hopping, Wildlife, Scenic
Visits: Brazil, Argentina, Peru, Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$18,556
Save 604
Per Person
View Trip
8 Day Adriatic Coastal Cruise with Travelmarvel
Cruise
 (2)

8 Days (7 Nights) Dubrovnik to Zagreb
Tour Operator: Travelmarvel
Ships: MV Princess Eleganza
Departures: Apr 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
Oceanview
$4,221
From (Per Person)
A$4,221
Save 1,108
Per Person
View Trip
8 Day Adriatic Coastal Cruise with Travelmarvel
Cruise
 (2)

8 Days (7 Nights) Zagreb to Dubrovnik
Tour Operator: Travelmarvel
Ships: MV Princess Eleganza
Departures: Sep 2026 to Oct 2028
Visits: Croatia
Exclusive Savings
Oceanview
$4,221
From (Per Person)
A$4,221
Save 2,078
Per Person
View Trip
13 Day Classical Greece with Iconic Aegean 4-night Cruise with Globus
Tour + Cruise
 (2)

13 Days Athens to Athens
Cruise Line: Celestyal Cruises
Tour Operator: Globus
Departures: Aug 2026 to Oct 2027
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visits: Greece, Turkey
Exclusive Savings
From (Per Person)
A$7,204
Save 237
Per Person
View Trip
7 Day Explore Croatia with Intrepid Travel
Tour
 (2)

7 Days Dubrovnik to Split
Operator: Intrepid
Departures: Aug 2026 to Oct 2028
Trip Styles: Adventure, Small Group, Island Hopping
Visits: Croatia
Exclusive Savings
From (Per Person)
A$3,097
Save 892
Per Person
View Trip
9 Day Galapagos Discovery with Intrepid Travel
Tour
 (2)

9 Days Quito to Quito
Operator: Intrepid
Departures: Jan 2028 to Dec 2028
Trip Styles: Adventure, Small Group, Island Hopping, Wildlife
Visits: Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$3,318
Save 73
Per Person
View Trip
11 Day Greek Island Hopping with Contiki
Tour
 (2)

11 Days Athens to Athens
Operator: Contiki
Departures: Aug 2026 to Sep 2027
Trip Styles: 18-30's, Island Hopping, Scenic
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,445
Save 110
Per Person
View Trip
8 Day Athens to Santorini Island Hopping with Contiki
Tour
 (1)

8 Days Athens to Santorini
Operator: Contiki
Departures: Aug 2026 to Sep 2027
Trip Styles: 18-30's, Island Hopping, Scenic
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,837
Save 100
Per Person
View Trip
10 Day Best of the Hawaiian Islands with Globus
Tour
 (1)

10 Days Honolulu to Maui
Operator: Globus
Departures: Oct 2026 to Dec 2027
Trip Styles: Coach, Island Hopping, Scenic
Visits: USA
Exclusive Savings
From (Per Person)
A$8,515
Save 490
Per Person
View Trip
15 Day Classical Greece Plus Island Hopper with Globus
Tour
 (1)

15 Days Athens to Athens
Operator: Globus
Departures: Apr 2027 to Sep 2027
Trip Styles: Coach, Island Hopping, Scenic
Visits: Greece
Exclusive Savings
From (Per Person)
A$7,704
Save 263
Per Person
View Trip
11 Day Croatia & Its Islands with Collette
Tour + Cruise
 (1)

11 Days Zagreb to Dubrovnik
Operator: Collette
Departures: Aug 2026 to May 2028
Trip Styles: Coach, Cruise, Island Hopping, Scenic
Visits: Croatia
Exclusive Savings
From (Per Person)
A$7,276
Save 1,180
Per Person
View Trip
8 Day Cycle the Dalmatian Coast with Explore Worldwide
Tour
 (1)

8 Days Kastel Kambelovac to Dubrovnik
Operator: Explore
Departures: Aug 2026 to Oct 2027
Trip Styles: Adventure, Cycling, Island Hopping
Visits: Croatia
Exclusive Savings
From (Per Person)
A$3,389
Save 329
Per Person
View Trip
14 Day Dubrovnik to Ljubljana with Intrepid Travel
Tour
 (1)

14 Days Dubrovnik to Ljubljana
Operator: Intrepid
Departures: Aug 2026 to Oct 2028
Trip Styles: Adventure, Small Group, Island Hopping
Visits: Croatia, Slovenia
Exclusive Savings
From (Per Person)
A$5,822
Save 1,251
Per Person
View Trip
9 Day Galápagos Adventure: Snorkelling & Sea Lions with G Adventures
Tour
 (1)

9 Days Quito to Quito
Operator: G Adventures
Departures: Aug 2026 to Dec 2027
Trip Styles: Adventure, Small Group, 18-30's, Camping, Island Hopping, Wildlife
Visits: Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$2,430
Save 700
Per Person
View Trip
9 Day Galápagos Island Hopping with G Adventures
Tour
 (1)

9 Days Quito to Quito
Operator: G Adventures
Departures: Oct 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Island Hopping, Wildlife
Visits: Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$3,974
Save 1,095
Per Person
View Trip
10 Day Galápagos – West & Central Islands aboard the Reina Silvia Voyager with G Adventures
Cruise
 (1)

10 Days (9 Nights) Quito to Quito
Cruise Line: G Adventures
Departures: Aug 2026 to Dec 2028
Visits: Ecuador, Galapagos
Exclusive Savings
From (Per Person)
A$9,564
Save 2,635
Per Person
View Trip
10 Day Greek Island Hopper with Trafalgar
Tour
 (1)

10 Days Athens to Athens
Operator: Trafalgar
Departures: Aug 2026 to Oct 2027
Trip Styles: Coach, Island Hopping, Scenic
Visits: Greece
Exclusive Savings
From (Per Person)
A$6,067
Save 1,060
Per Person
View Trip
8 Day Greek Isles Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Rome to Rome
Cruise Line: Royal Caribbean
Ship: Odyssey of the Seas
Departures: Aug 2026 to Oct 2027
Visits: Italy, Greece, Turkey
Exclusive Savings
Inside
$1,526
Oceanview
$1,754
Balcony
$1,785
Suite
$3,287
From (Per Person)
A$1,583
Save 1,951
Per Person
View Trip
8 Day Highlights of the Greek Islands with Explore Worldwide
Tour
 (1)

8 Days Athens to Santorini
Operator: Explore
Departures: Sep 2026 to Oct 2027
Trip Styles: Adventure, Island Hopping
Visits: Greece
Exclusive Savings
From (Per Person)
A$3,528
Save 301
Per Person
View Trip
Results: 1-30 of 269

No trips found. Try adjusting the search filters.




Cruises found! Scroll up to view.

Cruises

All Cruises Adriatic Cruises Aegean Cruises Africa Cruises Alaska Cruises Antarctic Cruises Arabian & Middle East Cruises Arctic Cruises Asia Cruises Australia Cruises Bahamas Cruises Bermuda Cruises Canada & New England Cruises Caribbean Cruises Central America Cruises China Cruises Croatia Cruises Cruises to the Falkland Islands Cruising Cape Horn Europe Cruises Hawaii Cruises Indian Ocean Cruises Japan Cruises Kimberley Tours & Cruises Mediterranean Cruises Mexico Cruises New Zealand Cruises Northern Europe & Baltic Cruises Northwest Passage Cruises Norway & Iceland Cruises Norwegian Fjords Cruises Patagonia Cruises South America Cruises South East Asia Cruises South Pacific Cruises Transatlantic Cruises UK Cruises USA Cruises Western Europe Cruises Worldwide Cruises

Trip Lengths

7 Day 10 Day 2 Week 3 Week 1 Month

Departure Months

July August September October November December January February March April May June

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