21 days in Caribbean Itinerary

21 days in Caribbean Itinerary

Created using Inspirock Caribbean itinerary planner

Make it your trip
Fly
1
San Juan, Puerto Rico
— 2 nights
Fly
2
St. Eustatius, St. Eustatius
— 3 nights
Ferry
3
Windwardside, Saba
— 4 nights
Ferry
4
Philipsburg, St. Maarten-St. Martin
— 3 nights
Fly
5
Basseterre, St. Kitts and Nevis
— 4 nights
Fly
6
San Juan, Puerto Rico
— 2 nights
Fly

S M T W T F S
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5

San Juan, Puerto Rico

— 2 nights

Walled City

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

For where to stay, traveler tips, ratings, and more tourist information, use the San Juan tour itinerary planner.

Sydney, Australia to San Juan is an approximately 28-hour flight. 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 catch the flight to St. Eustatius.

Things to do in San Juan

Historic Sites · Tours · Nature · Wildlife

Side Trips

Find places to stay Nov 15 — 17:

St. Eustatius, St. Eustatius

— 3 nights

Statia

Once a tax-free haven and the busiest seaport in the world, St.
Kick off your visit on the 18th (Wed): enjoy the sand and surf 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 stroll through Miriam C. Schmid Botanical Garden, and finally contemplate the long history of St Eustatius Historical Foundation Museum.

To see reviews, ratings, other places to visit, and other tourist information, read our St. Eustatius trip itinerary website.

You can fly from San Juan to St. Eustatius in 6.5 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 ride a ferry to Windwardside.

Things to do in St. Eustatius

Parks · Historic Sites · Beaches · Outdoors
Find places to stay Nov 17 — 20:

Windwardside, Saba

— 4 nights
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 trip includes some of its best attractions: take your sightseeing to a higher altitude at Mount Scenery, explore the activities along Well's Bay, take a stroll through Windwardside, and stroll through Saba National Marine Park.

To see more things to do, where to stay, reviews, and more tourist information, go to the Windwardside trip itinerary site.

You can ride a ferry from St. Eustatius to Windwardside in 4.5 hours. Alternatively, you can fly. In November, daytime highs in Windwardside are 32°C, while nighttime lows are 29°C. Wrap up your sightseeing by early afternoon on the 24th (Tue) to allow enough time to ride a ferry to Philipsburg.

Things to do in Windwardside

Nature · Parks · Wildlife · Museums

Side Trips

Find places to stay Nov 20 — 24:

Philipsburg, St. Maarten-St. Martin

— 3 nights
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 find other places to visit, photos, and other tourist information, read our Philipsburg online trip itinerary maker.

Traveling by ferry from Windwardside to Philipsburg takes 2.5 hours. Alternatively, you can fly. 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 fly to Basseterre.

Things to do in Philipsburg

Outdoors · Beaches · Parks · Wildlife

Side Trips

Find places to stay Nov 24 — 27:

Basseterre, St. Kitts and Nevis

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

For traveler tips, more things to do, and tourist information, go to the Basseterre trip itinerary planning site.

Traveling by flight from Philipsburg to Basseterre takes 4 hours. 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 fly to San Juan.

Things to do in Basseterre

Parks · Outdoors · Wildlife · Historic Sites

Side Trips

Find places to stay Nov 27 — Dec 1:

San Juan, Puerto Rico

— 2 nights

Walled City

Start off your visit on the 1st (Tue): revel in the low prices at Coach Outlet Store, pause for some serene contemplation at Catedral Basilica Menor de San Juan Bautista, and then get to know the fascinating history of Old San Juan. Keep things going the next day: scramble along the landscape 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.

To see more things to do, where to stay, maps, and other tourist information, go to the San Juan trip planning app.

Traveling by flight from Basseterre to San Juan takes 4.5 hours. On the 3rd (Thu), you'll have the morning to explore before heading back home.

Things to do in San Juan

Historic Sites · Tours · Neighborhoods · Outdoors
Find places to stay Dec 1 — 3:

Saba travel guide

4.6
Mountains · Bodies of Water · Museums
Tiny Saba encompasses just 13 sq km (5 sq mi), yet it represents one of the world's top scuba diving destinations. A trip to Saba takes you to an overseas dominion of the Netherlands, which houses fewer than 2,000 permanent residents and hundreds of species of native wildlife. In addition to 200 types of fish and 60 bird species, the island shelters at least nine different kinds of wild orchids. Visitors spot these fragile flowers everywhere they go during their Saba vacation, as they grow next to hiking paths and alongside the island's main road. To see what treasures the surrounding waters hide, bring your diving gear and head to the nearest beach.

St. Maarten-St. Martin travel guide

4.3
Gift & Specialty Shops · Beaches · Scuba & Snorkeling
A trip to St. Maarten-St. Martin allows you to discover two separate colonies occupying one small island of just 95 sq km (37 sq mi). Divided between France and the Netherlands, this tiny spit of land in the Caribbean treats visitors to a surprisingly diverse blend of native and European cultures. A tour of St. Maarten-St. Martin reveals a landscape of both urban and untamed areas, with sandy beaches and pristine rainforests often appearing as extensions of one another. The French north of the island offers a string of outstanding restaurants and lively beaches popular with a young party-loving crowd. The Dutch southern section lures visitors with its dynamic bar scene and casinos.

St. Kitts and Nevis travel guide

4
Beaches · Shopping · Scuba & Snorkeling
A trip to St. Kitts and Nevis takes you to the smallest country in the Americas. Although diminutive in size, the two Caribbean islands offer a distinct tropical experience to visitors. Rich in history, the islands feature forested hills, tranquil beaches, charming villages, and restored sugar plantations. On a tour of St. Kitts and Nevis you can visit historic forts and quaint colonial towns, lounge on picturesque stretches of sand, or enjoy hiking the dormant Mount Liamuiga, the islands' highest peak.