TripFinder

Compare multi-day small-group tours from independent operators, then ask a Canadian travel advisor for help.

Explore

Find tripsDestinationsTravel stylesDealsCompare trips

TripFinder

How it worksTalk to an agentAbout usContact

Good to know

Privacy PolicyCookie choicesTerms of UseTravel guides
TripFinder.ca helps you compare small-group trips from independent operators and book with a TripFinder travel advisor. Trips are operated by the tour companies under their own terms. © 2026 HighBar Enterprises Ltd.Made for adventurers in Canada 🍁
TripFinder
Find trips
DealsAsk TheoCompareHow it worksBrowse all trips
Greek Islands Bike & Boat
Find trips›Greece›Greek Islands Bike & Boat
UTOperated by UTracks

Greek Islands Bike & Boat

From
CAD 7,680
Duration
8 days
Countries
Greece
Activity
moderate
Rating
★ 4.8 · 24 reviewsvia UTracks →

The adventure

Greece Cycling & Sailing tour: Sail the Aegean waters and bike through the islands on this superb Greek cycle and sail holiday.

At a glance

Duration
8 days
Route
→
Countries
Greece
Activity level
moderate
Style
Beach & Islands, Cycling, Sailing & Marine
Group size
Ask
Flights
Not included
Solo travellers
Ask an agent

Day by day

Charming coastal town with hills and sea under a cloudy sky.
Your journey through

Greece

Showing Days 1-7

8-day itinerary

Day 1Day 1: Arrive AthensMake your own way to the embarkation port on Salamis Island. (an optional group transfer from Athens airport or town is available to the main port in Athens - supplement applies). From the mainland port of Piraeus, catch a local ferry to Paloukia Port on Salamis Island. Journey time approx. 35min. On arrival catch a taxi to the ship. Check in from 4.00pm. Dinner will be on board and the night will be spent in port. An optional extension in Athens is available before the trip.
Make your own way to the embarkation port on Salamis Island. (an optional group transfer from Athens airport or town is available to the main port in Athens - supplement applies). From the mainland port of Piraeus, catch a local ferry to Paloukia Port on Salamis Island. Journey time approx. 35min. On arrival catch a taxi to the ship. Check in from 4.00pm. Dinner will be on board and the night will be spent in port. An optional extension in Athens is available before the trip.
Day 2Day 2: Explore Kythnos Island (25km/15mi)This morning we cruise to Kythnos Island, known since ancient times for its traditional cheese and honey. Our first cycle ride begins from the harbour of Merichas and winds its way up to Chora, the island’s charming hilltop capital. Expect coastal views and classic Cycladic character – whitewashed lanes adorned with hand-painted flowers and geometric designs. From Chora, we continue to the quaint village of Driopida before looping back to Merichas. This evening, enjoy time at your leisure – perhaps in one of the welcoming tavernas by the water.
This morning we cruise to Kythnos Island, known since ancient times for its traditional cheese and honey. Our first cycle ride begins from the harbour of Merichas and winds its way up to Chora, the island’s charming hilltop capital. Expect coastal views and classic Cycladic character – whitewashed lanes adorned with hand-painted flowers and geometric designs. From Chora, we continue to the quaint village of Driopida before looping back to Merichas. This evening, enjoy time at your leisure – perhaps in one of the welcoming tavernas by the water.
Day 3Day 3: Cruise to SeriphosThis morning we cruise to Seriphos, a lesser-known island with rugged valleys, hidden coves and quiet sandy beaches. From the port of Livadi, our cycle route climbs a winding road to the main town, where whitewashed, cube-shaped houses sit perched high on a ridge above the sea. We ride on through an untouched landscapes to visit the Byzantine Monastery of Archangel Michael, before looping back to Livadi via a panoramic route along the island’s east coast. Later, we cruise to Syros, where you can wander the elegant old town and unwind at a café along the lively harbour promenade.
This morning we cruise to Seriphos, a lesser-known island with rugged valleys, hidden coves and quiet sandy beaches. From the port of Livadi, our cycle route climbs a winding road to the main town, where whitewashed, cube-shaped houses sit perched high on a ridge above the sea. We ride on through an untouched landscapes to visit the Byzantine Monastery of Archangel Michael, before looping back to Livadi via a panoramic route along the island’s east coast. Later, we cruise to Syros, where you can wander the elegant old town and unwind at a café along the lively harbour promenade.
Day 4Day 4: Explore Syros by bike then cruise to Kea (34km/21mi)Ermoupolis, the capital of the Cyclades, makes a striking first impression as it comes into view – set across two hills, it has a distinct character unlike other Cycladic towns. Pastel-coloured houses with neoclassical facades line its streets, adding to its charm. Today’s ride follows the scenic southern coast of Syros, passing a series of peaceful bays and coves enroute to the beach at Galissas. From here, we continue past the convent of Saint Barbara before returning to Ermoupolis. In the afternoon, we cruise onward to the nearby island of Kea.
Vibrant Greek architecture along the coast in Mandrakia, Milos, Greece.Kea (34km/21mi)
Ermoupolis, the capital of the Cyclades, makes a striking first impression as it comes into view – set across two hills, it has a distinct character unlike other Cycladic towns. Pastel-coloured houses with neoclassical facades line its streets, adding to its charm. Today’s ride follows the scenic southern coast of Syros, passing a series of peaceful bays and coves enroute to the beach at Galissas. From here, we continue past the convent of Saint Barbara before returning to Ermoupolis. In the afternoon, we cruise onward to the nearby island of Kea.
Day 5Day 5: Cycle to the white sand Otzias…We begin today’s ride from Korissia, a lovely natural harbour on Kea. Our route climbs steadily to the island’s capital, Loulis, a traditional village with scenic views. From there, we descend to the white-sand beach of Otzias, where there’s time for a refreshing swim before cycling back to Korissia. Later, we cruise to the island of Poros in the Saronic Gulf. With its hillside homes and vibrant waterfront, Poros offers a relaxed and authentic island feel – the perfect place to unwind for the evening.
We begin today’s ride from Korissia, a lovely natural harbour on Kea. Our route climbs steadily to the island’s capital, Loulis, a traditional village with scenic views. From there, we descend to the white-sand beach of Otzias, where there’s time for a refreshing swim before cycling back to Korissia. Later, we cruise to the island of Poros in the Saronic Gulf. With its hillside homes and vibrant waterfront, Poros offers a relaxed and authentic island feel – the perfect place to unwind for the evening.
Day 6Day 6: Explore Poros island by bike before…Today’s ride begins in the sheltered harbour of Korissia on Kea. We follow a gentle uphill route to Loulis, the island’s peaceful capital set among rolling hills. From here, we descend to the sandy beach at Otzias, where you can enjoy a swim in the clear Aegean waters. The ride then loops back to Korissia. In the afternoon, we cruise to Poros in the Saronic Gulf – a charming harbour town with traditional character and a laid-back island vibe, ideal for a relaxed evening by the water.
Today’s ride begins in the sheltered harbour of Korissia on Kea. We follow a gentle uphill route to Loulis, the island’s peaceful capital set among rolling hills. From here, we descend to the sandy beach at Otzias, where you can enjoy a swim in the clear Aegean waters. The ride then loops back to Korissia. In the afternoon, we cruise to Poros in the Saronic Gulf – a charming harbour town with traditional character and a laid-back island vibe, ideal for a relaxed evening by the water.
Day 7Day 7: Cycle on Aegina island…The island of Aegina is known far beyond the Greek borders for its incredible pistachio nuts! Our route takes us up to the Sanctuary of Aphaia, where the impressive temple stands proudly above the sea, offering views of the Aegean on both sides of the island. From here, we cycle through the island’s interior, passing the Monastery of Saint Nektarios before arriving in Aegina town. We rejoin the boat for our final cruise back to Salamis Island, where we share a farewell dinner and reflect on a memorable week of cycling and island discovery.
The island of Aegina is known far beyond the Greek borders for its incredible pistachio nuts! Our route takes us up to the Sanctuary of Aphaia, where the impressive temple stands proudly above the sea, offering views of the Aegean on both sides of the island. From here, we cycle through the island’s interior, passing the Monastery of Saint Nektarios before arriving in Aegina town. We rejoin the boat for our final cruise back to Salamis Island, where we share a farewell dinner and reflect on a memorable week of cycling and island discovery.
1 / 2

Traveller reviews

4.8
★★★★☆

Based on 24 reviews · via UTracks →

Discover Greece

A glimpse of the destination you'll explore.

Breathtaking aerial view of Kerkyra's lush landscape with hills, valleys, and ancient structures under a clear sky.
Breathtaking coastal landscape of Agios Stefanos, Greece featuring rocky hills and a tranquil sea.
Breathtaking view of a Greek island coastline with clear blue waters and vibrant nature.
Scenic view of Athens cityscape from a hilltop with clear skies.
Picturesque coastal scene with clear skies, azure waters, and distant mountains.

Upcoming departures

DatesPrice / personAvailability
21 Aug – 28 Aug 2026(price may vary)
CAD 7,680Available
Book my trip
28 Aug – 4 Sep 2026(price may vary)
CAD 8,180Available
Book my trip
UT
Operated by UTracks

TripFinder compares the available catalog facts and can help with the booking. You travel under the operator's terms; final price and availability are confirmed before purchase.

Book my trip →
Ask Theo about this trip
From
CAD 7,680 CAD / person
Twin share · prices may vary by departure
Next departures
Aug 21, 2026CAD 7,680 · available
Aug 28, 2026CAD 8,180 · available
Sep 11, 2026CAD 8,180 · spots left
See all 6 departures →
Book my trip
No payment now — tell us a few details and an expert confirms everything & finishes your booking.
✓No payment & no obligation to send a request
✓An expert confirms by email or phone — your choice
Prefer to talk first? Send a request and choose phone as your contact preference.
Operated by UTracks · view on operator site ↗

More Europe adventures

OpeningZagreb to Santorini: 35 Unforgettable Days image
GG Adventures
Save 20%

Zagreb to Santorini: 35 Unforgettable Days

Bosnia and Herzegovina, Albania, Greece, Montenegro, Croatia · 35 days · Easy

fromCAD 8,639
Next: 09 Aug
OpeningUltimate Europe: Berlin, Tuscany & Greek Temples image
GG Adventures
Save 35%

Ultimate Europe: Berlin, Tuscany & Greek Temples

Albania, Austria, Czechia, Greece, Netherlands, Montenegro, Germany, Italy, Croatia · 34 days · Easy

fromCAD 5,960
Next: 09 Aug
OpeningOne Month in Europe: Germany, Italy & Croatia image
GG Adventures
Save 25%

One Month in Europe: Germany, Italy & Croatia

Albania, Austria, Czechia, Greece, Netherlands, Montenegro, Germany, Italy, Croatia · 30 days · Easy

fromCAD 5,310
Next: 09 Aug
From
CAD 7,680/ person
Book my trip