The Caribbean has tempted travelers for centuries—sailors chasing trade winds, poets chasing light. January is peak dry season, which means dependable sun, calm seas, and rainforest scents carried on the breeze. You’ll embark from two classic non‑US homeports—Bridgetown (Barbados) and Philipsburg (St. Maarten)—to sample the Windward and Leeward Islands on a laid‑back 14‑day cruise plan.

Barbados brings British‑Caribbean history, a UNESCO‑listed Garrison, and beaches as pale as sugar. St. Maarten blends Dutch harbors and French bistros, with easy hops to nearby islands. At each stop, swap between reef snorkeling, volcanic hikes, and markets rich with spices and cocoa.

Practical notes: January seas are usually gentle, but pack motion bands if you’re wave‑sensitive. Barbados uses BBD (pegged to USD); St. Maarten widely accepts USD (and EUR on the French side). Driving is on the left in Barbados, right in St. Maarten. Book flights early for better winter fares; consider arriving a day before sailing to buffer any delays.

Bridgetown (Barbados)

Barbados’ capital marries colonial streets and coral-sand coves. Stroll the Careenage, explore 17th‑century fortifications at the Garrison Savannah, then slide into Carlisle Bay’s gin‑clear water. It’s the homeland of rum—tasting rooms and distilleries trace centuries of craftsmanship.

Days 1–3: Pre‑Cruise Barbados Stay and Embarkation

• Where to stay (pre‑cruise, beach access + easy port transfer): Search vacation rentals near Carlisle Bay, Hastings, or Worthing on VRBO Bridgetown or compare hotels on Hotels.com Bridgetown.
• How to get there: Fly into BGI (Barbados). Check fares on Trip.com flights or Kiwi.com. From London: ~8.5–9 h nonstop; Toronto: ~5.5 h; NYC area: ~4.5–5 h. Typical January economy fares bookable months out: ~$650–$1,050. Taxi to Carlisle Bay: ~25 minutes, ~$20–30.
• Top things to do before you sail:
  • Carlisle Bay swim and snorkel over shipwrecks; look for turtles in the seagrass.
  • Garrison Historic Area walk—George Washington House, cannons, and horse racing at the Savannah when in season.
  • Rum heritage: Foursquare Rum Distillery (award‑winning) offers tastings; book a driver for the ~35–45 min ride.
  • Sunset at Pebbles Beach; grab a fish cutter from the beloved Cuz’s stand nearby.
• Eat & drink (local flavor):
  • Breakfast: Bliss Café (St. Lawrence Gap) for Bajan bakes, pancakes, and strong espresso; ArtSplash Café (Hastings Boardwalk) for smoothie bowls and “bake & saltfish.”
  • Lunch: Cuz’s Fish Shack at Pebbles Beach—order a mahi‑mahi cutter with pepper sauce; Fisherman’s fare at Oistins (go midday if you’ll miss Friday Night Fish Fry).
  • Dinner: Champers (Worthing) for seafood with cliff‑edge views; Naru (Worthing) for sushi with Caribbean twists; The Tides (Holetown) for a refined oceanfront meal in a coral‑stone house.
  • After dark: Try a rum punch made with fresh nutmeg; Bajan soca often soundtracks waterfront bars on weekends.
• Embarkation morning: Arrive at the Bridgetown Cruise Terminal early; keep passports, printed cruise docs, and any e‑visas handy. Liquids rules apply at security; carry meds and a swimsuit in your day bag in case your luggage arrives later to your cabin.

Days 4–7: Windward Islands Ports (typical calls)

Ships from Barbados often loop the southern arc of the Eastern Caribbean. Your exact route depends on the line, but these ports are winter mainstays:

• Castries, St. Lucia: Take a coastal catamaran toward the Pitons; or hike Tet Paul Nature Trail for big views in under an hour. Lunch on green fig & saltfish; cap with local cocoa tea.
• St. George’s, Grenada: Wander the horseshoe harbor and climb to Fort George. At Grand Anse, swim then try oil‑down (breadfruit stew) and nutmeg ice cream.
• Fort‑de‑France, Martinique: French Caribbean vibes—markets selling Colombo spices. Consider a rum distillery tour or a beach day at Les Anses‑d’Arlet with snorkel‑friendly reefs.
• Roseau, Dominica: The “Nature Island”—tub along the Layou River, or chase waterfalls like Trafalgar Falls and Emerald Pool. Try mountain chicken (frog legs) if you’re adventurous, or fresh passionfruit juice.

Back on board, enjoy sea‑day rituals: sunrise coffee on deck, steel‑pan by the pool, and stargazing far from city lights.

Philipsburg (St. Maarten)

Half Dutch, half French, fully beachy—St. Maarten is a glorious blend of café culture and Caribbean color. Philipsburg’s boardwalk faces a sapphire bay, while the French side brings boulangeries and Grand Case’s fine dining scene.

Travel Day: Fly Bridgetown → St. Maarten (mid‑itinerary reposition)

• Morning flight: BGI → SXM nonstop is typically ~1 h 55 m (occasionally via Antigua). Expect ~$150–$280 one‑way in January if booked early. Compare on Trip.com flights or Kiwi.com. If you’re flying to/from Europe at either end of the trip, also check Omio flights.
• Transfers: SXM to Philipsburg is ~20–25 minutes by taxi; to Simpson Bay ~10–15 minutes.

Days 8–10: Philipsburg Stay and Second Embarkation

• Where to stay: For beach‑boardwalk convenience, base near Great Bay in Philipsburg or in Simpson Bay for more dining choices. Browse VRBO Philipsburg and Hotels.com Philipsburg.
• What to do ashore:
  • Rainforest Adventures at Rockland Estate: ride the Sky Explorer and, if you’re brave, the “Flying Dutchman” zip line with sweeping island views.
  • Maho Beach plane‑spotting: be there when jumbo jets skim the sand for a spectacular photo, then grab a drink at the beach bar.
  • Front Street and Old Street for jewelry and guavaberry liqueur; Fort Amsterdam for breezy bay views.
  • Ferry/day-trip ideas (time permitting): Pinel Island for shallow turquoise water and grilled crayfish; Grand Case for French bistros.
• Eat & drink:
  • Breakfast: Zee Best (Simpson Bay) for croissants and crepes; in Philipsburg, Coffee Lounge for espresso drinks and pastries.
  • Lunch: The Greenhouse on the Boardwalk for fish tacos and cold Caribs; Karakter (Simpson Bay Beach) for beach‑loungers and tapas.
  • Dinner: Emilio’s (historic sugar mill) for Caribbean‑Dutch dishes and a serious wine list; in Grand Case, Bistrot Caraibes for lobster thermidor and French classics.
  • Nightcap: Sunset Bar & Grill at Maho for golden hour; or a quiet rum on the Philipsburg boardwalk under the trade‑wind breeze.
• Second embarkation: Many winter itineraries sail round‑trip from Philipsburg—get to the cruise terminal early with printed boarding docs. Keep swimsuits and sunscreen in your day bag to hit the pool right away.

Days 11–14: Leeward Islands Ports (typical calls)

From St. Maarten, expect a northern loop with compact hops and striking variety:

• Basseterre, St. Kitts: Ride the scenic railway through old sugar estates, or head to Shipwreck Beach for volcanic‑sand lounging and green vervet monkey sightings.
• St. John’s, Antigua: “365 beaches”—pick one near Dickenson Bay or Pigeon Point. Don’t miss the views and steel‑band vibes at Shirley Heights Lookout if your timing aligns.
• Road Town, Tortola (BVI): Snorkel the Indians and Norman Island caves; on island, Cane Garden Bay offers mellow surf and rum shacks.
• Gustavia, St. Barts: Chic cafés, designer boutiques, and small coves like Shell Beach. Order a tartare and a glass of Sancerre, then watch the yacht ballet in the harbor.

Disembark in Philipsburg; if flying home same day, aim for afternoon departures to cushion customs and port traffic.

Getting in/out Flight Tips

• Outbound to Barbados: Compare fares and routes on Trip.com flights or Kiwi.com; if starting in Europe, also check Omio flights.
• Return from St. Maarten: Afternoon departures are plentiful in high season; look again at Trip.com flights, Kiwi.com, and, for trans‑Europe routes, Omio flights.

Coffee, Breakfast, Lunch, Dinner—Quick Picks by Port Day

• Bridgetown area: Bliss Café (breakfast), ArtSplash Café (coffee + light bites), Cuz’s Fish Shack (lunch), Champers or Naru (dinner).
• Philipsburg area: Coffee Lounge (espresso), Zee Best (pastries), The Greenhouse or Karakter (lunch), Emilio’s or Bistrot Caraibes (dinner).

Optional Add‑On If Your Flights Route via New England: Portsmouth (1 Day)

If your journey home connects through Boston, consider a day in Portsmouth, New Hampshire—an artsy harbor town with bike paths and historic architecture. Here are a few engaging activities:

• Public | Small Group | Islands & Harbor Sightseeing Tour 2-2.5hr — storytelling and waterfront views by bike.

  

• Self-Guided Portsmouth Scavenger Hunt: Pretty Portsmouth — an app‑led hunt that threads together landmarks and hidden corners.

  

• Historical Tastings at the Iconic Rockingham — sample regional flavors in a storied setting.

  

Two weeks, two classic Caribbean homeports, and a constellation of islands strung across sapphire water—that’s January at its best. With smart pre/post stays, great meals, and flexible shore days, this itinerary balances ease and discovery while keeping your departures firmly outside the US.