Journeys

Florida to Grenada, Five Islands

Ten nights south through the Caribbean, from the Florida Keys to Punta Cana, Antigua, Saint Lucia and Grenada.

  • 10 nights
  • Five stays
  • United States, Dominican Republic, Antigua and Barbuda, St Lucia, Grenada
  • Islands, beaches, colonial towns, rum, rainforest
Houses on a hillside by the water below the Pitons in Saint Lucia.

Two nights at each of five stops, moving south by short flights from a private island in the Keys to the spice island of Grenada. Whales in Samaná Bay, the old city of Santo Domingo and Grenada's rainforest and rum fill the days between beaches.

Length
10 nights
Pace
Five stays
Style
Islands, beaches, colonial towns, rum, rainforest
Route
Little Torch Key, Florida to Punta Cana, Dominican Republic to Antigua to Saint Lucia to St George's, Grenada
  1. Little Torch Key, FloridaTwo nights
  2. Punta Cana, Dominican RepublicTwo nights
  3. AntiguaTwo nights
  4. Saint LuciaTwo nights
  5. St George's, GrenadaTwo nights
An aerial view of the small wooded island ringed by shallow turquoise water and a jetty.
Photo: Little Palm Island

01

Days 1 to 3 · two nights

Little Torch Key, Florida

Start in the Lower Florida Keys, crossing by boat to a private island for two quiet nights of kayaking, paddleboarding and reef trips to Looe Key.

Where you stay

Little Palm Island

Little Palm Island is a small private island in the Lower Florida Keys, reached only by boat or seaplane, and is for adults only. It has 30 thatched-roof bungalow suites with no televisions or telephones, a spa, a pool and an oceanfront dining room.

A white beach and turquoise sea at Punta Cana under a blue sky.
Photo: Miltiadis Fragkidis / Unsplash

02

Days 3 to 5 · two nights

Punta Cana, Dominican Republic

A flight of about two hours brings you to Cap Cana. From mid-January to late March, humpback whales gather in Samaná Bay. Parque Nacional del Este covers more than 420 square kilometres of forest and empty beaches, some reached by small boat, and Santo Domingo keeps the first city the Spanish founded in the Americas, a UNESCO site. On the road, La Aurora in Santiago de los Caballeros, founded in 1903, is the country's oldest cigar factory.

Where you stay

Eden Roc Cap Cana

Eden Roc stands in Cap Cana at the eastern tip of the Dominican Republic, with a private sandy cove and beach club. Its 68 suites, bungalows and villas share lagoon-style pools, a spa, several restaurants and the Jack Nicklaus course at Punta Espada.

A curved white-sand beach lined with palms and thatched umbrellas, turquoise water and a jetty, green hills behind.
Photo: Curtain Bluff Resort

03

Days 5 to 7 · two nights

Antigua

About an hour and a half by air takes you to Antigua's south coast for two nights by the sea, with water sports, tennis and diving close at hand.

Where you stay

Curtain Bluff Resort

Curtain Bluff sits on a rocky promontory on Antigua's south coast, between two beaches. It has 72 rooms and suites, some on the beach and some with plunge pools, four tennis courts, a spa and a kids' camp, and all meals and nearly all activities are included.

The beach on Smugglers Cove below the hotel, white sand between green headlands and clear water.
Photo: Cap Maison

04

Days 7 to 9 · two nights

Saint Lucia

A 40-minute flight lands you in Saint Lucia for two nights in the north of the island, at Cap Estate, with dinners above the sea and on the sand at Smugglers Cove.

Where you stay

Cap Maison Resort & Spa

Cap Maison is built in Spanish-Mediterranean style among gardens at Smugglers Cove, Cap Estate, on Saint Lucia's north coast. It has suites and villas, some with their own pools, a spa, a clifftop restaurant serving French-Caribbean cooking and a beach grill on the cove.

An infinity pool lit at dusk, a pavilion and palms against a pink sky.
Photo: Calabash Hotel

05

Days 9 to 11 · two nights

St George's, Grenada

End in Grenada for two nights. Explore St George's, a colourful horseshoe-shaped harbour town founded in 1650, snorkel over the underwater sculptures at Molinière Point, set out in 2006 and slowly turning to reef, taste rum at River Antoine, a distillery of 1785 about an hour's drive away, and walk in Grand Étang National Park, with its crater lake and the Annandale Falls nearby.

Where you stay

Calabash Hotel

Calabash is a family-run hotel on the sheltered beach of L'Anse aux Epines on Grenada's south coast. Its 36 suites are spread through a garden that opens onto the beach, and it has a pool, a spa and three restaurants, including Rhodes.

Ways to make it yours

This is a sample. The hotels, the pace and the order are where we start, not where we finish: every journey is designed around the people taking it.

Made around you

Most travel is bought. This is designed.

Before anything is booked, we talk: who is travelling, how you like to spend a morning, and the hotel preferences below the obvious, from the kind of bath you like to the time you wake and how much daylight you need in a room. You see options where options matter and clean recommendations where they don't.

The same person remains your point of contact from the first reply to the trip after next. No handovers. No team.

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Aerial view of a palm-lined beach curving beside shallow turquoise water.

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