54 days in Caribbean Itinerary

54 days in Caribbean Itinerary

Created using Inspirock journey builder

Plan created by another user. Make it yours
1
San Juan, Puerto Rico
— 4 nights
2
Jost Van Dyke, British Virgin Islands
— 5 nights
3
The Valley, Anguilla
— 3 nights
4
Jolly Harbour, Antigua and Barbuda
— 5 nights
5
Willemstad, Curacao
— 11 nights
6
Oranjestad, Aruba
— 8 nights
7
Providenciales, Turks and Caicos
— 7 nights
8
Seven Mile Beach, Cayman Islands
— 8 nights

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4
nights
San Juan, Puerto Rico

San Juan ©

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Deepen your sense of the past at sights like Old San Juan and Paseo de la Princesa. You'll enjoy a bit of beach vacationing at Ocean Park Beach and Balneario El Escambron. There's still lots to do: contemplate the waterfront views at Condado Lagoon, kick your exploration up a notch at Campo Rico Ziplining Adventures, walk around La Marquesa Forest Park, and make a trip to Parque de las Palomas.

Plan my trip to San Juan with suggested itineraries provided by Inspirock.

Las Vegas, USA to San Juan is an approximately 12.5-hour flight. The time zone difference moving from Pacific Standard Time to Atlantic Standard Time is 4 hours. Plan for somewhat warmer nights when traveling from Las Vegas in September since evenings lows in San Juan dip to 78°F. Wrap up your sightseeing on the 23rd (Wed) to allow time to travel to Jost Van Dyke.

Things to do in San Juan

Outdoors · Parks · Historic Sites · Beaches

Side Trip

Find places to stay Sep 19 — 23:
Highlights from your plan
La Marquesa Forest Park ©
La Marquesa Forest Park
Old San Juan ©
Old San Juan
Paseo de la Princesa ©
Paseo de la Princesa

5
nights

Jost Van Dyke ©
Home to fewer than 300 residents and encompassing just 8 sq km (3 sq mi), Jost Van Dyke represents the smallest of the four main British Virgin Islands.
Kids will appreciate attractions like White Bay and Foxy's Charters & Water Taxi. You'll discover tucked-away gems like Ocean Spa Bvi and The Bubbly Pool.

For reviews, more things to do, ratings, and more tourist information, refer to the Jost Van Dyke trip planner.

Do a combination of flight and ferry from San Juan to Jost Van Dyke in 3.5 hours. In September, daily temperatures in Jost Van Dyke can reach 89°F, while at night they dip to 80°F. You'll set off for The Valley on the 28th (Mon).

Things to do in Jost Van Dyke

Outdoors · Parks · Adventure · Tours
Find places to stay Sep 23 — 28:
Highlights from your plan
White Bay ©
White Bay
Foxy's Charters & Water Taxi ©
Foxy's Charters & Water Taxi

3
nights
The Valley, Anguilla

The Valley ©
The Valley is the capital of Anguilla, one of its fourteen districts, and the main "town" on the island., it had a population of 1,067.HistoryHistorical landmarksThe Valley has few examples of colonial architecture due to the relocation of Anguilla's administration to St. Kids will enjoy Shoal Bay and Meads Bay. Step off the beaten path and head to Crocus Bay Beach and St. Gerard Roman Catholic Church. And it doesn't end there: kick back and relax at Cove Bay, stroll through Rendezvous Bay Beach, take a tour by water with Vigilant Divers Anguilla, and soothe aching muscles at some of the top local wellness centers.

For photos, maps, where to stay, and other tourist information, read The Valley road trip tool.

Do a combination of ferry and flight from Jost Van Dyke to The Valley in 4 hours. In September in The Valley, expect temperatures between 89°F during the day and 78°F at night. Wrap up your sightseeing on the 1st (Thu) to allow time to travel to Jolly Harbour.

Things to do in The Valley

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Sep 28 — Oct 1:
Highlights from your plan
Meads Bay ©
Meads Bay
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

5
nights

Jolly Harbour is a township on Antigua island, in Antigua and Barbuda.GeographyThe town is located in the southwest coast of the island in Saint Mary Parish, close to Bolans and south of Five Island Harbour.TourismIt contains shops, restaurants, holiday villas, private houses, golf-course and a marina and boatyard. Get outdoors at Scuba & Snorkeling and Deep Bay Beach. Explore hidden gems such as Ffryes Beach and Jolly Harbour Golf Club. Next up on the itinerary: kick back and relax at Jolly Beach, take in the exciting artwork at Art At The Ridge, get outside with jetovator Antigua, and stroll through Turners Beach.

For traveler tips, ratings, reviews, and more tourist information, read Jolly Harbour travel route app.

Traveling by combination of taxi, ferry, and flight from The Valley to Jolly Harbour takes 5 hours. Expect a daytime high around 87°F in October, and nighttime lows around 77°F. Wrap up your sightseeing by early afternoon on the 6th (Tue) to allow time for travel to Willemstad.

Things to do in Jolly Harbour

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Oct 1 — 6:
Highlights from your plan
Scuba & Snorkeling
Turners Beach ©
Turners Beach
Ffryes Beach ©
Ffryes Beach

11
nights
Willemstad, Curacao

Willemstad ©
Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Fort Beekenburg and Fortkirche - De Fortkerk - The Fortchurch in Fort Amsterdam will appeal to history buffs. Visiting Scuba & Snorkeling and Playa Jeremi will get you outdoors. Go for a jaunt from Willemstad to Barber to see Museo di Ka'i Orgel about 36 minutes away. There's lots more to do: tee off at Old Quarry Golf Course, explore the fascinating underground world of Boca Tabla, tour the pleasant surroundings at Playa PortoMari, and soothe aching muscles at some of the top local wellness centers.

To see reviews, maps, ratings, and other tourist information, read our Willemstad route builder app.

Getting from Jolly Harbour to Willemstad by flight takes about 9 hours. In October, daytime highs in Willemstad are 91°F, while nighttime lows are 80°F. On the 18th (Sun), you're off to Oranjestad.

Things to do in Willemstad

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Oct 6 — 18:
Highlights from your plan
Blue Bay Beach ©
Blue Bay Beach
Daaibooi Beach ©
Daaibooi Beach
Playa Jeremi ©
Playa Jeremi

8
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
You'll get in some beach time at Eagle Beach and Boca Cataavlina. Discover out-of-the-way places like Mangel Halto Beach and Malmok Reef. You'll find plenty of places to visit near Oranjestad: San Nicolas (Cosecha in San Nicolas, Baby Beach, &more). There's much more to do: see Aruba Off-Road Adventure, take in the dramatic natural features at Seroe Colorado, take a pleasant ride with The Gold Mine Ranch, and kick back and relax at Druif Beach.

For where to stay, reviews, and tourist information, refer to the Oranjestad day trip planner.

You can fly from Willemstad to Oranjestad in 4.5 hours. October in Oranjestad sees daily highs of 91°F and lows of 81°F at night. Wrap up your sightseeing by early afternoon on the 26th (Mon) to allow enough time to travel to Providenciales.

Things to do in Oranjestad

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Oct 18 — 26:
Highlights from your plan
Mangel Halto Beach ©
Mangel Halto Beach
Eagle Beach ©
Eagle Beach
Manchebo Beach ©
Manchebo Beach

7
nights
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Your itinerary includes some good beach time at Grace Bay Beach and Long Bay Beach. Your inner history buff will appreciate Cheshire Hall Plantation and Sapodilla Bay Hill Rock Carvings. Spend the 30th (Fri) exploring nature at Princess Alexandra National Park. The adventure continues: kick back and relax at Half Moon Bay, don't miss a visit to Leeward Beach, stroll through Smith's Reef, and tee off at Provo Golf Club.

For other places to visit, maps, photos, and more tourist information, read Providenciales trip itinerary maker website.

You can fly from Oranjestad to Providenciales in 9.5 hours. You'll gain 1 hour traveling from Oranjestad to Providenciales due to the time zone difference. October in Providenciales sees daily highs of 88°F and lows of 79°F at night. Wrap up your sightseeing by early afternoon on the 2nd (Mon) to allow enough time to travel to Seven Mile Beach.

Things to do in Providenciales

Parks · Outdoors · Wildlife · Nature

Side Trip

Find places to stay Oct 26 — Nov 2:
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
M & J's Charters ©
M & J's Charters
Half Moon Bay ©
Half Moon Bay

8
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Discover out-of-the-way places like Smith's Barcadere and Governors Beach. We've included these beaches for you: Seven Mile Beach and Cemetery Beach and Reef. Step out of Seven Mile Beach with an excursion to Davinoff's Concrete Sculpture Garden in North Side--about 40 minutes away. There's lots more to do: explore and take pictures at Kittiwake Shipwreck & Artificial Reef, push the limits with Jetpack Cayman, Head underground at Devil's Grotto, and discover the deep blue sea with a scuba or snorkeling tour.

To see traveler tips, photos, reviews, and more tourist information, read Seven Mile Beach online vacation builder.

You can fly from Providenciales to Seven Mile Beach in 9 hours. In November, daytime highs in Seven Mile Beach are 85°F, while nighttime lows are 77°F. On the 10th (Tue), you'll have the morning to explore before heading back home.

Things to do in Seven Mile Beach

Parks · Outdoors · Wildlife · Beaches

Side Trips

Find places to stay Nov 2 — 10:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Smith's Barcadere ©
Smith's Barcadere
Governors Beach ©
Governors Beach

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