A Greek Island vacation is one of those bucket list trips all travelers should make time for. The question is, what is the best way to see the islands? A cruise does all the complicated planning for you, while a self-organized trip gives unlimited freedom of choice and leisure.
Both options have merits, but they also have flaws. How do you choose? Read on to explore the pros and cons of a Greek Island cruise.
Pros
- Cruises offer incredible value with all-inclusive fares. Most cruise lines include unlimited on-board dining, activities and live entertainment. When you consider what you would spend separately on these amenities, the savings makes cruising a no-brainer.
- Greece has more than200 islands to chose from. For a first-time visitor, planning your trip can be overwhelming. Cruises take all the guesswork out of your trip. Experts have chosen the best islands to visit and crafted ideal itineraries to maximize your experience. You are taken directly to the most popular islands such as Crete, Santorini and Rhodes without having to worry about how you get there. While it is easy to get from island to island, arranging flights and ferry rides between the ones of your choosing can get complicated and costly as direct routes are not always available.
- Kids like to be entertained. No parent wants to see their child unhappy, especially on vacation. Cruises offer an endless supply of activities for young travelers, making the hours spent at sea fly by. Kids clubs, family-friendly entertainment, swimming pools and water slides make the boat a vacation in itself for young ones. Years later they will remember the onboard fun more than the islands visited.

© F8grapher | Dreamstime.com
Cons
- When you travel via cruise ship, you are at the mercy of someone else’s schedule. After working and saving all year to take our families on a well-deserved vacation, the last thing we want to do is have someone else tell us where to be and when to be there. Cruises stop for a limited time at each port. Greek Islands have a laid-back vibe — rushing through your visit almost defeats the purpose of visiting. If you lose track of time or get lost, your ship leaves without you.
- Cruising takes all the spontaneity out of a vacation. While it may be hard to decide which island to start with, once you get there you may love it and want to stay longer than a day. With a cruise, you don’t have that luxury. On the flip side, if you get to an island and absolutely hate it, just move on to another one. Ferries travel frequently between islands, especially during the summer, and tickets are relatively inexpensive, making it easy for a family to get around without blowing their budget.
- Greek Islands are famous for their nightlife. Islands may appear sleepy by day, but at night they come to life and the real fun begins. When traveling by cruise, you seldom get to stay in one port long enough to find out what happens once the sun goes down. A self-planned trip gives you the opportunity to see what the island is really like once the cruise ships pull out of port and the party gets started.
Read This Next
#WhereverFamily
Insta FeedDestinations / Caribbean
Sep 9, 2026The Bahamas is the Place to Be for the Ultimate Multigen Thanksgiving Experience
This Thanksgiving, family travelers should swap dishes and stress for sun and sand. The Bahamas is emerging as a multigen destination of choice thanks to short flights from the United States, making it easy for the whole family to gather and spend quality time together.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Hotels
Sep 9, 202613 Resorts to Consider for Your Babymoon
Expecting a bundle of joy and looking for a perfect spot for a babymoon? Consider these options:
North America
Sep 9, 2026This Golfing Destination Doubles as a Great Family Vacation Spot
A golf trip may not seem like the ideal place for a family vacation — unless the whole family loves to golf. While that isn’t always the case, everyone deserves to enjoy what they love when they get to take time away from life. Luckily, there are some amazing destinations offering the best of both worlds — great family getaways along with world-class golfing.
Sponsored Content
Celebrating 25 Years of The Peninsula Chicago
June marked The Peninsula Chicago’s 25th anniversary, commemorating a quarter century for the hotel as a pillar of luxury on North Michigan Avenue.
Destinations / North America
Sep 8, 2026Remembering Dolly at Dollywood
Unlike many entertainment stars, Dolly Parton appealed to all age groups. Her sparkling personality and family-friendly entertainment made her a universal favorite and her theme park in Pigeon Forge, Tennessee, like Dolly herself, appeals to all ages.
ShareThis