Two days in The Bahamas means Nassau and Paradise Island, full stop. Any itinerary that also tries to fit an Exuma pig tour or a Harbour Island overnight into that window is selling a rushed, expensive mess, the flight or ferry alone eats half a day this archipelago doesn’t give you. The real decision here is smaller and cheaper than the marketing suggests: skip the $195-260 Atlantis day pass if a water slide isn’t the point of your trip, since Cabbage Beach right next door is public and free.

The Bahamas is Nassau plus roughly 700 other islands you will not see in three days, and the real tourist trap isn’t a straw-market stall, it’s the operator who sells you an Exuma overnight when you don’t have the days for it. Three days means Nassau and Paradise Island done properly, with one full day given up entirely to a single ambitious trip out to the swimming pigs. US dollars work everywhere at par, so skip the currency exchange counter.

Four days is the point where a Bahamas trip stops being a resort weekend and starts being an actual island trip, if you use the extra day for a real overnight in the Exumas instead of another half-day on Cabbage Beach. Two days cover Nassau and Paradise Island properly, then you fly out to George Town, Great Exuma, for two nights built around the swimming pigs, Thunderball Grotto and the Compass Cay nurse sharks.

Five days is the point where The Bahamas stops being a resort weekend and starts being an actual island trip: two days in Nassau and Paradise Island, then three days based out on Exuma instead of a rushed day tour stitched onto the end. Bring a passport, not currency to exchange, the Bahamian dollar is pegged 1 to 1 to the US dollar and both spend everywhere at full face value.

Six days buys you Nassau plus two real Out Islands, Exuma and Harbour Island, but only if you accept that getting between them costs real time, not just money. This is The Bahamas: capital Nassau, an Atlantic archipelago where nothing connects by road, every inter-island hop is a flight or a ferry. The Bahamian dollar is pegged 1 to 1 to the US dollar, so bring a passport, not currency to exchange.

Seven days is the first length in this cluster honest enough to hold two Out Islands, and the honest version of that plan spends real hours on flights and connections getting between them, not just standing on them once you land. Two days cover Nassau and Paradise Island, three days move to Exuma for the swimming pigs, Thunderball Grotto and Compass Cay’s nurse sharks, and the last two land on Harbour Island for the pink sand and a Glass Window Bridge day trip.

Two days on Anguilla is not a rushed preview of a longer trip, it is the right amount of time to do three beaches and one proper beach-bar meal well: Shoal Bay East, Meads Bay, and Rendezvous Bay. Anguilla is a British Overseas Territory, not a district of neighboring St Martin, even though every visitor arrives through Sint Maarten’s Princess Juliana Airport (SXM) and crosses by ferry. That contrast, a quiet British island next to a livelier French-Dutch one, is worth understanding before you land.

Three days in Anguilla means two beach days and one cay day, not three beach days. Shoal Bay East and Rendezvous Bay already earn their “world’s best beach” rankings; a third or fourth beach afternoon on top of those doesn’t add much, but a morning on Sandy Island or Prickly Pear does. Anguilla is a British Overseas Territory, not a quieter corner of St Martin next door, even though most flights route through Sint Maarten’s SXM airport first.

Anguilla runs on East Caribbean dollars pegged at EC$2.70 to the US dollar, but almost nothing here is EC$2.70 cheap. It’s a British Overseas Territory built deliberately around no cruise ships, no casinos, no high rises, and it is not part of St Martin even though nearly everyone flies into Sint Maarten first and takes the ferry across. Four days is enough for the two beaches that genuinely earn the hype, one offshore cay, and Scilly Cay’s grilled lobster, without inventing a fourth “must-see” the island simply doesn’t have.

Anguilla runs on the East Caribbean dollar, pegged at EC$2.70 to the US dollar since 1976, but almost every price you’ll see quoted is already in USD, and that price runs higher than you’d expect. No cruise ships, no casinos, no high-rise hotels, that’s deliberate policy, not an accident of underdevelopment, and it’s why this British Overseas Territory (its own jurisdiction, not a satellite of St Martin/Sint Maarten next door) reads as upscale rather than cheap.

Anguilla runs on the East Caribbean dollar, pegged at EC$2.70 to the US dollar since 1976, but nearly every price a visitor actually sees is quoted straight in USD, and it runs higher than the peg alone would suggest. This is a British Overseas Territory, its own jurisdiction, not a satellite of St Martin/Sint Maarten next door, even though almost everyone flies into Sint Maarten first and ferries across. Six days covers the full spine of beaches and cays a 33-beach island genuinely has, plus one day that isn’t about Anguilla at all: a Sint Maarten ferry day, because by day 6 the checklist has run dry.

Book seven days in Anguilla expecting seven days of new sights and you’ll be disappointed by day 5. Here’s the honest heads-up: the island runs on roughly 33 beaches, two boat-out cays, one wave-down lobster shack, and a 45-minute island loop, and that’s genuinely the whole inventory. A week here works if what you actually want is pace, slower mornings, a repeat afternoon at whichever beach won on day 2, plus a St Martin day trip for a change of scene, not a longer list of must-sees the island was never going to produce.

Two days in the Dominican Republic gets you one base, not a country, and anyone pitching Santo Domingo and Punta Cana both in 48 hours is selling you a transfer day dressed up as a vacation, since the two sit 2 to 4 hours apart by road. Price things in Dominican pesos (DOP), running roughly 58 to 59 to the US dollar in mid-2026 (check the same-day rate; resorts and tours quote heavily in USD, but the peso is the real currency, not “the Dominican dollar”).

Three days buys two full days in Santo Domingo plus one honest beach day in Punta Cana, and that is the whole trip; Isla Saona needs its own day, so do not expect it to fit here. Price things in Dominican pesos (DOP, roughly 58 to 59 per US dollar in mid-2026, verify the same-day rate) rather than assuming the US dollar is the currency, it is only what resorts and tour desks quote in.

Four days is the shortest trip where Isla Saona actually makes sense, two days in Santo Domingo, one Punta Cana beach day, then a full day for Saona itself rather than squeezing it into an afternoon. Price things in Dominican pesos (DOP, roughly 58 to 59 per US dollar in mid-2026, verify same-day) since the peso, not the US dollar, is the actual currency, even though resorts and tour desks quote heavily in USD.

Five days adds Samana onto the Santo Domingo and Punta Cana base, and Samana is the day that separates a real country trip from an all-inclusive week: El Limon waterfall and Los Haitises National Park run year round, and humpback whales gather in Samana Bay only from mid-January through late March, so the extra day is not automatically a whale-watching day. Price things in Dominican pesos (DOP, roughly 58 to 59 per US dollar in mid-2026, verify same-day) rather than assuming USD is the currency; it is only what tourism quotes in.

Six days pushes this route on to Puerto Plata and Cabarete after Santo Domingo, Punta Cana, Isla Saona, and Samana, and the north coast is where the country stops looking like a resort brochure: kitesurfing, a real town instead of a resort strip, and a genuinely different identity from the east coast. Price things in Dominican pesos (DOP, roughly 58 to 59 per US dollar in mid-2026, verify same-day). The Dominican Republic has one of the world’s highest road-traffic fatality rates, roughly 65 to 67 per 100,000 people, worth knowing before you decide how you are covering these transfers.

Seven days is the length this route actually needs: Santo Domingo, Punta Cana and Isla Saona, Samana, then Puerto Plata and Cabarete, and it is still a brisk pace, not a lazy one, because the Dominican Republic is bigger and slower to cross than the map implies. Price things in Dominican pesos (DOP, roughly 58 to 59 per US dollar in mid-2026, verify same-day) rather than assuming the US dollar is the currency; it is only what resorts and tour desks quote in.

Trinidad and Tobago is one country split across two very different islands, and two days only covers one of them. Trinidad is the big, industrial, Carnival-mad half, home to the capital Port of Spain, sitting roughly 11km off Venezuela on the South American continental shelf, not on the volcanic island-arc most of the Eastern Caribbean sits on. This plan stays on Trinidad: Port of Spain’s food and culture, then Maracas Bay for the beach and the bake and shark.

Trinidad and Tobago is one country split across two very different islands, and three days still only covers one of them properly. Trinidad is the big, industrial, Carnival-mad half, home to the capital Port of Spain, sitting roughly 11km off Venezuela on the South American continental shelf, not on the volcanic island-arc most of the Eastern Caribbean sits on. Everything here prices in TT dollars, roughly 6.8 to the US dollar, not the Eastern Caribbean dollar most neighboring islands use.

Trinidad and Tobago is one country, not one island. Trinidad is the big, industrial, Carnival-mad half, home to the capital Port of Spain, sitting roughly 11km off Venezuela on the South American continental shelf rather than the volcanic island-arc most of the Eastern Caribbean sits on; that’s also why the country lies largely outside the main Atlantic hurricane belt. Tobago is the small, calm reef half, a 20 minute flight or a 3.

Trinidad and Tobago is one country, not one island. Trinidad is the big, industrial, Carnival-mad half, home to the capital Port of Spain, sitting roughly 11km off Venezuela on the South American continental shelf rather than the volcanic island-arc most of the Eastern Caribbean sits on; that’s also why the country lies largely outside the main Atlantic hurricane belt. Tobago is the small, calm reef half, a 20 minute flight or a 3.

Trinidad and Tobago is one country, not one island. Trinidad is the big, industrial, Carnival-mad half, home to the capital Port of Spain, sitting roughly 11km off Venezuela on the South American continental shelf rather than the volcanic island-arc most of the Eastern Caribbean sits on; that’s also why the country lies largely outside the main Atlantic hurricane belt. Tobago is the small, calm reef half, a 20 minute flight or a 3.

Trinidad and Tobago is one country, not one island, and a week is the minimum for doing both properly. Trinidad is the big, industrial, Carnival-mad half, home to the capital Port of Spain, sitting roughly 11km off Venezuela on the South American continental shelf rather than the volcanic island-arc most of the Eastern Caribbean sits on; that’s also why the country lies largely outside the main Atlantic hurricane belt. Tobago is the small, calm reef half, a 20 minute flight or a 3.