3 Months Cruising the Caribbean!


Last Updated on September 13, 2023 by Amy

It’s hard to believe our time in the Caribbean is over, but it is! We arrived in the BVIs on November 10th, 2015, and we left Grenada on February 17th.  That’s 99 days cruising the Caribbean! 

How Much Time is Right?

And before you say it – yes, we know our trip through the Caribbean was far too short and we skipped way too many islands.  

A Whole Season

It’s easy to spend an entire sailing season in the Caribbean. Boats usually depart from the US at the end of hurricane season (Nov/Dec) and leave the Caribbean to head north at the beginning of hurricane season (June/July). That’s 6-8 months of cruising time in the Caribbean.

Between the East Coast and the Pacific

Our trip was three months, designed to fit between the end of hurricane season on the East Coast (Nov/Dec) and the optimum time to cross the Pacific (March/April). We needed time to get from the leeward islands to Panama, through the canal, and to the Pacific Ocean.

Why Did We Do a Half Season instead of a Full One?

  1.  We aim to circumnavigate in about five years, and we did two seasons in the South Pacific, and one season in Southeast Asia.
  2. We will end our circumnavigation in the Caribbean/US, and plan to cruise there in 2020 and 2021.  Assuming we move back to land life in the States, we will forever have the Caribbean as our vacation playground.

Our Route Sailing the Caribbean

Our Caribbean Path

In the sailing season, the tradewinds blow in the Caribbean. This means there’s a very reliable east wind blowing almost all the time. Sailing from the BVIs to points directly west (like St Martin) is a little trickier, but after that, mostly it’s just pointing your nose south and riding just forward of the beam!

The islands of the Caribbean are close together, eliminating the need for overnight sailing if you so choose.


Countries visited:
BVIs, USVIs, St Martin, Antigua, Guadeloupe (Mainland and The Saints), Dominica (and a one-day tour), St Lucia (Sailing the coast and Soufrière), and Grenada (haul out and Carriacou).

Guests visiting:
Lisa, Bob, & Phil (Antigua); Bill, Christie, Carolyn, Jim, Lois (Antigua & Guadeloupe); Sarah (Antigua, Guadeloupe and Dominica); Madeline (St Lucia)

Click here for a spreadsheet with some technical information about our sailing in the Caribbean.

Virgin Islands

We spent 18 days in the British Virgin Islands; ten days sailing around the islands and eight days in the Nanny Cay yard.

Then we moved over to the USVI. We were there for 17 days before leaving on an overnight sail to the leeward islands.

Leeward Islands

We skipped many of the Leeward Islands because we’d been there before. We had chartered a sailboat in 2013 and cruising St Martin, Kitts & Nevis, and St Barts.

This time around, we stopped for three days in St Martin, the best place in the Caribbean to provision and buy marine supplies.

We took another overnight sail to Antigua where we spent ten days cruising with family over the holidays.

We day sailed over to Guadeloupe, where we spent nine days hopping down the western coast of the island.

Windward Islands

Dominica was up next, and we spent 14 days in Portsmouth.

We did an overnight sail, skipping Martinique and then spent 13 days in Saint Lucia.

We did another overnight sail, skipping St Vincent and the Grenadines to arrive in Grenada, where we stayed 11 days. A few of those days were spent in the Grenadan Grenadines before hauling out at Grenada Marine for a night, then back in the water to St George’s.

Highlights of 3 Months Cruising the Caribbean

Favorite Country:
Amy: BVIs; I think it’s a perfect mix. You can find quiet and peaceful anchorages like Brewer’s Bay or Peter Island, or rowdier places like Anegada or Jost Van Dyke. The anchoring is easy, the water clear, and great things to see like the Rhone and Baths.
David:  Guadeloupe; good anchorages (Deshaies, Pigeon Island, Anse a la Barque, and the Saintes) and good hiking.

Top 3 Anchorages:
Amy: Peter Island (BVIs), Brewer’s Bay (BVIs), Christmas Cove (USVI)
David:  Marigot Bay (St Lucia), Marigot Bay (St Martin), Peter Island (BVIs)

View over Marigot Bay
View over Marigot Bay, St Lucia

Favorite Snorkel/Dive:
Amy: Christmas Cove, because I got up close and personal with an octopus and we also saw a nurse shark.
David: Our dive at the Painted Walls (BVIs) with Noam and Dalit was pretty spectacular.

David on our dive with Noam and Dalit
David on our dive with Noam and Dalit

Favorite Meal:
Amy: Pizza Pi in Christmas Cove.
David:  Steak night at Big Chef, Rodney Bay St Lucia!


Favorite Hike:
Unanimous:  The lookout at the Saints.

Favorite Sail:
Unanimous:  From Carriacou to Grenada Marine, on the east coast of Grenada. It was a spirited sail, but not too rough. We sat at the helm the whole time and just enjoyed the day.  And it was our only downwind sail!

Best Customs Office:
David:  Jost Van Dyke, BVIs

The place we are most excited to revisit someday:
Unanimous:  St Vincent and the Grenadines

Guides for Cruising the Caribbean

I hope you enjoyed reading about our time in the Caribbean, and we can’t wait to keep sharing the rest of the world with you!

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  1. Hello from your home town of Houston! It is great to hear from you and I enjoyed reading about your Caribbean cruise. I’m looking forward to seeing you both again soon.

  2. Wow this is quite the trip, 3 months is a long time! Christmas Cove sounds awesome, how close to this octopus is close?! Thanks for sharing your trip!

  3. All your fabulous adventures sound like dreams come true! Sail on safely,
    you two, and we look forward to reading your experiences as you approach Panama and the Canal.
    Love always, Grandma and Grandpa

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