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Caribbean Islands for 40th Anniversary

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Caribbean Islands for 40th Anniversary

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Old Feb 16th, 2026 | 01:16 PM
  #1  
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Caribbean Islands for 40th Anniversary

Hello. I want to plan a trip to somewhere in the Caribbean for our 40th anniversary this November. We are looking for warm and sandy beaches, culture, good food, etc. I'll be still recovering from a knee replacement, so, I feel I need easy access to things, but maybe some hiking trails for my husband. I've read some input on staying one week on island is too long. Thoughts on that? We've discussed, but are not interested in a cruise at this stage. I'd appreciate any feedback, possible itineraries for a 2 or 2.5 or even 3 wk stay. Many thanks.
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Old Feb 17th, 2026 | 07:08 AM
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Whether you stay on any given island a few days, a week, two weeks or even longer is purely a personal decision - there is no right or wrong answer. It all depends on your particular travel style. how active or sedentary you are and how well you matched your "wish list" to the island(s) you visit. With one week, you'd probably want to stay on one island and perhaps visiting a second nearby island (if there is one) for a day trip. If spending 10 or more days you might consider splitting your time between 2 different islands. Keep in mind, that when splitting stays between different islands you lose a bit of "visiting time" packing, traveling between destinations and checking out of one hotel and checking in to another.

Now, among the islands you tagged in your subject line you indicated an interest in St. Martin/Sint Maarten and Anguilla. That's an excellent combination of islands if you are going for an extended trip (2 or 3 weeks). St. Martin has both a French side and Dutch side so it's like visiting two different islands. You can stay for a week on the French side and easily drive to the Dutch side any time during your visit. You can then take a short 20 minute ferry ride to Anguilla and stay there for the second half of your trip. It's has a completely different vibe and is much more laid back than St. Martin. You would also have the option of visiting St. Bart's while staying on either island. It's a short 10 minute flight from Anguilla or St. Martin. Depending on the length of your trip you could make it a day trip or spend a few days there.

You also tagged the US Virgin Islands as being of interest. Depending on the length of you trip you could easily island hop between St. Thomas, St. John and (with careful planning) St. Croix. You'd also have the ability to visit one or more of the British Virgin Islands as there's a very good ferry system which links both the USVI's and BVI's. Water taxis and island hopper flights are also an option for linking the two island chains.

Hope this helps.
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