Sailing Honeymoon in the Caribbean ? – 5 Most Romantic Islands!

A romantic getaway can be a couple’s dream, but where is the most romantic destination? There are hundreds of beautiful settings, but five of the most romantic islands for a couple to explore by yacht are located in one central location. If you are seeking a romantic setting for an anniversary, honeymoon, or vacation, look no further than the Caribbean.


5 most Romantic Caribbean Islands

The U.S. Virgin Islands are a cluster of islands in the Caribbean consisting of numerous little islands of varying size. There are three main islands that garner the most tourism, but other islands in the group are perfect settings for a romantic day or night with your partner.


Saint Croix

The largest of the Virgin Islands, Saint Croix has many activities for couples. You can go to Rhythms at Rainbow Beach for a fun night out, take a kayak or horseback riding tour, or hike to the Carambola Tide Pools. For a more sedate pace, take a sunset stroll down the Frederiksted Pier.

Saint John

A sailing honeymoon in the Caribbean must include a visit to Saint John, home to the appropriately named Honeymoon Beach. Scuba diving at Eagle Shoals or Carvel Rock is exciting, but if you are looking to get out of the water, shopping on the island offers a hodgepodge of handmade trinkets that are unique.

SAINT JOHNSaint Thomas

Saint Thomas has many fascinating dive sites, including sunken WWII navy barges, underwater tunnels and coral reefs, and the famous Cow and Calf rock formations.

Saint-Thomas island


Water Island

Located off of Saint Thomas, Water Island is small but isolated. This is the perfect choice for some private beach time away from everyone and everything.

Beach in the Caribbean

Buck Island

Buck Island is technically a National Park but has incredible exploration opportunities. Among the most popular and worthwhile is a snorkeling trip through the underwater reef monument.

Buck Island

Crewed Yacht or Bareboat?

The decision to skipper a bareboat yacht or charter a crewed yacht should boil down to experience, preference, and availability. Crewed yachts offer convenience and service, but the sailors must relinquish control of the boat to someone else. On the other hand, a bareboat means more privacy, but the responsibility of sailing the vessel falls on the passengers.




  • Privacy, especially for couples looking for a romantic getaway
  • More available space with no crew onboard
  • You get the experience of sailing and captaining the boat
  • Schedules and sudden changes are up to you and the other passenger


  • You must obtain a license to captain a vessel
  • Service is up to you and other passengers
  • Operation and other considerations are your responsibility for the duration of the trip

Crewed Yacht


  • Nothing but free time to spend with your special someone
  • A crew can provide top-notch service and help organize romantic activities
  • A chartered skipper will be more familiar with a locality and help find places that would be of interest


  • Lack of privacy
  • You must confer with the captain to set a schedule or visit a location

Sailing with romance in mind can be a private experience between a couple, or a pampered yacht trip with a full crew to make the experience more comfortable. Either way, sailing around the Virgin Islands is sure to make you fall deeper in love with your partner!


Have you been on a honeymoon in the Caribbean? If so, you are welcome to share your experiences in the comments below.

4 thoughts on “Sailing Honeymoon in the Caribbean ? – 5 Most Romantic Islands!”

  1. These are lovely places. I would love to go here someday 🙂
    I would just like to ask how much does it cost to stay here – Accommodation fees. How much is the food?

    • Hi Keye,

      It depends where you want to stay, for how long and what kind of food you order. A bareboat will be cheaper than a crewed yacht.
      I hope it helped

      Have a good day

  2. Hi Daniella,
    Romance is sewn into the very fabric of the Caribbean and makes for an unquestionably indulgent honeymoon. From Champagne catamaran cruises to petal-strewn sands in the balmy evening, the treat-upon-luxurious treat can be planned to celebrate your love in style.

    • Hi Taylor,

      Thank you for the comment!
      Yes, the Caribbean is the perfect place for a honeymoon trip, especially on a catamaran:)

      Thank you again and wish you a lovely day!


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