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Sailing holidays (8)

Family sailing holidays aren’t just an opportunity for budding skippers to wear silly hats and control the tiller all holiday long – the plus points are rather more numerous than that. Just think about it: you can set sail whenever you like, sailing from one beautiful location to another at the turn of a wheel. Best of all, you don’t have to put up with heaving beaches. Just find your own deserted stretch of sand or an isolated cove, moor up and enjoy the sunshine and quiet. Sailing doesn’t have to be an activity holiday, you know.

The more competent sailors among you might like to take the wheel yourself on one of our yachts in Spain or Greece. Or, for a little added luxury, you can hire your own private skipper.

For families in which there’s an even split between sea legs and landlubbers, there’s the sailing holiday compromise of renting a holiday home that has the use of its own boat and private mooring. Check out these sailing adventures in the Caribbean and along the coast of England.

But if sailing sounds just a little too involving for what’s supposed to be a relaxing holiday, there is the more tranquil option of a houseboat. Either stay put or pootle merrily around the waterways of England and the Netherlands. Whichever appeals more, you should definitely step aboard soon.

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Filters applied: Catered / B&B (8)

8 Results  |  
16 Photos

Yacht | 3 Bedrooms | sleeps 5

Very Good 4/5 

7 Nights min stay

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from £211 /night

£1474 - £2624 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Neverland is a 47ft luxury Moody Sailing Yacht, in pristine condition built in 2002 available for skippered charter. She can accommodate up to 5 guests. Breakfast light lunch, tea and coffee are included in the price. Cold drinks apart from water are chargeable. Yacht charter from Olbia Free skipper and hostess. Free breakfast, light lunch, tea coffee.  …see more

10 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
For a sailing holiday in the exotic spice islands of Zanzibar, Mafia and Pemba, Yacht CQ is your preferred accommodation and destination. Fully crewed with Skipper and Stewardess, all options can be considered to suit your needs for comfort, luxury or activity.  …see more

14 Photos

Yacht | 2 Bedrooms | sleeps 4

Excellent 5/5 

5 Nights min stay

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from £100 /night

£700 - £2800 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
We offer the chance to sail the Caribbean aboard a crewed Catamaran. You can stop in most harbours and inlets and explore the islands in the way they were meant to be seen - from the sea. As part of the package, we serve 3 homely meals a day onboard. A crewed yacht that sails the windward islands of the Caribbean ranging from Grenada through to Martinique.  …see more

Featured properties

24 Photos

Houseboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £75 /night

£522 - £1595 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Two luxury, 100% smoke-free rooms on a boat, and en suite bathrooms, free WiFI. After a busy day in the center you can enjoy the grand view of the eastern docklands on the deck terrace on a nice summer's day. Also suitable for 2 quests. Stay on the water in the Venice of the North: Amsterdam.  …see more

13 Photos

Yacht | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £114 /night

£798 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Holidays on a big multi-hulls, in the virgins San Blas Islands, 8 guests maxi in all inclusive, visit of the Indians Kuna villages and snorkelling. Sail, snorkelling , farniente, fishing, Indians villages on the trimaran La Mandragore.  …see more

21 Photos

Houseboat | 1 Bedroom | sleeps 2

Excellent 5/5 

2 Nights min stay

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from £98 /night

£684 - £763 / week

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Key info:

  • Nearest beach 15 km
  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Close to Central Station, comfortable, stylish, quiet and romantic. Three rooms for just the two of you. Own entrance. Great breakfast, bikes and Canadian canoe included.  …see more

24 Photos

Yacht | 5 Bedrooms | sleeps 12

Excellent 5/5 

2 Nights min stay

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from £827 /night

£5786 - £7439 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Impressive 120 foot Luxury Yacht based at Barcelona's Royal Yacht Club, right next to the Ramblas, Gothic Quarter and the Beach. Chef and maid onboard. Ideal for families, as a venue for small business meetings or groups of friends up to 10-12 people. Also for charter. This yacht can also be chartered for a day, weekend or an entire week cruising the Balearic Islands.  …see more

21 Photos

Houseboat | 49 Bedrooms | sleeps 5

1 night min stay

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from £16 /night

£106 - £742 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
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