Orca
The Leeward Loop
01 · Leewards · 7 nights

The Leeward Loop

Short hops between the most polished islands in the Caribbean. Six anchorages, five swim stops, and the best kitchens on the circuit.

Best season · December – April

The Chart
  1. 01St Barths
  2. 02Anguilla
  3. 03St Martin
  4. 04Saba
  5. 05St Kitts
  6. 06Nevis
Signature Moments
  • Shell Beach sundowners, Gustavia
  • Sandy Ground langoustines, Anguilla
  • Dive the Saba Wall, 2,000 ft of vertical reef
  • Pinney's Beach horseback ride at sunrise, Nevis
Day by Day
  1. 01
    Port de Gustavia, St Barths

    Embark · Gustavia

    Morning
    Met at St Jean airport, tendered aboard Orca by 1400.
    Afternoon
    Welcome canapés, safety brief, a lazy swim off Shell Beach.
    Evening
    Aperitifs on the bow terrace; first dinner at Bonito overlooking Gustavia harbour, light Provençal with a Caribbean accent.
  2. 02
    Anse de Colombier, St Barths

    Colombier & the North Coast

    Morning
    Short hop to Colombier — reachable only by boat or footpath. Seabobs out at 1030, snorkel the reef at the north headland.
    Afternoon
    Private lunch on the aft deck — local yellowtail crudo, chilled rosé, a long drift swim.
    Evening
    Tender into Gustavia for cocktails at Le Guanahani's rebuilt bar; simple dinner at Eddy's.
  3. 03
    Road Bay, Anguilla

    St Barths → Anguilla

    Morning
    Early departure at 0700. 4-hour crossing, breakfast underway. Clear in at Road Bay by noon.
    Afternoon
    Lunch at Veya — chef Carrie Bogar's West Indian tasting. Nap. Paddle into the mangroves at Little Bay.
    Evening
    Blanchards beach table at sunset; langouste and sea-urchin butter. Back aboard for a nightcap under the stars.
  4. 04
    Sandy Island / Shoal Bay East

    Sandy Island & Shoal Bay

    Morning
    Tender to Sandy Island — a sandbar with one beach bar. Jetski run down the north coast.
    Afternoon
    Orca repositions to Shoal Bay East while guests lunch at Shoal Bay Scilly Cay (a 40-ft cay the owner built by hand).
    Evening
    Chef's dinner aboard: lobster tagliatelle, passionfruit soufflé. Cognac on the flybridge.
  5. 05
    Ladder Bay, Saba

    Anguilla → Saba

    Morning
    Dawn departure, 7-hour passage south. Deep water, following seas; sightings of pilot whales common in January.
    Afternoon
    Arrive Saba. Dive the Pinnacle — a submerged seamount rising from 800 ft to 80 ft. Crew rig tanks off the swim platform.
    Evening
    Quiet dinner at anchor. Saba is empty at night — no beaches, no bars, just the sound of the reef.
  6. 06
    Pinney's Beach, Nevis

    Saba → Nevis

    Morning
    Late-morning passage to Nevis (4 hours). Lunch underway — grilled mahi, papaya salsa.
    Afternoon
    Tender in to Pinney's. Horseback ride through the hills at golden hour, arranged by the crew.
    Evening
    Sunset Bar at Nisbet Plantation; moonlit swim back at Orca.
  7. 07
    Basseterre, St Kitts

    Nevis → St Kitts · Disembark

    Morning
    Short 90-min crossing back to St Kitts. Full breakfast on the flybridge.
    Afternoon
    Farewell lunch aboard; luggage sent ahead to airport. Crew arranges tender and transfers.
    Evening
    Guests depart from Robert L. Bradshaw by 1600.
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