Just for fun I asked ChatGPT for a suggested itinerary. Seems like it is mostly good but with a few oddities (Norman then Peter?, Jost to Cooper?). I didn't "chat" with it to try and refine the results. I may give that a go (specify the number of days, tell it I don't want to do Norman and Peter on consecutive nights, etc.).

My Question: What is a good itinerary for a bareboat sail charter in the British Virgin Islands?

Answer:

A bareboat sail charter in the British Virgin Islands (BVI) offers a fantastic opportunity to explore beautiful islands, pristine beaches, and vibrant marine life. Here's a suggested itinerary for a week-long bareboat sail charter in the BVI:

Day 1: Tortola to Norman Island
Morning: Pick up your bareboat charter in Tortola and set sail to Norman Island.
Afternoon: Explore The Caves at Norman Island, a famous snorkeling spot.
Evening: Anchor in the Bight at Norman Island and enjoy dinner on board.

Day 2: Norman Island to Peter Island
Morning: Sail to Peter Island and explore the stunning Deadman's Bay.
Afternoon: Snorkel at the Caves at Little Harbor and enjoy water activities.
Evening: Anchor at Great Harbor, Peter Island, and have a peaceful evening on board.

Day 3: Peter Island to Virgin Gorda
Morning: Sail to Virgin Gorda and visit The Baths, a unique geological formation.
Afternoon: Explore Spanish Town and the shops at Virgin Gorda Yacht Harbor.
Evening: Anchor at Leverick Bay and dine at one of the waterfront restaurants.

Day 4: Virgin Gorda to Anegada
Morning: Sail to Anegada, the only coral island in the BVI.
Afternoon: Relax on the stunning beaches of Anegada, known for their pink flamingos.
Evening: Enjoy a seafood dinner at one of the beachside restaurants.

Day 5: Anegada to Jost Van Dyke
Morning: Sail to Jost Van Dyke and visit the iconic White Bay.
Afternoon: Relax on the beach, swim, and explore the beach bars.
Evening: Anchor in Great Harbour and experience the lively atmosphere at Foxy's or other local establishments.

Day 6: Jost Van Dyke to Cooper Island
Morning: Sail to Cooper Island and snorkel at Cistern Point or Manchioneel Bay.
Afternoon: Explore the island, visit the Cooper Island Beach Club, and relax.
Evening: Anchor in Manchioneel Bay and have dinner on board.

Day 7: Cooper Island to Tortola
Morning: Sail back to Tortola, stopping at Salt Island for a final snorkel at the wreck of the Rhone.
Afternoon: Return the bareboat charter and explore Road Town or relax on the beach.
Evening: Enjoy a farewell dinner at a local restaurant in Tortola.

This itinerary provides a mix of sailing, snorkeling, exploring on land, and enjoying the vibrant local culture. Keep in mind that weather conditions and personal preferences may influence your itinerary, so be flexible and make adjustments as needed. Ensure you have the necessary charts, navigational tools, and local knowledge for a safe and enjoyable sailing experience.

Not too bad, but returning the bareboat in the afternoon is a dead giveaway :-)

CHAT is good for some things but I don’t use it for travel planning. So many nuances and let’s be honest, an algorithm doesn’t understand your interests and preferences unless you spend a lot of time teaching it. For me the joy is in the research and planning. I don’t want an easy button.
😊

I tried some follow-ups...

Me: I don't want to go to Norman Island and then Peter's Island on consecutive nights.
It: Certainly, let's modify the itinerary to avoid consecutive nights at Norman Island and Peter Island. Here's an adjusted week-long bareboat sail charter itinerary for the British Virgin Islands:
(It then gave me a slight change but still had Norman then Peter)

Me: Make it for eight days
It: Certainly! Here's an extended eight-day bareboat sail charter itinerary for the British Virgin Islands:
(Added a Day at CGB but still had Norman then Peter)

Me: You've still got me going to Norman and Peter Island on consecutive nights.
It: Apologies for the oversight. Let's adjust the itinerary to avoid consecutive nights at Norman and Peter Island:
(It basically just swapped to Peter then Norman - Ha!)

So I tried something else.

Me: What are some secluded anchorages in North Gorda Sound?
It:
North Gorda Sound in the British Virgin Islands offers several secluded anchorages where you can enjoy privacy and tranquility. Here are some secluded anchorages in North Gorda Sound:

Saba Rock: Saba Rock is a small island with a quiet anchorage. It's known for its peaceful surroundings and proximity to other attractions like the Bitter End Yacht Club.

Eustatia Island: Eustatia Island provides a serene anchorage with beautiful views. It's a private island, so be sure to respect any boundaries and enjoy the secluded atmosphere.

North Sound, Virgin Gorda: While not entirely secluded, certain areas within North Sound offer quieter anchorages. Explore spots like Leverick Bay or quieter corners near Biras Creek for a more private experience.

Mosquito Island: Mosquito Island provides a more secluded anchorage away from the busier areas. Enjoy the peaceful surroundings and perhaps venture ashore for a quiet beach experience.

Prickly Pear Island: Prickly Pear Island offers secluded anchorages on its northern side. It's a beautiful spot with sandy beaches and clear waters.

Oil Nut Bay: While Oil Nut Bay is a private resort, the bay may offer anchorages with beautiful scenery. Exercise caution and respect any restrictions that may be in place.

Remember that the availability of anchorages can be influenced by weather conditions and the time of year. Always check local charts, weather forecasts, and any regulations or restrictions in the area. Additionally, respect private property and marine protected areas to ensure a positive experience for yourself and future visitors.


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So, kinda fun to play around with. Obviously it has some issues but overall not a bad job I think.

I agree but one could consider this part of the research and planning. Just one input on what the possibilities could be.

I'm not going to throw away the Scott book quite yet

But (Base Manager), my AI told me I could return the boat in the afternoon! What do you mean there's an extra charge!?!

Funny, I did the same but I was very specific. ChatGPT did fairly well. Of course then you get there and the wind is different and it all goes out the window!

That itinerary looks very familiar to some of our past trips - except the Norman>Peter thing and the upwind grind from Jost-to-Cooper. Just swap Cooper with Norman or Peter and I'd be good to go - though these days I might still skip Cooper and add an extra day in North Sound or at Anegada.

One other observation - not one mention of Boatyball.