Two days in the Bahamas is short, so make it count: Day 1 goes all-in on Paradise Island’s mega-resort energy, Day 2 works Nassau on foot plus a beach or boat trip. Want more? The 3-day , 4-day , 5-day , 6-day and 7-day versions all add a real Out Island. Book these before you go: Atlantis Aquaventure day pass : dynamic pricing, book the date you actually want before it climbs A Nassau boat or snorkel excursion : the genuine Day 2 sell-out risk, especially on cruise-heavy days A Paradise Island or Cable Beach hotel : lock the beach side you want, rooms here fill fast Day Focus Rough daily spend (USD) 1 Paradise Island: Atlantis/Aquaventure or Baha Mar, Cabbage Beach $60-280 2 Downtown Nassau: Bay Street, Straw Market, Queen’s Staircase, Fort Fincastle, plus a beach or boat trip $70-150 Day 1: Paradise Island, go big or go free Land at Lynden Pindling International Airport (NAS) with just a passport, nothing else to fill out.

Three days in the Bahamas is enough to do Nassau and Paradise Island right, plus one genuinely big bucket-list day out to Exuma. Capital is Nassau, on New Providence, and you’ll clear US customs right there at the airport before you fly home, not after landing. US dollars spend everywhere at par, this is an archipelago (flights and ferries connect the islands, not roads), and prices run at premium resort levels, not budget-Caribbean ones.

Four days in the Bahamas is enough to do Nassau properly and still get two real nights out in the islands. Spend the first two days between Paradise Island and downtown Nassau, then fly out to Exuma for the swimming pigs, Thunderball Grotto, and Compass Cay’s nurse sharks by chartered boat. Capital is Nassau, on New Providence; US dollars spend everywhere at par; this is an archipelago, so island-hopping means a flight, not a rental car; and prices run at premium resort levels, not budget-Caribbean ones.

Five days in the Bahamas is enough to do Nassau properly and still get a real Out Island in: two days working Paradise Island and downtown Nassau, then three more built around Exuma’s swimming pigs, Thunderball Grotto and nurse sharks by chartered boat. This is a premium, not a budget, trip either way. Too tight? Trim back to the 2-day , 3-day or 4-day versions. Got more time? The 6-day and 7-day itineraries stretch to a second Out Island.

Six days in the Bahamas is enough to work Nassau properly and still string together two real Out Islands: two days on Paradise Island and downtown Nassau, two more built around Exuma’s swimming pigs and Thunderball Grotto, then a final two on Harbour Island’s pink sand beach. Budget honest time for the two flight/ferry hops between them, this isn’t a road trip. Shorter window? Trim to the 2-day , 3-day , 4-day or 5-day versions.

Seven days in the Bahamas is enough to string together two Out Islands instead of settling for one: two days working Nassau and Paradise Island, three more in Exuma chasing the swimming pigs, Thunderball Grotto and Compass Cay’s nurse sharks, then two on Harbour Island for the famous pink sand and Dunmore Town by golf cart. Getting between all three means flights and a ferry, not a rental car, since the Bahamas is an archipelago and nothing here connects by road.

2 Days in Anguilla: First-Timer Itinerary Two days on Anguilla is not a warm-up for a longer trip you should have booked instead, it is a genuinely complete first visit. This route puts Shoal Bay East on day one and both Meads Bay and Rendezvous Bay on day two, three beaches that keep landing on real “best in the Caribbean” lists, closed out with one proper beach-bar meal. Anguilla is a British Overseas Territory, not a slice of neighboring St Martin, even though almost every visitor arrives through Sint Maarten’s Princess Juliana Airport (SXM) and finishes the last leg by ferry.

Anguilla doesn’t try to keep you busy, and that is the entire point. This British Overseas Territory sits a short ferry ride north of St Martin but is nowhere close to being part of it, a separate country under a separate flag. Three days here nails the headline beaches, Shoal Bay East, Meads Bay and Rendezvous Bay, plus your first offshore cay, enough to feel like a full trip rather than a preview.

4 Days in Anguilla: First-Timer Itinerary Four days is the sweet spot for a first Anguilla trip: enough time for the three headline beaches AND the payoff most short trips skip entirely, an offshore cay lunch on day three and Scilly Cay’s grilled lobster at Island Harbour on day four. Anguilla is a British Overseas Territory, not a slice of neighboring St Martin, and almost everyone arrives through Sint Maarten’s Princess Juliana Airport (SXM) before finishing the last leg by ferry.

5 Days in Anguilla: First-Timer Itinerary Five days is where an Anguilla itinerary stops chasing new sights and starts protecting pace. The first four days cover the headline beaches, a first offshore cay, and Scilly Cay’s grilled lobster at Island Harbour; day five is deliberately open, a repeat visit to whichever beach won you over, plus a Little Bay snorkel if the mood strikes. Anguilla is a British Overseas Territory, not a corner of neighboring St Martin, and almost every visitor arrives through Sint Maarten’s Princess Juliana Airport (SXM) before finishing the last leg by ferry.

6 Days in Anguilla: First-Timer Itinerary Six days is enough to run Anguilla’s entire spine, then know exactly when to stop inventing new stops. Days one through five cover the headline beaches, your first offshore cay, Scilly Cay’s grilled lobster, and a full island loop by rental car, the same route the shorter trips use with room to actually enjoy it. Day six leaves Anguilla altogether for a ferry over to Sint Maarten, because by then the checklist has genuinely run dry and a change of pace beats a manufactured fourth beach.

7 Days in Anguilla: First-Timer Itinerary Seven days in Anguilla is not seven days of new sights, the island simply doesn’t have that many, and pretending otherwise turns an itinerary into filler. What seven days actually buys you is the same route a shorter trip already nails, the headline beaches, a first offshore cay, and Scilly Cay’s grilled lobster, stretched out with a St Martin day trip and a day where the whole plan is picking a beach and staying on it.

Anguilla runs on the East Caribbean dollar, pegged at a steady EC$2.70 to the US dollar, though nearly every price you’ll actually see is already quoted in USD. There’s no big airport of its own for most travelers: you land at Princess Juliana (SXM) on Sint Maarten, then finish the trip by ferry or small plane. This is a British Overseas Territory, not part of St Martin or Sint Maarten despite sitting right next to it, and it’s built on purpose to stay quiet, no cruise ships, no casinos, no high-rises, just 33 beaches and a serious food scene.

Two days will not cover the Dominican Republic, and this route will not pretend otherwise. Pick ONE base: Santo Domingo’s Zona Colonial, the oldest colonial city in the Americas, or a Punta Cana beach stay. Everyday life runs in Dominican pesos, DOP, roughly 58 to the US dollar in 2026 (check the live rate before you fly), while resorts and tours quote USD directly. Tap water is not potable anywhere. The country sits at US State Department Level 2, and driving here means sharing the road with one of the world’s highest traffic fatality rates, so stay defensive behind the wheel.

Three days is a whirlwind, but it works: one day in Santo Domingo’s Zona Colonial, one day settling into a Punta Cana beach base, one day on Isla Saona. Everyday prices run in Dominican pesos, DOP, roughly 58 to the dollar in 2026, but resorts and tour desks quote straight USD. Tap water is not potable anywhere in the country, and the US State Department rates it Level 2, the same tier as France.

Four days is the sweet spot for a first pass at Santo Domingo and Punta Cana, with an actual rest day built in. One day in the Zona Colonial, one day transferring to the coast, one day on Isla Saona, and one full beach day before you fly out. Local life prices in Dominican pesos, DOP, roughly 58 to the dollar in 2026, resorts and tours quote USD directly. The country sits at US State Department Level 2, tap water is not potable, and the roads carry one of the world’s highest traffic fatality rates, so this route keeps self-driving off the table.

Six days is enough to actually see the country instead of one corner of it: Santo Domingo’s colonial core, a Punta Cana beach base with an Isla Saona day trip, a Samana detour for whale season, and the north coast’s canyoning circuit. Local life prices in Dominican pesos, DOP, roughly 58 to the dollar in 2026, resorts and tours quote USD directly. Tap water is not potable anywhere. The country sits at US State Department Level 2, and the roads carry one of the world’s highest traffic fatality rates, so lean on coaches and transfers rather than a rental car.

Seven days is the right length for the full country arc: two unhurried days in Santo Domingo, a Punta Cana beach base with an Isla Saona day trip, a Samana detour for whale season, and a north-coast finish around Puerto Plata’s canyoning. Local life prices in Dominican pesos, DOP, roughly 58 to the dollar in 2026, resorts and tours quote USD directly. Tap water is not potable anywhere. The country sits at US State Department Level 2, and the roads carry one of the world’s highest traffic fatality rates, so this route runs on coaches and transfers, not a rental car.

Two days is Trinidad territory only, and this route says so upfront: a real Trinidad and Tobago split needs more days plus a ferry or flight, not a rushed pit stop. You spend both days around Port of Spain, paying in Trinidad and Tobago dollars (TT$1 runs roughly US$0.147), timed best for the dry season (January-May) when the steelpan and soca energy runs highest. Trinidad also carries a real Level-3 US advisory and a 2026 State of Emergency, both worth a quick check before you fly.

Three days keeps you on Trinidad too, and that’s honest math: fitting Tobago into a 3-day trip means a rushed crossing that eats a full day for barely a night on the beach. This route runs Port of Spain, Maracas Bay, and a Caroni Bird Sanctuary sunset boat tour chasing the scarlet ibis, paid in Trinidad and Tobago dollars (TT$6.8 is about US$1), best timed for the dry season (January-May). Trinidad’s Level-3 US advisory and 2026 State of Emergency are both worth checking before you fly.

Four days is the shortest trip that fairly earns both islands: three days in Trinidad (Port of Spain, Maracas Bay, Caroni’s scarlet ibis) then a crossing to Tobago’s Crown Point on Day 4, either the roughly 20-minute Caribbean Airlines air bridge or the 3.5-4 hour TTITCo ferry. Prices run in Trinidad and Tobago dollars (TT$6.8 to US$1), best in the dry season (January-May). Trinidad’s real Level-3 advisory and 2026 State of Emergency deserve a check before departure, though Tobago runs far calmer.

Five days finally gives Tobago room to breathe: the same three-day Trinidad run (Port of Spain, Maracas Bay, Caroni), a Day 4 crossing to Crown Point, then a full Day 5 on the Buccoo Reef and Nylon Pool boat tour. Everything is priced in Trinidad and Tobago dollars (TT$6.8 to US$1), best visited in the dry season (January-May), Carnival aside. Trinidad’s Level-3 advisory and 2026 State of Emergency are real and worth checking, Tobago is consistently the calmer half of the country.

Six days adds Tobago’s wild side to the beach day: the same Trinidad opening (Port of Spain, Maracas Bay, Caroni) and Buccoo Reef afternoon, then a full Day 6 renting a car for the Main Ridge Forest Reserve and Argyle Falls. Prices run in Trinidad and Tobago dollars (TT$6.8 to US$1), best in the dry season (January-May). Trinidad’s Level-3 advisory and 2026 State of Emergency are genuinely worth checking before you fly, Tobago stays noticeably calmer throughout.

A full week covers both islands properly: three Trinidad days (Port of Spain, Maracas Bay, Caroni’s scarlet ibis), then four Tobago days covering Buccoo Reef, Main Ridge Forest Reserve, Argyle Falls, and a quiet finish at Englishman’s Bay. Prices run in Trinidad and Tobago dollars (TT$6.8 to US$1), best in the dry season (January-May), or around Carnival (16-17 February 2026) if you want the country at full volume. Trinidad’s Level-3 advisory and 2026 State of Emergency are real, Tobago stays calmer throughout.