Sailing holidays

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Sailing holidays (179)

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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£370 Average

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179 Holiday homes

Filters applied: Walking holidays (179)

(2) Excellent 

1 / 28

Yacht rental in San Sebastian de la Gomera

La Gomera / San Sebastian de la Gomera

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £40 / night

£280 / week

Book Book View

from £40 / night

(6) Excellent 

1 / 16

Sorrento holiday yacht rental

Province of Naples / Sorrento

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from £250 / night

£1563 - £11954 / week

Book Book View

from £250 / night

(2) Excellent 

1 / 10

Holiday yacht in Southampton

Hampshire / Southampton

  • 3 bedrooms
  • Sleeps 5
  • 1 night min stay

from £90 / night

£400 - £1030 / week

Book Book View

from £90 / night

(5) Very Good 

1 / 41

San Diego holiday yacht rental

California / San Diego

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £189 / night

£1165 - £1856 / week

Book Book View

from £189 / night

(1) Excellent 

1 / 8

Holiday yacht rental

Hampshire / Southampton

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from £90 / night

£400 - £1240 / week

Book Book View

from £90 / night

(3) Excellent 

1 / 24

Holiday houseboat rental

North Holland Province / Amsterdam

  • 3 bedrooms
  • Sleeps 12
  • 2 nights min stay

from £411 / night

£2735 - £3625 / week

Book Book View

from £411 / night

(12) Excellent 

1 / 24

Houseboat rental in Amsterdam

Amsterdam / Eastern Docklands

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £180 / night

£1258 / week

Book Book View

from £180 / night

(24) Excellent 

1 / 20

Holiday narrowboat rental

Warwickshire / Rugby

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from £470 / night

£2000 - £2980 / week

Book Book View

from £470 / night

(1) Excellent 

1 / 6

Worsley holiday narrowboat rental

Salford / Worsley

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from £150 / night

£795 / week

Book Book View

from £150 / night

(1) Excellent 

1 / 19

La Linea de la Concepcion holiday yacht rental

Andalucia / La Linea de la Concepcion

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from £196 / night

£1368 / week

Book Book View

from £196 / night

(2) Excellent 

1 / 9

Boston holiday yacht rental

Massachusetts / Boston

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from £343 / night

£2055 / week

Book Book View

from £343 / night

(9) Excellent 

1 / 19

Narrowboat rental in Nantwich

Cheshire / Nantwich

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £80 / night

£799 - £1799 / week

Book Book View

from £80 / night

1 / 27

Holiday yacht in Gijon

Asturias / Gijon

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from £196 / night

£1094 / week

Book Book View

from £196 / night

(2) Very Good 

1 / 50

Holiday yacht in Barcelona

Barcelona / Barcelona Beach

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from £59 / night

£352 - £2352 / week

Book Book View

from £59 / night

(13) Excellent 

1 / 24

Holiday houseboat rental

Amsterdam / Central Amsterdam

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £172 / night

£1250 - £1969 / week

Book Book View

from £172 / night

(5) Excellent 

1 / 23

Great Billing holiday narrowboat rental

Northamptonshire / Great Billing

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from £80 / night

£520 - £540 / week

Book Book View

from £80 / night

1 / 12

Holiday yacht with golf nearby in San Diego

California / San Diego

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £168 / night

£1028 - £1548 / week

Book Book View

from £168 / night

(1) Excellent 

1 / 9

Holiday yacht in Ta' Xbiex

Island of Malta / Ta' Xbiex

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from £40 / night

£274 / week

Book Book View

from £40 / night

(2) Excellent 

1 / 11

Holiday yacht in Alimos

Athens / Alimos

  • 10 bedrooms
  • Sleeps 10
  • 1 night min stay

from £352 / night

£2461 / week

Book Book View

from £352 / night

1 / 23

East End holiday yacht rental

St. Thomas / East End

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from £69 / night

£432 / week

Book Book View

from £69 / night

(21) Excellent 

1 / 30

Yacht rental in Dubrovnik

Dubrovnik / Gruz

  • 12 bedrooms
  • Sleeps 24
  • 7 nights min stay

from £159 / night

£1110 - £13282 / week

Book Book View

from £159 / night

(16) Excellent 

1 / 7

Holiday houseboat with golf nearby in Loch Ness

Scottish Highlands / Loch Ness

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from £167 / night

£770 - £1362 / week

Book Book View

from £167 / night

(2) Excellent 

1 / 23

Yacht rental in Petersburg

Alaska / Petersburg

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from £478 / night

£3340 - £40099 / week

Book Book View

from £478 / night

(1) Excellent 

1 / 24

Yacht rental in East End

St. Thomas / East End

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from £69 / night

£432 / week

Book Book View

from £69 / night

(4) Excellent 

1 / 25

Holiday yacht in Kas

Antalya Province / Kas

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from £704 / night

£4922 - £5469 / week

Book Book View

from £704 / night

(12) Excellent 

1 / 21

Holiday houseboat in Amsterdam

Amsterdam / Central Amsterdam

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay

from £102 / night

£204 - £610 / week

Book Book View

from £102 / night

1 / 15

Holiday houseboat in Montgomery

Texas / Montgomery

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from £185 / night

£1028 / week

Book Book View

from £185 / night

(2) Excellent 

1 / 67

Holiday yacht in Road Town

Tortola / Road Town

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £1644 / night

£11302 - £19932 / week

Book Book View

from £1644 / night

1 / 5

Palmetto holiday yacht rental

Florida / Palmetto

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min stay

from £103 / night

£685 - £1405 / week

Book Book View

from £103 / night

1 / 11

Holiday houseboat in Montgomery

Texas / Montgomery

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £116 / night

£473 / week

Book Book View

from £116 / night

(119) Very Good 

1 / 15

Holiday houseboat in Alappuzha

Kerala / Alappuzha

  • 4 bedrooms
  • Sleeps 12
  • 1 night min stay

from £209 / night

£1233 / week

Book Book View

from £209 / night

1 / 14

Holiday yacht in Miami

Florida / Miami

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from £257 / night

£1798 / week

Book Book View

from £257 / night

(2) Excellent 

1 / 29

Holiday yacht in Bacvice

Split-Dalmatia County / Bacvice

  • 12 bedrooms
  • Sleeps 24
  • 7 nights min stay

from £1228 / night

£8594 - £13282 / week

Book Book View

from £1228 / night

(2) Very Good 

1 / 20

Holiday narrowboat with golf nearby in Lancaster

Lancashire / Lancaster

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from £125 / night

£820 / week

Book Book View

from £125 / night

1 / 8

Central Palermo holiday yacht rental

Palermo / Central Palermo

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay

from £46 / night

£318 - £3172 / week

Book Book View

from £46 / night

1 / 9

Holiday narrowboat rental

Aude / Marseillette

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from £79 / night

£469 / week

Book Book View

from £79 / night

1 / 24

Holiday yacht in Zadar

Zadar / Poluotok

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from £659 / night

£4610 / week

Book Book View

from £659 / night

1 / 7

Palermo holiday yacht rental

Province of Palermo / Palermo

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay

from £46 / night

£318 - £3172 / week

Book Book View

from £46 / night

1 / 29

Yacht rental in Brewers Bay with shared pool

Tortola / Brewers Bay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay

from £1600 / night

£6395 / week

Book Book View

from £1600 / night

(2) Very Good 

1 / 6

Holiday houseboat in Draveil

Essonne / Draveil

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay

from £55 / night

£313 / week

Book Book View

from £55 / night

(2) Poor 

1 / 18

Holiday houseboat in Amsterdam

Amsterdam / Central Amsterdam

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from £227 / night

£1485 / week

Book Book View

from £227 / night

1 / 15

Holiday yacht in Galveston

Galveston Island / Galveston

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay

from £137 / night

£720 / week

Book Book View

from £137 / night

1 / 58

Holiday yacht rental

St. Thomas / East End

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £1644 / night

£11302 - £19932 / week

Book Book View

from £1644 / night

1 / 18

Fethiye holiday yacht accommodation

Mugla Province / Fethiye

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from £547 / night

£4922 - £5469 / week

Book Book View

from £547 / night

(2) Excellent 

1 / 30

Zagreb holiday yacht rental

Croatia / Zagreb

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay

from £3237 / night

£22657 / week

Book Book View

from £3237 / night

1 / 11

Holiday houseboat in Montauban

Tarn-et-Garonne / Montauban

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £1340 / night

£9375 / week

Book Book View

from £1340 / night

(1) Excellent 

1 / 30

Holiday houseboat in Marigot Bay

Castries Quarter / Marigot Bay

  • 3 bedrooms
  • Sleeps 2
  • 4 nights min stay

from £55 / night

£385 / week

Book Book View

from £55 / night

1 / 28

Pontevedra holiday yacht rental

Pontevedra / Vigo

  • 2 bedrooms
  • Sleeps 10
  • 1 night min stay

from £204 / night

£1172 / week

Book Book View

from £204 / night

(1) Excellent 

1 / 14

Holiday yacht in Stintino

Stintino / Tanca Manna

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from £547 / night

£3829 - £4219 / week

Book Book View

from £547 / night

(2) Very Good 

1 / 17

Houseboat rental in Redding

California / Redding

  • 4 bedrooms
  • Sleeps 15
  • 7 nights min stay

from £346 / night

£2420 / week

Book Book View

from £346 / night

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