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an aerial view of an island in the middle of the ocean

Explore Sailing Voyages in Cayman Islands 🇰🇾

Cover photo by @ernests on Unsplash

Voyage photo from Smooth operator Voyage photo from Smooth operator Voyage photo from   Off I go Offshore ☀️🌖☀️🌖Voyage photo from   Off I go Offshore ☀️🌖☀️🌖Voyage photo from   Off I go Offshore ☀️🌖☀️🌖Voyage photo from   Off I go Offshore ☀️🌖☀️🌖Voyage photo from Georgetown, Grand Cayman to Isla Providencia, ColumbiaVoyage photo from Georgetown, Grand Cayman to Isla Providencia, ColumbiaVoyage photo from Georgetown, Grand Cayman to Isla Providencia, ColumbiaVoyage photo from Georgetown, Grand Cayman to Isla Providencia, ColumbiaVoyage photo from Georgetown, Grand Cayman to Isla Providencia, ColumbiaVoyage photo from Kaibo to Fisherman’s rock, Grand Cayman Voyage photo from Kaibo to Fisherman’s rock, Grand Cayman Voyage photo from Georgetown to Sting Ray City, Grand Cayman Voyage photo from Georgetown to Sting Ray City, Grand Cayman Voyage photo from Georgetown to Sting Ray City, Grand Cayman Voyage photo from Georgetown to Sting Ray City, Grand Cayman Voyage photo from Georgetown to Sting Ray City, Grand Cayman
Brandon Williams

Brandon Williams

1 June 2021 at 05:45

Calico Skies
Voyage map
284.1NM
2 days 15 hours

Caribbean Sea, Cayman Islands to Caribbean Sea, Colombia

Brandon Williams

Brandon Williams

29 May 2021 at 11:00

Calico Skies
Voyage map
330.9NM
2 days 15 hours

La Carbonera, Mexico to Caribbean Sea, Cayman Islands

Jaroslav Barnik

Jaroslav Barnik

10 June 2026 at 12:48

Smooth operator
Anapa

2

Smooth operator
94NM
1 day 3 hours

Caribbean Sea to Rock Hole, Cayman Islands

Chris Lobel

Chris Lobel - Well done 💪🏻

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Jaroslav Barnik

Jaroslav Barnik

2 June 2026 at 10:08

Off I go Offshore ☀️🌖☀️🌖
Anapa

4

  Off I go Offshore ☀️🌖☀️🌖
149.2NM
1 day 22 hours

Box, Jamaica to West End, Cayman Islands

Chris Lobel

Chris Lobel - Well done Cpt Jaro - your first solo passage - full marks

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Katharine Smith

Katharine Smith

21 May 2026 at 10:00

Georgetown, Grand Cayman to Isla Providencia, Columbia
Sea Stray

6-20 knots of true wind with up to 10 foot waves. Motored 1st 12 hours and then sailed from close reach to beam sail in rough seas. We decided to sail further away from Nicaragua point. Became rougher with motor sail into waves. We encountered 3 fishing boats in middle of the night as sailing without lights. Mark diverted around one and I was not feeling well. The next day I developed a migraine and was vomiting and weak . We pulled into Providencia around 8:30 pm with a well lit channel and anchored in the dark. I was just recovering from my incapacitating headache.

5

Georgetown, Grand Cayman to Isla Providencia, Columbia
362.8NM
2 days 11 hours

Rock Hole, Cayman Islands to Mountain, Colombia

DG
Nick W.

Nick W. & DG

30 April 2026 at 12:30

Grand Cayman - Bermuda
Vingilot

Head winds until we got to the Windward passage on day 5. Wind speed everything from 3 - 20+ knots. Heading N to NNE across the trades after passing between Cuba and Haiti was pleasant though we had little wind at times. As we approached Bermuda the weather deteriorated and we had head winds up to 18 knots. The last few hours were exhilarating sailing close hauled in 18 knots.

Grand Cayman - Bermuda
1558.2NM
13 days 2 hours

Upper Land, Cayman Islands to Saint George, Bermuda

Katharine Smith

Katharine Smith

18 May 2026 at 09:08

Kaibo to Georgetown, Grand Cayman
Sea Stray

Wind 4-20 knots. 2 ft waves. Motored and tried to raise the spinnaker. Only 3 knots SOG. As rounded to inlet and made it across the pass, wind arrived and sailed south on a close reach while tacking.

Kaibo to Georgetown, Grand Cayman
18.7NM
3h 57m

Water Cay to Rock Hole, Cayman Islands

Katharine Smith

Katharine Smith

17 May 2026 at 14:48

Fisherman’s Rock to Kaibo, Grand Cayman

Motored back to the anchorage after trying to kite surf

Fisherman’s Rock to Kaibo, Grand Cayman
5.7NM
1h 6m

Fisherman’s Rock to Water Cay, Cayman Islands

Katharine Smith

Katharine Smith

17 May 2026 at 10:34

Kaibo to Fisherman’s rock, Grand Cayman

Wind 13-16 knots on broad reach sail. Used asymmetrical spinnaker for the 1st time and was fantastic. 6.5-9 knots apparent wind with 5-6.5 knots SOG. 2 foot waves. Anchored to kite surf but sargasm and untangling lines were too difficult.

2

Kaibo to Fisherman’s rock, Grand Cayman
4.4NM
60min

Water Cay to Fisherman’s Rock, Cayman Islands

Katharine Smith

Katharine Smith

16 May 2026 at 16:46

Sting Ray City to Kaibo Anchorage (starfish point), Grand Cayman Islands

Flat conditions motor to anchorage in 8-6 feet of water.

Sting Ray City to Kaibo Anchorage (starfish point), Grand Cayman Islands
1.9NM
30min

Rum Point Channel to Water Cay, Cayman Islands

Katharine Smith

Katharine Smith

16 May 2026 at 09:52

Georgetown to Sting Ray City, Grand Cayman
Sea Stray

10-20 knots of true wind on the beam. Waves up to 3 feet. Reefed and then unreefed. Passed through coral cut and watched for 6 ft depths. Sting rays were very tame upon the snorkel.

5

Georgetown to Sting Ray City, Grand Cayman
23.6NM
4h 12m

Rock Hole to Rum Point Channel, Cayman Islands

David Carlson

David Carlson

21 April 2026 at 21:45

Grand Cayman to Key West
Pangolin
Grand Cayman to Key West
555.6NM
6 days 21 hours

Dog City, Cayman Islands to Man of War Harbor, United States

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