21 days in Caribbean Itinerary

21 days in Caribbean Itinerary

Created using Inspirock Caribbean itinerary planner

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Route & dates

Start: Sydney, Australia
Fly:  27 h
1
San Juan, Puerto Rico
— 2 nights
Fly:  3 h
2
St. Eustatius, St. Eustatius
— 3 nights
Fly:  15 min
3
Windwardside, Saba
— 4 nights
Fly:  30 min
4
Philipsburg, St. Maarten-St. Martin
— 3 nights
Fly:  45 min
5
Basseterre, St. Kitts and Nevis
— 4 nights
Fly:  3 h 45 min
6
San Juan, Puerto Rico
— 2 nights
Fly:  27 h
End: Sydney, Australia

2
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Venture out of the city with trips to Monkey Threads (in Luquillo), El Yunque Rain Forest (in El Yunque National Forest) and Trollbeads (in Canovanas). There's lots more to do: get to know the fascinating history of Old San Juan, scramble along the landscape with a canyoning and rapelling tour, view the masterpieces at La Casa de los Contrafuertes, and pause for some photo ops at Juan Ponce de Leon Statue.

To find ratings, reviews, and more tourist information, use the San Juan tour itinerary planner.

Sydney, Australia to San Juan is an approximately 27- hour flight. You can also do a combination of flight and car; or do a combination of flight, car, and shuttle. The time zone difference moving from Australian Eastern Standard Time (AEST) to Atlantic Standard Time (AST) is minus 14 hours. Plan for a bit warmer temperatures traveling from Sydney in November, with highs in San Juan at 36°C and lows at 28°C. Cap off your sightseeing on the 17th (Tue) early enough to travel to St. Eustatius.

Things to do in San Juan

Historic Sites Tours Parks

Side Trips

Monkey Threads, El Yunque Rain Forest, Trollbeads
Find places to stay Nov 15 — 17:
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Food Tours

3
nights
St. Eustatius, St. Eustatius

St. Eustatius ©
Once a tax-free haven and the busiest seaport in the world, St.
Kick off your visit on the 18th (Wed): identify plant and animal life at Zeelandia Beach, then explore the wealth of natural beauty at Quill/Boven National Park, and then steep yourself in history at Fort de Windt. On the next day, contemplate the long history of Fort Oranje, kick back and relax at Oranje Bay Oranjestad Beach, then admire the natural beauty at Miriam C. Schmid Botanical Garden, and finally contemplate the long history of St Eustatius Historical Foundation Museum.

For other places to visit, reviews, more things to do, and other tourist information, read our St. Eustatius trip itinerary website.

You can fly from San Juan to St. Eustatius in 3.5 hours. Expect slightly colder weather when traveling from San Juan in November: highs in St. Eustatius hover around 32°C, while lows dip to 28°C. Finish your sightseeing early on the 20th (Fri) to allow enough time to fly to Windwardside.

Things to do in St. Eustatius

Parks Historic Sites Beaches
Find places to stay Nov 17 — 20:
Highlights from your plan
Quill/Boven National Park ©
Quill/Boven National Park
Fort de Windt ©
Fort de Windt
Miriam C. Schmid Botanical Garden ©
Miriam C. Schmid Botanical Garden

4
nights
Windwardside, Saba

Windwardside ©
Windwardside is the second largest town on the island of Saba, aptly named for being on the windward side of the island.GeographyThe hike up the stairs to the top of Mount Scenery can begin from the road just outside Windwardside.TourismTwo banks and several dive shops as well as multiple grocery stores, gift shops, etc. Windwardside is known for nature, museums, and shopping. Your plan includes some of its best attractions: take your sightseeing to a higher altitude at Mount Scenery, shop like a local with Jo Bean Glass, don't miss a visit to Tent Reef Wall, and explore the activities along Saba National Marine Park.

For maps, where to stay, photos, and more tourist information, go to the Windwardside trip itinerary site.

You can fly from St. Eustatius to Windwardside in 2.5 hours. Alternatively, you can do a combination of flight, car, and ferry; or ride a ferry. In November, daytime highs in Windwardside are 32°C, while nighttime lows are 29°C. Finish your sightseeing early on the 24th (Tue) to allow enough time to travel to Philipsburg.

Things to do in Windwardside

Parks Nature Wildlife

Side Trips

Saba, The Bottom, Saba National Marine Park
Find places to stay Nov 20 — 24:
Highlights from your plan
Mount Scenery ©
Mount Scenery
Saba National Marine Park ©
Saba National Marine Park
Ladder Bay ©
Ladder Bay

3
nights
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Kick off your visit on the 25th (Wed): appreciate the history behind Brown Pelicans, kick back and relax at Maho Beach, and then get some thrills on the water with a speed boat tour. Get ready for a full day of sightseeing on the 26th (Thu): enjoy the sand and surf at Orient Bay Beach, then enjoy the sand and surf at Great Bay Beach, and then don't miss a visit to Frontstreet.

To see where to stay, reviews, traveler tips, and other tourist information, read our Philipsburg online trip itinerary maker.

Philipsburg is just a short distance from Windwardside. Expect a daytime high around 35°C in November, and nighttime lows around 30°C. Wrap up your sightseeing by early afternoon on the 27th (Fri) to allow enough time to travel to Basseterre.

Things to do in Philipsburg

Outdoors Beaches Parks

Side Trips

Simpson Bay, Mullet Bay Beach, Maho Beach, Orient Bay Beach
Find places to stay Nov 24 — 27:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Mullet Bay Beach ©
Mullet Bay Beach

4
nights
Basseterre, St. Kitts and Nevis

Basseterre ©
Step out of Basseterre to go to Charlestown and see Pinney's Beach, which is approximately 56 minutes away.

For traveler tips, maps, where to stay, and tourist information, go to the Basseterre trip itinerary planning site.

Traveling by flight from Philipsburg to Basseterre takes an hour. In November in Basseterre, expect temperatures between 36°C during the day and 28°C at night. Wrap up your sightseeing on the 1st (Tue) early enough to travel to San Juan.

Things to do in Basseterre

Parks Outdoors Wildlife

Side Trips

St. Kitts, Pinney's Beach
Find places to stay Nov 27 — Dec 1:
Highlights from your plan
Brimstone Hill Fortress National Park ©
Brimstone Hill Fortress National Park
Pinney's Beach ©
Pinney's Beach
Cockleshell Beach ©
Cockleshell Beach

2
nights
San Juan, Puerto Rico

San Juan ©
On the 1st (Tue), revel in the low prices at Coach Outlet Store, then take in the architecture and atmosphere at Catedral Metropolitana Basilica de San Juan Bautista, and then appreciate the extensive heritage of Old San Juan. Keep things going the next day: skim along the rocks with a canyoning and rapelling tour, then indulge in some culinary diversions at a local gastronomic tour, and then appreciate the extensive heritage of Sitio Histórico de San Juan.

For more things to do, where to stay, maps, and tourist information, use the San Juan day trip planning site.

Getting from Basseterre to San Juan by flight takes about 4 hours. Other options: do a combination of ferry, taxi, and flight. You'll have a few hours on the 3rd (Thu) to wrap things up before traveling home.

Things to do in San Juan

Historic Sites Tours Neighborhoods
Find places to stay Dec 1 — 3:
Highlights from your plan
Old San Juan ©
Old San Juan
Food Tours
Canyoning & Rappelling Tours

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