Sailnboat
United States

Eastern Seaboard

Yacht charter in United States

Choose from 4 yachts across United States. Spread over 1 sailing regions. Prices from €8,627 per week.

  • 4
    Yachts available
  • €8,627
    From / week
  • 1
    Charter regions
  • 1
    Marinas

Why this country

Sailing in United States

We should be precise about this one: we list four boats in the United States and all four are at Annapolis, Maryland, on the Chesapeake Bay. There is nothing in Florida, New England, California or the US Virgin Islands. If you came here looking for the Keys or San Diego, this is not that page.

What it is instead is one of the better-kept secrets in American sailing. Annapolis sits where the Severn River opens into the bay and calls itself America's sailing capital with some justification — the Naval Academy is here, the boat shows are here, and the bay behind the town gives hundreds of miles of protected, mostly flat water. The Chesapeake is a drowned river valley rather than a coastline: a shallow estuary of islands, marshes, tidal creeks and sand flats that rearrange themselves with every wind shift. The skill it asks for is reading depth, not handling weather.

The season runs opposite to the way most people would guess. July and August are often hot and light — poor sailing. The good months are spring and autumn, and September is widely reckoned the best of the year: steady wind, lower humidity, comfortable temperatures. April and November are the quiet shoulders, cooler, with better light and fewer boats. The one caution is that the second half of the hurricane season overlaps the best of the autumn, so a long cruise in late September or October carries more weather risk than the sailing conditions alone suggest.

The four boats average 13.5 metres and 3.3 cabins with an average build year of 2018, and weekly rates run roughly €8,600 to €11,100 — high for the size, which reflects a small, well-equipped fleet in an expensive market.

On the water

Sailing conditions in United States

Where this actually is
Annapolis, Chesapeake Bay

All 4 boats. No listings in Florida, New England, California or the US Virgin Islands.

Best month
September

Steady wind, lower humidity and comfortable temperatures. Spring and autumn are the seasons here; July and August are often hot and light.

Shoulder months
April and November

Cooler, quieter and cheaper, with better light. The trade calls April shoulder season for exactly this reason.

The water
Shallow estuary, not coastline

A drowned river valley of islands, marshes, creeks and sand flats. Protected and mostly flat, but depth is the constant consideration.

Hurricane season overlap
Late September – November carries risk

The best sailing months overlap the second half of the hurricane season. Short trips are fine; a long cruise then is a weather gamble.

Worth the detour

Where to drop anchor in United States

  • 1

    Annapolis

    The base: an intact 18th-century town with the Naval Academy at one end and City Dock at the other, where the water comes up to the pavement. Worth a night either side of the charter.

  • 2

    St Michaels

    Across the bay on the Eastern Shore, up the Miles River — a small town built on oystering with the Chesapeake Bay Maritime Museum on the waterfront. The standard first destination.

  • 3

    Oxford and the Tred Avon

    South of St Michaels: a village of about seven hundred people, a ferry that has run since 1683, and a river with deep water right up to the shore.

  • 4

    Wye River

    A branch of the Miles River with anchorages on both sides and almost nothing built on them. The best quiet night within a day of Annapolis.

  • 5

    Rock Hall and the Chester River

    North-east across the bay. Working watermen's harbours rather than restored towns, and a different side of the Chesapeake.

  • 6

    Solomons Island

    South down the western shore at the mouth of the Patuxent. A deep, sheltered harbour and the usual turning point for a week that heads south.

  • 7

    The Chesapeake Bay Bridge

    Four miles across, just north of Annapolis. Passing under it is the first thing most crews do and the mental boundary between the upper and middle bay.

  • 8

    Blue crabs

    Not a sight but the point of several stops. Steamed crabs at a waterfront table in September is the Chesapeake experience, and most of the good places have a dock.

Suggested routes

Where a week in United States could take you

The Eastern Shore from Annapolis

7 days

Short crossings and long rivers. The bay is wide but the destinations are up the creeks, so the week is more about pilotage than passage-making. Best in September.

  1. 1

    Annapolis

    Saturday handover at the city; move out past the Naval Academy and anchor off.

  2. 2

    St Michaels

    Across the bay under the Bay Bridge approach and up the Miles River.

  3. 3

    Wye River

    A short move to the quietest anchorage on this side.

  4. 4

    Oxford

    South round to the Tred Avon; deep water and a very small town.

  5. 5

    Solomons Island

    The long leg, south-west across the bay.

  6. 6

    Back north — Herring Bay or Rhode River

    Work up the western shore toward base.

  7. 7

    Annapolis

    Final leg for the Saturday handover.

Find a boat for this route

Before you book

Local rules and paperwork in United States

Skipper qualification
No federal licence; the operator decides. The United States has no national pleasure-craft licence for bareboat charter. Operators ask for a sailing resume instead, and on the Chesapeake they will want to know you can read a chart for depth.
Depth is the hazard
Shoals move; charts lag. The bay is shallow and its sand flats shift. Stay in the marked channels up the rivers, and treat the chart as a guide rather than a guarantee on the edges.
Season — not the summer
Spring and autumn, with September best. July and August are hot and often windless. If your dates are fixed to school holidays, be realistic that you will motor a good deal of the week.
Hurricane watch in autumn
The best months overlap the risk. Late September through November is the back half of the season. Operators monitor it; ask what the policy is if a storm is forecast during your week.
Thunderstorms
Sudden and local in summer. Chesapeake squall lines build quickly on hot afternoons and pass fast. The anchorages up the creeks are the reason they are not a serious problem.
Four boats only
Availability is narrow. One base, one changeover day. Enquire early, and be flexible on the week rather than booking flights first.

Checked October 2026. Rules change — confirm the detail that matters for your trip when you book.

What is here

The United States fleet at a glance

The fleet in United States is made up of 2 catamarans, 1 sailing yachts and 1 motor yachts.

Most boats here are catamarans, averaging 12.1 metres.

Weekly prices start in the €6,000 – €12,000 range, where 4 boats are listed.

Boats sleep between 6 and 10 guests, with cabins up to 4.

The most common size band is 10 – 13 m, with 2 boats.

The fullest month on the calendar right now is Oct 2026: 50% of the fleet already has at least one booking, while 2 boats are still completely open.

Budget

Charter prices in United States

Weekly rate, set by the operator. No booking fee.

Space on board

Boat sizes

Sleeping 6–10 guests

  • 10 – 13 m 2
  • 13 – 16 m 1
  • 16 – 20 m 1

Availability

How full is the calendar in United States?

Share of the United States fleet that already holds at least one reservation, for each of the next twelve months. Taken from the operators' own calendars and refreshed daily — a boat with one week booked can still be chartered in the others.

Months further out look emptier simply because they are further away — most charters are booked a few months ahead, not a year.

Most booked month

Oct 2026

50% of the fleet already booked

Most still open

Nov 2026

3 boats with no booking yet

The fleet

Yachts in United States

4 yachts available · from €1.232 / day

6
catamaran

Sia

Annapolis

3 cabins 8 guests 11.33 m 2022
From €1.580 / day €11.057 / week
View
6
sailboat

Slowdown

Annapolis

4 cabins 10 guests 13.24 m 2019
From €1.232 / day €8.627 / week
View

Where to sail

The one sailing region in United States

Every region we have boats in, largest fleet first — with the number of departure bases so you can see where a week actually starts.

Good to know

Frequently asked questions

Weekly prices in our catalogue break down as: €6,000 – €12,000 (4). The lowest published weekly rate is €8,627. These are the operators' own prices — we add no booking fee.
Our United States catalogue currently lists 2 catamarans, 1 sailing yachts, 1 motor yachts.
Booking pressure is highest in Oct, when 50% of the fleet already holds at least one reservation. Dec is the quietest month in our calendar. Availability shown on this site is synchronised daily from the operators' own reservation systems.
4 of the 4 boats we list in United States are available bareboat, meaning you sail them yourself. A recognised licence is required; the listing states which. 0 boats can be chartered with a skipper.
Boats in United States sleep from 6 up to 10 guests, with the largest offering 4 cabins. Most groups book a boat in the 10 – 13 m size band.

Ready to explore United States by sea?

4 verified yachts across 1 regions.