2025/2026 Caribbean Calendar

Extra Early Bird Rates until August 30

We will be adding Tour de Martinique and Antigua Sailing Week to our April 2026 calendar when event organizers have finalized details.

Booking Packages available now!

Our Booking Packages offer enormous value, and the opportunity to maximize sunshine sailing this winter. Space is limited on each Package. Details available on any of the relevant event pages, but here’s a sneak peek:

Booking Package A: Grenada to St.Lucia, Mango Bowl Regatta, St.Lucia to St.Maarten

Booking Package B: St.Maarten to Barbados, Barbados Sailing Week

Booking Packages C: Rum to Spice Race, Grenada Sailing Week

Ultimate Adventure Package: Booking Packages A + B together!

Booking Package D: St.Maarten to BVIs, BVI Spring Regatta, BVIs to St.Maarten

Featured
Cruise 'n Learn 1: Grenada, Carriacou and Petite Martinique
Nov 1
Cruise 'n Learn 1: Grenada, Carriacou and Petite Martinique
Cruise 'n Learn 2: Grenada, Carriacou and Petite Martinique
Nov 10
Cruise 'n Learn 2: Grenada, Carriacou and Petite Martinique
Offshore Mileage Builder: Grenada to St.Lucia
Nov 19
Offshore Mileage Builder: Grenada to St.Lucia
St.Lucia's Mango Bowl
Nov 26
St.Lucia's Mango Bowl
Offshore Mileage Builder: St.Lucia to St.Maarten
Dec 2
Offshore Mileage Builder: St.Lucia to St.Maarten
Offshore Mileage Builder: St.Maarten to Barbados
Jan 5
Offshore Mileage Builder: St.Maarten to Barbados
Barbados Sailing Week
Jan 15
Barbados Sailing Week
Rum to Spice Race: Barbados to Carriacou
Jan 22
Rum to Spice Race: Barbados to Carriacou
Grenada Sailing Week
Jan 24
Grenada Sailing Week
Offshore Mileage Builder: Grenada to Antigua
Feb 5
Offshore Mileage Builder: Grenada to Antigua
RORC Caribbean 600
Feb 19
RORC Caribbean 600
Offshore Mileage Builder: Antigua to St.Maarten
Mar 1
Offshore Mileage Builder: Antigua to St.Maarten
St.Maarten Heineken Regatta
Mar 3
St.Maarten Heineken Regatta
Cruise 'n Learn 3: St.Maarten to BVIs
Mar 16
Cruise 'n Learn 3: St.Maarten to BVIs
BVI Spring Regatta & Sailing Festival
Mar 22
BVI Spring Regatta & Sailing Festival
Offshore Mileage Builder: BVI to St.Maarten
Mar 31
Offshore Mileage Builder: BVI to St.Maarten

+1 604-283-5343*

ahoy@seatoskysailing.com


WEST VANCOUVER, BC, CANADA

*monitored voicemail

Latest on Instagram

A hard earned rest for our crew after the mania of @mangobowlregatta … just chillin’ in Martinique for a few days before our last leg of 2024 to Barbados! #learntosail #saileverywhere #sailinglife #caribbeancruising #vivelafrance #lesvoilesdemartinique #frenchwestindies #sailing #Panacea😘
First time at @mangobowlregatta and first in class for #Panacea😘 We had a fantastic time throwing our big blue boat around the courses in Rodney Bay, St Lucia in a great warm-up for a long season ahead on the Caribbean race circuit. I’m beyond proud of our very rookie crew that came together to make a really great team, able to do hard things in close quarters at serious speed while a bit shorthanded!! This was a super fun regatta across the board, with wonderful hospitality from @stluciayachtclub making it all possible. #learntosail #saileverywhere #learntorace #raceeverything #sailing #yachtracing #caribbeansailing #seatoskystyle #snowbird #escapeartist #salona45
Wrapping up a wonderful island hopping cruise today, from Grenada to St Lucia with all stops in between 🙌 Fresh lobster BBQ in #TobagoCays, exploring beautiful little #Bequia and sunset swims by St Lucia’s iconic #Pitons all add up to a pretty
Wrapping up a wonderful island hopping cruise today, from Grenada to St Lucia with all stops in between 🙌 Fresh lobster BBQ in #TobagoCays, exploring beautiful little #Bequia and sunset swims by St Lucia’s iconic #Pitons all add up to a pretty great week! Today we’ll finish up in Rodney Bay and start the prep to get #Panacea😘 race ready for our first event of the season: @mangobowlregatta next weekend! #learntosail #saileverywhere #learntorace #raceverything #seatoskystyle #islandhopping #caribbeansailing #grenadines #windwardislands #neverstopexploring #escapeartist #sailinglife #salona45
#ChathamBay on little Union Island was our first stop in the Grenadines this season, 4 months after Beryl stomped all over this gorgeous corner of the world. The bay is still here and still beautiful, but man what a difference a cat 4/5 hurricane mak
#ChathamBay on little Union Island was our first stop in the Grenadines this season, 4 months after Beryl stomped all over this gorgeous corner of the world. The bay is still here and still beautiful, but man what a difference a cat 4/5 hurricane makes 😢 The vegetation has clearly been brutalized, every proper sized tree is stripped and dead, the few palm trees left standing like toothpicks on the beach- and most of those are actually replanted rather than survivors. I’ve never been in here with fewer than maybe 40 other boats… this time it was us, 2 catamarans and one pirate-y vibes ketch. The beach bars are gone without a trace. The ‘resort’ is the only business left, hard at work on reconstruction of their 4 cottages and little beach restaurant. All their buildings were destroyed except for one room of the staff housing where the manager-couple is now based as they try to get things back up and running. As a side business in these tricky times, they offered customs clearance which we gratefully used! Chatham offered a tranquil stop after the bustle of Grenada… plus a perspective on just how fragile our human enterprise can be when nature takes a turn. #grenadines #caribbeansailing #sailinglife #posthurricane #hurricaneberyl #learntosail #saileverywhere #seatoskystyle #sailing #salona45 #Panacea😘
After some bonus hiccups to the start of the season, including engine starter battery failure at anchor, jump starting adventures, hand-bombing up the giant anchor and 50m of chain, discovering a failing water pump in the engine and spending extra qu
After some bonus hiccups to the start of the season, including engine starter battery failure at anchor, jump starting adventures, hand-bombing up the giant anchor and 50m of chain, discovering a failing water pump in the engine and spending extra quality time in the always-wonderful @portlouismarinaofficial to get ourselves sorted out… #Panacea😘 is casting off for her first cruise of the season. Grenada to St Lucia, via the beautiful Grenadines. This is a true adventure as we don’t know what awaits us in this island chain so recently devastated by Hurricane Beryl. Into the wide blue yonder we go, as kitted out and self-sufficient as we can get! #learntosail #saileverywhere #caribbeansailing #snowbirds #salona45 #seatoskystyle #sailing #sailinglife #grenada #grenadines #exploring #escapeartist
Another boat yard marathon of upgrades to #Panacea😘 is done! A litany of projects complete, all kinds of adventures in wiring, waterproofing, smoothing / speeding up and generally getting the big blue beauty ready for a great Caribbean season in th
Another boat yard marathon of upgrades to #Panacea😘 is done! A litany of projects complete, all kinds of adventures in wiring, waterproofing, smoothing / speeding up and generally getting the big blue beauty ready for a great Caribbean season in the sweltering heat of Trinidad ✅✅✅ We’re a little late posting, as we launched Tuesday and sailed up to Grenada Wednesday, but working on catching up to current events. As per usual, it’s one for the memoirs!! #learntosail #saileverywhere #learntorace #raceeverything #seatoskystyle #caribbeansailing #sailinglife #haulout #diyboating #sailing #herewegoagain
Just one training course left on our BC schedule for this year 🤯 Our last #StartSailing session of the season runs in early November with just 3 spots left, bookable online 👆Last chance to dip your toes into sailing so you’re all set to fully
Just one training course left on our BC schedule for this year 🤯 Our last #StartSailing session of the season runs in early November with just 3 spots left, bookable online 👆Last chance to dip your toes into sailing so you’re all set to fully launch by next spring! #sailingschool #learntosail #saileverywhere #optoutside #allseasonsailing #sailing #PauHana #hotfoot27
Early bird rates expire on Monday!!!! Lead the pack. Be part of an amazing team. Full send. Explore & enjoy an exquisite part of the world. Fill up that bucket from your List ✅✅✅ Join us this winter for nautical Caribbean adventures of all ki
Early bird rates expire on Monday!!!! Lead the pack. Be part of an amazing team. Full send. Explore & enjoy an exquisite part of the world. Fill up that bucket from your List ✅✅✅ Join us this winter for nautical Caribbean adventures of all kinds: international racing, offshore experience builders, island hopping cruising… #Panacea😘 is ready for all of it! Full schedule online here: https://www.seatoskysailing.com/sailing-overseas
Bonus with today’s #spinnakerschool was some extra seal spectating… or as I like to call them, nautical sausages 🦭
Winding down a spectacular summer sailing season in #beautifulbc September is pretty much the best month round here with decent breeze and empty anchorages 🙌. Just a few courses left on the BC training calendar (and a few spots left in some of them!
Winding down a spectacular summer sailing season in #beautifulbc September is pretty much the best month round here with decent breeze and empty anchorages 🙌. Just a few courses left on the BC training calendar (and a few spots left in some of them!), before we wrap things up here and head south to the sunny Caribbean 😎☀️ #learntosail #saileverywhere #bestcoast #ohthosesummernights #Paragon #xyacht #gulfislands #canadiansailing #ryatraining #competentcrew #dayskipper #sailing #seatoskystyle
A hard earned rest for our crew after the mania of @mangobowlregatta … just chillin’ in Martinique for a few days before our last leg of 2024 to Barbados! #learntosail #saileverywhere #sailinglife #caribbeancruising #vivelafrance #lesv
First time at @mangobowlregatta and first in class for #Panacea😘 We had a fantastic time throwing our big blue boat around the courses in Rodney Bay, St Lucia in a great warm-up for a long season ahead on the Caribbean race circuit. I’m beyond
Wrapping up a wonderful island hopping cruise today, from Grenada to St Lucia with all stops in between 🙌 Fresh lobster BBQ in #TobagoCays, exploring beautiful little #Bequia and sunset swims by St Lucia’s iconic #Pitons all add up to a pretty #ChathamBay on little Union Island was our first stop in the Grenadines this season, 4 months after Beryl stomped all over this gorgeous corner of the world. The bay is still here and still beautiful, but man what a difference a cat 4/5 hurricane mak After some bonus hiccups to the start of the season, including engine starter battery failure at anchor, jump starting adventures, hand-bombing up the giant anchor and 50m of chain, discovering a failing water pump in the engine and spending extra qu Another boat yard marathon of upgrades to #Panacea😘 is done! A litany of projects complete, all kinds of adventures in wiring, waterproofing, smoothing / speeding up and generally getting the big blue beauty ready for a great Caribbean season in th Just one training course left on our BC schedule for this year 🤯 Our last #StartSailing session of the season runs in early November with just 3 spots left, bookable online 👆Last chance to dip your toes into sailing so you’re all set to fully Early bird rates expire on Monday!!!! Lead the pack. Be part of an amazing team. Full send. Explore & enjoy an exquisite part of the world. Fill up that bucket from your List ✅✅✅ Join us this winter for nautical Caribbean adventures of all ki
Bonus with today’s #spinnakerschool was some extra seal spectating… or as I like to call them, nautical sausages 🦭
Winding down a spectacular summer sailing season in #beautifulbc September is pretty much the best month round here with decent breeze and empty anchorages 🙌. Just a few courses left on the BC training calendar (and a few spots left in some of them!
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