Sailing & Hiking Vacations 


Tortola Sailing & Sights offer great vacations for people who want to learn to sail and also explore the beautiful Virgin Islands by foot. It is great to get ashore and take a walk to absorb the history and culture of local communities. British Virgin Islands isn't known for it's 'Everest' like mountains, however Sage Mountain is the highest in this part of the eastern Caribbean at 1,760ft. With around 60 islands, there is a lot to explore, weather you want an easy wander through the beautiful Sandy Cay to see the hermit crabs or a steep climb of 1000ft to see the sunrise over Jost Van Dyke. 


Sample Itinerary For Hike & Sail

(This sample itinerary will never be 100% accurate, your skipper will always have flexibity because of weather, seasonality, student needs etc.)

Day 1: 9.30am Arrive at our classroom in Soper’s Hole Marina to meet your fellow students and instructor. After completing your Health & Safety paperwork, your instructor will take you to your boat and get you settled into your cabin. Then it's time for the safety briefing, provisioning etc. before setting sail. 

Afternoon sailing will get you to Norman Island in time to visit The Caves before picking up a mooring ball at 'The Bight' .There will be time for a swim and a sundowner on Willy T's. Crew (the students and skipper) will decide on the nights they cook onboard or eat ashore - At Norman Island there is the choice to eat at Pirate's Bight or Willy T's.  

Day 2 : After an early breakfast onboard it's time to dingy to Norman Island to start 1 hour hike to Spyglass Hill or 2.5 hours to West Hill returning to the boat in time for lunch before lifting the anchor and sailing to 'The Indians' for a snorkel. Anchoring in one of the many bays off Peter Island. Dinner will be onboard.

Day 3  The day will start with breakfast onboard, before a full day of sailing, allowing you to build your confidence at the helm. Lunch and dinner onboard, with time for a snorkel in the bay where you drop anchor for the night.   

Day 4 Another early breakfast will allow you time to hike for 4 hours to the top of Peter Island. After lunch onboard, the afternoon will be spent back on the winch and the helm. You will drop anchor before dark at Trellis Bay. It is a quick dingy ride ashore to one of several restaurants. 

Day 5 After an early breakfast and a dingy ride ashore, you will take on Mount Alma & Trellis Bay hike. This 3.2mile will take approx 3 and 1/2 hours (extra 1 and 1/2 hours if you want to reach Mount Alma). Exploring Beef Island before you return to the boat for lunch. The afternoon will see you tightening your main sail as you get more sailing in. Tonight picking up a mooring ball off Scrub Island. 

Day 6  Breakfast either on  the boat or ashore at the beautiful Scrub Island resort, then it's time to set sail for a full day of sailing to Virgin Gorda. A visit to the 'Baths' is a must. After a few hours at the Baths it's back onboard for an afternoon of sailing. Depending on which course you are taking, you will have exams to do every few days, but don't worry, your instructor will talk you through all of this so it won't be a surprise to you. Anchoring in Spanish Town, the choice of dinner will be onboard or eat at the beautiful Coco Maya.  

 Students having a break after a busy day of docking practice

Students having a break after a busy day of docking practice


Day 7 A full day of sailing to learn new skills as you make your way around Virgin Gorda to North Sounds, with breakfast and lunch onboard. Once you drop the anchor you will have time for a snorkel and a sundowner. Choices for dinner at North Sounds include Leverick Bay, Saba Rock or Bitter End Yacht Club. 

Day 8 After breakfast you will have time to complete one of four beautiful hikes on Virgin Gorda. For example, a 2.5 hour walk to  Gorda Peak will allow you views all across Virgin Gorda. Ask your skipper to point out Richard Branson's islands, Nector and Mosquito, before heading back to the boat for lunch. You will sail west after lunch, continuing to build your knowledge. Dropping anchor in Monkey Bay, Guana Island. Here you will have time for a swim or a snorkel before dinner and sundowner will be onboard tonight.

Day 9 After a leisurely breakfast, it's another full day of sailing. You will follow the north coast of Tortola, as you sail west. This evening you will anchor in the beautiful Cane Garden Bay. A busy bay with lots of bars, live music and restaurants. Your instructor will have lots of info and recommendations about Happy Hours, dinner, etc. 

Day 10 After a very early breakfast there is a short sail west to Smugglers Cove, where you can really 'go wild'. There are 3 Arawak trails in this area, not always a path to follow, but well worth the effort. You will definitely need sturdy boots, long sleeves and pants for this part of the island (your instructor will need his machete and a compass). At the top you will be rewarded with views over Smugglers Cove and Long Bay. This trek is hard walk, so you will enjoy a swim & a snorkel at Smugglers Cove before you set sail for the afternoon. Your instructor will make sure you get to Great Harbour to drop anchor before dark. Here you can enjoy a night at the world renown 'Foxy's bar'.

Day 11  You will have a full day of sailing around Jost Van Dyke, practicing 'man overboard', passage planning etc. You might have time to put a dollar in your pocket as you swim ashore to spend that soggy dollar at 'Soggy Dollar' (I'd say put a few of them in your pocket for your Pain Killer). You will another night at Jost Van Dyke in preparation for the walk the ext morning.

Day 12 An early start before breakfast will allow you to get to the top of Jost Van Dyke's Mahjonny Hill to watch the sunrise over the beautiful Caribbean. This walk can be extended to a 3 hour hike depending on how the learning is going - or you will be back on the boat for breakfast before you set sail. You will make a quick visit to Sandy Cay - a beautiful little island great for a walk through, a snorkel and view for lunch (on the boat).

Day 13 The day will start with revision after breakfast, checking you remember the 'rules of the road'. The day will be spent practicing everything you have learnt and focusing on docking skill. 

Day 14 An early breakfast in Sopers Hole marina will allow you time to complete the 3.5mile hike, to Smugglers Cove over the hill from Sopers hole and returning to the boat in approx 2.5 hours (it could take longer if you stop in at Fish & Lime for lunch and a refreshing juice). The afternoon will then be spent doing your practical sailing exam before finishing your exam paper in time for a sundowner (or 2)

Day 15 The last day of your trip will be spent polishing of skills on anything your instructors may feel you need practice on, before returning to Sopers Hole Marina in time for you to catch your taxi to the ferry dock or airport. 

This will be the hardest task of your whole trip......leaving the beautiful BVI and the new friend's you have met :-) 




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