Anniversary Trip in November
 

My wife and I are looking at options to celebrate our 20th anniversary in November and are interested in a Caribbean destination. We are interested in relaxation, good beaches, good food and outdoor activities. We don't have an interest in casinos or shopping and are leaning away from all-inclusive resorts. Our experience in the Caribbean is limited. She's been to the Atlantis in the Bahamas and is not interested in a similar experience. We've been to Puerto Rico (I've been multiple times myself on business). I like PR and the people but am interested in something different. Our initial thoughts are for the BVIs, Turks and Caicos, or possibly Barbados or Grenada. St John and the Caymans maybe too. For activities, we'd be into hiking, fishing, sailing excursions, jeeping around, snorkeling (more me than her), historical or nature tours and similar outdoor pursuits - really trying to convey that while we LOVE sitting and walking on a beach, we don't want to do that all day, every day. Food for us can be a mix of local (i.e. street food/food trucks) and fine dining. We are not paranoid about crime or hurricanes - we live in the southern US and know that those are a fact of life.

As an experienced cruiser on the Caribbean islands, I have few places to recommend. By far, and considering the activities you want to do, I would suggest Barbados, St. Thomas and St. John (super close to each other), Grand Cayman, Grand Turk and Antigua (beautiful beaches). Have fun!

Each island you list has it's own pros/cons.

Turks & Caicos- my 1st visit last year and loved it, the beaches are just beautiful and the snorkelling/diving excellent. But there is no hiking or historical sites, it is a dry scrubby island with the main appeal being the sea. Lots of great hotels & restaurants, very comfortable especially for Americans with all home comforts and familiar amenities. We started off wanting to try local/street food etc but the experiences were not good so we stuck to hotel restaurants which were very good and all in all much better standard and value.

Barbados has beautiful beaches on the west coast, great hotels and upscale dining options too, the east side is windy and great for an excursion, the island has a bit of hiking and many historical sites. A great intro to the Caribbean, snorkelling is not fantastic but you will see fish and maybe turtles. Lots of street food (fish fry in Oistins for instance.)

Grenada is the island that has everything (well almost), gorgeous beaches, great hotels, a rainforest jungly interior, hiking, friendly local people, snorkelling not fantastic sadly. Food options very good.

Caymans is a bit like T&C, dry hot arid island with beautiful beaches, beautiful hotels & restaurants, well off island that is very comfortable, snorkelling and diving excellent. Alot of upscale dining but also some less expensive gems, it's an expensive island, the supermarket prices were just astounding (to me.)

You can rent a jeep on all the islands I've mentioned, they drive on the left.

Have you thought of any of the French islands? St Barts is just lovely for an anniversary, so is Guadeloupe and Martinique, esp for hiking, historical sites with very nice beaches, lots of street food. Haven't been to BVI or St Thomas/St John so can't comment.

This is factually incorrect.
Annual Amount of Precipitation by Caribbean Island
Days of Rainfall by Caribbean Country + TCI

I'm sure it is, I'll try to remember to consult raincharts before making factually incorrect statements. Obviously I cannot go by what I observe, they may appear to be hot.dry arid islands but the raincharts say they are not.

Not singling any poster(s) out, but it is a common misstatement on this forum for the Cayman Islands to be described as arid and scrubby. Many people may get that impression since they are flat, exempting Cayman Brac, and incorrectly associate them with other other flat islands that may be "arid and scrubby" more along the veins of Aruba, Turks and Caicos, Curacao, Anegada, Bonaire, etc...

I'd hate for visitors to have the wrong impression of what conditions during their visit may be like.

Just returned from TCI. Had a great time, but cross it off your list as it doesn't really fit most of your criteria.