A sailing-led passage through the Grenadines

Wind & Water

When to Go

November-May

Trip Length

8 days/7 nights

Price Guide

from $5,950 pp

This 7-night journey through St. Vincent and the Grenadines is built around sailing and time on the water. Spend full days aboard a private boat, cutting across open channels to the Tobago Cays, snorkeling shallow reefs, and swimming from the stern into clear blue shallows. Evenings return you to Bequia for quiet dinners near the sea, with space to rest, watch the light fade, and feel the distance from everything left behind.

Trip Highlights

Share two secluded seaside dinners arranged just beyond the tide line

Snorkel shallow reefs among sea turtles and coral gardens

Spend unstructured days in a private plunge pool villa on Bequia

Sail by private boat across open channels to the Tobago Cays

Day by Day

Anchorage, open water, and quiet shores

Bequia

Day 1: Arrival on Bequia
Arrive in St. Vincent and continue by small aircraft or ferry to Bequia. Settle into your villa at The Liming, where the sea stretches wide beyond your terrace. Spend the afternoon swimming, walking the beach, or resting by your private plunge pool as boats drift quietly through Admiralty Bay.

Day 2: Sailing into open water
Board a private sailboat and leave Bequia behind, crossing open channels toward the southern Grenadines. Spend the day under sail, stopping to swim straight from the boat and snorkel clear reefs along the way. Return to Bequia in the late afternoon with the evening free to enjoy the calm of the island.

Day 3: Tobago Cays by sea
Set out early for a full-day private sail to the Tobago Cays, one of the Caribbean’s most striking marine reserves. Anchor near uninhabited islands, snorkel among sea turtles and reef fish, and step ashore on white sand beaches with nothing built in sight. Lunch is taken on board before the return sail in the afternoon light.

Day 4: A slower pace
Keep the day close to Bequia. Swim in the bay, explore quiet stretches of sand, or spend time at your villa with no plans to follow. In the evening, enjoy a private dinner arranged near the water, with simple food and the sound of the sea close at hand.
Day 5: Reefs and nearby islands
Sail again, this time to nearby cays and reefs around Bequia. Snorkel in shallow water, float alongside the boat, and move easily between anchorages. The afternoon is spent at anchor or back on shore, depending on the weather and your preference.

Day 6: Sunset on the water
Spend the morning at leisure before heading out for a late-day sail along Bequia’s coastline. As the sun drops, the hills soften in color and the water grows still. Return ashore for a quiet evening and a second private dining moment arranged in a secluded setting.

Day 7: Time left open
Your final full day is intentionally unstructured. Swim, walk the beach, or remain close to your villa, letting the pace slow naturally before departure.

Day 8: Departure
Return to St. Vincent for onward travel, carrying with you the memory of open crossings, clear water, and long hours spent at sea.
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Best trip of our lives

We had the absolute best trip of our lives thanks to ROAM! Our hotels and excursions were unbelievable, truly I can’t thank them enough.

— Sara T.

Jungle to paradise

Our trip went off flawlessly. We enjoyed every venue, excursion, every minute. We went from the jungle in Belize to a private island

— Charles M.

A logistical relief!

Adrienne and team were so easy to work with, and truly took the detailed logistical stress off of planning AND getting through our vacation.

— Darcy T.

Unreal experience

An absolutely unreal experience. Attention to detail was exceptional. The service Roam provides is worth every penny and more.

— Mike T.

The perfect trip

You planned the perfect trip, the accommodations were first class and the guides were very good and knowledgeable. I will be spreading the word.

— Laura L.