13 days in Simpson Bay, Gustavia & The Valley Itinerary
Created using Inspirock Caribbean trip itinerary planner
Start: Toronto, Canada
Fly
1
Simpson Bay, St. Maarten-St. Martin
— 3 nights
Ferry
2
Gustavia, St. Barthelemy
— 5 nights
+3
Ferry to Marigot, Saint Martin, Foot to St. Martin, Ferry to Anguilla, Taxi to The Valley
3
The Valley, Anguilla
— 4 nights
Fly
End: Miami, United States
Sun, Jan 29 - Fri, Feb 10
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Simpson Bay, St. Maarten-St. Martin — 3 nights
Simpson Bay offers luxury resort living and good access to the main areas of the island.Simpson Bay is known for wildlife, adventure, and nightlife. Your trip includes some of its best attractions: discover the deep blue sea with a scuba or snorkeling tour, contemplate the waterfront views at Mullet Bay Beach, take in the waterfront activity at Isle Del Sol Marina, and kick back and relax at Cupecoy Bay Beach.
To see more things to do, other places to visit, reviews, and more tourist information, read Simpson Bay attractions planning website.
Toronto, Canada to Simpson Bay is an approximately 8-hour flight. Due to the time zone difference, you'll lose 1 hour traveling from Toronto to Simpson Bay. Expect much hotter temperatures when traveling from Toronto in January; daily highs in Simpson Bay reach 33°C and lows reach 28°C. Finish your sightseeing early on the 1st (Wed) so you can ride a ferry to Gustavia.
Side Trips
Find places to stay Jan 29 — Feb 1:
Highlights from your trip
Gustavia, St. Barthelemy — 5 nights

Gustavia is known for parks, wildlife, and shopping. Your trip includes some of its best attractions: stroll through Shell Beach, kick back and relax at Anse du Gouverneur, and see some colorful creatures with a scuba or snorkeling tour.
To find photos, traveler tips, other places to visit, and tourist information, refer to the Gustavia route maker tool.
You can ride a ferry from Simpson Bay to Gustavia in 1.5 hours. Alternatively, you can fly. Wrap up your sightseeing on the 6th (Mon) early enough to travel to The Valley.
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To find photos, traveler tips, other places to visit, and tourist information, refer to the Gustavia route maker tool.
You can ride a ferry from Simpson Bay to Gustavia in 1.5 hours. Alternatively, you can fly. Wrap up your sightseeing on the 6th (Mon) early enough to travel to The Valley.
Side Trips
Find places to stay Feb 1 — 6:
Highlights from your trip
The Valley, Anguilla — 4 nights

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. The Valley is known for nightlife, adventure, and wildlife. Your trip includes some of its best attractions: stroll through Shoal Bay, soothe aching muscles at some of the top local wellness centers, get interesting insight from Tours, and kick back and relax at Crocus Bay Beach.
For more things to do, maps, where to stay, and other tourist information, read our The Valley attractions website.
Traveling by combination of ferry and taxi from Gustavia to The Valley takes 3 hours. Alternatively, you can do a combination of ferry, car, and flight; or do a combination of flight, shuttle, ferry, and taxi. In February, daily temperatures in The Valley can reach 33°C, while at night they dip to 26°C. Cap off your sightseeing on the 10th (Fri) early enough to travel back home.
more
For more things to do, maps, where to stay, and other tourist information, read our The Valley attractions website.
Traveling by combination of ferry and taxi from Gustavia to The Valley takes 3 hours. Alternatively, you can do a combination of ferry, car, and flight; or do a combination of flight, shuttle, ferry, and taxi. In February, daily temperatures in The Valley can reach 33°C, while at night they dip to 26°C. Cap off your sightseeing on the 10th (Fri) early enough to travel back home.
Side Trips
Find places to stay Feb 6 — 10:
Highlights from your trip
Anguilla travel guide
A peaceful set of islands with a pristine, bespoke tourism infrastructure, Anguilla offers a restful vacation for beach-lovers, honeymooners, and diving enthusiasts. A scattering of historic attractions in Anguilla stand as testament to the native and colonial histories of the set of paradisal islands, but the focus here lies much more on coastlines rather than timelines. The beaches of Anguilla remain relatively untouched, allowing the scenery to speak for itself. However, this is no back-to-basics place, with whatever tourist developments there are being made to luxury standards, and priced accordingly.