Caribbean Holiday – Which One to Choose?

Sep

Caribbean Holiday – Which One to Choose?

The Caribbean isn’t just one holiday – it’s dozens of different worlds. From bustling resorts in the Dominican Republic to the peaceful lagoons of the San Blas Islands in Panama. To choose the right Caribbean getaway, consider three things: (1) when you’re traveling, (2) what kind of stay you’re looking for (hotel, cruise ship, private yacht…), and (3) how much time you want to spend in nature versus cities. Below you’ll find a comparison of destinations and holiday types, plus smart tips on how to put it all together.

Where in the Caribbean: Overview of Key Regions

Bahamas & Turks and Caicos – Iconic white beaches and turquoise waters straight out of a postcard. Best from December to April. In summer and autumn, there’s a higher hurricane risk; some islands are more expensive for accommodation and transfers.

Greater Antilles (Dominican Republic, Jamaica, Cuba, Puerto Rico) – The most accommodation options and great package deals. DR = all-inclusive resorts and long beaches; Jamaica = music, excursions, waterfalls; Cuba = history and atmosphere. More crowds during peak season, and longer travel distances.

Northern Lesser Antilles (Antigua, St. Martin, Anguilla, St. Barth, Guadeloupe/Martinique) – Beautiful beaches, great cuisine, and French flair on Guadeloupe/Martinique (EU territory). For sailing lovers, it’s a “playground” of nearby islands.

Windward Islands (Barbados, Saint Lucia, Saint Vincent & the Grenadines, Grenada) – Lush mountains, dramatic scenery (the Pitons in Saint Lucia), great snorkeling, and island-hopping sailing (Grenadines). In summer and autumn, a higher chance of hurricanes.

Southern Caribbean – ABC Islands (Aruba, Bonaire, Curaçao) – Outside the main hurricane belt, a very stable year-round choice. Bonaire offers diving and kitesurfing; Aruba and Curaçao have more infrastructure and restaurants.

Central America – Caribbean Side (Belize, Panama) – Belize: the world’s second-largest barrier reef and the idyllic “cayes”. Panama – San Blas (Guna Yala): hundreds of tiny islands with minimal tourism, outside the hurricane zone, and home to the authentic Guna culture. Ideal for peace and nature lovers.

What Type of Holiday Do You Want

1) All‑inclusive resort

– Pros: “no worries,” kids’ clubs, pools. Advantages: easy planning, consistent standards, often great deals. Drawbacks: limited contact with nature outside the resort, crowds in high season; excursions are often short and organized.

2) Cruise Ship

– Pros: a quick “taste” of several islands. Advantages: great onboard facilities, no need to pack and unpack. Drawbacks: short port stops, extra charges (drinks, excursions), less authenticity.

3) Boutique hotel / eco‑lodge

For: couples and small groups seeking design and tranquility. Pros: personal service, sense of place, connection with nature. Cons: limited capacity, higher price, experience tied to one location.

4) Private Yacht with Experienced Crew (Panama, San Blas)

For: those who want privacy, freedom of route, and closeness to nature.
Pros: sleep where you like (anchored by corals or in quiet lagoons), plan your own program (snorkeling, paddleboarding, visiting Guna communities). Comfort like home: our 19m Hanse 630e has a generator, watermaker, air conditioning, and Starlink; the crew has a separate cabin with private access. The Yacht • What the Cruise Looks Like.

Seasonality and Weather (in short)

December–April: best weather for most of the Caribbean (dry season), also the highest prices.
May–November: more rain and a hurricane risk in the eastern Caribbean (June–November).
Stable year-round: Panama – San Blas and the ABC islands lie outside the main hurricane belt.

How to Choose a Destination by Style

White beaches & easy comfort: DR (Punta Cana), Barbados, Aruba.
Nature & dramatic scenery: Saint Lucia, Grenada, Guadeloupe.
Diving & snorkeling: Bonaire, Turks & Caicos, Belize (reef), San Blas (corals and lagoons).
Sailing & “island-hopping”: Antigua, Grenadines, San Blas.
Off the beaten path & authentic: San Blas (Panama), some Belize “cayes,” smaller Grenadine islands.

Sample Itineraries (7–10 Nights)

Resort (DR/Barbados): 7 nights by the beach, 1–2 paid excursions (island, waterfalls, catamaran). Relaxed but fewer “wow” moments outside the resort.
Cruise (from Miami/Barbados): 7 nights, 4–5 stops, quick island experiences, back on board every evening.
Boutique Hotel (Saint Lucia): 5 nights in the mountains + 3 nights by the beach, trips to the Pitons, snorkeling; romantic, but more logistics.
Private Yacht (Panama, San Blas): 7 nights – lagoons, snorkeling, paddleboarding, Guna visits; no crowds, fully personalized itinerary. What’s Included.

How to Get There

To “classic” islands (Barbados, Saint Lucia, Aruba…) fly via European hubs (AMS, CDG, LGW) or the USA.
To Panama (PTY): conveniently with Condor via Frankfurt – our sailing dates are synchronized with this connection for smooth timing. For more details, see the article “How to Fly to Panama” and the section Travel Information.