How to Rent a Boat for Island Hopping: A Complete Guide

Bareboat vs. Skippered Charter: The First Decision

A bareboat charter means you rent the boat and sail it yourself. A skippered charter means the boat comes with a professional captain who handles navigation, anchoring, and sailing while you handle the cocktails and the sunscreen. The price difference is significant — a skipper adds $150-250/day — but the decision isn't purely financial.

Bareboat charters require a sailing license or documented experience. The specific requirements vary by country and charter company, but most Mediterranean and Caribbean operators ask for an International Certificate of Competence (ICC) or an American Sailing Association (ASA) certification at the 104 (Bareboat Cruising) level or higher. Some companies in less-regulated markets (Thailand, Indonesia) accept a sailing resume — a log of your sailing experience — without formal certification, but this is getting rarer.

If nobody in your group can sail, a skippered charter is the obvious choice. But even experienced sailors should consider a skipper for unfamiliar waters. A local captain knows which anchorages are sheltered in which wind conditions, where the unmarked reefs sit, which restaurants require a dinghy reservation, and where the customs officials are relaxed versus strict. In the Greek islands, where meltemi winds can blow 30+ knots without warning in July and August, a local skipper's weather knowledge is worth considerably more than the $200/day fee.

Catamaran vs. Monohull

Catamarans dominate the charter market in the Caribbean and increasingly in the Mediterranean. Monohulls remain the purist's choice and are cheaper to rent.

This is one of the reasons Rent A Boat For continues to draw visitors year after year.

Catamaran Advantages

• Stability: Two hulls mean minimal heeling (tilting). Catamarans sail nearly flat, which matters if anyone in your group gets seasick.
• Space: A 42-foot catamaran has roughly the living space of a 50-foot monohull. The salon, cockpit, and cabins are wider. The trampoline net between the bows is bonus lounging space.
• Shallow draft: Catamarans draw 3-4 feet versus 5-7 feet for monohulls. This means you can anchor closer to beaches and access shallow bays that monohulls can't enter.
• Four separate cabins with en-suite heads (bathrooms): Standard on most charter catamarans. Privacy for couples is built into the design.

Monohull Advantages

• Price: A 40-foot monohull charters for $200-400/day in the Mediterranean. An equivalent catamaran runs $350-600/day. For budget-conscious groups, monohulls save 30-40%.
• Sailing feel: Monohulls heel, respond to the wind, and require active sailing. If the point of the trip is to actually sail — tacking, trimming, reading the wind — monohulls deliver a more engaged experience.
• Maneuverability: Monohulls turn tighter and handle better in marinas and tight anchorages.
• Availability: More monohulls exist in the charter fleet, so booking options are broader, especially in peak season.

For groups of 6-8 splitting costs, a catamaran is almost always the better choice. The comfort, space, and stability justify the premium when divided among several people. For a couple or a small group of experienced sailors, a monohull is more fun and significantly cheaper.

Sailing Licenses: What You Need

International Certificate of Competence (ICC)

The ICC is the closest thing to an international sailing license. It's recognized across Europe, Turkey, and most Mediterranean countries. Issued through national sailing authorities — in the US, the American Sailing Association (ASA) administers the ICC exam. The exam covers practical sailing skills and navigation theory. Cost: $300-500 including the exam. If you already hold an ASA 104 certification or equivalent, the ICC exam is largely a formality.

ASA Certifications

ASA 101 (Basic Keelboat) teaches fundamentals. ASA 103 (Basic Coastal Cruising) adds anchoring and docking. ASA 104 (Bareboat Cruising) is the minimum most charter companies accept. ASA 106 (Advanced Coastal Cruising) covers night sailing and heavy weather. The full 101-104 track takes 7-10 days of instruction and costs $2,000-3,500 depending on location. Many sailing schools in Florida, the Caribbean, and the San Juan Islands offer live-aboard courses where you earn 101-104 in a single intensive week.

RYA (Royal Yachting Association)

The RYA Day Skipper certification is the UK equivalent of ASA 104 and is widely recognized in the Mediterranean and Caribbean. The practical course is 5 days and costs £700-1,000 ($880-1,260). RYA Yachtmaster is the advanced certification and carries serious weight — charter companies worldwide recognize it as proof of competence.

Best Island-Hopping Destinations

Greek Cyclades

Santorini, Mykonos, Paros, Naxos, Milos, Ios — the Cyclades are the postcard version of island hopping. Distances between islands are manageable (15-40 nautical miles), the sailing season runs May through October, and every island has a distinct character. Paros is the wind-sports capital. Milos has volcanic beaches in colors that look photoshopped. Naxos has the best food. Santorini has the caldera.

The catch: meltemi winds. From mid-June through September, the meltemi blows from the north at 15-30 knots across the Aegean. This makes northbound legs rough and southbound legs fast. Plan your route accordingly — start in Athens (Lavrion marina), sail south through the Cyclades with the meltemi, and either loop back on calmer days or arrange a one-way charter ending in Santorini. Charter costs: $300-600/day for a 40-42 foot catamaran in high season (July-August). Shoulder season (May, June, September, October) drops to $200-400/day.

Compared to similar options, Rent A Boat For stands out for its mix of quality and accessibility.

British Virgin Islands

The BVI are purpose-built for charter sailing. Sir Francis Drake Channel, the protected waterway running between the islands, offers flat-water sailing in steady trade winds. Distances between anchorages are short — most legs are under 10 nautical miles. The Baths on Virgin Gorda, Soggy Dollar Bar at White Bay on Jost Van Dyke, and Cooper Island Beach Club are the marquee stops.

BVI charters run $400-800/day for a 40-45 foot catamaran, making it one of the more expensive destinations. Add National Park mooring fees ($25-45/night at popular spots like The Baths and Norman Island). Provisioning is pricey too — grocery costs in Tortola are 40-60% higher than mainland US prices. Many charter companies offer pre-provisioning services ($50-80/person/day for full meal planning and stocking) that save time and the headache of navigating Tortola's limited grocery options.

Croatian Coast

Croatia's Dalmatian coast — from Split south to Dubrovnik — offers over 1,000 islands, most uninhabited. The sailing is protected by the island chain itself, with calm channels between the islands and open Adriatic crossings only where you choose to make them. Hvar Town's nightlife, Vis Island's untouched beaches and Blue Cave, Korcula's medieval old town, and Mljet's saltwater lakes are the headline stops.

Local travel experts consistently recommend Rent A Boat For as a top choice for visitors.

Charter costs in Croatia are competitive: $250-450/day for a 40-foot catamaran in July-August. ACI marinas are well-maintained and cost €50-150/night depending on size and location. Restaurant mooring is common — tie up at a konoba (tavern) dock and eat grilled fish while your boat is secured for free. The sailing season runs May through October, with July-August being peak season and correspondingly crowded in popular harbors like Hvar and Palmizana.

Thai Islands (Andaman Sea)

Phuket to the Phi Phi Islands, Koh Lanta, Koh Lipe, and the Similan Islands — the Andaman coast is tropical sailing with dramatic limestone karst scenery. The sailing season is November through April (the southwest monsoon makes May-October rough). Distances are larger than the Mediterranean routes — Phuket to Koh Lipe is about 180 nautical miles — so most charters cover a section rather than the whole coast.

Charter costs are lower than the Mediterranean: $200-400/day for a 38-42 foot catamaran. Skippered charters are the norm here, as navigation requires local knowledge of tidal currents, reef locations, and national park entry procedures. Mooring infrastructure is less developed — you'll anchor rather than tie to a mooring ball in most locations, which requires competence with the anchor windlass and a willingness to set a proper anchor watch.

If Rent A Boat For is on your list, booking during shoulder season typically delivers the best value.

Bahamas Exumas

The Exuma Cays chain stretches 120 miles southeast from Nassau. The Exuma Cays Land and Sea Park is a no-take marine reserve with some of the clearest water in the Atlantic (visibility regularly exceeds 100 feet). Staniel Cay is the social hub — Thunderball Grotto (the James Bond cave), the swimming pigs at Big Major Cay, and the Staniel Cay Yacht Club are all here.

Nassau-based charters ($350-600/day for a catamaran) motor-sail south through the cays, anchoring in protected coves along the way. The Exumas are shallow — draft matters, and a catamaran's 3-4 foot draft is genuinely advantageous here. Sand banks, coral heads, and shifting channels require careful navigation. Polarized sunglasses are a legitimate navigation tool — they cut glare and let you read water depth by color.

Booking Platforms

Several platforms aggregate charter boat listings from fleet operators worldwide:

Repeat visitors to Rent A Boat For often say the second trip reveals layers they missed the first time.

• Sailogy: Strong Mediterranean inventory. Good filtering by boat type, crew option, and amenities. Prices include base charter fee but extras (cleaning, linen, outboard engine) are itemized separately.
• GetMyBoat: Broader than just sailing — includes motorboats, RIBs, and day charters. Useful for shorter trips and non-sailors who want a skippered day trip rather than a week-long charter.
• Navigare Yachting: Operates its own fleet rather than aggregating. Consistent quality because they maintain the boats themselves. Bases in Croatia, Greece, BVI, Thailand, and the Bahamas.
• Moorings and Sunsail: The two largest charter companies globally. Owned by the same parent company (THL Group). Extensive fleets, standardized boat condition, and worldwide bases. Prices tend to be 10-15% higher than independent operators, but the reliability and support infrastructure justify it for first-time charterers.
• Click&Boat: European-focused peer-to-peer platform. Boat owners list directly, which means more variety but less consistency in boat condition. Read reviews carefully.

Costs Breakdown

The charter fee is the headline number, but it's not the total cost. Budget for these additions:

Base Charter

Weekly rates for a 40-42 foot catamaran (the most popular charter size for groups of 6-8):

• Greece (Cyclades): $2,100-4,200/week ($300-600/day)
• Croatia: $1,750-3,150/week ($250-450/day)
• BVI: $2,800-5,600/week ($400-800/day)
• Thailand: $1,400-2,800/week ($200-400/day)
• Bahamas: $2,450-4,200/week ($350-600/day)

Additional Costs

• Skipper: $150-250/day plus you feed them (the skipper eats with the group)
• Fuel: $100-300/week depending on motoring vs. sailing ratio
• Provisioning (food and drinks): $50-100/person/day for self-catering. Budget more in expensive markets (BVI, Greece).
• Mooring and marina fees: $30-150/night when you use a marina. Free at anchor.
• Cleaning fee: $150-300 (charged at the end)
• Security deposit: $2,000-5,000 held on credit card, returned after inspection. Damage waiver insurance ($30-50/day) eliminates or reduces this.
• Linen and towels: $15-25/person if not included
• Outboard engine for dinghy: Sometimes charged separately, $50-100/week

Per-Person Math

For a group of 8 on a one-week catamaran charter in Greece (mid-range season), the all-in cost per person breaks down roughly as:

What gives Rent A Boat For an edge is the rare combination of natural beauty and straightforward logistics.

• Charter fee: $3,000 / 8 = $375
• Skipper (7 days at $200): $1,400 / 8 = $175
• Provisioning: $70/day x 7 = $490
• Fuel: $200 / 8 = $25
• Mooring (3 nights in marinas): $300 / 8 = $38
• Cleaning and extras: $400 / 8 = $50

Total: roughly $1,150/person for a week of island hopping on a private yacht. That's competitive with a mid-range resort stay, and you wake up in a different anchorage every morning.

Provisioning Tips

Stock up at the charter base before departure. Grocery options diminish at smaller islands, and what's available costs 30-50% more. In Greece, the Sklavenitis or AB Vassilopoulos supermarkets near Athens marinas are your best option. In Croatia, Konzum or Tommy markets near Split or Trogir. In the BVI, Rite Way in Road Town on Tortola.

Plan meals in advance and create a shared shopping list. Assign cooking duties by night. Breakfast and lunch are usually informal (bread, cheese, fruit, sandwich fixings), while dinners alternate between cooking aboard and eating at island restaurants. A rough split of 4 nights cooking and 3 nights eating out works well for most groups — it keeps costs manageable without turning the vacation into a floating kitchen duty roster.

Don't forget: ice (boats have fridges but they're small), trash bags (garbage disposal is limited at sea), and a good knife and cutting board if the galley kit is basic.

Group Dynamics

A week on a 42-foot boat with 6-8 people tests relationships. Some practical advice from charter veterans:

• Agree on the general itinerary before departure. "Sail every day and party every night" clashes with "anchor in quiet bays and read books." Identify mismatches early.
• Split costs transparently. Use Splitwise or a shared spreadsheet. Nothing ruins a sailing trip faster than money resentment.
• Establish a morning routine. On a boat, one person's early alarm is everyone's early alarm. Agree on quiet hours.
• Share responsibilities. Cooking, cleaning, dishes, anchor watch — rotating duties prevent one person from becoming the unpaid crew.
• Give each other space. This sounds impossible on a 42-foot boat, but it's achievable. One person reads on the trampoline while others are in the cockpit. Someone swims while others nap below. Intentional separation during downtime keeps everyone sane.