All at sea

Socially distanced, small groups and a sense of freedom: sailing holidays and boating breaks are perfect for 2021


Fleewinter Ltd. Tel 00 44 207 112 0019

Sun glinting on the water, the gentle swell of the waves and the knowledge there’s a new adventure to be found just over the horizon: the freedom of sailing off into the sunset is always tempting. But after endless travel restrictions and time away from family and friends, it’s even more enticing this year.

With the chance to charter a boat for a group of friends or a multigenerational holiday, or to join a small group of like-minded fellow travellers, it’s also perfect if you’re looking to steer clear of crowds.

Choose from holidays with skippers and crews on hand if you’d rather relax in the sun than sail yourself, brush up your own navigation skills, or stick with a canal or river boat trip if you prefer to stay closer to home: we’ve found ten of the best breaks on board.

Greek island hop

Island-hopping through Greece has long been a staple for everyone from backpackers to cruisers, but nothing compares to sailing your own yacht between these beautiful islands, stopping at deserted coves and revelling in the crystal clear water. And the super yachts from Fish & Pips come with their own private chef and skipper, and sea toys from paddleboards to water-skis.

The route can be tailored to the group, usually starting and finishing in Corfu, then visiting the northern Ionian islands of Paxos and Antipaxos, whether you fancy a chilled-out leisurely break or want to sail further south. The menu can be tailored too, with locally sourced ingredients, including freshly caught fish.

Seven nights costs from £1,450 per person, based on a group of six with exclusive use of a 57ft yacht.

Luxury narrowboat in Wales

There’s nowhere quite like the UK for a narrowboat holiday, with around 4,700 miles of navigable canals and rivers, more than half connected on a network across England and Wales. And Beacon Park Boats has five-star narrowboats sleeping from two to seven people, to combine comfort and style with some of the UK’s most beautiful countryside,

Cruise along the Monmouthshire & Brecon canal, starting near Abergavenny, to explore the beautiful Usk Valley and the Brecon Beacons National Park — perfect for families, wildlife spotting and for lock-free stretches. New for 2021, you can hire your own personal skipper too.

Three nights costs from £927 on a boat sleeping two.

  • Canal boating across the UK

With more than 550 narrowboats to hire at 45 bases in England, Scotland and Wales, including a new base in Staffordshire for 2021, Drifters Waterways Holidays are another great canal boating option. Rates start from £540 for a short break on a boat sleeping four.

Lake cruise in Portugal

Portugal’s sun-baked Alentejo region is home to sleepy villages surrounded by olive groves and vineyards, fortified towns like Monsaraz and Europe’s largest manmade lake, created when the Guadiana River was dammed. And the best way to explore is by motorboat, on a self-drive cruise.

With control of your own itinerary, a huge expanse of water where you’ll see no-one for hours and kayaks to paddle to deserted little islands (actually the top of submerged hills), it’s also fantastic for star-gazing, as the first Starlight Tourism Destination in the world.

The boats sleep two to ten people, and there’s a training session beforehand, plus onboard equipment to make it easy for novices.

A week costs from £1,345 per person based on two sharing. Book with Sunvil.

Sailing Finland’s lakes

Finland is known as the land of 188,000 lakes and the only tricky decision about a sailing holiday there is where to start. The eight-day archipelago sailing holiday from Responsible Travel lets you visit remote bays and islands on an ocean sailboat, marvelling at the midnight sun, feasting in a Viking Hall or discovering Finnish traditions in a floating sauna.

Groups can book the whole boat which sleeps up to ten, perfect if you’re looking for family time with grandparents and cousins, or join a small group tour of eight focused on meeting local communities and experiencing nature along the way.

With a skipper on board, there’s no previous experience required, although you’ll be encouraged to join in.

The eight-day holiday costs from around £950 per person. 

Cruise Scotland’s highland waterways

Discover Scotland’s spectacular mountain scenery from the deck of your own boat on a self-drive Caledonian cruise, heading from Laggan to Fort William, Fort Augustus and lochs in the valleys along the Great Glen.

The holidays from Le Boat mean you’ll have your own space rather than having to share, and the freedom to decide where to go. Hilltop castles and highland scenery are perfect with kids; add some thrills with mountain biking and white-water rafting, or try a relaxed mix of waterside towns and whisky tasting. Dog-friendly and no experience needed.

A seven-night self-catered cruise costs from £673 per boat, available from April 1 to October 31.

Sail the Canary Islands

Uncover another side to the Canary Islands with a new sailing holiday from G Adventures, part of a collection of European trips exploring beyond the best-known beaches.

Designed for sailors of all levels, travellers spend a week aboard the 56ft yacht, with a skipper tailoring the itinerary depending on the group and the weather, so travellers can decide if they want longer to enjoy being at sea or to explore the islands. Departing from Tenerife, the trip includes stops at San Sebastian de La Gomera and Santa Cruz on La Palma, plus snorkelling and hiking.

The seven-day break costs from £899 excluding flights, with a maximum group of ten, or book a private departure, chartering the boat for your own group.

Sail the south coast

If you’re longing to sail away but aren’t ready to book a trip beyond the UK for now, Hampshire-based Fairview Sailing has sailing holidays around the south coast. Head along the Jurassic coast, explore the Isle of Wight and the New Forest, or even pop over to northern France.

Experienced sailors can book a self-sail holiday, or arrange a skipper to manage all the hard work — and show you the ropes, if you’d like to learn a little more.

Larger families can hire several boats for a big get-together if you’re making up for missed time over the past year, with options for short breaks and week-long escapes.

Prices start from £1,116 for a two-night break on an Oceanis 37, sleeping up to six. A skipper costs £250 per day.

Escape to the Caribbean

A holiday enjoying the sparkling turquoise waters of the Caribbean Sea as you explore the 60-plus British Virgin Islands (BVIs), with a professional crew at the helm, is pretty close to paradise.

You can book a cabin as part of a group trip or there are exclusive yacht charters from Turquoise Holidays, with the itinerary tailored to your group. Visit the Baths marine park, the flamingos of Anegada, take rainforest hikes and snorkel with turtles, as well as finding the best beaches on the mostly uninhabited islands and the bars with the best rum punch.

Seven nights costs from £1,999 per person, including captain and chef, all food, drinks with meals, watersports equipment and flights.

Sail around Scilly

One of the sunniest corners of the UK, the Isles of Scilly have always been the perfect place to get away from it all — and the best way to explore the five inhabited islands is on board your own boat.

With more than 20 vessels in the fleet from Venture Sail, including classic sailing boats, join a group or book a private charter, with most boats sleeping six to 12 people.

With a full crew on board, you don’t need to have sailed before; food is also included (with options for vegetarians).

Seven nights costs from £3,724 to charter Pettifox, sleeping four, on dates from June to August. There are also Boat Bubble Holidays in Cornwall during April and May, designed for up to six members of one family/bubble.

Luxury gulet in Sicily

Explore the Unesco-protected Aeolian archipelago near Sicily on an island-hopping trip aboard a luxuriously upgraded classic wooden gulet boat.

The tailored week-long escape from Cognoscenti Travel visits the volcanic islands of Lipari, Salina, Filicudi, Vulcano and Stromboli. There’s also local vineyards, the chance to meet a poet and swimming in the unspoiled waters of the little-known islands.

The gulet has six double en-suite cabins, although you can also sleep under the stars on deck, with a Sicilian family to act as crew and chef.

Seven nights’ exclusive charter costs from around £1,416 per person based on 12 guests sharing in June, with six nights on board and one night B&B at Monaci delle Terre Nere hotel on Mount Etna. Excludes flights.


Like this? Sign up for more with our JC Life newsletter here.

From fabulous recipes to parenting tips, travel and West End entertainment; insightful interviews and much more: there’s more to the JC than news!

Share via

Want more from the JC?

To continue reading, we just need a few details...

Want more from
the JC?

To continue reading, we just
need a few details...

Get the best news and views from across the Jewish world Get subscriber-only offers from our partners Subscribe to get access to our e-paper and archive