31 days in Caribbean Itinerary

31 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

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Make it your trip
1
Pointe-a-Pitre, Guadeloupe
— 6 nights
Fly to V.C. Bird International Airport, Drive to English Harbour
2
English Harbour, Antigua and Barbuda
— 5 nights
Fly
3
Basseterre, St. Kitts and Nevis
— 6 nights
+2
Fly to St Maarten, Drive to Simpson Bay, Ferry to Gustavia
4
Gustavia, St. Barthelemy
— 5 nights
Ferry
5
Philipsburg, St. Maarten-St. Martin
— 8 nights

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Pointe-a-Pitre, Guadeloupe

— 6 nights
Pointe-à-Pitre is the largest city of Guadeloupe, an overseas région and département of France located in the Lesser Antilles, of which it is a sous-préfecture, being the seat of the Arrondissement of Pointe-à-Pitre.Although Pointe-à-Pitre is not Guadeloupe's administrative capital (that distinction goes to Basse-Terre), it is nonetheless the region's largest city and economic capital. Explore the numerous day-trip ideas around Pointe-a-Pitre: Ranch de Moreau (in Goyave), Sainte Rose (Regy Balade, Scuba & Snorkeling, &more) and Pointe de la Grande Vigie (in Anse-Bertrand). Next up on the itinerary: get engrossed in the history at Memorial Acte, indulge your thirst for a good beer at Les Bieres de la Lezarde, get outside with Grand Cul-de-Sac Marin, and admire the sheer force of Cascade aux Ecrevisses.

For more things to do, where to stay, photos, and tourist information, read our Pointe-a-Pitre online trip maker.

If you are flying in from Brazil, the closest major aiport is Pointe-à-Pitre Le Raizet. In May in Pointe-a-Pitre, expect temperatures between 36°C during the day and 27°C at night. Finish up your sightseeing early on the 7th (Fri) so you can travel to English Harbour.

Things to do in Pointe-a-Pitre

Outdoors · Parks · Nature · Museums

Side Trips

Find places to stay Apr 30 — May 7:

English Harbour, Antigua and Barbuda

— 5 nights
Venture out of the city with trips to Devil's Bridge (in Willikies) and Galley Bay Beach (in St. John's). Spend the 9th (Sun) exploring nature at Nelson's Dockyard.

To see photos, more things to do, reviews, and tourist information, you can read our English Harbour attractions website.

Explore your travel options from Pointe-a-Pitre to English Harbour with the Route module. In May in English Harbour, expect temperatures between 34°C during the day and 28°C at night. Cap off your sightseeing on the 12th (Wed) early enough to catch the flight to Basseterre.

Things to do in English Harbour

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay May 7 — 12:

Basseterre, St. Kitts and Nevis

— 6 nights
Change things up with these side-trips from Basseterre: Nevis (Nevis Peak Hike & Oualie Beach).

To find maps, reviews, more things to do, and more tourist information, go to the Basseterre holiday maker website.

You can fly from English Harbour to Basseterre in 2.5 hours. In May in Basseterre, expect temperatures between 35°C during the day and 28°C at night. Finish your sightseeing early on the 18th (Tue) to allow enough time to travel to Gustavia.

Things to do in Basseterre

Parks · Outdoors · Nature · Beaches

Side Trips

Find places to stay May 12 — 18:

Gustavia, St. Barthelemy

— 5 nights
Gustavia is known for parks, wildlife, and shopping. Your trip includes some of its best attractions: stroll through Colombier Beach, get a taste of the local shopping with Sea Spice, enjoy the sand and surf at Anse des Flamands, and discover the deep blue sea with a scuba or snorkeling tour.

For reviews, other places to visit, where to stay, and more tourist information, read Gustavia trip itinerary planning website.

Traveling by combination of flight, car, and ferry from Basseterre to Gustavia takes 4.5 hours. Alternatively, you can fly. Wrap up your sightseeing on the 23rd (Sun) early enough to ride a ferry to Philipsburg.

Things to do in Gustavia

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay May 18 — 23:

Philipsburg, St. Maarten-St. Martin

— 8 nights
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
When in Philipsburg, make a side trip to see Cupecoy Bay Beach in Cupecoy Bay, approximately Cupecoy Bay away. Next up on the itinerary: race across the water with a speed boat tour, see the interesting displays at Yoda Guy Movie Exhibit, don't miss a visit to Frontstreet, and enjoy the sand and surf at Maho Beach.

To see traveler tips, reviews, maps, and tourist information, use the Philipsburg trip planner.

Traveling by ferry from Gustavia to Philipsburg takes 2 hours. Alternatively, you can fly. In May, plan for daily highs up to 34°C, and evening lows to 29°C.

Things to do in Philipsburg

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay May 23 — 31:

Antigua travel guide

4.2
Scuba & Snorkeling · Beaches · Lookouts
A true tropical getaway, Antigua attracts travelers from all over the world with its innumerable beaches, coves, and bays. Although an important cruise ship destination with upscale resorts and facilities, Antigua doesn't lack tranquility. With picturesque and secluded stretches of sand and sleepy villages waiting at every corner, a vacation in Antigua is the perfect opportunity to lounge on the waterfront, enjoy swimming and snorkeling, and indulge in delicious seafood.