Dodecanese Island Hopping: Kos, Lipsi, Kalymnos & Pserimos
Explore the Dodecanese on a two-week island-hopping route that takes you from bustling Kos to tiny, peaceful Pserimos. This itinerary links Kos, Lipsi, Kalymnos and Telendos, finishing on Pserimos — all connected by easy local ferries. Expect a mix of relaxed beaches, traditional harbour towns, dramatic landscapes and genuine island life. No car needed: these islands are best explored on foot, by bike, or from the deck of a small boat.
The Dodecanese archipelago stretches along Turkey’s Aegean coast, and while Kos serves as a popular tourist destination for large tour operators, it also provides a gateway to some of the most beautiful islands in Greece. Lipsi is a small island with a traditional and yet vibrant centre. Its beautiful sand beaches are protected and unorganised, enabling them to retain their natural charm. Kalymnos, once known for its sponge diving industry, now draws rock climbers to its dramatic cliffs. A short hop from the small island of Telendos, connected by water taxi, you almost get two islands for the price of one. Tiny Pserimos has just a handful of tavernas and a small permanent population. Yes, the tourist boats descend upon Pserimos, but by 5 pm, they’ve gone, leaving just you and the locals.
What Makes This Itinerary Special
This 2-week itinerary takes you from the developed to the barely-there, all connected by local ferries that islanders actually use. No hire car needed—these islands reveal themselves best on foot, by bike, or from the deck of a small boat. While Kos gets the package tourists, the islands in between—Lipsi, Kalymnos, and micro-islands like Pserimos—remain refreshingly normal. Fishermen still fix nets in the harbour, taverna owners remember your name by day two, and the biggest excitement is the ferry arrival.
Throughout this post, you’ll find links to excerpts from my travel diary — feel free to click through and follow my journey as it unfolded.
The Route at a Glance
Islands: Kos → Lipsi → Kalymnos → Pserimos (with return to Kos)
Duration: 2 weeks, flexible depending on ferry schedules and how long you want to stay
Transport: Blue Star Ferries, Dodekanisos Seaways and other local ferries connect all islands. Local excursion boats to Pserimos from both Kos and Kalymnos (Hmmm!)
Best Time: May-October (shoulder season has fewer tourists, weather ‘usually’ good well into October)
Who It’s For: Travellers who want variety—beaches and a bit of nightlife alongside quiet villages, dramatic landscapes and authentic island life
What Makes This Itinerary Special
Variety – Beach resort, climbing mecca (not compulsory), fishing village, and desert island vibes all in two weeks
Good connections – Regular ferries make island hopping straightforward (mostly)
Authentic Dodecanese – Experience traditional sponge-diving culture and island life
Manageable distances – Short hops between islands, easy to adjust your plan
Mix of activity and relaxation – Hike Kalymnos’ Kastro one day, doze on Pserimos beach the next
The Island by Island Itinerary
Day 1: Arrival on Kos
The gateway island and the largest in this chain. Kos has proper beaches, nightlife if you want it, excellent cycling paths, and enough ancient ruins to keep archaeology fans happy. It’s touristy, yes, but also a comfortable starting point with all amenities.
Getting There: Direct flights from many European cities, or ferry from Piraeus/Rhodes
Where to Stay: Kos Town for convenience and ferry connections, or beachside villages for quieter vibes. I recommend the Kosta Palace Hotel at the other end of the harbour to the port and Hotel Astron next door – both walkable to the port.
Don’t Miss: If you decide to have a few days on Kos, visit the Ancient Asclepion by choo choo tourist train, cycling to Zia village, dine by the Plane Tree of Hippocrates
Onward Travel Connection: There are ‘almost’ daily connections from Kos Town to Lipsi with Dodekanisos Seaways even out of season. This is supplemented by the occasional Blue Star Ferry that tends to sail in the midst of the night.
→ Why this itinerary?
→ Read about my arrival on Kos
Days 2-7: Lipsi
Population: Around 700. Feeling: Greece 30 years ago. Lipsi is the antidote to Kos—one harbour village, a few beaches you can walk to, tavernas where you’ll eat the same fresh fish the locals eat, and not happening after 10 pm unless, of course, there is a Panagiri or music event in the square.
Getting Around: Walk. The whole island is walkable. There’s a taxi and a kind of bus.
Where to Stay: Anywhere in Lipsi village. I recommend the Aphrodite at the back of Lientou Beach and Rizos Studios and Niriides Houses just up the hill. Don’t go in August as the island gets very busy.
What It’s Really Like: Quiet. Possible to find empty beaches. Bring books
Don’t Miss: Platis Gialos Beach, the Five Island boat trip on the Rena, the award-winning Manolis Tastes restaurant and doing absolutely nothing
Onward Travel Connection: Again, a very good ferry service along this line usually Dodekanisos Seaways 6 days per week.
🏩 Book the Aphrodite Apartments and Studios Here
Days 8-10: Kalymnos
Dramatic. That’s the word for Kalymnos. Sheer limestone cliffs plunge into deep blue water, colourful sponge-diving boats line the harbour, and rock climbers from around the world scale the island’s famous routes. Even if you don’t climb, the landscapes are spectacular. Traditional villages still exist.
Getting There: Ferry from Lipsi via other islands (check schedule), or direct from Kos Town or Mastichari
Getting Around: Local buses connect Pothia (main town), Myrties, and Masouri. Scooter rental available
Where to Stay: Myrties/Masouri for beaches, access to Telendos via water taxi. Pothia for culture and museums, though less peaceful. My top recommendation is the family-run Nefeli Hotel in Myrties, with easy access to Telendos.
Don’t Miss: Sponge diving museum, the fjord at Vathi, a hop over to Telendos for the day
The Reality: This can be a lively island—it’s rugged, active, and full of character, but tranquillity can be found. Embrace it all
Who this island is for: Active travellers, photographers, anyone who appreciates dramatic scenery. Not for pure beach lounging (but definitely possible).
→ A flying visit to Kalymnos and a hop over to Telendos
Days 11-13: Pserimos
Population: About 20 in summer, nearly zero in winter. Tavernas: Several good ones. Entertainment: The sea. One sandy beach, one village, and the kind of silence you didn’t know still existed. Pserimos is a day-trip island where many pirate-type ships bring the hordes from Kos and Kalymnos. If people watching is your thing, you’ll love it. If you want complete isolation, you’ll only get it when the day trippers leave at 5 pm – then it’s like a desert island. Means of escape from the day trippers – excellent hiking trails to almost deserted Vathy and Tafos Beach.
Getting There: Ferry connections from Kalymnos and Kos. If you want to ‘try before you buy’ daily excursion boats from Kalymnos and Kos, though, why visit with the hordes? Or ask a fisherman
Where to Stay: There are a few rooms available—ask at the taverna. I recommend Hotel Tripolitis for an authentic Greek/Aussie experience (either phone or turn up) or the Nammos Sunset Apartments at the other end of the beach.
What to Bring: Everything you need (cash, supplies, entertainment)
Don’t Miss: Swimming in crystal-clear water, the walk to the church, sunset solitude, chatting with the locals selling shells on the beach.
Why come here: To experience a truly tiny Greek island before they all disappear.
Day 14: Return to Kos
Return to Kos by ferry (check schedules). If flying home from Kos, consider an overnight buffer in case of ferry delays (especially if travelling off-season).
Budget
Total Cost: £1,540 (£770 per person for 2 travelers – July 2023)
This includes flights, accommodation, ferry tickets, and airport/port transfers. It does NOT include daily meals, on-island transport, activities, or sundries.
What’s Included in £1,540:
✈️ Flights (return)
🏨 Accommodation (all nights across Kos, Lipsi, and Pserimos)
⛴️ Ferry tickets (all inter-island travel)
🚖 Airport/port transfers
What’s NOT Included:
• Daily meals and drinks (budget €25-30/day per person) (can be less when sharing starters)
• On-island transport (buses, taxis – minimal costs)
• Activities (boat tours, museum entries, etc.)
• Sundries
Budget Tips:
💡 Kos: Has the widest range of accommodation – you can splurge or save depending on where you stay
💡 Lipsi & Pserimos: Simple, affordable accommodation and reasonably priced tavernas
💡 Ferries: Very manageable costs (€5-38 per hop)
💡 Dining: Eat where the locals eat for the best value
💡 Daily costs: Drop significantly once you’re on the smaller islands
The Bottom Line: This is a very budget-friendly itinerary outside of Kos. The smaller islands keep costs low, and even on Kos you can find good value if you avoid the resort areas.
Why Skip the Car Rental?
Kos: Bicycles are cheaper, more fun, and the island is flat. Buses connect major sites. There’s also a little choo choo train that goes from Kos Town to the Asklepion.
Lipsi: You can walk the entire island in a day
Kalymnos: Buses run regularly between main towns. Scooter if you want, but not essential
Pserimos: There are not many roads. Mainly sand and footpaths
These islands are small enough that renting a car is overkill. Save the money, enjoy the slower pace and think of the environment.
Note: The hotels and guesthouses recommended here are places I’ve either stayed in myself or vetted through my work as a travel consultant with Hidden Greece. No generic recommendations – only authentic experiences.
Now follow this journey by clicking the next post below ↓
