Caribbean Yacht Charter & Boat Rental | Luxury Private Crewed Charters & Island Hopping

Choose a private crewed charter for island hopping in the Caribbean, and you’ll enjoy a turnkey week with a captain, chef, and steward attending to every detail during your escape.

Their team meets your needs with precise planning, being attentive and proactive, flexible routing, and on-board service that keeps your days flowing smoothly from dawn swims to sunset dinners.

In the usvi, port towns offer pristine coves and tranquil anchorages, with larger yachts delivering comfort and rental options for intimate days on board. The crew handles provisioning, parts for gear, tender transfers, and safety checks so you can focus on everything you want to do, with free water toys on select charters.

We blend Caribbean flavor with international touches–indian-spiced curries, fresh seafood, and locally sourced produce–delivering exceptional service on every voyage. If you’ve compared to amalfi or sardinia, you’ll notice the Caribbean pace lets you linger in town squares or explore a quiet port, without rush.

To tailor your itinerary, specify preferred islands, snorkeling sites, dining ambitions, and the number of ones in your party; we’ll craft a plan that fits your schedule, your preferences, and your rental needs, with flexible options and add-ons ready to cover contingencies.

Caribbean Yacht Charter & Boat Rental: Luxury Private Crewed Charters & Island Hopping; - SICILY

Choose a 7-night Caribbean private crewed charter aboard a larger yacht with a captain, a chef, and a stewardess to guarantee exceptional service aboard. Your plan should center on captivating islets, crystal-clear coves, and miles of beautiful coastline, with daily routes that return to anchor every sunset.

Under the guidance of Grigory, our lead sailor, the crew delivers careful provisioning and vigilant safety checks, ensuring your days run smoothly. Being aboard feels effortless as you glide between sheltered bays, snorkel in crystal-clear waters, and relax in shade under palm fronds. Temperatures sit comfortably in the high 20s Celsius, making water activities a daily highlight for six to eight hours of cruising and stops.

• Your crew and on-board service: captain, chef, stewardess, and a dedicated watersports specialist; Grigory coordinates the deck for a seamless flow from dawn to dusk.
• Ship and gear: larger motor or sailing yacht, air-conditioned cabins, snorkeling gear, inflatable tenders, and a selection of paintings and plants that add a welcoming touch to interiors.
• Route framework: day trips span 12–25 miles between anchorages, with time to explore islets, bays, and coastal towns while keeping the daily rhythm comfortable for all ages.
• Standards and safety: pre- and post-cruise checks, licensed crew, and full compliance with maritime regulations, ensuring a secure backdrop for unforgettable moments.
• Captivating experiences: private beach picnics, sunset cocktails, and guided snorkeling on pristine reefs; every day offers a new spot to treasure.

Sample Caribbean itinerary highlights you can expect to tailor: St. Barts, Anguilla, Antigua, Nevis, and Grenada, with optional stops at small islets off the main routes. You’ll discover rich culinary contrasts between seafood-forward menus in protected coves and bold Creole flavors ashore, all curated to your preferences. Each day presents a new option to mix up viewpoints–from panoramic hillsides to crystal-clear water coves–while the same crew attends to your comfort below deck and on deck.

For travelers seeking a broader horizon, consider adding a Mediterranean extension. Naples offers access to larger ports and charming shore excursions, while Dubrovnik provides dubrovnik spots along the Dalmatian coast waiting to be explored. In Croatia, islands like Korčula and Hvar offer a different charm, with limestone coastlines and long, winding harbors. A deal that blends Caribbean charm with a Sicily-based leg can deliver a diverse experience, allowing you to compare the overall vibe, service, and scenery across regions.

1. Deal fundamentals: confirm the yacht size (larger yachts provide more deck space and stability), crew count (captain, chef, stewardess, and a dedicated deckhand), and the number of days you’ll sail. Ensure the plan includes at least two isolated islets or crystal-clear bays each day for immersive time ashore.
2. Route planning: map your choices between Caribbean routes and optional Mediterranean add-ons. Prioritize spots with calmer days and predictable currents, then layer in a Sicily or Naples departure for a longer program if your schedule allows.
3. Yacht amenities: verify air-conditioned cabins, reliable Wi-Fi, water toys, snorkeling equipment, and a robust wine list. Check that your package covers fuel, port fees, and on-shore experiences with a single, clear billing structure.
4. Crew quality: request a captain who has hands-on experience with both open-water crossings and coastal hops, plus a chef who can adapt menus to dietary preferences and local markets. Ask about a dedicated on-board sailor who can lead guided shore walks and light watersports coaching.
5. Booking flexibility: confirm cancellation terms, window options for weather-scale adjustments, and a back-up plan for alternate spots should seas or winds shift unexpectedly.

Your choice should reflect how you want the days to flow: a more relaxed pace with longer swims and slower sightseeing, or an active schedule centered on back-to-back dives, hikes, and culinary tastings. The overall experience hinges on the trio of a capable crew, a versatile yacht, and carefully curated itineraries that maximize time ashore while preserving a steady rhythm aboard.

If you plan to weave in a Mediterranean leg, start from Naples, explore Capri’s charm, and then sail to Dubrovnik and other Croatia coastlines. This approach yields a rich contrast between Caribbean warmth and European elegance, maintaining the same high service standards and attention to detail you expect. With this structure, you can return to a familiar port or stay longer in your favorite spots, enjoying the same level of care and the same family-like atmosphere aboard.

Bottom line: your best value comes from a larger yacht with a seasoned crew, a strong emphasis on safety and standards, and a flexible itinerary that blends captivating Caribbean islets with selective Mediterranean extensions. This approach keeps the experience fresh across days and miles of sailing, while ensuring the service and atmosphere stay consistently warm, welcoming, and memorable for everyone aboard.

Spots to consider for island hopping include islets off Antigua and Grenada, verdant Corisca-style coves near Sicily, and coastal Dubrovnik experiences that highlight Croatia’s rich history and scenic harbors. By balancing your deal, ranges, and preferred pace, you ensure a memorable escape that aligns with your dreams and your budget.

Caribbean & Sicily Crewed Charters: Practical Planning for Island Hopping

Book a сrewed charter that blends Caribbean routes with Sicily legs and lock in a flexible, 3–4 port itinerary to satisfy different interests, from Saint lucia to coastal Sicily towns.

To maximize atmosphere and ease, choose an agency that confirms a known captain and crew with Caribbean and Mediterranean experience. The crew should include provisioning options, water toys, and clear plans for island stops that meet your group’s priorities. This approach keeps the process easy to manage; variable weather in these regions means you need a flexible captain and adaptable shore calls. In the planning phase, specify a minimum of 7–10 days for a relaxed pace across legs; late changes can complicate schedules. Include activities such as snorkeling time, beach picnics, and cultural stops along the riviera and balearics where permissions allow.

Prices vary by season and itinerary. If you’re renting, ask what the base rate includes (skipper, crew, meals, fuel) and which items are optional; this helps you avoid surprises. For those with flexible travel dates, consider shoulder periods to secure favorable prices while temperatures remain comfortable for outdoor activities. In rentals, check if port fees, provisioning, and taxes are included, and what the minimum crew hours are to guarantee service. A well-structured plan across Caribbean and Mediterranean routes increases value and satisfies expectations for holiday guests.

Booking tip: coordinate with your agency to align ports with weather windows and guest interests, and confirm whether rentals include provisioning, taxes, and port charges. If you are willing to adjust dates, you can optimize itineraries and minimize long passages, making the holiday flow smoothly for all onboard.

Choosing Your Charter Type: Crewed vs Bareboat vs Mixed Crews

Choose a mixed crew charter for a balanced Caribbean experience. A captain sails while an onboard crew handles meals, provisioning, and tender operations, giving you space for island adventure and downtime that suits what you want. This option shines in usvi and stkitts, where intimate coves and lively ports demand steady navigation and local insight, and it also works well for saint martin, where you can connect with local guides and sunset shows.

Crewed charters provide a full crew and a tailored day-by-day plan. You enjoy chef-prepared meals, daily provisioning, and shore excursions organized by the crew, plus a captain who knows reefs, anchorages, and local weather. On a 50-foot yacht with six guests, this translates to comfortable cabins, reliable WiFi, and ready access to pristine beaches, fruits markets, and historical sites. Costs include crew salaries and port charges, but the total often remains predictable because meals and activities are bundled on board. Superyachts frequently run this model on long routes, showing how it scales from coastal hops to island chains, a setup that represents diverse itineraries for different groups throughout the region.

Bareboat puts control in your hands, ideal for experienced sailors who want maximum independence. You must have a valid license and experience to handle navigation, anchoring, and weather decisions. Provisioning is on you, so costs stay lower on the yacht, but fuel, marina dues, and provisioning add up. Plan for august heat and Caribbean temperatures; bring extra water, reef-safe sunscreen, and a robust safety plan. In places like martin and saint martin, you can anchor in protected bays and adjust routes quickly, since you’re not tied to a fixed crew schedule.

Mixed crews blend structure with freedom. You get a captain plus a lightweight crew or a chef for select legs, providing both reliability on long passages and flexibility in lagoons and coves. This approach suits diverse groups and budgets while still offering onboard groceries, healthy options, and curated activities. The usvi, stkitts, and saint martin ports offer consistent shore experiences, and you can also tailor provisioning to fruits and snacks, which helps keep costs predictable. For longer routes, you’ll discover options that maximize time on the water, including charters that run around dubrovnik as a benchmarking example.

Seasonal Best Itineraries: Caribbean Island-Hopping Routes by Weather

Plan a February–April window to maximize calm seas and steady trades: begin in Antigua and Barbuda, then loop through Saint Kitts & Nevis, Guadeloupe, and Dominica, with a possible touch on Martinique or St. Lucia before returning. For each leg, target 20–40 nautical miles to keep daily sailing simple and maintain a comfortable length of sailing time per day, boosting value across the Caribbean vacations and holiday.

The Leeward Island sequence offers diverse anchorages and reliable shelter. Antigua → Barbuda runs 25–35 nm, Barbuda → St. Martin or Anguilla 40–60 nm, then St. Martin → Guadeloupe adds 50–70 nm. This option keeps seas manageable, yields pristine beaches and calm bays, and even passes close to canals near sheltered harbors. For flexibility, a bareboat rental fits well; if you prefer support, a crewed option adds reliability while you prefer indian-flavored markets and fresh produce.

The Windward arc adds exciting contrast. Martinique → Dominica 40–60 nm, Dominica → Guadeloupe (Les Saintes, Marie-Galante) 25–40 nm, Guadeloupe → St. Lucia 25–50 nm, St. Lucia → Grenada 50–90 nm. This broad loop favors protected anchorages and a rich mix of landscapes, from rainforests to pristine beaches. If you have 10–14 days, finish back near your start with relaxed pacing that keeps vacations on track and lets you savor the scenery below the surface and above.

Weather snapshot: the northeast trade winds during the dry season (December–May) run 15–25 knots, with seas generally 2–4 ft. Morning conditions are calm, afternoons build a comfortable breeze. May–June bring more shower risk; plan legs under 60 nm on heavier days and book reliable marinas for refueling and provisioning. The egadi comparison helps planners gauge options, but the Caribbean abundance of sheltered bays and island ports keeps options flexible.

Practical notes: choose a rental that matches your crew, then map anchor days to avoid long passages. Carefully check fuel consumption for your boat type and carry extra water; many ports offer free Wi‑Fi and easy access to markets with fresh seafood. Among options, national harbors tend to deliver reliable services while private marinas add cost savings and flexibility; this helps keep costs down and issues rare on well-planned vacations.

Know that you can tailor routes among Antigua, Barbuda, Guadeloupe, Dominica, Martinique, St. Lucia, Grenada, and Barbados to suit your pace. For families or groups, a mid-size catamaran balances length, living space, and value, while a bareboat is isnt a viable choice for experienced crews. This approach offers an abundance of diverse ports, pristine anchorages, and simple logistics, with below-average fuel charts and a year-long supply of fresh provisions. If you prefer a more relaxed experience, stick to 3–4 anchor days per island and adjust as weather dictates.

Luxury Provisions Onboard: What to Pack, Stock, and Request

Create a full provisioning plan three days before departure to cover peak demand and keep the atmosphere aboard relaxed.

• Pack for comfort and ease
  • Personal kit: prescription meds, seasickness remedies, sunscreen (reef-safe), hats, sunglasses, a light rain shell, two changes of dry clothes, and a compact laundry bag.
  • Beach and shore days: two pairs of sandals, sand-friendly footwear, a quick-dry towel, a small daypack for onshore activities.
  • Tech and safety: power bank, universal adapter, waterproof phone pouch, a first-aid kit with motion-sickness meds, and extra batteries.
  • Extras: pack extra toiletries and a small stash of holiday treats for moments of celebration, if you like.
• Stock the galley with pantry and perishable items
  • Pantry staples: pasta, rice, canned tomatoes, tuna, beans, olives, capers, pesto, tomato paste; oils and vinegars; salt, pepper, chili flakes, dried herbs, sugar, coffee, tea, and cocoa.
  • Spice kit and flavor boosters: paprika, cumin, garlic powder, dried basil, saffron, and a small hot sauce collection.
  • Fresh provisions: seasonal fruit, greens, zucchini, tomatoes, cheese (including mozzarella or feta), bread, yogurt, and dairy-free options if needed.
  • Buffer and ranges: aim for a three- to five-day stock with a mid-week refresh; this keeps everything flexible for port calls and weather. Include example menu ideas to guide the chef.
  • Apart from routine staples, add budget-friendly items as needed, so you can adapt to the crowd without overstocking.
  • Holiday-friendly snacks or kid favorites can lift the mood during longer passages.
• Beverages and bar essentials
  • Water supply: still and sparkling, plus electrolyte drinks for hot days.
  • Wine and spirits: a small selection of white and rosé, Caribbean rum, neutral vodka, and a versatile liqueur for sunset moments.
  • Coffee and tea: whole beans or ground coffee, decaf, and a selection of herbal teas.
  • Local touches: request a few regional items from ports you visit to elevate the welcome on board.
• Regional flavors and sample menus
  • Plan for routes with broad regional options; include croatian olive oil and dutch cheese as examples of imported flavors that pair well with seafood and pasta, especially ocean-fresh options when you visit coastal ports.
  • Draft an example weekly menu to streamline provisioning: day 1 light lunch, day 2 seafood, day 3 vegetarian, day 4 grill night, day 5 pasta night.
  • September heat calls for lighter fare and more refreshing drinks to maintain the same energy on deck and in the galley.
  • Part of the holiday mood: offer small chef-driven touches that make guests feel welcome and relaxed, even during long passages.
• What to request from the crew
  • Share a full provisioning list with the captain or chef to ensure everything you want is found and ready before you board.
  • Ask for a welcome pack with basic toiletries and fresh towels, plus a snack tray for arrival.
  • Coordinate above-deck and below-deck storage plans, confirm fridge and freezer space, and designate items for each guest so there’s something for everyone.
  • Request exceptional service and a tailored experience; explain dietary restrictions for each guest, including kids, and provide a called-for list of items for clarity and planning.
  • When ports include pockets like kitts or naples, specify local provisions you’d like to try and note any special requests; this helps the crew tailor a regional touch while keeping the same high standard.

Port Calls & Anchorages: Top Marinas and Hidden Coves in the Caribbean

Secure reliable moorings at Simpson Bay Marina, Saint Martin, in june to enjoy a warm coastline and abundant sheltered anchorages. Due to june demand for prime berths, book early. The official port staff coordinate a smooth berthing process, and the well-maintained chain keeps superyachts and charter yachts comfortable after long sails. Grigory, our local dockmaster, ensures timely berthing and reliable moorings for every leg.

From the riviera vibe of Gustavia (Saint Barthélemy) to Antigua's Jolly Harbour, there is a balanced mix of sophisticated facilities and practical access. Jolly Harbour provides protected anchorages, long quay spaces, and straightforward provisioning, plus a beverage service that rounds out evenings. Port Louis Marina in Grenada opens up calm coves and legitimate marina services for longer hops. The coastline around the main ports delivers an exciting rhythm for crews and guests, with festival nights in Gustavia and Bequia.

Hidden coves around Tobago Cays and Saint Vincent offer quiet, protected options apart from the main routes. Finding calm water among the islands makes it easy to stage island-hopping itineraries that are comfortable for all aboard, with warm evenings and a beverage program ready to go ashore or aboard. The island cluster around Saint Vincent & the Grenadines provides reliable moorings and a straightforward chain for owners and captains alike.

Sicily Leg: Key Ports, Legalities, and Local Mooring Rules for Private Yachts

Recommendation: Reserve marina slots in Palermo, Messina, Catania, Trapani, and Milazzo six weeks ahead, especially in June, to guarantee space for a private crewed charter. These berths provide a stable base for provisioning, refueling, and handling the legalities directly with harbor masters. Confirm each port's requirements via these official sites (источник Capitaneria di Porto) and keep a lightweight crew checklist ready.

Palermo sits on the northwest coast as a primary gateway, with two main marinas offering full services, security, and reliable provisioning. Book early, as peak days fill quickly; mooring in the marina is straightforward for mid to large private yachts. Fees and availability vary by season and length, so obtain quotes in advance and confirm reservations in writing.

Messina provides a protected harbor on the Strait and easy access to Lipari, Vulcano, and Salina for island hopping. Expect a mix of marina berths and buoy moorings; plan ahead in June when demand rises. The harbor master requires vessel details and a quick port clearance; ensure VHF Channel 16 readiness and clear communication. These steps apply across the eastern coast to avoid delays during busy times.

Catania Port combines city amenities with straightforward east-coast berthing. Porto di Catania offers marina facilities, fueling points, and shore power, plus strict rules on anchoring beyond designated zones. Always check with the harbor office and carry updated documents; in windy conditions near the Etna foothills, pre-booking and local guidance streamline berthing and exit procedures.

Trapani and Milazzo serve as excellent bases for western Sicily and the Egadi or Aeolian routes. Trapani's marina and adjacent buoy options provide flexible berthing, while Milazzo handles frequent ferries and is the main hub for Lipari, Vulcano, and Stromboli. Use licensed moorings and respect designated zones; anchoring outside permitted areas around the protected coastline is restricted.

Aeolian Islands and virgin coves around Lipari, Vulcano, Stromboli, Filicudi, and Salina offer gorgeous, secluded anchorages, yet most areas lie within marine protected zones. Mooring permissions usually flow through Capitaneria di Porto or licensed operators. If you plan to anchor, choose designated zones only, avoid sensitive seabeds, and carry waste-disposal arrangements on board. These rules apply throughout these islands and can shift with seasonal restrictions till late spring and early summer.

Local mooring rules emphasize prudence: use designated berths in busy ports; outside marinas, many shore zones prohibit anchoring or require explicit permission. Always file a temporary plan with the Capitaneria di Porto and respect environmental guidelines in protected areas. These practices apply here and throughout Sicily, supporting safe operations for private yachts as you visit these ports and windward bays.

These official sources and port sites provide the latest regulations, and it pays to review them before each hop. The variety of cultures across Sicily, plus overseas connections with croatia and other Mediterranean routes, makes this leg a true option for experienced crews and owners. By planning with these considerations in mind, you’ll enjoy smooth visits, clear views, and memorable charters along the coast and beyond.

Cost, Booking Windows, and Flexibility: How to Budget for a Private Crewed Charter

Lock in a 12–18 month planning window for peak-season weeks to guarantee the right crewed charter and the best value. Expect weekly rates in the Caribbean from roughly $40,000 to $70,000 for 70–100 ft yachts, and $80,000 to $180,000 for larger vessels with a full crew. Provisioning adds about 15–25% of the base rate, including fruits and a beverage package, while port fees, fuel, marina dues, and taxes push the total higher. Ask for a detailed, up-to-date information packet and a valid, itemized contract before you sign.

Booking windows vary by season, but there is a practical rule: lock peak weeks early, typically 12–18 months out; there are off-peak options if you are flexible. If you are flexible, you can either secure a reduced rate with last-minute slots or opt for shoulder-season weeks, usually 4–8 weeks out on mid-sized yachts. Especially important: verify inclusions–meals, beverages, and excursions vary by yacht; ask if fruits, wine, or a curated beverage list is included or billed separately. Further, request bundled provisioning and excursions where possible to reduce on-board friction.

Flexibility matters in routing: Grenada can anchor at St. George's and hop to Carriacou, Union Island, and the Grenadines, while the yacht can pivot toward the croatia coast or Bavaria lake regions in a later season for captivating yachting experiences. Each leg offers places for beaches, hikes, or shopping, and the captain should adjust sails with minute precision to balance sailing time, anchor stops, and tender trips. grenada anchors again as a base for next hops, keeping the itinerary dynamic and relaxed for the group.

To meet your level of service, ask for a detailed crew roster and daily schedule; the right operator should call the crew by their roles and deliver with calm reliability, keeping promises and transparent provisioning lists. Specify the beverage list and dietary options; ensure there are valid checks for provisioning, including fruits and specialty items. Port calls should be confirmed in advance, and you should have options for on-shore experiences at each place. There is flexibility to adjust if a port gets crowded or seas are rough.

Keep the information current by asking for up-to-date itineraries and weather forecasts; compare yachts against riviera benchmarks and yachting standards, and use grenada as a base to evaluate service levels; you can also compare with croatia or the bavaria coast for context on upkeep and design quality. A well-planned charter balances price and experience across season, with a relaxed vibe onboard and well-curated beverages, along with fresh fruits and healthy options. Yachts were designed for extended voyages, not just short hops; ensure the contract remains valid for the dates and ports you want, including the calls and moments you want to capture on this yachting itinerary.