Top 5 Caribbean & Bahamas Luxury Vacation Ideas – and When to Book Them

By Shanna Dickerson

by Elysian Magazine

This time of year, it’s easy to get lost in dreams of warm, white sand and crisp, clear blue water. But to make the most of an island getaway, you need to start planning pretty far in advance.

Blue Sky Luxury Travels CEO Shanna Dickerson shares that, “Knowing when to book the most popular weeks in the Caribbean & Bahamas is essential in making sure you get the best villa rentals, yacht charters, rental cars, private chefs and other fun activities and services.”

Certain times of the year actually require extensive planning. If you are considering a vacation in the Caribbean or the Bahamas, it is highly recommended that you book the following weeks at least a year in advance:

  • Christmas and New Year’s Eve (Rates during festive weeks are at least 30% higher than high season rates.)
  • President’s Day (high season rates) 
  • Spring Break (high season rates)
  • Thanksgiving (high or low season rates, depends on the villa owner)

Once you settle on when you are going, let’s think about where you’d like to spend your getaway. These are Shanna’s Top 5 Luxury Vacation Ideas in the Caribbean & Bahamas:


  1. Estate Solenborg — St. John, U.S. Virgin Islands

Located on the north shore of St. John, Solenborg is a luxury Caribbean vacation rental villa that sits in a breathtaking setting. This amazing retreat overlooks the Sir Frances Drake Passage and Denis Bay. As you drive down the historic road that leads to this secluded estate, you will feel like you are approaching your own private paradise. As you arrive, a cocktail reception and chef-prepared dinner await. But that’s only the beginning. You will have your whole vacation to enjoy swimming in the two heated pools, perfect your tan lounging on the terrace, and enjoy a leisurely evening in the outdoor living and dining areas.

The villa’s seven bedrooms all have an en-suite bathroom, al-fresco showers, and ocean views. Five bedrooms have king beds, including the master suite, one bedroom has a queen bed, and one has two double bunk beds, making Solenborg the perfect vacation rental for a family reunion, birthday celebration or a group of friends.

Read more about Estate Solenborg.


  1. Weeklong charter on Bella Vita — British Virgin Islands

Coming in at a massive 105 feet, this super luxury catamaran can accommodate up to ten guests (eight adults and two children) with a crew of six. It was formerly named Necker Belle and was owned by Richard Branson. Now this sleek cat has a new name – Bella Vita – and in 2010 she underwent such a beautiful refit that she won a World Superyacht Award.

Whether you’re an adventure-seeker into sailing, paddleboarding or sportfishing, or you’re just looking for some serious suntanning space, Bella Vita is the charter yacht for you. It was built to maximize fun, featuring a spacious trampoline, a diving board and a unique crow’s nest that can lift you to the top of her mast.

Well-known charter captain Oswaldo Cruz and gourmet chef Briar Smith, along with a crew of four, share their passion and knowledge of the islands to ensure that you and your guests have an unforgettable experience.

Read more about Bella Vita here.


  1. Sandpiper Beach House — Antigua’s Jumby Bay

Overlooking Davis Bay and the hills of mainland Antigua, the Sandpiper Beach House occupies an unrivaled beachfront position and boasts truly dramatic views. Surrounded by majestic palm trees, the five-bedroom residence encompasses 9,700 square feet and rests serenely within beautifully manicured tropical gardens. It is located just a short distance away from the resort’s restaurants, bars and amenities.

Sandpiper features a light and airy ambience that flows gently from room to room and is enhanced by an island-inspired interior palette that includes artwork by local artists, as well as interesting books and fresh flowers from the garden. The retreat also features a spacious great room that opens to the outdoors, a modern kitchen and an indoor sitting/media room with a pool table. 

Each of Sandpiper’s bedrooms boasts an ocean view, a private terrace and a lushly planted outdoor shower room. Three of the bedrooms open straight onto the white sands of Harbour Beach. The residence offers four king beds and a set of twin beds, all dressed in luxurious linens.

Read more about Sandpiper Beach House here.


  1. Long Bay Villas — Anguilla 

Located on beautiful Long Bay on Anguilla, Sea Villa is one of a trio of newly transformed beachfront villas that can be rented by itself or together, making it the perfect vacation rental villa for your family vacation, dream wedding or corporate event. Sea Villa is the largest and closest to the beach of the three Long Bay villas. No matter which one you choose, though, each villa offers you the privacy of a villa, plus the amenities and service of a luxury boutique resort.

Sea Villa accommodates 11 guests in six bedrooms, five of which have king beds (with the option to convert to two twin beds in two of the bedrooms), and one with a single bed that’s ideal for a child. 

From the outdoor terrace, a private staircase leads down to the soft white sands of picture-perfect Long Bay Beach. Relax with a good book in one of the comfortable lounge chairs or enjoy a refreshing swim. Beach drink service with complimentary soft drinks and water is provided.

Read more about Long Bay Villas here.


  1. Weeklong charter on HOME — Exuma, the Bahamas

HOME is a stunningly beautiful megayacht offering luxury accommodations for 12 guests. The full-beam master cabin on the main deck features a dressing room, en-suite bathroom with shower and a private office. On the lower deck is a full beam VIP cabin, two double cabins and two twin cabins.

Her gorgeous styling by Omega Architects features floor-to-ceiling glass in the main living areas and the master cabin, creating an airy ambience with natural light shining onto clean, contemporary Ibiza-style interiors by Cristiano Gatto.

A large sun deck is equipped with sun loungers and glass screens to shield the breeze. Located aft is a Jacuzzi and a stylish sit-up bar with designer lounge shaded by the hardtop in the middle. The upper deck’s casual sky lounge has beanbags, day beds and teak decking that, together with the glass walls and sliding glass doors, link the space seamlessly with the open-air dining area.

Read more about HOME here.

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