The Caribbean - 21 Day Yacht Charter Itinerary
- Aruba
- Barbuda Island
- Caribbean Itinerary
- Cayman Islands
- Dominica
- Guadeloupe
- Haiti
- Hot Caribbean Yacht Charter Spots
- Montserrat
- Puerto Rico
- Spanish Virgin Islands
- St Kitts and Nevis
- St Martin
- Top 10 Caribbean Dive Sites
- Trinidad and Tobago
- Turks and Caicos Islands
- Anguilla
- Antigua
- Bahamas
- Barbados
- Bermuda
- British Virgin Islands
- Cuba
- Exumas
- Grenada
- Grenadines
- Leeward Islands
- Martinique
- St Barts
- St John
- St Lucia
- St Thomas
- The French West Indies
- US Virgin Islands
- Windward Islands
Read the full Caribbean Charter Guide.
A 21-day private yacht charter itinerary visiting Martinique, Dominica, Guadeloupe, Antigua, Barbuda, St Kitts, Anguilla and St Martin.
Day 1
Board in Le Marin, Martinique and cruise to Anses d’Arlets, a typically pretty fishing village south of Grand Anse which makes the most of its gorgeous beach front. Places of interest are the 18th century Roman Catholic Church in its centre as well has a handful of laid back beach shacks selling snacks at the northern end of the village. There is some excellent snorkeling around an offshore rock that juts out of the sea.
Day 2
Cruise to Martinique Central East Coast where you’ll find a mini-version of the Grenadines with one anchorage reminiscent of the spectacular Tobago Cays. This coastline is protected from the Sea by a reef so offers some nice anchorages.
Day 3
Enjoy some shore based activities in Martinique such as horseback riding. The Captain can move the yacht to a new anchorage whilst you’re ashore. Spend the night in the North at St. Pierre.
Day 4
Iles de Saint – Located a short distance to the south of Guadeloupe are the small group of islands known as the Les Saintes - some are inhabited some are not. Terre-De-Haut is the largest of the 8 islands that make up the Les Saintes. The island was too hilly and dry for sugar cane so slavery never took hold here. Consequently the descendants can trace their ancestry to the early seafaring Norman and Brenton colonists. Terre-de-Haut is quaint and unhurried, very French in nature and almost Mediterranean in appearance. It has a beautiful landscape of volcanic hills and deep bays with plenty of protected beaches for good swimming.
Day 5
Iles de Saint – Terre de haut – Enjoy some snorkelling before heading back to Dominica in time to collect Amanda from her flight.
Day 6
Dominica - Nature Isle - Whale watching, Diving, Hot River Bathing.
Day 7
Remain in Dominica to meet the Bowlers from their flight. We recommend a boat ride on the Indian River and a tour of the island to explore the local culture and see the stunning rainforest and waterfalls this island is famous for. There will be a handful of Rowers standing by just south of town ready and willing to be your guide for the trip. The boats wind up a shady river through tall swamp blood trees, whose buttress trucks rise out of the shallows. This can be a fascinating outing, taking you into an otherwise inaccessible habitat and offering a close up view of the creatures that live at the water’s edge. Try to pick a guide/boater who works with the Park Service as you will get a lot more out of the trip. The cost will be about $35EC per person and it will take about 1.5 hours. (Usually with a stop for a drink at a jungle hut bar)
Day 8
Guadeloupe – Grand Terre. Long stretches of beautiful sand, beach bars, plenty of activity
Day 9
Guadeloupe – Spend the day at Pigeon Island Cousteau Marine Park which offers excellent snorkelling. Continue onto Deshaies in the north of the islands for the evening. Deshaies is known as the gourmet capital of Basse–Terre. It is a beautiful harbour side village surrounded by green hills and dotted with waterside restaurants. Deshaies is a popular “Yachty” haven.
Day 10
Montserrat – Explore a live volcano
Day 11
One day free to spend where ever you are enjoying – Dominica, Guadeloupe, Iles de Saint or arrive one day early to Antigua. There is plenty to do around Antigua which you may not have done when you were there ashore. Uninhabited Green Island is great for a day and there are many nice anchorages.
Day 12
Cruise to Antigua and stop to enjoy a snorkel at Cades Reef which offers large amounts of soft corals and colourful marine life. Continue to St John for the evening. St John’s offers shopping, hotels, restaurants and casinos.
Day 13
Head to Barbuda to explore the lagoon and the Frigate bird colony
Day 14
Return to Antigua and enjoy lunch at the Italian restaurant perched on a cliff (name TBC). Take a berth for the evening in English or Falmouth Harbour. The Bowlers depart Antigua.
Day 15
Head to St Kitts early and anchor off. There are some nice restaurants ashore that you may wish to enjoy.
Day 16
Take a tour of St Kitts exploring Brimstone Hill fort and Rawlins Plantation.
Head to St Kitts – although you’ve been there it may be different to see the island from another perspective. I’d suggested at least one day and night here.
Day 17
Cruise to Anguilla and experience the unspoiled Caribbean at its best. This pristine island boasts charming villages, serene harbours and long stretches of white powdery beaches. A short cruise from Road Town brings you to the Prickly Pear Cays and Seal Island Reefs. This is a wonderful snorkeling spot with crystal clear water and vibrantly colored living reefs.
Day 18
Anguilla – Enjoy the luxurious spa facilities ashore and 5 star resort dining at Malliouhana Spa on Meads Bay or CuisineArt Resort and Spa in Rendezvous Bay.
Day 19
One spare day to enjoy where you like – St Kitts, St Barts or Anguilla.
Day 20
St Martin - Anchor in the pretty bay of Grand Case for the evening. This is a calm bay, perfect for relaxing, sunbathing and enjoying some water toys. Its waterfront is lined with brightly coloured houses in true Caribbean spirit.
Enjoy an afternoon stroll down the vibrant narrow main street lined with great little boutiques and galleries. In Grand Case you can enjoy some of St Martin’s best gourmet restaurants such as Le Tastevin which offers traditional French cuisine and a wonderful Degustation menu.
Day21
St Martin – Perhaps take a taxi to the hillside retreat, Lottery Farm for an adventure of the Mango Tree tops. Enjoy some lunch at the excellent organic Tapas at the Hidden Forest Cafe. Tonight berth in Marigot Bay and perhaps enjoy an evening out at Mario's Bistro.
Day 22
Enjoy a leisurely breakfast before preparing to disembark before midday.
Charter Yachts in Caribbean Itinerary
Client Testimonials
What our clients say about their charter experience.
Dear Crossed Sabre team, we were VERY happy with the entire experience and very appreciative of all that you, your crew and your chef did to accommodate our religious requirements and to provide our family with a beautiful experience. Captain Simon was the best we have had yet, and we liked our previous captain very much. We liked your calm demeanour, your humility and your genuine desire to make sure we had a great experience. We also appreciated how good you were with the children, including playing chess with them and just in general how you were very easy to speak with. All the crew were excellent and very service-oriented and super respectful. I was especially grateful for the sincere concern all the crew had to be sure our religious needs were fully met, and everyone went above and beyond in this regard, which was very much appreciated. The chef had a calm and easy demeanour and was easy to communicate with, and the meals were excellent. As for my father, it was fantastic that he was able to work out regularly with a crew member. We want to make sure you know how much we appreciated all that you and your team did for us; we were very happy with everything. We know that accommodating strict kosher requirements was not easy, but it was done very well.
They absolutely loved the boat and described it as phenomenal. The meeting with the captain at a café the day before departure was excellent and helped establish a great rapport. They loved the flexibility of having the captain tailor each day around their preferences. The boat would typically move in the morning, although some evenings they would travel as well. The food onboard was exceptional. They did not want to miss a single meal and were consistently impressed with the quality. The crew's service was a major highlight. They loved that the crew knew one another well and were all Croatian, which created a very warm and cohesive atmosphere. The crew offered two massages each day, allowing everyone to take turns enjoying them. The captain would regularly go into town to purchase fresh produce and local fish, which added a wonderful local element to the experience. One day, the captain went out diving for octopus and later enjoyed it as part of their onboard meal. Overall Takeaway: The clients were exceptionally positive about the trip, with the yacht experience, crew, flexibility, food, and personalised service standing out above everything else. They repeatedly emphasised how much they loved being onboard and how little they wanted to leave the boat.
What can we say? Unbelievably amazing experience. You are all such wonderful people whom we can now consider friends we hope to have long into the future. Thank you for sharing your hospitality and incredible country with us; we could not have asked for a better experience. We look forward to seeing you all in the very near future – in Croatia or Florida. All the very best and with much affection
To the Reverie team: We want to say a huge thank you for everything you have done for us on this trip. You are the best crew we have ever had on a yacht, hands down. Everything has been flawless. Keith’s food has been healthy, tasty, voluminous, and so varied. The toys and tenders were always ready for us when we needed them, and we loved having 3 Sea-Bobs, 3 efoils and 2 jet skis. Always charged and ready to go, from the moment we woke until we went to bed. Our rooms were cleaned so fast we often wondered if there were fairies who appeared and did it. Our washing was done and returned so quickly we wondered if we dreamed it. Service was perfect (thanks Megan and team!) - always nearby when we needed it, and invisible when we didn’t. We aren’t sure how we will survive at home, and there won’t be a drink, a cold towel and a smile waiting for us. Shane - you found us the best anchorages - exactly where we wanted to be - out of the way, out of the wind, but close to everything. We wanted adventures, and you went out of your way to source e-bikes, which ended up being a highlight. We know it wasn’t easy to find or to get them on and off the boat. The smaller things: remembering everyone’s names; the printed AllTrails maps; taking our kids jet skiing. They have all been noticed and appreciated. We know that it isn’t easy to build a team that can create such an exceptional experience. Congratulations to everyone on board - including those behind the scenes we don’t get to see as much. We would love to come back again next year - only if the crew is the same! Thanks so much!
Thank you all so much for such an amazing week! We had such a fabulous time thanks to each & everyone of you! Looking forward to seeing you in Dublin.
You guys knocked it out of the park again – we had such a super time! Thanks again to all for looking after us so well and all welcome in Dublin at any time!
