One Way Thessaloniki to Rhodes - FP Isla 40 Catamaran

April & November
Cabin or whole boat with Skipper Instructor
Fountain Pajot 2022 Isla 40
4 double ensuite cabins
Incredible route 500+ miles

Join this wonderful low season catamaran one way adventure on ‘Prodigy’, a 2022 model Isla 40 by Fountaine Pajot. Following the success of the first trip in November 2024, we’re doing it all again each spring and autumn in both directions. Incredible islands, ports, bays along the way, beautifully quiet & tranquil at this time of year. Sail the Dodecanese, Cyclades, North Aegean, Sporades & Northern Greece regions in one amazing catamaran experience. Mixed weather of course, this is no easy summer holiday trip! Professional Skipper. Boat handling, sail trim & all aspects of catamaran life. 14 days (southbound) or 18 days going north.

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One Way Thessaloniki to Rhodes - Dufour 530

 

April & November
Cabins £1800 / £2000 for 14 nights
Dufour 530 monohull 2023
4 double cabins & 1 twin bunks
Incredible route 500+ miles

Join this wonderful low season one way adventure on Splash, a Dufour 530 monohull sailing yacht. Following the success of the November trip in 2024, we’re doing it all again but in the opposite direction! Incredible spots along the way, Dodecanese, Cyclades, North Aegean, Sporades & Northern Greece regions in one amazing 2 week sailing experience. Trip should be largely downwind!

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Athens - Corinth Canal - Kefalonia - Corfu
2 x 10 days April 2026

Athens - Corinth Canal - Kefalonia - Corfu

Cabins & Bareboat options
11 yacht fleet split into 2 trips of 10 days
Athens - Corinth Canal - Galaxidi - Trizonia - Navpaktos - Mesalonghi - Ithaca - Kefalonia
Kefalonia - Ithaca - Levkas - Paxos - Sivota - Corfu
Bedding & small towels provided
Kitty for provisions, fuel, harbours & Corinth Canal
Bring own wet weather gear - life jackets provided
Bring own gas inflated life jacket if preferred

Our signature ‘Jolly’ - the multi-yacht, one way, low season run every April from Athens to Kefalonia and on to Corfu 2026 will see us run this event twice, on 2 consecutive 10 day events from 9-19 April and again from 20th to 30th April. Option to continue in the Corfu area for the week May 2-9 and beyond, either by taking a cabin or if qualified and confident, by taking your own bareboat.

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May 2nd to 9th, 2026 - “Birthday Week Flotilla” - Corfu

Corfu - Sivota - Lakka - Gaios - Parga - Plataria
7 nights - cabin or bareboat

Corfu - Sivota - Lakka - Gaios - Parga - Plataria

Cabin or Bareboat options, ask
Flotilla with informal training, guidance & support
Corfu - Paxos - Antipaxos - Sivota - Corfu (no fixed route)
On board kitty for provisions, fuel, harbour dues
Bedding & small towel provided
Life jackets on board or bring your own
Bring own sailing gear
Fantastic event - ideal for beginners & new Skippers

Rich’s birthday event, since its inception at his 50th in 2023 with 12 yachts and by chance, 50 people, this has become a popular annual event. Join by the cabin or take a bareboat - ask for details. SPECIAL OFFER - every week in May 2026 at April one way prices on Omegasail bareboats!

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Every May & October - Catamaran Experiences & Training - Corfu area

Corfu - Sivota - Lakka - Gaios - Parga - Plataria
7 or 14 nights

Corfu - Sivota - Lakka - Gaios - Parga - Plataria

Cabins £2000/£2400 for 2 sharing. Bareboat possible, ask
Flotilla format - join by the cabin or add your own bareboat
Corfu - Paxos - Antipaxos - Sivota - Corfu (no set route)
On board kitty for provisions, fuel, harbour dues
Bedding & towels provided
Life jackets on board or bring your own
Bring own sailing jacket
Fantastic event - ideal for beginners, those training for purchase or future charter

Join our catamaran experience special week - take a cabin on with us on our Lagoon 42 & 40 catamarans, or ask about taking one yourself as a bareboat group. Assistance, support and training can be given on the event for those taking a catamaran for the first time or just wanting some tips on improving your boat handling and berthing.

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Oct 18th to 25th - “Pre-Delivery Flotilla” - Corfu

Corfu - Sivota - Lakka - Gaios - Parga - Plataria
7 nights - cabin or bareboat

Corfu - Sivota - Lakka - Gaios - Parga - Plataria

Cabins £800 solo, £1100 for 2. Bareboats POA
Flotilla format - join by cabin or take a bareboat
Corfu - Paxos - Antipaxos - Sivota - Corfu
On board kitty for provisions, fuel, harbours
Bedding & small towel provided
Life jackets on board or bring your own
Bring own sailing gear
Excellent week for first time Skipper or Mate

Due to huge demand, and the one way selling out months ahead, we are laying on this additional ‘flotilla’ style week in the Corfu area. A pleasant, easy trip, ideal for those stepping up to Mate or Skipper roles. Omegasail’s fleet of monohulls is our first port of call for bareboats, but we can add any others, including catamarans, as you wish. Talk to Rich for more info.

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October 25th to November 1st - Corfu to Kefalonia

Corfu to Kefalonia one way 11 yachts
7 nights

Corfu to Kefalonia one way 11 yachts

£750 solo, £1200 for 2 persons
11 yacht fleet all going together
Corfu - Sivota - Paxos - Levkas - Ithaca - Kefalonia - Ithaca (among others)
On board kitty for provisions, fuel, harbours
Bedding & small towels provided
Life jackets on board
Bring own wet weather gear
Bring own gas inflated life jacket if preferred

Our signature ‘Jolly’ - the multi-yacht, one way, low season event that runs every October from Corfu to Kefalonia (1 week) and on to Athens (10 further days 1-11 Nov). Option to add a week before, in the Corfu area for the week October 18-25, either by taking a cabin on a Skippered boat, or if qualified and confident, by taking your own bareboat.

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November 1st to 11th - Kefalonia to Athens

Kefalonia to Athens one way 11 yachts
10 nights

Kefalonia to Athens one way 11 yachts

£1000 solo, £1600 for 2 persons
11 yacht fleet all going together
Kefalonia - Corinth Gulf & Canal or Peleponnese & Monemvasia - Athens
On board kitty for provisions, fuel, harbours, canal fee where applicable
Bedding & small towels provided
Life jackets on board
Bring own wet weather gear
Bring own gas inflated life jacket if preferred

Our signature ‘Jolly’ - the multi-yacht, one way, low season event that runs every October from Corfu to Kefalonia (1 week) and on to Athens (10 further days 1-11 Nov). This is the second leg, 10 days Kefalonia to Athens, hopefully via the Corinth Canal, but if closed for winter, around the Peleponnese.

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November 12th to 30th - One Way Rhodes to Thessaloniki

 

Rhodes to Thessaloniki
18th to 30th November 2025

Rhodes to Thessaloniki

£3600 for 18 days
Fountain Pajot 2022 Isla 40
4 double ensuite cabins
Incredible route 500+ miles

Join this huge catamaran one way adventure on a 2022 model Isla 40 by Fountaine Pajot. Following the success of the 14 day version in 2024, we’re doing it all again but extending it to 18 days. Incredible spots along the way, too many to list! Dodecanese, Cyclades, North Aegean, Sporades & Northern Greece regions in one amazing experience!

More Catamaran Trips

How do I join?

 

By the cabin

Book a cabin on one of our larger boats with a professional or established Skipper. Join other like-minded people, all there for the right balance of sailing, seeing beaufiul places and the social side. Make new sailing friends for life and pick up many tips & tricks along the way.

Your own bareboat group

If suitably qualified & experienced, you may bring your own group and take one of the 6 yachts we make available to bareboat charter parties within the events. Minimum Day Skipper (with ICC) but you’ll need at least 2,000 miles and 4+ weeks of experience under your belt.

Professional Organisations - Be our Guest

If you run professional sailing trips yourself or are a sailing school, you may be invited to join us by taking one of our boats and selling the places to your own clients.
Nobody can book onto a Jolly without first speaking to Rich on the phone. Think of it as a friendly introduction chat, however it is important for everyone on board that we don’t get square pegs in round holes, so you can go forward confidently knowing that Rich will have had ‘the chat’ with everyone else on the event too. Prepare all your questions and have a pen and paper ready!

Use the contact form or WhatsApp